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Host Ian Hathaway interviews Brian Requarth, co-founder of VivaReal and Latitud, about building one of Latin America’s leading real estate marketplaces and later creating a founder support system for the next generation of entrepreneurs in the region. Brian traces his path from Sebastopol, California, to Bogotá, Colombia, where a one-way trip became six years, a language school helped pay the bills, and a chance meeting in an immigration office led to his first co-founder. He explains how the 2008 financial crisis pushed him to rethink the business, why Brazil became the market for VivaReal, and what it took to build a company through cold calls, investor rejection, bootstrapping, and $87 in the bank. They cover scaling VivaReal from a scrappy startup to more than 500 employees, learning the CEO job in real time, stepping back from the role for family, negotiating the Zap merger, and selling the company to OLX for roughly $550 million. Brian also discusses the post-exit search for purpose, the origins of Latitud, why founders need community earlier than they usually get it, the rise of globally ambitious Latin American founders, San Francisco’s role in accelerating learning, and how outsiders can turn their perspective into an advantage.

Show Notes:

(06:05) Teaching English And Meeting A Co-Founder In Immigration

(11:00) Pivoting After The 2008 Financial Crisis

(12:05) Engineering Serendipity

(15:00) Cold Calling Brazil And Bootstrapping VivaReal

(18:15) Scaling From Startup To 500 Employees

(19:10) Learning Fast As A First-Time CEO

(21:20) Stepping Back From The CEO Role

(24:30) Negotiating The Zap Merger

(28:00) Lessons From A $550M Exit

(30:30) The Origins Of Latitud

(36:45) Latin American Founders Building Globally

(39:15) San Francisco And The Velocity Of Learning

(42:15) Latin America’s Founder Mindset Shift

(47:10) Beyond The Bio with Brian Requarth

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Brian Requarth - Co-Founder, VivaReal & Latitud

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Brian Requarth: We really did need the capital. We had bootstrapped, and we had $87 in the bank. Either you get capital or you die. I’m moving to a new country, and I’m starting a business, and trying to get pregnant at the same time. So, that was absolutely brutal.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Brian Requarth, co-founder of Latitud, Latin America’s leading pre-seed fund that has become critical infrastructure for the next generation of founders in the region. But Brian’s journey to Latitud is about as unconventional as it gets. He grew up in a small town in Northern California’s wine country, dropped out of college, went back, and graduated with a degree in Spanish. Everyone assumed he’d become a Spanish teacher. Instead, at twenty-three, he drove to Costa Rica, sold his car, and bought a one-way ticket to Bogota to see a woman he’d met in college. The three-month plan became six years. [00:01:00] He married her, and he ended up teaching English door to door. He met his first business partner in line at the immigration office, both of them paying fines for overstaying their visas. Everything after that got built from the outside. VivaReal, one of Brazil’s leading real estate marketplaces, came together while Brian cold-called agencies in a Portuguese language he could barely speak. He got turned down by dozens of investors early on, and sold his apartment to keep the lights on. He eventually converted those very same investors, including the top funds in Latin America and brand-name firms in the US, on his way to selling the company in twenty twenty for roughly five hundred and fifty million dollars, one of the largest tech exits in Latin American history. But what he did next is what interests me most. Instead of going quiet, he built Latitud, the support system he wishes he’d had, whose fellowship alumni have now raised over a billion dollars. He wrote a book, Viva the Entrepreneur, to pass on the hard lessons. He’s even sat [00:02:00] as a guest investor on Shark Tank Mexico. And there’s an interesting turn in where this story has landed. The man who spent 15 years proving you could build from anywhere now lives back near his hometown, part of the greater San Francisco Bay Area. Today, we’ll get into all of it, the transformative years in Colombia, the building of VivaReal from Brazil, what he’s learned the second time around with Latitud, where he thinks the Latin American ecosystem is headed next, and the personal side of building that almost nobody talks about. Brian, welcome to Outsider Inc.

Brian Requarth: Hey, Ian, it’s Good to see you, man. It’s been too long.

Ian Hathaway: Yeah. It’s good to see you again, man. Thanks for being here. I wanna start before all of the companies. You grew up in Sebastopol, California, small town in Sonoma County. You grew up middle class, yet you were hustling from the beginning. In grade school, buying bulk candy and reselling for a markup, and teaching swim lessons [00:03:00] in the neighborhood. It may have been by a different name, but you seem to have an entrepreneurial DNA from pretty early on. So what do you think was actually driving that for you? Was it money, or was it something else you were kinda chasing? And maybe do you recognize that kid in the person you are today?

Brian Requarth: Oh yeah, I’m definitely a product of my environment. I was well supported, and I had a role model in my dad. My dad was an entrepreneur, and so I love the chase, I love the creation, I love the challenge, I love making things. I like building. Maybe just being around an entrepreneurial, household planted the seed, but it’s something that I’ve, always really gravitated towards. A lot of what you described it stems from a very scrappy nature, and I’ve kinda carried that forward and I probably look for founders that, have a little bit of the scrappiness inside them, too. There’s no shortage of those in Latin America. We call it in Portuguese, “Gaja,” which is kinda claw is [00:04:00] the translation. You gotta hustle to make things happen. So yeah, I don’t know where it comes from, but it’s definitely an intrinsic part of me and something I value in other people as well.

Ian Hathaway: We’re gonna dig into it throughout the show, but you definitely have plenty of gaha. You went on to San Diego State, dropped out your second year. You eventually went back to school and chose to study Spanish. Everyone thought you were gonna be a Spanish teacher. Then you graduated, worked six months in your father’s paving business to save money, and drove to Central America with a friend. The plan was Patagonia. You made it to Costa Rica, sold the car, bought a one-way ticket to Bogotá to see Andrea, a woman you met in college. You had a few thousand dollars and a three-month plan. You stayed six and a half years. When you look back at that 23-year-old getting off the plane in Bogotá, no job, no network, no real plan, what do you think he understood about himself that made him willing to do that?

Brian Requarth: I think a couple things. First, like an appetite [00:05:00] for adventure. Absolutely. Just always interested in figuring out how do I expose myself to something unique. And then I also had this realization as a kid that when you put yourself in different circumstances that are way different than your typical life, it’s a forcing function to learn and accelerate your perspective on seeing the world differently. And so I knew that I could drop myself into a different environment, and it would force me to evolve as a person. And so there was a keen awareness about that as a young adult, and then obviously there’s a strong attraction to a woman, which is a very powerful force. And so, that was also a variable and an element to kinda, want me to extend my stay from three months to six years and eventually another six and a half in Brazil

Ian Hathaway: You mentioned appetite for adventure evolving as a person, these are critical elements of being an entrepreneur. Sure you’re looking for those things in the founders you back today. But back to [00:06:00] Colombia, early on, nobody will hire you, so you invent a job. Read a story about you going to a book fair in Bogotá, you bought a business book, used it as a curriculum, and you start knocking on doors. It wasn’t easy, but that little language school paid the bills for a little while. And it’s what put you in line at the immigration office, paying a fine for overstaying a visa, standing next to a German backpacker. You ask him to teach German in your school. He turns out to have a technical background. You have sales, the scrappiness, the hustler mentality. You have coffee the next day, and that becomes a company which takes a few turns before landing on something that works: bilingual websites for American real estate agents serving Spanish-speaking market, sold over VoIP, from Colombia. None of that looks like a plan. It looks like a guy scrambling to make rent over and over until something finally sticks. So take me back to that time. What were you trying to accomplish then? And was there a [00:07:00] moment when you realized that maybe you were actually building something real?

Brian Requarth: You’re taking me way back, man, and I love it. It’s obviously a pivotal moment. Look, it’s pretty simple. You move to a new place. You don’t have any money. You’re eating cheap, shitty food and, you want to be in a better position. And so frankly, the motivation was how do I live better? I didn’t have this like grand vision of oh, I’m going to build a tech company or a startup or... Literally the first necessity point was pay rent. The second necessity point was be able to have money to have fun because if you don’t have any money, you can’t get on a plane and go explore the country. And I think that what happens is you have a little degree of success. You get a taste of something working. Well, now maybe I should increase my ambition a little bit. I was able to, teach some English classes and then, I can hire a teacher and, I can, make a little bit of money. And so I think all of these things in the [00:08:00] beginning, they’re really just a baseline for the next thing. And then I think that you start realizing what the world of possibilities are out there when you achieve a certain degree of, success. And success is defined differently probably in the beginning because in the beginning there was this thing called the menu ejecutivo, which is like you’d go to these little restaurants and they’d serve like the cheap like rice, beans, meat, salad. And it was like cool at the beginning. I was like, “Actually, I really like this. It’s good food.” But then I was like, “I’m so sick of eating it,” but it was the three dollar meal. I think the motivation was figure it out so I could have freedom.

Ian Hathaway: It’s funny you mentioned that meal. I spent four months in 2006 in Colombia as well to learn Spanish. I was a poor grad student with no money, and that was literally my lifeline. I was in Cartagena, and so it was mangoes on the beach and then the executive meal at night once a day. So I definitely know what that’s like. But I think, as I was reading your background it reminded me of something when someone asked me [00:09:00] recently, “How did you end up in tech and venture?” It was always following the best opportunity in front of me. And it seems like there is this through line for you. You had this entrepreneurial DNA early. Even when you dropped out of college, you were working for a company that was dealing with real estate websites, and Spanish is what brings you to Colombia, where you see this opportunity. So, I know there’s this kinda prototypical, image of this Stanford-trained, entrepreneur, computer science, tech. But there’s also this other side of just really smart people who are experiencing a problem and then start building a solution around that. And that’s kinda what I see with, your story as well.

Brian Requarth: I had lunch the other day with a mentor of mine named Greg Waldorf, and, I remember he was an early investor in VivaReal, wrote the first check, kinda like made me legit, connected me to a big network of people like Mickey Mauka and other folks. And I remember very specifically a phone call I had with him where I’m in my shitty office in Sao Paulo. It’s like very early, it’s hard, I’m grinding, and I’m feeling [00:10:00] insecure about my academic trajectory. I didn’t go to a top school, and everyone I’m meeting is like from Stanford, Harvard, all these very polished people. And I remember confessing that to him, and he’s like, “Brian, ten times out of ten, I’d rather back some with your, hustle and drive and motivation over any, elite grad, from a top university.” I needed that little belief in me to get belief in myself. Everyone has their own internal things that hold them back. And I think that the best entrepreneurs and the most successful people just figure out how to have the courage to address those things head-on, and then just identify that “I’m actually not gonna die. I’m gonna be uncomfortable.” And if you get comfortable with the uncomfortable, then you can overcome whatever obstacle you face.

Ian Hathaway: Beautifully said. It’s what this show’s all about. So, You’re building these websites. 2008 hits you pretty hard. Your customers are American real estate agents [00:11:00] and home builders, precisely the population the subprime crisis vaporizes. But instead of throwing in the towel, you think bigger, You realize that your customers don’t just need websites, they need more customers, a marketplace. And then two things happen at once. You start doing some research online about the real estate market in Brazil. You’re blown away by how much online search volume there is, how poorly that’s being serviced by existing sites, and the size of the market, right? There are more real estate agencies in the state of Rio alone than in all of Colombia, and it made Brazil a compelling opportunity for you. Around the same time, Diego Simon a guy you studied abroad with in Argentina, cold messaged you to catch up. You were flying to Rio the next week, you just start to tell him about this idea and ask him what he thinks. You hire him for market research, eventually becomes the third co-founder. That 2008 crash destroyed [00:12:00] the business you actually wanted to keep running, but fate brought you both of your co-founders through the side door. So looking back on all of that how much do you think of VivaReal exists because you were curious, smart, and hardworking, and how much of it was just simply good fortune and dumb luck?

Brian Requarth: It’s absolutely both. I do know that a lot of it you gotta manufacture and the way you engineer serendipity is you have forward progress you test things you gotta make things happen. You gotta get on the plane sometimes. When the door opens, you gotta walk through. Sometimes things go your way, and sometimes you’re in the right place at the right time and you don’t have control over that all the time. But I do think that it’s definitely a combination and, fate is gonna take its course. Certain things are, naturally gonna unfold. But standing still won’t get you there, so you have to make your bet. I don’t know how much of it is luck but I do know that none of it happens if there’s not forward movement and progress and, willingness to hop on the plane or make the phone call or show up to [00:13:00] the event, the cocktail party that you’re invited to that you’re like, “Ah, I don’t really wanna go.” You have to have movement.

Ian Hathaway: Well you’re certainly a good evaluator of talent. What made you wanna jump in headfirst with these two and start the company?

Brian Requarth: That’s one thing that I feel like is a skill. I’ve always been very good at identifying people that fill gaps that I have, and, I’m down to put effort in things. I’m actually a hard worker, grinder, but at the same time, if I can figure out a way to do it more efficiently, assembling a team, people that will make you more competitive as a unit. And Thomas, I remember early on in my first conversation with him, we met in my little tiny apartment in, Bogota, and at our first meeting, he brought all of this like structure to the meeting. He’s like this German guy, classic kind of stereotype. He had this framework of idea, analysis and a list of questions that we went through. And I was like, “Oh, this is what I need.” ‘Cause I could be all over the place. I got a lot of ideas. My brain is working really fast. It was like a great symbiotic [00:14:00] relationship because I had a lot of the creativity, he had a lot of the structure, and then together we, made it work. For Diego, Diego was an entry point into a market that I’d knew nothing about. To pick up as an American, living in Colombia and go to Brazil and start a business, like there’s just a lot of question marks in terms of how to do that. And so, there was, boots on the ground understanding of what it’s like in Brazil. And I’m like a believer in partnerships. “What are your skill sets?” “How do you complement each other?” And I think I’m very good at finding people that have the right motivations and have the right skill sets I don’t know if I systematically was aware of it, and it was more instinctual than anything, but retrospective rationalization tells me that I’ve done a good job of that.

Ian Hathaway: Well, Obviously you’re good at it. Other than setting the vision, it’s the most important job of a CEO is building out that team, right? The team that complements you. VivaReal is on its way. You launch in 2009. Diego moves to São Paulo and works out of this, studio apartment, [00:15:00] cold calling for over a year. Your Portuguese is not very good so he’s writing scripts for you, and you’re reading them phonetically from Colombia, seven months in, trying to solve the cold start problem, and then finally you get this first customer. Things start working, and you guys start believing that this is gonna work. At the same time, almost no one will fund it. You’re getting turned down by a few dozen investors. You go the friends and family route, scrape together what you can, sell your apartment in Colombia, put all the money into the company, and by 2011, you move to Brazil with Andrea. So you have this belief this thing is starting to work on the one hand, and on the other hand, the capital that would be really helpful for getting it going and getting it scaling. You’re having a hard time getting people to believe in that vision and that reality that you see. So how do you hold those two things simultaneously in a way that allows you to keep pushing forward?

Brian Requarth: It comes down to like, an insane belief and conviction and [00:16:00] just obsession that things will work. There’s definitely a moment of doubt. We really did need the capital. We had twenty five employees on the payroll at one point bootstrapped, and we had $87 in the bank. So there became a moment where it was like, yeah, either you get capital or you die. It got to that point. I’ll add another layer of complexity. We’re trying to have a family, and I’m moving to a new country, and I’m starting a business, and trying to get pregnant at the same time. Nico came a couple years after that he was born in 2013. So that was absolutely brutal. In terms of how those things kinda live together, Man, it’s it’s just so hard. And I think that it gives me such empathy and understanding for entrepreneurs, and I think I have credibility with entrepreneurs because almost every founder I’ve ever met can relate to , just the struggle and hardship of getting things going in the early days. As an entrepreneur, there’s a couple things that happen. There’ll be a couple aha [00:17:00] moments all of a sudden this like glimmer of hope. It’s almost like my golf game, my golf game is pretty atrocious, but every so often I’ll just put it three feet from the cup, and I’m just like, “Actually, I can figure this game out.” And then it keeps me coming back. And I think that like those little moments like, your first customer that surprises you and tells you how great you are and then you hone in on what is it they’re, appreciating so much, and then you double down on that. Or, the hire that you’re trying to make and they’re like, really, really complimentary to what you’re doing, and they decide to take a leap of faith and leave their more comfortable job. These are things that provide confidence. The first check you get after 34 no’s, and then all of a sudden someone kinda co-signs on what you’re building. You have to stay in the game long enough to be able to knock in a nice shot, that gives you the confidence you should keep going. It’s a series of events that you can build confidence on [00:18:00] and self-belief.

Ian Hathaway: I can definitely relate. I always think of that line I’m sure you’ve seen “Finding Nemo,” you know, you’ve had young kids. Whenever times are tough for me, there’s this line saying, “Just keep swimming.” I just repeat it to myself, and that’s it. Just keep moving forward. That’s all you can do.

Brian Requarth: 100%.

Ian Hathaway: So those were the hard times. Things start working, right? You land a key angel investment from an executive in Australia. Kaszek and Monashees, the stellar standout funds from the region co-led your first institutional round. Things begin accelerating. You go from low single-digit valuation to raising it nine figures, in about two years. You’re raising money from some name brand US funds. Things are going well, but along with that money, the company shape also changes, You quickly go from just a few people to over 500 employees, and it’s a totally different job from cold calling agencies in phonetic Portuguese to managing this [00:19:00] large team and having, these sort of, established firms on your cap table. So tell us about that transition, going from the guy that was doing everything to get by to the guy that was running this rapidly growing company.

Brian Requarth: It’s like a new hard. It doesn’t get easier, it’s just different. And, as a first-time CEO, you’re getting on-the-job training, you know, you’re making a lot of mistakes, but you’re hopefully learning quickly and no fatal mistakes. You wanna reduce the size of the impact of the mistakes you make. But I had a lot of good mentors. I think I surrounded myself by smart people that, were great executives, great operators. You have to build a team, and you have to run exec meetings, you have to hold people accountable, and you have to have investors, and you have to communicate to investors, and you have to run a board meeting. I remember my first board meeting before I had a head of finance, I was the head of finance, right? And I remember I had the, former CFO of Mercado Libre that took Mercado Libre public on my board, and I stayed [00:20:00] up all night the night before trying to produce some financial model that I could communicate in my board meeting with confidence, and I didn’t know how to work Excel hardly and I remember showing up just like super embarrassed because I had this perfectly ten percent month over month graph I like apologized to the board, so I’m like: “This sucks. I know how bad this And I remember Nico Sakazi was like: “Listen, we didn’t invest in you because you’re, some financial wizard. We invested because you have all these other skills.” He explained to me the difference between a finance director that’s FP&A versus an accounting, person, ‘cause I just didn’t even know what the difference was. So I think the key thing that I look for in founders is like the velocity of learning, how quickly do you learn. And then also secondly, where do you spike? Finding founders that spike somehow, that are just insanely good at something that will move the needle for their business, and then assembling a team around them, with people that can fill in the gap of just the, fundamental things that make the company work. [00:21:00] So I leaned into my strengths, which were selling, recruiting, marketing building the team, setting the vision, as you said before. I just leaned into those things, and then everything else, I just found people that could do it better than me, and I think that’s what good, founders do. hopefully I learn quick enough to figure some things out

Ian Hathaway: It’s the second example of investors saying things in your ear at critical moments, mentors really that gave you the confidence to, push forward in light of this uncertainty. right? Flash forward a little bit 2016 arrives, two things collide, the business is working but you begin asking yourself a tough question: Do I wanna be super rich and 100% all into this company, or do I wanna have a happy family life? What happens next is unusual. You tap Lucas Vargas, then VP of sales, to meet with you every Sunday essentially shaping him into becoming CEO. Then you tell him your plan you tell your board, you get some mixed reactions, and then you rip the [00:22:00] Band-Aid off at the Rio Olympics. Everyone’s reporting to Lucas now, and you move over to executive chairman. Big change. Walk us through that decision and course of events as you’re preparing to hand off this thing that made you. I have to think there was a lot of mixed emotions, some ego some identity tangled up in that, maybe some relief. It couldn’t have been a easy decision to make either way, but, what was that like for you, and why did you do it?

Brian Requarth: It was a super hard decision. There was a lot of internal tug of war going on. The whole kind of identity piece. You’re the CEO of this successful company, respected in your tiny universe, which is, a speck of, sand in the cosmos. But, it feels good and I had a good stock plan too, so I had incentive to stay longer. And, super candidly, I mean, look, my wife and I moved to Brazil. She’s Colombian. We had kids, and we wanted to raise our kids in the US around grandparents and other things. And she gave me an [00:23:00] ultimatum, really. We said we would be there for five years. We got on year six and then she was like, “Hey.” It’s funny because in the moment It’s so easy for you to be like the only thing that matters is my company. And, I had built a really good team. Lucas was, highly capable. In fact, Lucas has now made a career of going into companies that are, like, Series A he’s the CEO of Nomad, which I’m an investor in. Totally killing it. He was able to take over. But really, it was taking a step back and realizing kinda what’s important in my life, and then obviously my relationship with my wife. I didn’t wanna push her good faith in me too far. That would be contentious in our relationship, it was really hard. I remember being back and feeling like I didn’t wanna relinquish the company and the decisions, but it became super clear after a year or two that, it was, the best decision for me personally for my happiness, and the company was in good shape. And it actually worked out really well because I was able to negotiate the sale [00:24:00] later on. So Lucas became this internal CEO, and I became this external CEO, if you will. Executive chairman was my title. So it actually was very complimentary. And frankly, Lucas, at some point, even a year or two before that, he had taken on a little bit more of a president/internal CEO role. It became a natural progression. I think I knew that eventually I wanted to move back. So those are, like, the variables. Didn’t make it an easy decision. I’m very loyal to the people that back me, so I felt guilty, but I remember, the whole kinda put your oxygen mask on yourself, before worrying about other people, and that was something I did.

Ian Hathaway: You hinted at it, Lucas is running the day-to-day. You as executive chairman were able to negotiate, first this, merger of equals, I guess you could call it, with Zap before the acquisition by OLX. Would love for you to talk a little bit about that merger just ‘cause I, I think your role in that was really interesting. They were your biggest competitor backed by one of the biggest, media families in Latin [00:25:00] America, and you convinced them to let your group, a group of outsiders, run the merged - entity, and you even gave up some of the equity to make that operational control happen. Tell us a little bit about that, how that went down, why you chose that path of control versus more equity, and then what was it like to be on the front lines of integrating these two major companies?

Brian Requarth: It’s funny because I approached them years ago before the actual merger ‘cause Mickey Malka , runs Ribbit Capital. He was like, “Hey, why don’t you try to buy a Zap?” And I’m like, “Mickey, that’s just absolutely nuts.” They’re 10 times bigger than us. And I remember reaching out to the CEO and of course, I got no response, and later on I would hear that they talked about it one time, and it was like, “oh, that’s so cute,” “brian wants to buy our company.” Like, David and Goliath, right? fast-forward a couple years we actually were making a dent, and I remember the first phone call I had with the CEO where it was, like, real serious discussions. I was in my house in California at this point, [00:26:00] and we’re on the call, and I’ve got my spreadsheet open, and we’re going through the top KPIs of our business quarterly. Okay, Q1, revenue, traffic, leads, the main me-metrics that we’re both monitoring. And I would give my numbers, he would give his numbers. and it was interesting because they had a huge gap. And in fact, internally, I had this mantra that was, “ close the Zap gap,” ‘cause they were bigger than us. But you could extrapolate out and you could see a scenario where we were gonna pass them based on our growth rate. We were growing at a much faster clip and I think they were super surprised. It was quite a, revealing moment and then we got into negotiation. It was like a very long and, difficult negotiation. And for me, I really cared about the team, and I really believed in our team. The CEO was non-negotiable to me, making sure Lucas was the CEO of the combined entity. But we were too diplomatic, where we’re like, “ your head of [00:27:00] sales, our, our head of engineering,” At the end of the day, it should have just been all our team because it’s like putting together two competing, soccer teams, like Palmeiras and São Paulo. These teams kinda hate each other, and like the cultures are different. It just didn’t mix, and so anyways we learned a lot from that process, and if I were to do it again, it would’ve been better for us to absorb the team and just had one team because it was a lot of operational overload and it was too heavy and like we had to fire a lot of people and there was politics. Just absolutely brutal and painful.

Ian Hathaway: Definitely some very meaningful lessons So you stayed on as the executive chairman of the merged entity, Grupo Zap for a couple years. And then comes, I guess we could call this some good news, bad news. You’re acquired by OLX. Agreement was signed March 4th, 2020. If it was a week later, maybe would’ve been disrupted by the pandemic So sounds good, right? But couple of difficult things happened. First, the deal was [00:28:00] denominated in Brazilian reals which was decoupling from the dollar pretty quickly. The original deal was around $735 million at signing, but by the time it closed, it had fallen to five hundred and fifty million. On top of that, VivaReal was a Delaware C Corp because that’s what US investors had advised early on, but no one thought about what the tax implications would be on an exit. You end up paying over $100 million in US capital gains taxes for a company with essentially no US presence, right? Really no US customers.

Brian Requarth: Thanks for bringing it up.

Ian Hathaway: So I brought up two really painful things for you. I feel almost bad, but I, had to ask you about these. Maybe this is almost a silly question, what it’s like to watch nearly $180 million of value evaporate. But the second thing about the tax, you’ve been really open in talking about it even saying the numbers, that’s [00:29:00] something that a lot of founders would not be so open about with people. Makes it real, makes it tangible. It is a good news story, but there were some pain points involved. Talk to me a little bit about the experience of both of those things, why you’ve been open about it, and then maybe how being open about it has surprised you. Maybe how it’s helped other founders and maybe how it’s even helped you.

Brian Requarth: I think that it’s just part of my nature to be open and authentic with what’s going on. I respect realness and people that are, open about, the challenges and frankly, growth happens when go through struggle. If anything, it’s like these are stripes that I’ve earned, and it’s also easier to talk about struggle when there’s a big number attached to it also, right? So I get to kinda be like, “Yeah, I got crushed in this process, but there’s some silver lining, right? Things went well.” But look, I appreciate when people share different things that I can learn from. So I got on the mic and I just-- I talked through some of [00:30:00] my stuff, I value that as someone who’s learning from other people. The big lesson I learned from that is there’s an expression, lo barato sale caro, which is being cheap is expensive at the end. If you can do the research yourself and then hire one person to audit what you’re understanding and hypothesis just to save you some money, like probably should, spend the energy and the time and the money to make sure that you do things right. But yeah, it’s nice to learn from other people and, so if I can share my experience and let people know, I think founders value that authenticity.

Ian Hathaway: I appreciate you sharing that. Shifting gears to a chapter I know you’re excited to talk about and so am I, the Latitud beginnings really spawn out of this. You start taking Zoom calls, we’re all locked down during COVID restrictions, and you keep hearing the same things. The same questions are coming up. How do I raise a seed round? How do I manage stock options? How do I structure my company correctly so I don’t have huge tax bills down the road? And that’s really where the Latitud story begins. Instead of [00:31:00] just writing angel checks and doing mentoring calls, you start building. I know the early vision evolved, figuring out what the business model was. Then in December 2020, you do an offsite in Rio, and you start drafting a memo about what this could become. Tell me about that initial vision, that room, who was in it, what was being discussed, and how did that memo come together, that original concept before Latitud became a fund and a founder support platform?

Brian Requarth: Look the genesis of Latitud is, you’re grinding out, you’re working hard, you sell your company, you go from having a job to being jobless and no purpose. And you’ve gotta figure out what your purpose is and, what is energizing. I got a little bit down and depressed after I sold my company because I’m like, “I don’t know what to-- How do I put my energy?” I’m very creative and very energetic, so that didn’t last that long. I wrote a book, and, I really reflected on what I care about, what’s energizing for me, and what do I wanna spend my time on. And kept coming [00:32:00] back to what I get energy from is helping founders and talking to founders, learning from founders, and then supporting them on their journey. And so that became very clear to me that this is something that I wanted to do. I didn’t have a roadmap exactly of what that would look like and how I’m gonna do that. So I just started having conversations with founders, and I started listening. And, those 150 Zoom calls that I took from April to July 2020 Basically were the roots of hearing that people are kind of lonely they needed support. I reflected back on my journey in terms of not having a community of founders that could help me , and I benefited dramatically from, some early supporters that had been in the trenches and emerged successfully and learned a bunch on the way. So I figured, is there a way that I can reverse engineer a little bit of the magic that I had, in the early days of getting some support from other founders? Not just mentors and people that have been successful, but other people that were [00:33:00] also in the struggle. And so, that became apparent that was what I wanted to put my energy into. And the manifestation of that, resulted in these kind of cohort-based, program that we launched which, you were involved in and you met a lot of the founders, especially when I was in Mexico and that kinda was just like born out of this interest and desire to kinda reach back and kinda elevate the next generation of founders. And then it’s morphed into a bunch of stuff which I can talk about, it’s had multiple iterations and like any good entrepreneur, you learn, you adjust, you adapt, and then you kinda have a rebirth. And so there’s been a couple things that we’ve learned along the way that’s, resulted in what we’re building today. But it all started from a place of, what do I wanna do that’s gonna enable me to be energized for ten, fifteen, twenty years? And how can I make a difference? How can I make money, too? I like to keep score. I’m not gonna lie. It’s not a nonprofit. There’s a for-profit motive. But I do think that there’s an intersection of impact, capitalism [00:34:00] learning, all these things that I can wrap into one thing.

Ian Hathaway: Let’s talk about that evolution. At first it was pretty broad, There was, this idea of becoming the operating system for VC-backed startups in Latin America, community education, software, a fund. So just walk us through the whole evolution of where things are today.

Brian Requarth: Latitud today is the premier pre-seed fund. We have a pre-seed vehicle that we invest first check partner usually targeting, 5% ownership, and we write, usually on average about 250k first check. Then we also run the fellowship. The iteration of the fellowship now is that we used to run this equity-free program, around 100 founders per cohort. We did 13 cohorts. They collectively went on to raise a billion dollars, as you mentioned earlier, and then we would pick off a handful of those founders and invest in them. We knew that we wouldn’t Be able to attract the best founders if we had terms in the very beginning, ‘cause [00:35:00] we didn’t have a brand. So we spent five years building the brand in an equity-free model so that there’s no adverse selection in terms of who would apply to the fellowship. And about a year and a half ago, we flipped the switch, and now out of the thousand plus applicants we get, we, handpick the top one percent, and we do two cohorts a year, eight to ten founders, and we write them their first check, and that’s inception stage investing. And so those are the two products we have, negative one to zero and then zero to one. And, gonna raise our third fund here. We’re just finishing up deploying the second fund, and it’ll be to double down on the fellowship and pre-seed investing. We exclusively are pre-seed, and then we help the founders connect with seed capital after us. One evolution to this, historically, we’ve invested in Brazil, Colombia, Mexico, Argentina, a lot of like, fintech, stuff that’s, very local in the LatAm ecosystem. We have followed talent, [00:36:00] and the last year and a half, the evolution of our applicants for our fellowship has gone from three percent of the applicants building globally to forty-six percent of them building for the US or the world from day one. So the amount of O-1 visas, people moving to San Francisco, that is just like a natural evolution. And so our Latitud Global One, which is our new fund that we’re currently raising is focused heavily on top talent from Latin America. It’s a region with over six hundred and fifty million people, great universities, great schools from top companies, we basically write that first check, and we get them plugged into the Silicon Valley and connect with downstream capital with the, top funds. that’s what we are doing now. And now I’m a hundred percent focused on the fund, on the fellowship, and no side quests, and it’s taken me five or six years to realize that this is what I wanna do for the next, fifteen, twenty [00:37:00] years.

Ian Hathaway: I’d like to just unpack this whole, trend, founders going from, 3% globally focused to forty-six percent. So when you say globally focused is it about serving customers on a global basis, or is it about serving investors on a US basis? Is it the same thing? Are they different?

Brian Requarth: there’s a couple buckets. I’ll just put names to this so it’s easier to exemplify it. Robson from Be Confident is a founder from Brazil. He’s building an AI language, learning app, he ended up scaling really fast in Brazil and then started getting demand in other countries and, now they’re in 40 countries. He moved to San Francisco ‘cause it’s very heavy AI driven, and so that’s like a global company that started with a domestic market with very fast evolution into global markets, and that’s one profile. And so Robson was like, robotics champions from Brazil, not hyper networks in the Silicon Valley big ambition, super technical, smart young guys. So we wrote the first check and then we helped them plug [00:38:00] into, downstream capital and they had global ambitions from day one with their first customer being Brazil. That’s one example. Another example would be someone like Thais Castello Branco, who’s the founder and CEO of Taste Labs. She was part of our fellowship, three years ago, working on a company that didn’t go as, planned, and she ended up joining Exa in San Francisco, which is Benchmark backed , search engine for AI agents, part of the founding team, raised a Series B, kinda hot AI company. She’s working with the labs very closely, and then she ended up identifying an opportunity where the taste layer, if you will, like the LLMs are very bad at subjective domains, starting with design and other things. And so she built, a data infrastructure, data labeling company selling into the labs as well as application layer companies. And so she is already deeply connected into the Silicon Valley and she’s, selling into the labs [00:39:00] mostly and, top AI companies. And so that’s a different profile. Both Brazilians, both global, but different flavors of global

Ian Hathaway: Maybe this is a broader question on the state of the ecosystem in Latin America. Something we’ve seen with a couple of our portfolio companies who are LatAm founders who are servicing US customers feel the need to move to the US or spend significantly more time in the US to raise capital. What do you think about the state of the early-stage funding market in Latin America? And for founders who wanna raise, where do you think they should best spend their time?

Brian Requarth: I think there’s great investors in LATAM, and I’m an LP in a handful of the funds, and I’m still very bullish on the LATAM VC market. It’s still underdeveloped in my mind, but there is capital, and there is sophisticated investors now. I think that what happened for me, and I was in denial about this, [00:40:00] and it’s funny because I live really close to San Francisco, and it wasn’t until last year when I spent significant time in San Francisco where something just clicked for me, and it’s the urgency, it’s the speed, the velocity of change that just dramatically accelerates your thinking, your network. So if you’re selling into accountants in Brazil, do you need to be based in San Francisco? Probably not. You need to be where your customers are. But, an example is Kamu, who I’m a shareholder in and co-founder of the company. They have a tax solution for mid-market companies. The team comes up to San Francisco three times a year. Goes and visits all the labs. Andreessen invested, so spends time with Andreessen, NFX, and their investors, and also meets other investors too just to quickly understand. As an example, this whole forward, deployed engineer taking the labor piece. Is that something I should accelerate? Should I do that? Versus more of a classic AI SaaS play , or should I actually execute the work? These discussions [00:41:00] and debates are happening at a faster rate and with interesting insights and examples. People are, testing things and some things are working. the velocity of learning is faster in San Francisco. So I think that if you’re a serious entrepreneur, regardless of where you’re building from, if you’re building from Poland or you’re building from, São Paulo, spending some time in the Bay Area, is recommended. You don’t have to build your research team , or your engineering team in San Francisco, but you should probably bring your best engineer, and they should camp out for a month at one of these residencies and, ac-accelerate your understanding of what’s happening, and I think that will be beneficial and advantageous to any entrepreneur. So I’m an advocate of that. We have an in-person component to our fellowship, And now we have a house in Pac Heights. The founders come. We drop by Andreessen, we drop by YC, we drop by, OpenAI, Anthropic, fill in the blanks. And it’s [00:42:00] dramatic accelerator for the thinking of these founders. So I don’t think you need to be in San Francisco to be successful, but I do think that if you’re ignoring what’s going on in the Bay Area, it’s a blind eye to really what’s happening at the frontier.

Ian Hathaway: One of the things I tell founders all the time is a much lazier version of what you said, which is you need to spend time in San Francisco just to understand the pace of what you’re up against. You said the velocity of learning, but I also think it’s the velocity of execution, Just to see the pace at which, the frontier is moving is valuable, even if your customers are in Brazil and you’re best served being there. So really well said. Last question on Latitud, what are you most excited about besides what you just talked about now? How do you see the next few years evolving for the firm?

Brian Requarth: I’m excited about the caliber of founders, there’s been a mindset shift, and it’s a mindset shift that’s taken 10 years. Two thousand [00:43:00] sixteen maybe, I went to China, with a bunch of entrepreneurs from Brazil, and I remember it became clear the dimension of the entrepreneurs in China, like how big they were thinking. And I came back to Brazil and like, “Oh, we’re thinking way too small.” And I wrote a blog post about this on LinkedIn years ago. And what’s happened is that there’s these success stories, like you build on the shoulders of giants, right? There’s Gui from Vercel. There’s Enrique from Brex. There’s Luana from Cauchi. There’s, Mati from Office Zero. There’s the Runway, guys from Chile, where it’s oh, I can actually compete on a global stage. So I think as a theme for me, what excites me the most is the level of ambition that I’m seeing. The talent has always been there in Latin America. Like you’ve got really smart people, on par with anyone, anywhere in the world. But the limitation of the mindset is a real factor, and when you unshackle your thinking about what’s possible, your upside is infinite. that’s what I’m most [00:44:00] excited about. We just released our applications to the Latitud fellow, the SF cohort. Shameless plug, apply.latitud.com. And, the quality and the caliber of some of these founders, it’s something I haven’t seen before. that’s what probably excites me the most is the caliber, the size of the thinking, the ambition, and the fact that they’re going all in on this.

Ian Hathaway: I wanna end where we began, which was this, 23-year-old leaving Sebastopol with a Spanish degree, a few thousand dollars in his pocket, and really no plan or not much of one. Spends six and a half years in Colombia, six and a half in Brazil, finds a wife, begins raising two kids, builds a company in a language he doesn’t initially speak, in a market nobody was really paying attention to, and you won big, And today, you’re back, a few miles away from where you grew up, about an hour north, from the place where founders from around the world are flying in to stake it all. [00:45:00] You went a long way out and you came back. If you think about, that person who you were building without those resources, without the network, without the supports, eventually those things came along with the success, and what you’re building today in Latitud, your book, “Viva the Entrepreneur,” was really written with these people in mind, saving them from some of those headaches. If you look out, let’s say a decade or two what do you hope you will have achieved, and how do you hope that you’ve changed the game?

Brian Requarth: If I were to project out what I hope happens and what I firmly believe will happen, is that we become the starting point for the most ambitious entrepreneurs that wanna change the world in some way, and that we’re able to provide this catalyst and shortcut for them to be able to achieve what they want, and we get to participate in that. That gives me energy, and I think that also will be quite lucrative because the talent is amazing. If I were to take a step back, I would love [00:46:00] for literally the GDPs of all these countries to have grown because the impact that the entrepreneurs made. We know that entrepreneurship is one of the greatest levers for economic and social mobility, And so if we can accelerate the journey of these, frankly, are outsiders to the Silicon Valley because they’re from this region, and we become this on-ramp to, building the most impactful companies that transform these economies I’d say I’ve done my job successfully. If we make it and we become this bridge for the most ambitious entrepreneurs in the corners of Latin America, where the talent resides, and we’re able to put them front and center and enable them to achieve the ambitions that they have, there’s an opportunity for us to literally elevate the economies of these countries. We’ve seen what’s happened with a company like Nubank. It’s a benchmark for the world.

And if we can find, a couple of those, [00:47:00] the lasting impact will be significant

Ian Hathaway: Very well said and a great way to end. We’re almost out of time, but before I let you go, here on Outsider Inc., we like to finish with a little segment called Beyond the Bio. Just some quick-hit questions that let us step beyond your resume. Sound good

Brian Requarth: Yeah, let’s do it.

Ian Hathaway: What’s a quick piece of advice from a mentor that stuck with you throughout your journey?

Brian Requarth: I had lunch with Greg Waldorf. He was the former CEO of eHarmony back in the day, and he was an entrepreneur in residence at Excel Partners, and he was a guy that really shaped my journey, early check and mentor as a CEO. And he told me at one point, he said, “At some point in your career, you’re gonna hit some milestone of success, and you’ll get a little bit older, and you’ll wanna surround yourself by highly ambitious, talented young people because it’ll keep you young and energized and give you purpose.” And I had lunch with him and I said, [00:48:00] “Hey, Greg, this is exactly what I’m doing right now with Latitud.” It’s something that I was exposed to from him, and so a big inspiration for me. So I’m grateful for that

Ian Hathaway: Yeah that’s, a really good one. Who is an unsung hero in your life and what has been the impact they’ve had on you?

Brian Requarth: my dad is an entrepreneur, definitely someone that I sing his praise on podcasts like this. But really beyond that, my mom I learned so much from her about integrity, about, serving other people. She’s basically a social worker. She ran the children’s program at hospice, which is very hard work and very difficult. And I think that I’m a juxtaposition of the kind of entrepreneurial piece of my dad and business acumen and, customers at the center learned all these things from him. And then at the other side of the spectrum is this whole like, serve your community. And so I think that, my mom gets a lot of credit for that because I remember delivering, meals to AIDS patients in the ‘80s, with her. I remember, her always just helping people out and, making an impact in our [00:49:00] community. And so I think that the combination of those two have formed me, and I think my mom doesn’t get enough credit for that because I get a lot of respect on the business side. But her contributions as a person are huge.

Ian Hathaway: Who’s someone in the startup community or maybe your broader network who doesn’t get enough credit and deserves a shout-out from you?

Brian Requarth: I get to be the face of Latitud, but the team is really what makes it happen. So Louisa, she’s on our investment team and, Tommy and I just recently made her a partner in the fund, which is like a big deal because, she’s been there for three years and she’s moving to San Francisco and, she’s the glue in a lot of ways. So I- I’d have to give her a shout-out. You build these things for continuity, all great things require long-term effort, and when you’re building an institution or a fund like this, you need to have this continuation of consistency over time ‘cause it compounds. Huge shout-out to Louisa and everything that she’s [00:50:00] done in the background to make Latitud successful and, looking forward to building another 10 years.

Ian Hathaway: Tell us something most people don’t know about you, something outside of work. Could be a hobby, a favorite travel spot, a guilty pleasure, or maybe even a hidden talent.

Brian Requarth: This is like an embarrassing one, because it’s a sport associated with old people, but I love playing pickleball. I played tennis and then I started playing pickleball two years ago. And my son and I actually play tournaments together. He’s 13, and we take on adults, and it’s always fun because he’s tiny and we would be, starting the match, and they would ask where my partner is and then they’d look down ‘cause he’s a 12 year old. So him and I play pickleball tournaments together, which is pretty fun and, we get to compete at a high level. I play pickleball now fairly regularly, not so much in the last couple months, but I love that. So a dorky sport, which is associated with the older people but it’s, definitely a super fun thing for me to do.[00:51:00]

Ian Hathaway: We’ve had multiple people give different versions of the same answer, so you’re in good company, I guess. so what are one or two songs you’d like to add to our Spotify Founders playlist? Something that fuels your workday or has inspired you on your journey as an entrepreneur?

Brian Requarth: I gotta say, you said Journey, so I’m just gonna say Don’t Stop Believin’,

Ian Hathaway: Yeah. That’s perfect. Other than your own book what’s a book you recommend, maybe something that was valuable along your way or something that you think every first-time founder should read as they’re getting going?

Brian Requarth: Man trying to think of something more recent that I’ve read, or I could go way back. Chris Anderson wrote a book called “The Long Tail,” and I don’t even know how relevant it is today, but that was a book that shaped me. I haven’t visited for fifteen or twenty years, so I don’t know the relevancy of the concepts in there. If there’s anything else that I’ve read- I still go back to “The Hard Thing About Hard Things,” every year and it still impacts me.

Ian Hathaway: I also love another one by [00:52:00] Ben is What You Do Is Who You Are, the ultimate book on culture. So last question. If you could give one piece of advice to someone who’s about to start their first company today, particularly someone who’s a bit of an outsider, what would it be?

Brian Requarth: I guess there’s two things. One, leverage your outsider perspective as an advantage because outsiders typically disrupt markets, right? David Velez was not from banking, carlos from Kavak was not, from the car world. You look at all the most successful entrepreneurs, and they have a fresh look. One thing is take that outsider as an advantage. But you do wanna become an insider eventually because you wanna be in those circles, and you wanna access capital, talent, and networks. And so there is a path to engineering your entrance into these more elite circles, and you wanna basically identify people that can catalyze or accelerate your, path and where you land. [00:53:00] And I think that one way to do that is if I were to go back to my journey, I was able to find, I mentioned Greg Waldorf, you mentioned Simon Baker, the guy from Australia that built the biggest, real estate marketplace in Australia, Mickey Malka. So find a couple high signal people and get those people to believe in you first because it’ll basically reduce your, path to resistance of being in the right rooms that will facilitate your journey

Ian Hathaway: It’s a great answer and couldn’t agree more. Awesome way to end. Brian, it was so good to see you. Thanks for joining me today. I really appreciate it.

Brian Requarth: Awesome. Thank you. Great to see and I love the concept of the podcast. Despite growing up in the Bay Area, I always felt like an outsider it’s a state of mind that you’ve got a little bit of a chip on your shoulder. You’re out to make it work. So I love the concept and I think that, the best companies are founded by outsiders.

Ian Hathaway: Yep. Couldn’t agree more. Thanks, Brian.

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big [00:54:00] thank you to Brian Requarth for joining us and sharing his incredible story. Having chased that same $3 executive meal in Colombia myself, I felt a real connection with where Brian’s journey takes off. I love how little of it looked like a plan in the moment. A language school cobbled together to pay rent, a co-founder met in line at the immigration office. Careers get built by people willing to get on the plane and follow opportunity. Nothing happens standing still. But what stays with me isn’t the exit or the eighteen years of building. It’s the decision he made at the height of it to hand over the company and put his marriage and kids ahead of the title, and to be as candid about the hundred million in unexpected taxes as he is about the wins. That honesty is rare, and it’s why founders trust him now that he’s the one writing checks. Brian didn’t just build a marketplace in a language he could barely speak. He built the support system he never had. So take his advice. Let your outsider’s eye show you what everyone else missed. Then find [00:55:00] the few high signal people who believe in you first, who can open the rooms you can’t enter alone. If you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn at outsiderincpod. You can also follow me on X at Ian Hathaway. Outsider Inc. is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation. Until then, thank you so much for listening, and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features Khatija Ali. She’s the founder and CEO of BioSapien, a biotech company built on the premise to stop flooding the entire body with chemotherapy and put the drug where the cancer actually is.

BioSapien’s flagship product is the MediChip, a 3D-printed, biodegradable implant placed at the tumor site that releases chemotherapy locally over weeks. Khatija calls it a Band-Aid for cancer. About 30% of cancer patients quit treatment because of what the treatment does to them. The company is aiming at a million patients by 2035.

Khatija was born in Saudi Arabia, where her father spent eighteen years engineering the Kingdom’s oil refineries. The family then moved to Canada, where her father later became an entrepreneur out of necessity, her mother worked two jobs, and by sixteen Khatija was COO of the family staffing business. She went to McMaster to study philosophy and planned to become a professor. At the end of her first year, her father was diagnosed with colorectal cancer. She left school to care for him and lost him three years later, when she was twenty-one.

That loss brought her to medicine. She earned her MD, fell in love with surgery, but never practiced, chased out by an idea about the tumors no surgeon could reach. Her first check was $10,000 from her attending, Dr. Marshall, who brought a centrifuge to the restaurant and pulled out a checkbook at the end of dinner. Her mother wrote the second one the next morning. What followed was a pivot from pancreatic to rectal cancer, a few dozen deals done inside a New York biotech venture firm, a thousand investor no’s, a stretch driving for Uber to keep the company alive, and a move almost no biotech founder would make.

In this episode, we get into the question that had hold of her before she had language for it, why she left the operating room she loved, what sitting on the money side of the table taught her that medical school never could, what a thousand no’s does to a person, why the fastest route to a patient ran through the Gulf, and the line she draws between suffering you can engineer against and suffering that simply has to be lived. ⤵️

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Episode Highlights

Here are some highlights from the show. In this first clip, Khatija goes back to the question she was chasing as a kid, which was what it actually means to become who you really are. That one comes loaded, because you have to know who you are before you can become it. Philosophy wasn’t an elective in her house. Her parents ran a social group that met on weekends to argue about philosophy, politics, and religion. She took her first formal course in grade 11, fell madly in love with it, and paired it with physics, because that combination is where abstract thinking gets dangerous and also useful. She’s still chasing the same question. You can see it in how she runs the company, what she angel invests in, and the nonprofit work she does for free.

In this next clip, Khatija explains the MediChip the way she’d explain it to a patient. The current standard of care is a chair, a machine, and several hours of IV chemo running through your whole body to reach a tumor sitting in the corner of your stomach. An IV bag holds a thousand milligrams. Ten to fifteen percent of it arrives where it’s needed. So her question is why push all of it through a body hoping a sliver lands, instead of taking the fifteen percent, putting it in a simple mechanical chip, and setting it directly on the tumor to break down there. For the patient that turns months of treatment into a scope, a three-week wait, and a phone call to check the chip is still in place. You eat, you sleep, you keep your hair.

Khatija then does the math on rejection. The first no costs you a week of feeling terrible. The second one costs you five days. By the third you’ve mostly stopped counting. She went in assuming no was the default anyway, on the logic that unless you ask, the answer is already no, which turned every pitch into an invitation to be surprised. Each rejection became a note on the story, or the business, or the way she was explaining the thing. A number of the people who passed on her are on the cap table now. None of it works if you take it personally.

And here, she describes the hardest conversation she’s had with her team, which was telling them they were picking up everything and moving to a part of the world that shows up in the news more often than it should. It got easier once she took the geopolitics out and left only the question that mattered, which was how to get the product to patients fastest. The UAE’s regulatory timeline runs about thirty days, the fastest in the world. Cleveland Clinic is there. Sanofi, Pfizer, and AstraZeneca all run trials there. What she found strange was that no startup had gone after any of it, which left an opening to run a first-in-human oncology trial in a region she was born in and hadn’t lived in since she was small.

Finally, the exchange I’ve thought about most since we recorded. I asked whether suffering is a problem to be solved, and where she draws the line between the kind you can engineer against and the kind you just have to live. Her view is that suffering is necessary and nobody gets asked for consent, and the mistake is staying in it. Sit there long enough and it becomes a dark cloud, a very Schopenhauer path. Convert it into struggle and you’re in Nietzsche’s territory instead, the examined self, and at least you’re moving. Most people live reactively, running on values and fears they never chose, which is how you end up suffering on a loop. Trace the impulse back to where it came from, choose differently on purpose, and you get struggle. Struggle is where you find out who you are.

I’m grateful for this conversation with Khatija. The regulatory arbitrage is clever and the Abu Dhabi bet is bold, but what stays with me is that every real decision in this story runs back to a room she couldn’t leave. She was eighteen when her father was diagnosed and twenty-one when he died, and she spent most of the years in between in hospitals with him. The philosopher who wanted to live under a tree came out of that with an MD. The surgeon who loved the operating room walked away from it because she’d seen its ceiling from the inside. The first company she ever ran, she ran with her father. Her mother wrote BioSapien’s second check.

The suffering-and-struggle distinction is the part I keep coming back to, because for her it isn’t a slogan. She’s built a company on the belief that some suffering is an engineering problem, and a life on the acceptance that the rest of it isn’t, and she seems to know which is which. It’s also why she’s taken on more than the job asks of her, helping build a biotech ecosystem in a region that doesn’t have one yet. When I asked why, she said: why not. Same answer she once wrote on a philosophy exam in undergrad when the question was “why.” Her line is that if they won’t let you sit at the table, you make your own. So when she tells you the answer is always no unless you ask, believe her, because she has the receipts. And when the MediChip goes into that first patient, I hope she lets herself feel all of it, the relief and the grief and the quiet vindication of a daughter who turned the worst thing that ever happened to her into the reason someone else might be spared it. Her advice for anyone about to start a company is not the encouraging kind.

“Don’t do it unless you really mean it. It’s not worth the fame. Only do it if you can handle that suffering.” — Khatija Ali

Khatija’s Library

Khatija named two books, and split them cleanly by purpose: one for understanding people, one for understanding the business she happens to be in.

The Laws of Human Nature: Robert Greene’s 2018 book on the drives and motivations underneath behavior — including the ones people can’t see in themselves. It’s organized as a set of laws, each anchored to a historical figure: detaching from your own emotions rather than reacting from them, developing the empathy that produces insight, reading what sits behind the mask someone is wearing, resisting the pull of conformity. Khatija credits it directly for how she learned to absorb a thousand no’s without taking any of them personally — the emotional-intelligence frame that lets you hear what a rejection is actually about and treat it as information rather than a verdict.

For Blood and Money: her pick for anyone building in biotech specifically. Nathan Vardi, a MarketWatch editor and former Forbes senior editor, reconstructs how a small, unlikely company produced a breakthrough blood-cancer drug — and how members of the team who were cut out of the proceeds turned around and did it a second time with a rival compound. It’s a story about scientists, patients, hedge funds, and venture capitalists all pulling on the same molecule at once, and it doubles as an unusually clear-eyed explanation of why new drugs take so long, cost so much, and so often never reach the people who need them. Which is, more or less, the gap Khatija built a company to close.

Khatija’s Playlist

I always ask guests what’s been fueling them. Khatija gave me two, and the gap between them is wide. Eminem’s “Lose Yourself” is the pre-stage ritual, the thing she puts on right before she walks out to pitch.

The other is Bach, which she puts on for the long grind: decks, financial models, and once upon a time, memorizing anatomy. She called it “Symphony 5,” which I’m reading as the Brandenburg Concerto No. 5, since Bach never wrote a symphony. Khatija, correct me if I’ve got that wrong.

Up Next: Brian Requarth

Next up is Brian Requarth, co-founder of Latitud, Latin America's leading pre-seed fund and by now a piece of infrastructure for founders across the region. Brian grew up in Sonoma County wine country. He dropped out of San Diego State, went back, and graduated with a degree in Spanish, which had everyone assuming he'd teach. Instead he drove to Costa Rica at twenty-three, sold the car, and bought a one-way ticket to Bogotá to see a woman he'd met in college. The three-month plan turned into six and a half years. He married her. He taught English door to door. And then he met his first business partner in line at the immigration office, where both of them were paying fines for overstaying their visas.

Viva Real, one of Brazil's leading real estate marketplaces, got built out of that, on cold calls he read phonetically off scripts because his Portuguese wasn't good enough yet. A few dozen investors turned him down. He sold his apartment in Colombia to keep going. At one point there were twenty-five people on payroll and $87 in the bank. He converted most of those investors eventually, and sold the company in 2020 for roughly $550 million, one of the largest tech exits in Latin American history. But, rather than go quiet, he built the support system he wishes someone had built for him. Latitud's fellowship alumni have now raised more than a billion dollars. Don't miss it.

Listen on: Spotify, Apple Podcasts, Amazon Music

Host Ian Hathaway interviews Khatija Ali, founder and CEO of BioSapien, about building a biotech company on a mission to change the way the world treats cancer. Ali shares how her path began in philosophy and physics at McMaster University, where she was drawn to metaphysics, Nietzsche, and big questions about why we are here, before her father’s colorectal cancer diagnosis redirected her life toward medicine. After earning her MD and falling in love with surgery, she left that path to build BioSapien, whose flagship product, MediChip, is a 3D-printed biodegradable implant designed to deliver chemotherapy directly to a tumor site instead of flooding the entire body through an IV. She describes the personal loss behind the company, the early support from physicians and her mother, the realities of raising capital as a woman founder in biotech, hearing a thousand no’s, driving Uber to keep the company alive, and learning to treat rejection as data. They discuss BioSapien’s pivot from pancreatic cancer to rectal cancer, why Ali moved clinical operations to Abu Dhabi, the advantages of building between San Diego and the UAE, preparing MediChip for first-in-human trials, building the Gulf region’s biotech ecosystem, leading with curiosity and compassion, and the difference between suffering and struggling.

Show Notes:

(03:00) Philosophy, Physics, And The Question Of Becoming

(05:15) Building A First Company With Her Father

(08:30) Grief, Cancer, And A New Path

(11:35) Leaving Surgery To Build BioSapien

(15:03) MediChip And Treating Cancer Locally

(19:25) Pivoting From Pancreatic To Rectal Cancer

(21:40) Learning Biotech From The Money Side

(23:25) A Thousand No’s As Data Points

(25:20) Moving BioSapien To Abu Dhabi

(32:20) What The West Gets Wrong About The Gulf

(35:00) Preparing For The First Human Patient

(38:25) Leading With Curiosity And Compassion

(41:20) Building A Biotech Ecosystem From Scratch

(44:25) Suffering, Struggle, And The Founder Journey

(49:30) Beyond The Bio with Khatija Ali

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Khatija Ali - Founder & CEO, BioSapien

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Khatija Ali: [00:00:00] I think the transition for me becomes not staying too much in suffering and turning that into struggling. Because if you’re struggling, then you can at least get somewhere, and along the struggle you learn more about yourself. But if you’re suffering, then you’re consistently in this dark cloud of mentally suffering, and, goes down a very Schopenhauer path.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Khatija Ali, founder and CEO of Biosapien, a biotech company on a mission to treat cancer locally Biosapiens’ flagship product is the MediChip, a 3D-printed biodegradable implant, placed directly at the site of a tumor that releases chemotherapy slowly and locally over weeks instead of flooding the entire body through an IV. Khatija calls it a Band-Aid for cancer. The problem it attacks is one most of us know through someone we love. Roughly [00:01:00] 30% of cancer patients stop treatment because of the side effects. Biosapien’s goal is to treat one million patients by 2035. But Khatija’s path here is anything but conventional. She was born in Saudi Arabia, moved to Canada as a young child, and grew up in suburban Ontario, starting her first business with her father at sixteen A philosophy major who planned to spend her life as a professor, she was redirected by tragedy. Her father’s colorectal cancer, diagnosed when she was 18, took his life just three years later. That loss redirected her towards medicine. While earning her medical degree, she fell in love with surgery, but walked away before ever practicing it. Instead, she chased an idea that hit her, sleep-deprived, in an operating room with $10,000 from an attending physician who believed in her and her mother as her first investors. What followed is an outsider story on nearly every axis. A founder in an industry where only 2% of funding goes to female [00:02:00] founders. A self-taught operator who learned the business of biotech doing deals inside a New York venture firm. A CEO who heard a thousand noes and drove a taxi to keep her company alive. And then the boldest move of all, she left America, where, in her words, you don’t get funded in biotech unless you’re in AI or gene therapy. She moved the company to Abu Dhabi, where Biosapien is now preparing for clinical trials and where Khatija is helping build the region’s biotech ecosystem from scratch. In this conversation, we’ll talk about the losses that shaped her, how a philosopher thinks about building a company, what she learned about why medical innovation so rarely reaches patients, the realities of being a woman founder building in the Gulf, and the decision to put a cancer trial in a city nobody had on the biotech map. Khatija, welcome to Outsider Inc.

Khatija Ali: Thank you, Ian. That was a perfect intro.

Ian Hathaway: It’s so good to see you Thanks so much for being here. I wanna start [00:03:00] broader than the company. Before medicine, you were a philosophy major and a physics minor at McMaster in Ontario, deep into metaphysics, reading Nietzsche, planning to become a professor and basically live under a tree. I know philosophy is your first love to this day. Before any of the cancer work, the thing pulling at you was this big unanswerable stuff. Why we’re here, how we perceive reality, what reality even is, and it traces back to a kid in suburban Ontario who wanted to be an astronaut, thought about black holes, built potato clocks, drawn to the unknown before you had language for it. Looking back on that, what was the question that had a hold on you as a kid back then, and do you find you’re still chasing some version of that now?

Khatija Ali: Wow, what a way to start this conversation. Yeah, look, I think ultimately the question I was trying to answer at that [00:04:00] time was what does it really mean to become who you really are? That’s a loaded question because obviously you have to understand who you are to begin with, and then what it means to actually become something, and what does that mean externally. And so that’s been the fundamental question I’ve been chasing. And then of course, why are we actually here? I’m still driven towards that. You can see parts of that in my curiosity and how I operate with the business, with some of the angel investing that I do, and some of the non-profit stuff. There’s always a question of why and what’s the purpose and who does this benefit, and who do we become in the process of building towards something? I think that’s the question in itself. I grew up actually in a household where philosophy wasn’t entirely just a subject in undergrad. more like a weekend activity where basically, my dad and my mom had the social group where we would all come together and essentially debate different topics around philosophy and politics and religion. And really, I think by the time I got to grade 11 I dove in and took the first [00:05:00] philosophy course in high school fell madly in love with it and realized that, okay, I formally want to start studying it alongside physics. Because that was where it becomes dangerous but also potentially useful, and that abstract thinking was what really, got me excited towards that.

Ian Hathaway: So I wrote down building towards something. We’ve talked in the past about stoicism and, focusing on what you can control. I feel like that’s a really consistent theme through your life, you have a good nose for opportunity and then putting in the work to make that opportunity a reality. You mentioned your parents. Your first company wasn’t BioSapien. At 16, you and your father started a family staffing business together. He was the CEO. You were out there chasing contracts and getting meetings. You credited that period as kind of your entrepreneurial spark, Tell me about that time, about him, about what working side by side with your dad that early on in your life [00:06:00] taught you that maybe you didn’t realize at the time, but looking back on it now, that you were learning?

Khatija Ali: Honestly, very interesting experience as a whole. I think maybe to answer that I can go back a little bit around sort of his background and how we ended up in that situation to begin with. So my dad was actually an engineer for the Kingdom of Saudi, and basically spent 18-plus years over there building out their oil refineries and essentially leading the charge. So that was the prestigious chapter of his life. And I think Canada, when we moved, that essentially became the reinvention chapter. And so he became an entrepreneur out of necessity, not so much by choice, but that’s what, the circumstances demanded from him. And my mom worked two jobs to keep the food on the table. And so how that came into being in terms of building the first business with him is his idea was basically to become the middleman of large corporations like Coca-Cola, Minute Maid, and on the other side with general laborers, So protecting their interests, their salaries, their [00:07:00] wages and everything around that. He found this niche market in which there was a lot of appetite for large corporations like these factories to require hands-on general labor. And then there was a lot of general laborers that he knew as a part of his adventure and journey that could be potentially useful to these such corporations. And so he bridged that gap and put together a company called Tiger Force, which still makes me laugh till today. My brother was the CFO I was the COO running the operations, in charge of scheduling, in charge of people management trying to find contracts, putting together decks trying to get a meeting in front of these factory owners, et cetera. And so what my summer really looked like when I was 16, besides summer school, was I would basically go with him to these factories, knock on the door and trying to get in a meeting with somebody to say, “Hey, look at this value proposition. We can help you get general laborers. We can improve your productivity. We can improve your wages [00:08:00] and just your overall packaging that you offer and help you with cost reductions, et cetera.” So that was the thesis behind it. That was sort of my first experience in what I call the grand building, right? Where you essentially roll up your sleeves and you get it done and I think that’s something that’s always been a message that both my parents have instilled in me over the years, and I couldn’t be more grateful for that.

Ian Hathaway: It’s pretty wild that you had that level of responsibility and initiative at 16. But I, can definitely see that, ability to knock on doors and just make it work served you well later when it came to raising capital. No doubt we’ll get to that in a minute. But at the end of your first year of university unfortunately, your father was diagnosed with cancer. You were just 18 years old. I know that you were the youngest child. You were, to a large degree, his primary caregiver. You took time off of school to look after him. He went through the whole course: [00:09:00] chemotherapy, radiation, surgery. I know that you even took an experimental treatment in China. he passed away in January 2011 when you were just 21 years old. I have to imagine that was the worst moment of your life but it changed you, right? You became hell-bent on pursuing medicine when you originally had planned to be a professor in philosophy. It feels like the curiosity that had once been about why are we here turns to dealing with what’s in front of us now. What did caring for him do to you, that philosophy student who just wanted to live under a tree, and how did it redirect your entire life?

Khatija Ali: Honestly, I think that was definitely a very catalystic moment in my life. left a, tremendous mark on me for sure. So much so that I, to your point not only did I leave philosophy, I eventually left surgery to basically go and, start a biotech company [00:10:00] to try and alleviate human suffering. I grew up very bubbled, I would say, right? In the sense of like I had a great family. Youngest of four. My summers were playing street hockey and those were the concerns that the, popsicles are melting faster than I could eat them. And so having to have that reality check of like human suffering to watch someone who you love who’s been the guiding compass of both morality and just how to navigate the world I think was definitely a really hard challenge I think the suffering became less theoretical. Schopenhauer was no longer words on a piece of page that I read. Schopenhauer was what I was living in terms of nihilism and this horrendous dread of life and its capabilities and what we can’t control and basically coming to terms with the reality of mortality as a whole and we’re all here to eventually die. And so that was really dark I think at 21. But really once you get over the cloudy, [00:11:00] depressing phase of grief and what it does to you, I think what it allows you to understand is that there’s an opportunity here, We’re sort of the ones that are left behind, and either we can do something with that and make an impact and try to change or alter the world in a better way, or we can just let that suffering, engulf us and basically become Schopenhauer 2.0. And for me, as tempting as that latter was at times it wasn’t the most feasible path because it wouldn’t do justice to him or me or anybody else. And so, kind of had to pick up my shit and, move on.

Ian Hathaway: Well, so you did, you fell in love with surgery in medical school, and then I read about a moment you had in a Houston operating room where you’re, like, literally saving someone’s life, holding their beating heart in your hands, which just seems, wildly intense. But, it also revealed to you that surgery has, a ceiling. There was sort of a, helplessness. You’re dealing with pancreatic tumors, spreading into arteries [00:12:00] and nerves that a surgeon could never touch. And somewhere in that, this idea hit you that you could create and embed, this drug in a printable biodegradable material delivered right to where it’s needed. Looking at that time, we’ve got this philosopher, this grieving daughter, this surgeon, and this stubborn idea all in the same person. At what point did it stop being something that you were just researching or had a curiosity about to become this thing that you were going to go out and pursue?

Khatija Ali: I have an MD and basically right as I was graduating from medical school, decided to open Biosapien and pursue that. So I never actually ventured down the path of surgery, which is like my second and first love, I would say. Surgery I think is a beautiful way to combine art and medicine with human gratification all in one nice little bubble. So it definitely fulfills me in a different manner for sure. I [00:13:00] think the driving factor for me as to wanting to leave something that I love so much to pursue this was ultimately that conversation with my attending, Dr. Marshall, and a few others along the way, including Dr. Rapanos, who’s a vascular surgeon over at McMaster University, basically telling me these three things. One, the idea is incredible and much needed. It’s something that they would use and they would support. And so that was, validating for me that, hey, colleagues of mine feel like this is a tool that surgeons need in their hands, especially when it comes to pancreatic or other kind of surgical oncologies where the tumor’s too large and you can’t resect it and it’s a failed surgery for the surgeon, so that was nice and validating to hear that I was actually solving a problem for my colleagues. Then the second part of it was essentially a dinner conversation I had with Dr. Marshall who wrote me that first $10,000 check, and literally she brought a centrifuge to the restaurant. I still have it. I don’t know what to do with it, but, it was momentum and symbolic, and I think if [00:14:00] I remember correctly the conversation went something like, “There’s so many surgeons in the world, and you can always pursue medicine and become a surgeon when the time is right. But fundamentally there’s this problem that you can solve for a lot of people. You have the drive. It’s something personal.” And I-- at that point, I had about four startup companies under my belt. So I had some idea of how to build a business and what, it entailed. And then to see her actually take out a checkbook at the end of dinner and write me a $10,000 check, I think was definitely a nice push. Then the last really came from my mom, who wrote the second check of $10,000 the next morning as I’m telling her this conversation over the phone and she’s saying to me, “She’s right. This is a good product. You should definitely give it a shot. Try it for six months or a year and see where it takes you.” And, here I am still chugging away at it. So, I think it was, definitely the driving confidence of my colleagues, of people who are close to me validating that the product in itself could exist and there was a market [00:15:00] and working towards that. And of course, just being a stubborn person that I am, so

Ian Hathaway: Yeah. Persistence pays. Okay, so you mentioned the product. Let’s talk about that. Give me the simplest possible version of what MediChip actually is. Maybe explain it in a way that you would to a patient, what it does, what it could change about the experience that a person would have going through a cancer treatment.

Khatija Ali: Certainly, yeah. Current traditional standard of care treatments right now means that you go to a hospital, you sit in a chair tied to a machine for several hours on end, and they’re basically giving you IV chemo that’s going in through your entire body, even though the cancer might be located in the very corner of a stomach, for example. And so what we aim to do at MediChip is essentially remove that entire paradigm altogether and say, “Look, patients don’t need to be suffering sitting in a hospital trying to get IV chemo and blasting the entire body [00:16:00] for hours on end. Instead, why don’t we take the bioavailable drug that’s required in its dose form?” So let’s say taking a step back, that IV bag has 1,000 milligrams. When you look at bioavailability and how drugs break down and where it needs to go, you essentially end up with about 10 to 15% of drug at the actual site. And so the thesis is instead of trying to, put 100% of drug throughout the entire body in the hopes that 15% get to it, why don’t we just take that 15%, put it in a simple chip, directly on top of it allowing it to release and break down at the actual site. And so what this looks like for patients is they basically, they get a scope. Someone says, “Oh, you’ve been diagnosed with cancer, but don’t worry, someone out there in the world created this product called MediChip. We’ve put this in as you’re waiting to see your surgeon to have the tumor removed and essentially it’s providing chemotherapy directly to the site. You don’t need to come see us for another three weeks. You can eat, sleep. You keep your hair. Everything is great, and we’ll do a check-in a week from now to just make sure [00:17:00] the chip’s in place and ensure that there’s no additional harm.” So that’s the value proposition for the patient and the value proposition for pharma on the back end of that is that 30% that you mentioned that don’t want systemic chemo. Not to sound too much of a business, but ultimately that’s revenue being lost for a pharma company and that’s an opportunity for patients as well that we could pull back and open that market for. So MediChip can unlock that as well.

Ian Hathaway: So cancer is a disseminated disease, we talked about how some patients will drop out because they’re essentially exhausted by it. so is MediChip, is it a complementary tool or a replacement for systemic treatment?

Khatija Ali: Yeah, no. Our plan is not to replace systemic treatment this is really meant for localized disease, right? So if we take a subset, for example, rectal cancer. In rectal cancer, you go through the paradigm of getting chemo, you get radiation, and you still get left by what’s called a near complete response, meaning that you still have a little bit of tumor [00:18:00] left, roughly the quantity of one to two centimeters large and it’s a small nodule that remains. And so what you do in that scenario is a process under the OPRA trial called Wait and Watch. You just watch to see if the cancer will go away, and generally, in half of the patients it does. And that’s great. But the other half of the patients, it does not. And what their treatment options include is essentially going to surgery and having their rectum potentially removed. And so they’re pooping in a bag for the rest of their life. That’s the paradigm that we wanna change. We want to be able to give patients an option to say, “Before we take the extreme measure of chopping things out let’s try this chip and see if we can provide some local therapy at the site.” Now, zooming out MediChip is a platform, and so we think it’s anticipated for all localized solid tumors down the line. So, It’s something that could be used in tangent in therapy with chemo and with radiation. And so a part of our Phase II clinical design is to give MediChip with chemo, to give MediChip without chemo, to give [00:19:00] it with radiation, to give it without radiation, and then give it as a stand-alone monotherapy, essentially meaning by itself. Obviously the data will drive whether this is something that goes in conjunction with chemo, with rads, or monotherapy. The way that I see it is it’s ultimately complementary to chemo. So you have some disseminated disease, but you’ve got some nodules in your lung and liver that really could be, hyperfocal that need some high dosages, and you just plug those in at that site. And it degrades over a course of one month releases the chemotherapy to the site.

Ian Hathaway: Very helpful. Thank you. you mentioned colorectal cancer, which as we discussed before, is what your father had , but that wasn’t the original vision, right? It was pancreatic cancer in the beginning. So obviously, founders have to pivot constantly. This seems higher stakes and definitely more scientific. So talk to us a little bit about that evolution and what it took for you to make that pivot.

Khatija Ali: Yeah, definitely. So y- you’re right on in terms of [00:20:00] pancreatic cancer was our first line of indication that we wanted to target, and the reason why is it came from the clinical need. So when you’re doing a Whipple procedure and you’re trying to remove parts of the cancer that sit on the pancreas, it’s a five-hour procedure. It requires removal of multiple organs. It’s very stressful. You have to be super specialized to do it. And so imagine going through all of that as a patient and as a surgeon, only at the end to find out that, “Oh, I’m sorry. It’s impending upon a blood vessel and we can’t remove the cancer altogether,” and so the surgery was a fail. That’s, lost morale for the surgeon, but more so lost opportunity for the patient. And so we built Medichip with that in mind, that if a surgeon is standing at the OR, he has no other tools, he can’t cut out the cancer, how else can you downsize it? You could take the chip, throw it on, downsize the tumor, and potentially go back and retrieve it along with the tumor in three, four weeks’ time. And if you think about it, it makes sense. It takes five hours to go to the pancreas. Let’s say we put a chip inside and something goes wrong in a Phase 1 safety. [00:21:00] It’s gonna be very difficult to retrieve that chip. And so we thought, what’s the lowest hanging fruit in terms of ease of access from an anatomical perspective that also has the highest unmet need and could also fulfill the opportunity in the market as well. And so that’s where rectal cancer came to the forefront as the lead indication of our pipeline.

Ian Hathaway: So you touched a little bit on early funding sources, opportunities. I know when you were getting Biosapien off the ground in New York, you were pulled into biotech venture capital. You did a few dozen deals. Three of the companies went public. You had some outlier successes, some write-offs, and I know it left you with this lens where y- you saw where physicians understand these unmet needs but are often not considering the business side in a complete and comprehensive way, while the VCs are just focused on only chasing these biggest markets, which can sometimes mean they overlook rare or pediatric diseases. [00:22:00] What did sitting on the money side of the table teach you that medical school never could have? And how has it affected the way that you’re thinking about and building the company today?

Khatija Ali: I think that experience was extremely valuable. For me initially, it was a survival mechanism, ‘cause it was a job that paid where- whereas my company, is a little bit bootstrapped. But in a way, it was actually a form of like due diligence on myself and what we’re building. And so I wanted to see the same problem from both sides of the table, right? And what the investment side really gave me was pattern recognition, I would say, at scale. Whereas hundreds of companies, you see what breaks them, you see what they build, you get a particular lens, like you said of founders and their approaches, and I kept thinking that there’s a gap of what the science could actually do versus what actually reach patients versus what actually makes money. And so for me, I think the exciting part was, acknowledging that gap and then realizing that to pivot from this full-time, venture capital where I love what I was [00:23:00] doing, wasn’t really this dramatic moment, but it was more of this reckoning of I’d like to spend more time to build the thing that is meaningful for me. And so I just stopped working in the VC space although I really enjoyed it and hope to go back to it one day just so that I can, build out Biosapien and give it the full attention that it needed.

Ian Hathaway: I know then flipping back to the other side of the table, trying to raise for Biosapien, and it was brutal, You got a thousand no’s. You were Ubering around New York just to keep the company alive against the odds. Take me back to that period, those early days when you’re trying to raise that critical early capital. What does the one thousandth no do to a person? Was there a moment when you thought about walking away, and what actually kept you in the game?

Khatija Ali: Look, hearing no is n- is never fun, but I think if you hear it the first time, you’re like, “Oh man, that sucked.” And then you’re depressed for a week. You hear it the second time, you’re depressed for five days. You hear it the third, [00:24:00] you’re like, “Okay, whatever.” So that’s what it was in magnitudes. I think I’ve always been of that philosophy that unless you ask, the answer’s always no, always was anticipating a no anyways right? And so it’s more of, “Hey, can you surprise me in saying yes?” Was my mindset and how I approached it. Look, every no for me is a data point, right? To try and improve either the story, the business, the problem or just in how we articulate the solution. And so I think every single person who said no to us along the way, some converted and, had a yes down the line and are now our investors for which we’re grateful for. Along the way we’ve just learned, how to pivot and how to get better at taking nos. And I think I really have to thank Robert Greene There’s a book that’s called The Laws of Human Nature that really helped me understand the importance of emotional intelligence and really understand as long as you don’t, take things personally, you can always learn from the experience. And so I embodied that 100%. And I’ve got some funny stories I can tell you about [00:25:00] people I’ve chased and the nos I’ve gotten and

Ian Hathaway: Yeah.

Khatija Ali: but we’d be here for hours, so

Ian Hathaway: I’m a huge Robert Greene fan. He actually has a s-somewhat recent book called “War,” which is a great book, I think, for someone in your shoes right now as a CEO or just really any human being who’s out trying to do something. So I kinda wanna flash forward a bit to where I feel like this story really becomes like true heart of what we’re trying to do here on Outsider Inc. The obvious play for a biotech founder is to be in Boston or San Francisco. Instead, your next chapter is in Abu Dhabi which is where things really start to take off for you. Part of that was a diagnosis you had about America, That unless you’re in AI or gene therapy, you’re not gonna get funded. But I, know another part of that was this opportunity that Abu Dhabi specifically presented for you. And of course, there’s this [00:26:00] interesting third layer because in a way it’s you returning to the region where you were actually born. So looking at that whole decision, from the outside, this looks like a bold, contrarian strategy bet, but I know in these conversations with you it’s actually quite sensible. So walk us through that decision and what it was like to actually follow through with it.

Khatija Ali: I think that was one of the most difficult pivoting moments of my life to try to explain to my team we are now picking up everything and going all the way across the other end of the world in which the Middle East appears in the news more frequently than it should. And so that was a difficult conversation to have. It became a lot easier when you take away the sort of political and geopolitical elements of the story. Ultimately what we were trying to achieve is what’s the fastest way to get this product to patients? And so we looked at the world and said, “Okay, on the map here, which regions or which countries could potentially accelerate that?” So Japan was on there, Australia was on there, India was on [00:27:00] there, and UAE had appeared as itself as an opportunity. The reason why we didn’t move forward with Japan, is, one, they move a little bit slower than anticipated. Their regulatory speed is six to nine months, and there’s a very obvious language barrier in its regulatory submissions and parties and so on and so forth. And we thought, “Okay, that might be a heavier lift than we can potentially manage at this time.” We started looking at Australia and thought, “Okay, that could be a potential opportunity,” but that required obtaining R&D credits from the US, setting up a whole operational team in Australia which was very disconnected from the world. And so the logistics and supply chain of trying to make the chips in the US and ship them, it just seemed like a nightmare for us at that point, and thought, “Okay, maybe that’s not the best solution. We looked at other places in Southeast Asia and just decided that from a regulatory perspective, there’s been a little bit of scrutiny around that, and so maybe not the best for us to put our first in human in there. From the UAE side, the thing that was really intriguing for us was, one, [00:28:00] is their regulatory framework and timeline is roughly 30 days. And so that’s the fastest in the world. And given that they have all these infrastructures with Cleveland Clinic all pharmas are out there like Sanofi, Pfizer AstraZeneca, et cetera, conducting clinical trials. For me, I thought it was fascinating that startups had not infiltrated or activated that ecosystem. And so to your point, it, one, it was a way to give back, but two, is this opportunity to be a pioneer in a phase one oncology trial in a country or in a region that was near and dear to me. Plus it was extremely, cost effective. And so it just made the most sense that we would move the operations there And they were actually allowed us to do our IND approvals and filing. We’ve gone through that process and happy to say came out the other end with an approval.

Ian Hathaway: So that’s super interesting. You said you needed to leave the country in order to accelerate your development. What were structural reasons, advantages to leaving the US or the [00:29:00] deficiencies in the US, and then just general lessons about operating in a, quote-unquote, “less developed ecosystem”?

Khatija Ali: Look, we’re still a US company. We’re still based here but our operations did move to the UAE. A-and I think one of the driving factors for that in 2023, if you recall was FDA was a little bit of a black box. There was a lot of uncertainty and I think that was the driving factor for us from a structural standpoint to say, “Yes, this makes more sense.” If we’re going to have ambiguity and we’re gonna have uncertainty around how this is gonna play out, let’s try it in an ecosystem that gives us the opportunities and sort of a launchpad including grant funding, including connections, including accelerated pathways, rather than, to try and get this trial rolling in a black box regulatory framework. I would say that was the ultimate driving factor behind it. The second was New York has changed. New York I now see more as growth capital. It’s not really early stage. I think San Francisco is very tech-focused. San [00:30:00] Diego actually is more of a biotech hub which is where we’re housed now. So we’re basically between San Diego and Abu Dhabi and trying to interlink our manufacturing here in the US with our clinical operations in the UAE. From a structural standpoint- I think the biggest benefit for us was really being part of the Hub71 program. So this is a Mubadala-backed Mubadala is the sovereign wealth fund of the UAE, backed accelerator program, which actually provided us a launchpad. So when we got there, we got a grant to set up the companies through the ADGM, through a freehold. Essentially had some incentives to do visas, housing, and just the basic living elements of it. And then not to mention that through their Techstar program, I believe that’s where we met, Ian.

Ian Hathaway: Yeah.

Khatija Ali: But through their Techstar program, they sort of introduce you to their ecosystem, and look, there’s no denying it, this is something I’ve been vocal on every panel in the UAE. It is a small ecosystem. It is new, it is growing it has its flaws, but I would say [00:31:00] that the drive is there, the passion is there, and the infrastructure, for the most part, is there to get the ball rolling for a clinical phase company to move their assets forward and reach their milestones. So the last thing is, I would say in regards to my message to founders, it doesn’t have to be about UAE. Look, I think UAE’s been wonderful to us. I’ve have more awards from them than I can handle, and the recognition has been tremendous. Honestly, the support was amazing. We were trying to close $100,000 bridge round with angels. We ended up closing 950,000 in three weeks. So I think capital was not the problem. I think it was really more around understanding the problem that you’re solving, having conviction in that, and to your point, the person spearheading that and their conviction in what they’re building. So I would say to founders, take the leap of faith. The answer is always no unless you ask, right? And you’re always gonna fail if you don’t try. And so worst case scenario, you come out as someone who has a bunch of battle scars a, bunch of cool stories to share over beer versus somebody who [00:32:00] doesn’t. So from a philosophical standpoint, it’s a journey worth going on. It’s worth having the experience and staying out of that bubble of I have to build the traditional New York way and, raise my Series A on a private jet, all these crazy stories that you hear which, are not really realistic for the rest of us who are building on the ground.

Ian Hathaway: Most of our listeners are in North America and carry a lot of assumptions about the Gulf region and maybe what it’s like to be a woman building a company there. So just, kinda give me your honest assessment as a woman running a biotech company in the Middle East. What do Westerners get wrong about the region? What do they get right? What do you wish they knew about the region, both its strengths and maybe where it still falls short?

Khatija Ali: I think there’s a lot. I’ll tell you a funny story, and then I’ll answer it. I went to JPMorgan last year and met some of my old friends and one of them came up to me and said, “Oh, Khatija, it’s so nice to see you here.” I said, “Oh yeah, likewise.” He said “Oh my God, I have to ask you [00:33:00] this. He said, “I know you love driving, so do you still drive?” And I just started laughing, where do we start? So yeah, I think there’s some fundamental things that I think the West is way off about for sure. I would say to anybody listening to this, don’t believe everything you read. Everything that you read on the internet or everything that you see in movies the Middle East is not as backward as people think. I think people forget that it was actually the Arab civilization that generated algebra, scientific theories calculus, the fundamental frameworks on which we do financial deals. The concept of a bank is Islamic. And so I think it’s important to not fall for those narratives and really to re- remain open-minded. That’s something I definitely wish people knew more of. Now, looking on the other side of things, everything in the US or in North America as a whole is a little bit transactional. I show you a deck, you give me the money. That’s not how things work in Abu Dhabi or in the Middle East. It’s more of, “Hi, we’re [00:34:00] gonna sit down and have seven coffees, and in those seven coffees I’m going to get to know you.” And those seven coffees are, weeks apart, months apart, and you have to have patience and tenacity to be able to develop a relationship which is based on trust. And I think once you develop that, then it’s a different story because then, you’re an insider at that point and no longer an outsider. The last thing I’ll say regarding that is, there’s always insane stories that you hear about different parts of the world, and so you just have to be open-minded and experience it for yourself. So again, anyone who’s interested, happy to have a conversation, happy to make introductions and, come visit us in Abu Dhabi. I’ll take you around for a nice gin. We can drive in my car and blast some music with the, windows down.

Ian Hathaway: Obviously, having spent time in Abu Dhabi, I can’t say enough, really special people and special place. Definitely encourage everyone to check it out. Look, everything in this story, The abstracts, the lots of nos, moving [00:35:00] across the world, it points to this moment, this one thing, the first time the MediChip goes into a human being. I know the trial is coming in Abu Dhabi in low GI cancers. It’s the line that every biotech company has to cross, and most don’t make it past. You have to go from belief to evidence. It’s a critical juncture. You’re raising a Series A behind it. Just reflecting on this moment what does the first patient mean to you? How does it change the weight of the job as the founder, as the doctor, as the person who’s carried this idea for so long? And then maybe what does success look like for you scientifically and commercially for the, company?

Khatija Ali: Honestly, Ian, I’ve said this probably the last six weeks nonstop to anyone who’ll hear me, I’ve spent 12 years of my life to try and get to this next milestone, which is like unfolding in the next month. It’s unreal. It’s unbelievable. It’s like the light at the end of the tunnel because [00:36:00] everything in my mind at least, was to get to this point. And I’ve said this to all my investors, is I would love to be in that OR when the MediChip goes into the first patient. And for me, it’s going to be a series of things, and I think about this a lot philosophically. One, it’s going to be excitement around, okay, hey, we’ve made it to this milestone, which most people don’t because we’ve crossed the valley of death twice along our journey of biotech building. That’s obviously one. Two, we’ve made a huge impact and potentially opened the doors for other patients, other indications, other pharmaceutical companies. And so this can become revolutionary and actually change the way that delivery occurs across the globe in various cancers for everybody. And so that’s an excitement a reality that I think will only unfold once we get back the cohort one safety data. But the third thing I think is honestly a little bit of relief. Like, Hey, we actually said to our investors in the GCC that we were going to reach these milestones, and despite all the bumps and hurdles along the [00:37:00] way, here we are. We proved the infrastructure works. We’ve turned on the machine and, we’ve done the thing that we said we would. And if I’m just being real with you, Ian, I’ve put on my, philosophy hat probably a little bit of grief because, I would say that I would love to have a time machine in which I could take a chip back. Without getting too sentimental about that. I think that part is something, that’s very fascinating and I’m excited to see how I feel on that day. To answer your question on what success looks like. Success for me from an endpoint is, look, phase one, our primary endpoints are safety, feasibility, tolerability. Is this thing safe? Can it stay inside the patient? Is the patient able to, keep it and tolerate the treatment? Then next we’re looking at, okay let’s look at the PK of the product itself, meaning how does it actually release the drug? Does it actually get to the site? And the tissue aspects of bioavailability, et cetera, and that’s our secondary endpoint. And then the tertiary is, okay, did it have an efficacy signal? I think success for me is that nobody gets hurt. We show that the product is [00:38:00] safe. We walk away with a strong safety profile and a signal that says, yes, we can move on to phase two to now look at efficacy where we can measure how effective this treatment is in comparison to standard of care. I think for me, that is success in a nutshell.

Ian Hathaway: I’m excited to see how things evolve over the next few years and have you back, and hopefully we’re all celebrating a successful IPO of the company, right?

Khatija Ali: We’ll go to New York Stock Exchange together. I actually know, them fairly well,

Ian Hathaway: Oh, wow. I would love that. That would be amazing. I wanna shift gears now to you as a leader. You have a real philosophy, of course of leadership, and I think it comes from seeing the industry from a lot of different angles, From the VC side, the clinical side, from this founder operator side. Even inside of Biosapien, the way you hire is unconventional. What’s the thing that you [00:39:00] do most differently as a leader in a deliberative way, and what do you think the credential default version of this industry keeps getting wrong about who belongs in the room when hard medical problems need to get solved?

Khatija Ali: That’s a tough one. Because if I tell you, what I think about what a great leader I am, that would be absolute BS, I think the thing that I do well that I’ve gotten feedback from my team and just everyone around me, consultants, investors, is that I probably over-communicate and I think that’s something that maybe not a lot of leaders do or leading from a perspective of curiosity and compassion rather than direction and authority, ? I think if you lead with compassion and understanding and trying to work on the problem together rather than, “Hey, this is your problem and you need to solve it, and you dropped the ball,” it’s a collective, “Hey, we have this problem as a team. How do we overcome this issue?” And then we’ll deal with whoever dropped the ball later, I think that’s [00:40:00] something that is not very common in the VC world. That’s not something that’s very common in industry. I think people can learn and be a little bit more forgiving in terms of just the process, the mistakes the thoughts. Having a space where people can say, “I don’t know the answer, but I’ll go find one,” is, I think, something that we do very well in our company culture. And we actually encourage that. That’s something maybe the industry is missing. Also we’re about to go into bio, and I guarantee every room I’m going to walk into is gonna be 56-year-old white men. And so I would say the industry needs to be a little bit more diversified. It needs to be a little bit less judgmental around who’s in the room. And you never know when a great idea will pop up from someone who doesn’t maybe have the background or the knowledge to bring that idea to reality. But that doesn’t mean that the idea itself cannot come to reality if you bring the right experts ar-around the table, if you’re trying to build an app, I don’t have to be the one that codes the app and [00:41:00] understands the app and all the infrastructures and frameworks of how it’s put together. I just need to have an idea and find a really good coder that can do that for me. So similarly, that concept of remaining open, remaining confident, remaining compassionate and clear and understanding we’re all working towards making human lives better, I think is something that the industry can definitely learn from.

Ian Hathaway: So continuing on that thread of changing the operating environment for entrepreneurs, operators, employees. There’s a version of your story where you prove the platform, you build Biosapien, the company, and you stop there. But I know you are frequently talking about creating something bigger. You’re actively helping to build the biotech ecosystem in Abu Dhabi and beyond. we talked before about how nascent that ecosystem is. You’re involved at Hub 71. You’ve done some angel investing. I know you’re part of a [00:42:00] industry group of life science investors and CEOs that has talked about getting a early stage biotech fund off the ground. An ecosystem needs startups, needs institutions, needs investors, particularly in the MENA region where a lot of this stuff is still nascent and lacking. You mentioned you’ve been at this 12 years, It’s been hard work. You’ve had to make a lot of sacrifices to get to this moment. After everything it’s cost you to break into this industry, why take on that extra work? Why take on the harder job of building the ecosystem itself? And maybe what do you wish had existed when you were a founder getting the door slammed in your face a thousand times by investors?

Khatija Ali: Wow, that’s a good question. I’m gonna say something that’s gonna sound so silly and limited, but like, why not?

Ian Hathaway: Yeah.

Khatija Ali: But like really, why not? I wrote that on a, one of our philosophy exams in undergrad was the question [00:43:00] was why, and I wrote why not as the answer, and I stand by that 100% today. I think if there’s an opportunity to build something, you should definitely go and take it. And try to make an effort in leaving a dent into the universe. I think that for me, supporting other founders, supporting tech, especially in the region, is something that’s really meaningful and exciting and definitely something that I’m working on in the background currently as well. I’m trying to create a space in which founders and the ecosystem as a whole can come and collectively work together and grow and learn from one another. I find that the current biotech industry is a little bit groupie, if I may. And, trying to essentially establish our own group. If they won’t let you sit at the table, you make your own. When I was building and getting doors slammed in my face, there were not a lot of people that I could turn to and say, “Hey, I need help,” or, “Hey, how do you navigate this?” Or, [00:44:00] “Hey, can you look at this for me and help me out?” I think I had some really good founders and mentors and advisors that I leaned on, and so I think if I can combine all of those together, essentially loop them into an ecosystem, we can grow that together.

Ian Hathaway: Continuing on that thread, this pondering of why we’re doing what we’re doing, chasing these questions about why we’re here, how to make sense of reality. You began there philosophically, , And then you’ve spent your whole career turning suffering into something that at least you could in part engineer against. A material you can print, a tumor you can treat locally, side effects you might reduce. So you believe that at least some suffering is an engineering problem. But you’ve also sat with your father through the part of it that no technology was ever fully going to fix. So my question to you: Is suffering a problem to be solved Where’s the line for [00:45:00] you between the suffering that’s an engineering problem and the suffering that just simply has to be lived?

Khatija Ali: Wow, I wish I had a beer for this one.

Ian Hathaway: Go ahead, crack one.

Khatija Ali: I think suffering is something that’s absolutely necessary. Suffering is something that is a part of life, and I think it’s something that we all fundamentally have to go through without anyone’s consent We have no choice but to go through it. I think the transition for me becomes not staying too much in suffering and turning that into struggling. Because if you’re struggling, then you can at least get somewhere, and along the struggle you learn more about yourself. But if you’re suffering, then you’re consistently in this dark cloud of mentally suffering, and, goes down a very Schopenhauer path. Where I think struggling for me turns it into more of a Nietzsche’s framework, where when you strip it to the core of it all is about your examined self, and who you are, and the idea that people mostly live reactively. Their inherent values, their fears, their [00:46:00] self-concept, all of that combined. And so everyone reacts from it, and therefore falls into the state of suffering perpetually. For me, , the goal is to try and actually look at that and say, “What if you trace back every impulse back to where it came from and asked what if you chose a different outcome consciously? Would that lead you to suffering?” Most likely not. It would lead you to struggle, and struggle would allow you to find out who you are during that suffering, rather than just sitting in it, if that makes sense.

Ian Hathaway: I just would say, holy shit, that was probably one of the best exchanges I’ve had on this show. That was very enlightening. great answer.

Khatija Ali: A lot of suffering came from it.

Ian Hathaway: Yeah. Actually, it’s interesting. I was explaining to one of my sons about music and there’s this rapper that we like. He passed away. His name was Mac Miller, and you can hear the real struggle in his voice. And I was explaining to my son about how [00:47:00] suffering and struggle actually are almost prerequisites for beautiful art And he said to me Dad, I can really feel the pain in his voice.” And so, suffering, struggle, it’s all part of the human existence, but it ultimately creates meaningful new forms that we can all benefit from. So thank you for sharing that.

Khatija Ali: Of course

Ian Hathaway: I wanna end where we began. Before medicine, the question that had a hold on you was why we’re here, why do we exist? And you’ve had an entire life happen since then. You lost your father, you left medicine, you built this amazing thing. You bet the company on a place most biotech founders would never even have considered, let alone been able to find on a map. Your first business was with your father. Your mother wrote Biosapiens’ first check. The company’s founding question is whether fighting cancer can be about regaining control instead of losing control, which is [00:48:00] something your father never got. So let me ask this way not to the person you were then, the person you are now, not the philosophy student under the tree, the CEO who has this lived experience. After all of it, do you feel like you have a clearer answer for why we’re here? What we’re doing when you imagine the version of this company where everything works, massively successful, looking ahead, the patients you reach, the ecosystem you help build, the thing you leave behind, what do you hope it’s all for?

Khatija Ali: I wish I’d gotten these questions in advance, Ian, so like at least I had... at least I could say something, ‘cause wow, you just like... Wow, that was a great question. What is it all for, right? I think ultimately the purpose of human life is for us to be able to experience the divine in whatever way, shape, or form you think it exists, in a way that the divine could not experience itself. [00:49:00] And so I think for me the purpose of life is to be able to live it in every way possible, to experience the things that are meant to be experienced, to be curious, to build, to break, to cry, to fall apart, to rebuild, to fail, to get up, to have that human experience and essentially meet your maker at the end, and for him to say, “Well fucking done with what I gave you.

Ian Hathaway: That was beautifully said. Well Look we’re, almost out of time, but here on Outsider Inc., we like to finish with a little segment we call Beyond the Bio. These are just some quick-hit questions that let us step away from your resume and learn more about what makes you, you. Sound okay?

Khatija Ali: Perfect. Let’s do it

Ian Hathaway: All right. What’s a quick piece of advice -- from a mentor that stuck with you throughout your journey?

Khatija Ali: It will always take twice as long, you’ll need twice as much the money, and everything that can go wrong will go wrong.

Ian Hathaway: Only twice as long and twice as [00:50:00] much as it’s probably more than that.

Khatija Ali: My God, he was wrong. It took three times.

Ian Hathaway: Yeah, exactly. Who is an unsung hero in your life and what has been the impact they’ve had on you?

Khatija Ali: Unsung hero would have to be my mom. She thinks I definitely don’t like her, and I’m gonna take this moment to tell her that I love her a lot, and I actually look up to her a lot. I would say that all of my hard work ethics, everything that I’ve done has been through that unsung hero.

Ian Hathaway: Amazing. Who’s someone in your local startup community or your broader network who doesn’t get enough credit and deserves a shout-out?

Khatija Ali: Michael Lynds from Golden Gates Venture, who has been an absolute rock throughout this entire rocky road that we’ve had over the last six months. And his response to me when I said, “Thank you, Michael, for everything,” he said, “Rocky is what we do. Keep on rolling.”

Ian Hathaway: Oh, amazing.

Khatija Ali: So he’s awesome.

Ian Hathaway: Oh, yeah. Tell us something most people don’t know about [00:51:00] you, something outside of work. Could be a hobby, a favorite travel spot, a guilty pleasure, or maybe even a hidden talent.

Khatija Ali: Okay. Let’s see here. I’ve got a bunch. I write poetry in my free time. That a lot of people would never expect from me. The fastest I’ve gone on a vehicle is 210 miles an hour, and I enjoyed that a lot. And I like adventure, so I skydive. If I could combine the two together, oh, if I could do a haiku while falling, oh, that’s a dream.

Ian Hathaway: Oh, wow. yeah, Curing cancer skydiving, poetry. Cool. Check, check, check. Okay, what are one or two songs you’d like to add to our Spotify founders playlist? Something that fuels your workday or maybe has inspired you on your journey as an entrepreneur

Khatija Ali: Oh my God, there’s so many, but I have to give a shout-out to Eminem for Lose Yourself because nothing like that gets me pumped up right as I’m about to go on stage to pitch. And the second one I would say [00:52:00] is a little boring but I would say it’s Bach Symphony 5. It’s an incredible thing to continuously work to, especially if you’re trying to get through decks or financial models or trying to memorize anatomy.

Ian Hathaway: That’s excellent. Good range. I know this one’s gonna be tough, this next one. What’s a book you might recommend? Something that’s been especially valuable to you on your journey, or maybe one that you think every first-time founder should read as they’re getting going?

Khatija Ali: I think I mentioned this, The Laws of Human Nature by Robert Greene, 100%. And For Blood and Money if you’re building in biotech

Ian Hathaway: That’s great. Okay. Last question. If you could give one piece of advice to someone who’s about to start their first company today, particularly someone who’s maybe a bit of an outsider, what would it be?

Khatija Ali: Don’t do it unless you really mean it. It’s not worth the fame. Only do it if it’s, if you can handle that suffering. That’s all I can [00:53:00] say.

Ian Hathaway: That’s a great way to end. Khatija, thank you so much for joining me today and sharing your incredible story. I am so excited to share it with our listeners.

Khatija Ali: Awesome. Thank you for having me here, Ian. It was an honor. I really appreciate it.

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big thank you to Khatija Ali for joining us and sharing her incredible journey and wisdom. What stays with me isn’t the regulatory arbitrage or the move to Abu Dhabi. It’s that every consequential decision in this story traces back to a room she couldn’t leave. A father’s diagnosis at 18, three years as his caregiver, a young philosopher who wanted to live under a tree but instead got an MD, a medical student who fell in love with surgery but pivoted to build a company around an idea for a better cancer treatment. A thousand no’s later, she’s still here. What Khatija understands better than most is the difference between suffering and struggling. That one engulfs you, and the other reveals [00:54:00] you. She’s built a company on the belief that some suffering is an engineering problem and a life on the acceptance that the rest of it isn’t. So when she says the answer is always no unless you ask, believe her. She has the receipts. And when the meta-chip goes into that first patient, I hope she lets herself feel all of it: the relief, the grief, and the quiet vindication of a daughter who turned the worst thing that ever happened to her into the reason anyone else might be spared it. If you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn at outsiderincpod. You can also follow me on X at Ian Hathaway. Outsider Inc. is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation. Until then, thank [00:55:00] you so much for listening, and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features Tony Summerville, founder and executive chairman of Fleetio — a fleet optimization platform he built in Birmingham, Alabama that recently crossed a valuation of more than $1.5 billion.

Tony grew up in an entrepreneurial family in Huntsville, spending his summers stocking supplies in his father’s electrical supply warehouse in the Alabama heat, and tagging along to the office on Sundays to watch his dad go through the books. He was a serious competitive swimmer as a kid — ranked fifth in the nation in the 100-meter freestyle at age ten. After Auburn University and a short, uninspiring stint at a regional bank, he landed at Daxko, one of Birmingham’s early SaaS companies, where he got a front-row education in how software businesses actually get built.

In 2011, Tony quit his job on a one-year deal with his wife Brittany: she’d keep her income, he’d go build, and if it didn’t work, he’d get another job. He didn’t have the idea fully formed. He had a conviction and a regret-minimization framework — better to look back as an old man having tried than never to have tried at all. What followed was months of customer conversations before a line of code was written, four years of bootstrapping before a dollar of outside capital was raised, a hard call to kill a product that was half-working, and eventually the hardest call of all: handing the CEO seat to someone else while the company was thriving.

In this episode, we get into the wrong kind of validation and why he never chased it, what he was actually listening for in those early customer interviews, why he thinks founders have to leave the office to understand a problem, how he came to know that Fleetio needed something from him he couldn’t give, and his conviction — proven out — that you can build a great business anywhere. ⤵️

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Episode Highlights

Here are some highlights from the show. In this first clip, Tony names the trap he watched other founders fall into — treating a term sheet as proof the idea was good. He never bought it. An investor’s yes doesn’t build anything; you still have to go make a great business, and that’s the hard part. So he put his energy where it counted: the mission, the ROI for customers, a repeatable way to win more of them. Get those working, and the money stops being something you chase. It comes looking for you.

In this next clip, Tony describes the three or four months he spent almost entirely on customer interviews before building anything. He wasn’t hunting for validation — he was hunting for a problem people genuinely ranked among their biggest, and a way to reach those people at scale. His first test was simple: will they even respond? People vote with their time before they ever vote with their wallet. If someone’s too busy to talk about a problem, that problem probably isn’t a big one for them. Only after they’d given him their time was there any point talking about their money.

In this next clip, Tony makes the case for getting out from behind the desk. You learn what someone actually cares about by standing in their physical space — the sticky notes, the ringing phones, the giant whiteboard dedicated to managing a few dozen vehicles by hand. A whiteboard, at a Birmingham nonprofit that drove underprivileged kids to medical appointments, told him the problem was real in a way no survey could. And it changed the goal: not just to solve the problem, but to build something that fit the way people already worked, so they could set the whiteboard down without being asked to change much at all.

In this next clip, having spent twelve years as founder and CEO, Tony talks about the loneliest call a founder can make. The CEO job, he says, is the one that changes the most — what the company needed from him shifted almost monthly across a decade. By 2022 he was burned out and honest enough to admit that the person who built Fleetio might not be the person to run its next phase. Rather than sell, he brought in a seasoned leader, watched him thrive, and then stepped back into the chairman seat. The company has more than doubled since. He says he pinches himself most days that it worked out this well.

Finally, Tony explains the conviction he carried from the start: you can build a great business anywhere. Birmingham’s talent pool was smaller, so he and a handful of like-minded founders built intentionally hybrid cultures that let them hire the best people wherever they were, while still bringing everyone through Birmingham early and often. Companies, he says, are just people aligned on a mission. There’s a reason he thinks that group has all had outsized success. Fleetio is proudly headquartered there still.

I’m grateful for this conversation with Tony. What impresses me most isn’t the billion-and-a-half valuation from Birmingham. It’s how much of Fleetio was already written in a Huntsville warehouse, with a teenager watching his dad go through the books on a Sunday. Tony refused the shortcut everyone else was chasing. No silver-bullet investor, no validation from a term sheet — just months of conversations before any code, a whiteboard that told him the problem was real, and the patience to let a good business earn its own capital.

The part I keep returning to had less to do with the building than the letting go. It takes a rare kind of humility to admit, years in and with the company thriving, that the founder who made the thing might not be the one to lead its next chapter, and to step back not because Fleetio needed less of him, but because it needed more of something else. Everything underneath that story is available to anyone willing to work the way he did. None of it required a coastal zip code or permission from someone with a checkbook. His closing advice was simple: start. Decide what you actually want. And trust that when you build something real, the money will find you.

“It’s funny how it works out. You build a good business, and people throw money at you.” — Tony Summerville

Tony’s Library

Tony’s a re-reader. His favorite business book is Shoe Dog, Phil Knight’s Nike memoir — he’s been through it more than once and swears by the audiobook. He keeps a stack of Andy Grove’s High Output Management on hand to give to the founders he invests in (so do we). That book is short, he says, and it puts you in the right mindset. And the one he recommends for any walk of life is the old-school Dale Carnegie, How to Win Friends and Influence People. Timeless habits, he figures — bake them in and you’ll do better at whatever you end up doing.

Shoe Dog: A Memoir by the Creator of Nike: Phil Knight’s memoir of building Nike, tracing the company from its 1963 origins — when Knight, fresh out of business school, was importing Japanese running shoes out of the trunk of his car — through decades of near-bankruptcy, supplier betrayals, banking crises, and legal fights to its emergence as a global brand. It's less a business how-to than a candid, often anxious account of what the early years actually felt like: the constant cash shortages, the ragtag group of misfits and former runners who built the company alongside him, and Knight's own doubts and stubbornness. The throughline is his idea of following a "crazy" calling and refusing to stop, told with unusual honesty about how close the whole thing came to failing.

High Output Management: this book by Andy Grove, the longtime CEO of Intel, is a management classic that treats running a team like an engineering problem. Its central idea is that a manager's output is the output of their whole organization plus the organizations they influence — so the job is to find the highest-leverage activities that improve everyone's performance. Grove works through practical mechanics: production principles applied to any workflow, why meetings are a medium of managerial work rather than a waste of it, how to run effective one-on-ones and performance reviews, and how to think about training and delegation. Written in the 1980s, it remains popular in tech circles precisely because its framework for leverage, decision-making, and measuring what matters holds up regardless of industry.

How to Win Friends and Influence People: first published in 1936, is one of the best-selling self-improvement books ever written and remains a fixture in business and personal-development circles. Its premise is that success in work and life depends far more on how you handle people than on technical skill, and it lays out a set of durable principles for doing so: become genuinely interested in others, remember and use people’s names, listen more than you talk, avoid criticism and argument, and make the other person feel important and understood. Carnegie illustrates each idea with anecdotes drawn from history, business, and everyday life. The advice can read as simple or even obvious, but the book’s staying power comes from how consistently people find those basics hard to actually practice — which is exactly why founders like Tony keep recommending it.

Tony’s Playlist

Tony’s an indie-rock guy at heart — The Strokes, some electronic-leaning stuff like MGMT. And, by his own admission that he’s getting older, a lot more country than he used to allow himself. He grew up rolling his eyes at what his dad played in the car; now he’s a devoted Chris Stapleton fan. We’re adding picks to the Outsider Inc. Founders Spotify founders’ playlist. In the meantime, I’ll post here a few well-known tracks from each of these three groups.

Up Next: Khatija Ali

Tune in next time for Khatija Ali, the founder and CEO of BioSapien — a very different kind of outsider story. She grew up in suburban Toronto, the daughter of immigrants, planning a quiet life as a philosophy professor, until her father’s colorectal cancer redirected everything. He was diagnosed when she was eighteen, gone three years later, with Khatija as his primary caregiver. That loss made her a doctor. She fell in love with surgery, then walked away from it to build a “Band-Aid for cancer” — the MediChip, a 3D-printed, biodegradable implant placed at the tumor site that releases chemotherapy locally over weeks instead of flooding the whole body. She heard “a thousand no’s” from investors, drove a taxi to keep the company alive, and eventually left America — where, in her words, biotech doesn’t get funded unless it’s AI or gene therapy — to move the company to Abu Dhabi and build a first-in-human trial in a city nobody had on the biotech map. It’s an incredible episode. Don’t miss it.

Listen on: Spotify, Apple Podcasts, Amazon Music

Host Ian Hathaway interviews Tony Summerville, founder and executive chairman of Fleetio, about building a $1.5 billion fleet optimization platform from Birmingham, Alabama. Summerville traces his Huntsville upbringing, summers spent working in his father’s electrical supply business, competitive swimming background, early career at Regions, and time at Daxko, where he saw the shift toward web-based software and learned how SaaS businesses are built. After leaving a stable job with a one-year agreement with his wife Brittany, he spent months interviewing customers before writing a single line of code, using those conversations to validate fleet management as a painful, underserved problem. He describes Fleetio’s early product discovery, the whiteboard moment that shaped its direction, capital-efficient growth, content-driven marketing, the discipline of building before chasing investor validation, and the difficult decision to kill a product that was pulling focus from the core business. They cover the transition from founder-CEO to executive chairman, scaling Fleetio while preserving culture, building from Birmingham, hybrid team design, supporting the next generation of local entrepreneurs, and the personal framework that helped him decide to start in the first place.

Show Notes:

(02:33) Huntsville Roots And Early Work Ethic

(08:43) Leaving Daxko And Taking The Leap

(11:53) Customer Interviews Before Code

(15:22) The Whiteboard That Became Fleetio

(20:19) Bootstrapping And Capital Efficiency

(22:52) The Wrong Kind Of Validation

(24:05) Killing A Product That Half Worked

(29:15) Knowing When To Step Aside

(35:34) Building From Birmingham

(39:44) Investing Back Into The Ecosystem

(43:56) Beyond The Bio with Tony Summerville

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Tony Summerville - Founder & Executive Chairman, Fleetio

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Tony Summerville: What I saw in others that I didn’t necessarily agree was, the most fruitful use of time was like to constantly be fundraising, looking for some silver bullet, some investor that’s gonna give you money and, oftentimes validate your idea, because they gave you money. But that’s just the wrong kind of validation. You still have to go build a great business. And then, it’s funny how it works out when you build a good business, people will throw money at you.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Tony Summerville, founder and executive chairman of Fleetio, a fleet optimization platform built in Birmingham, Alabama that recently reached a valuation of more than one point five billion dollars. But Tony’s story starts long before Fleetio. He grew up in an entrepreneurial family, spent his summers working in his father’s electrical supply business in Huntsville, and developed an early understanding of how real operating businesses [00:01:00] work from the inside, the kind of understanding that most software founders simply don’t have. Later, after Auburn University and an early career stop at a regional bank, he made his way to Daxko, one of Birmingham’s early SaaS companies, where he learned not only how software businesses are built but what he might do differently if he ever built one of his own. In 2011, Tony quit his job with a one-year agreement with his wife Brittany and the belief that he could tackle a massive underserved market. What followed was a founder journey defined by disciplined customer discovery, capital-efficient growth, content-driven marketing, hard product decisions, and the difficult transition from doing everything himself to building a company that could scale beyond him. Today, Tony is no longer the day-to-day CEO of Fleetio, but he remains deeply connected to the company’s future and to Birmingham’s next chapter. He and Brittany are now helping support Birmingham AI as it grows from a grassroots meetup into a [00:02:00] structured nonprofit aimed at making sure the city is ready for the next major platform shift. And he’s betting on the next generation of Birmingham entrepreneurs through capital, connections, and mentorship. I’m looking forward to talking about what growing up inside his father’s business taught him, why he spent months with customers before writing a single line of code, how Fleetio found growth in an overlooked market, what it takes to let go as a founder, and what building outside the traditional tech hubs can give you that you might not get anywhere else. Tony, welcome to Outsider Inc

Tony Summerville: Thank you very for having me Ian.

Ian Hathaway: You have an amazing story. I can’t wait to dig into it all. Obviously the centerpiece of this discussion will be Fleetio, but before we get to that, I wanna start with the world you grew up in. Your dad and both of your grandfathers started their own businesses, and you spent summers working in your father’s electrical supply business in Huntsville, stocking heavy supplies in [00:03:00] Alabama warehouse heat, and occasionally driving vehicles out to contractor job sites. Outside of summer work, you were a serious competitive swimmer, ranking fifth in the nation in the 100-meter freestyle at age 10. Well done. A lot of people have summer jobs or childhood sports, but not everyone grows up around entrepreneurship or self-measured competition at that level. So what did those two worlds teach you about hard work, and how did they shape the kind of founder that you eventually became?

Tony Summerville: I’ll start with the swimming. That was just a sport I was drawn to. In Huntsville, where I up, there’s a pretty large summer swimming culture. Pretty much everybody swims on their summer swim team, and I just started doing it year-round at a relatively young age. But I think you’re always just to some degree competing with yourself always trying to improve your time. The outcomes are largely dependent upon the work you put in. And swimming and similar sports teach you, at a relatively young age how to [00:04:00] grind. As you sort of get into the pre-teen and teenage years in a sport like that, I was swimming before school at 5:00 a.m., multiple times a week pretty much every day after school, Saturdays. And so, you sort of learn how to, work hard, how to wake up and do something you’re not really excited to do every single morning. Swimming, I think really at the end of the day taught me how depend on myself, know that I could work hard and grind more or less. Growing up In a family where there was an entrepreneurial father a- and entrepreneurial grandfathers. I saw what my dad not only did every day going into the office, but, he was always at night going through the books. And even on, Sundays too, he would go in pretty much most Sundays. As I got older, I would go to the office with him and, bring my skateboard or my bike and kind of mess around in the warehouse. Probably at a very young age, started learning how to drive a forklift ‘cause it’s just something to do. I think what I got to see was the work effort it truly takes to build something. And I think a lot of entrepreneurs, business owners there’s a lot of work that people never see, and certainly those are some of the [00:05:00] things that I took forward with me, knowing what it takes when I was building Fleetio. I think the other thing that I didn’t realize it at the time, but now reflecting back I think I realized how important an entrepreneur is for the community. Dad built a business and still runs it to this day. There’s, I don’t know, 700 or 800 employees there now. And it is a wonderful culture, really sort of family business, very earnest people, and it’s important, to everybody that earns a paycheck there and their broader families. And I think I felt that at an earlier age seeing how important, Dad was in not just building a business but being an important part of the community and now communities as they’re in many states and, just what that responsibility entails. Those were some things I got to see behind the scenes just growing up in a family like I did.

Ian Hathaway: Being a part of the community, I know that’s a big part of what you’re doing now. We’ll get to that a bit later. Continuing on that theme of hard work, you eventually attend [00:06:00] Auburn University, graduate in 2004 with a degree in information systems, and you take a first job at Regions, a large corporate bank, which by your own account taught you pretty quickly that’s not the environment you were looking for. I heard a story that a big turning point for you was the day that you first saw Google Maps, and you were blown away by it, and you’re kinda looking around the office and nobody else seemed to care. And that was a catalyst for you a moment where you started thinking about doing something different. So what did that moment clarify for you about the kind of environment that you wanted to be in? And then what made Daxko, which was a relatively early-stage SaaS company right there in Birmingham, what made that feel like the right next move for you at that time?

Tony Summerville: I would classify myself as a pretty curious person. Curiosity plus sort of interest or passion is important, and I was just never super passionate about school. One of the things that was somewhat of a [00:07:00] turning point was after my sophomore year I was not excited about going back and working in the very warm hot, muggy warehouse at my dad’s company. And so I kinda walked in one day to the co-op office in the business school and found myself that next summer working at a paper mill in Brewton, Alabama, of all places. Very small town, just north of the Florida Panhandle. What was neat about that experience was I realized what I enjoyed was actually working, and I enjoyed, putting effort into something and sorta seeing results manifest in more reality versus kind of a score on a test. I got a lot more exposure to programming in that job at the paper company, and you could build these little internal, visual Basic apps and things like that. Got some exposure to programming, fell in love with ended up having my first job doing sort of web development. And that’s what I was doing at Regions. What I realized your point about the Google Maps and just really that Web 2.0 era, I had all this context of the challenges of managing a large operation, a giant paper mill, and [00:08:00] the amount of client server, computational effort it took to run something like that. And you could just see, Google Maps, it was a true application feel, but it was like the website was the application. That was just a major stopping point like, this is gonna be important. And so that led me to Daxko because it was a true tech company, a software company that was building a software application. And this was before, software as a service, that, phrase took off. We were calling it on-demand software because it of lived in the cloud and you used it on demand. But again, those few years there where things like Google Maps show that you’re gonna be able to build really impressive, application caliber things in the web. And then my years at Daxko, I mean, that was what we were doing i- is building software that was delivered, over the web and not done, via the traditional client services. So all those things helped me feel the major shift that was coming.

Ian Hathaway: So you spend about six years at Daxko moving through roles as software engineer, new market [00:09:00] strategist, where you were able to work directly with the CEO on an acquisition before finally ending up in product management. A lot of seeds were planted there for what would come next. But I know that also by your last few years at Daxko, you were increasingly trying to tinker on the side, working nights and weekends, getting up early. You came to realize along the way that you couldn’t actually validate a real business idea without being able to go out and talk to customers during real business hours. You had to let go in order to pursue a new business idea. So in the summer of 2011 you quit. You and your wife Brittany, who was also working at Daxko, had an agreement that you’d give it a year, and she’d keep working, she’d have the income, you’d go out and build, and if it didn’t work out, you’d just go back and get another job. Founders realize that they have to be all in, but also have personal [00:10:00] responsibilities to manage. What was it like to walk away from a stable career without the company even being fully formed yet or even having a, a full idea, just with this conviction that you needed to go and find it? And what do you recall about those discussions with your wife about the decision to go all in?

Tony Summerville: She saw it progress, over the course of years, just wanting to strike out on my own and try something. I was approaching the age of 30, and we didn’t have kids yet. It was a moment in time that was as good as it was gonna get as far as the timing aspect. one of the things that was also helpful for me, and I’ve certainly, tried to convey this to others that are thinking about making the jump into entrepreneurism is regret minimization framework. Fast-forward to the future. In my case, looking back as an old man, what am I gonna regret? Most of the time, people regret not trying something [00:11:00] way more than they regret trying and failing. And that’s exactly what ultimately motivated me, was, I would much rather be later in life looking back and have tried something and it not worked out not trying at all. And that ultimately is what, helped me have the confidence to go and, like you say, quit a good, stable job and forge ahead with this. Really kind of had a few ideas, but, none of them were necessarily gonna be the one. But I knew I needed to go out, talk to people. I need to devote, every ounce of my being to this and, give it a real effort. and, all those things led me to have the confidence to just go and do it

Ian Hathaway: The regret minimization framework. Which I guess in this context could be the pain of opportunity versus the pain of regret, which is really about short-term pain, long-term gain. That’s a great Way to view it. So timing is everything. When you quit, I know fleet management wasn’t necessarily the only idea on the table that you were exploring. It was potentially the one with the most opportunity [00:12:00] and one that you had a strong connection from your upbringing. But before you built anything, you spent, three or four months almost entirely on customer interviews. No code, just conversations. You used Eric Ries’ The Lean Startup as your guide, creating one-pager interview sheets and turning those into strategy documents. I know you’ve talked about how if people wouldn’t respond to your outreach or wouldn’t meet with you, it was something that you could treat as a signal. Maybe the problem wasn’t big enough to build for. So at that time, if you could go back, what were you actually trying to learn in those conversations? And what would have made you walk away from an idea entirely?

Tony Summerville: I was looking for a problem that people truly thought was like a top 10, if not a top five, maybe even in certain days the top problem that they would have. And then I was also looking for a way to get customers in a scalable [00:13:00] fashion, are people, one, willing to admit or do they believe that this is a problem? And then If I’m talking to you, Ian, would I even get you as a customer? Are you looking for this, solution to this problem actively? Do you visit, do you talk with, peers that have similar type companies that you might get advice from? And ultimately at the end of the day that, framework level of thinking is do you have a problem we’re solving and do you have a potential go-to-market strategy that can acquire customers and get distribution? ‘Cause at the end of the day I think you have to have a great fundamental, product or solution to a problem. You have to have great distribution. And when I was having a lot of those conversations, you’re obviously putting on the product manager hat and trying to figure out , how you do this, show me your computer. I’m a big believer in just having those conversations if you can, in When you go into somebody’s office you immerse yourself in their full experience and you can sort of see, what’s happening. And in the world our customers their phone’s ringing, their cellphone’s going off, there’s sticky notes, in a lot of places. And it’s not all just about fleet management, but it helps you kinda [00:14:00] understand them ‘cause you’re trying to get in their head. And then you’re also trying to understand in a broad category like fleet management, what are the things that you actually feel like, you need to solve today or like what’s kind of a weekly problem that you wish you could, have a better solution for? And then, how do they describe it? What are the words that they use? Because at the end of the day, we need to make sure that our marketing, is using those same words too so that we show up in, back then, Google search results. You’re just, listening, documenting these things as best you can. But you’re gonna use those insights to hopefully dial in what you need to build and how you need to build it. So all those conversations were important to, zero in on, is this a pain point worth solving? And that starts with will people even respond to me? Because people vote first with their time. And then later hopefully you can get them to vote with their wallet. And it also just, you either decide whether or not you want to build this product and this company. Like, do you want to serve these people? There’s a lot of things that I like and I’m passionate about. There’s a lot of things that I probably, would have a hard time caring deeply about. Are [00:15:00] these the people I wanna spend time with, and do I want to help these people? Not to say that that’s the only thing that matters, but it makes it a lot easier to build something that’s gonna be very difficult to do if you enjoy being around the people that you want to build for and solve for and all those types of things.

Ian Hathaway: So earlier you talked about being curious, Having these customer conversations, listening for the right cues, seeing the right behaviors, observing the environment, then the passion, Do I wanna serve these people? Do I wanna solve this problem amongst many? I feel like in so many of these founding stories, along with that comes a spark, you have this aha moment where it all clicks. I know that in one of these early conversations, there was this defining story for you from Fleetio’s beginning, when you walked into the office of Kid One Transport, which is a Birmingham nonprofit that transports underprivileged kids to medical appointments, and the operations manager there , who was managing a fleet of, a few dozen vehicles, is using this hand-drawn grid [00:16:00] on a whiteboard and that’s how they were managing their entire fleet for this business, that was their core function, managing a fleet, moving people around. You said that moment told you that this was the problem that was worth solving. So what did that whiteboard reveal that a structured interview or a carefully worded survey might not have? I think this might go a little bit to your point of getting into that environment, getting out of your office and sitting with people. But what did that moment change your understanding of what Fleetio actually needed to go out and solve?

Tony Summerville: People will reveal their priorities or what they care about if you just get to see more of their physical context. And you can spend a little bit more time with them in a more structured, yet still informal environment. Okay, they have a huge whiteboard dedicated to fleet management. May not be the biggest, most important thing that they do all day, every day, but from Patrick, that was the guy that was working there at the time, it’s clearly a big part of his, job because he’s got a huge [00:17:00] whiteboard dedicated to it. It’s not just about figuring out what problem to solve, it’s like how do we build a, as perfect as we can get product that, fits like a glove to them? Of course, you’re never gonna be perfect there, but you at least have a much better understanding of how you’re gonna make something that actually solves the problem for them in their context. ‘Cause I’m not a huge believer of trying to make people change dramatically. Show me what you’re already doing, and let’s go find a way to build something that you can incorporate, pretty easily. One of the nice things about web-based software too, back in the early days, you could instrument it with analytics and start to see what are people clicking on? How are they using it? And if you can find usage and people are continually using something, that inherently probably has some value. Hopefully then they’re willing to pay for that usage because they’re getting value for it. Started meeting with Patrick regularly, starting to build things, and you could watch him start to use it more and more and more because it was starting to solve not just solve the problems, but solve it in a way that he could actually use it and start to get value and, stop using the [00:18:00] whiteboard and start using Fleetio.

Ian Hathaway: As you were evolving on these, the shape of the early product, you actually started building it. You get a working version in early 2012. A few months in, you were still the only employee doing everything. Development, sales, support, doing it all yourself. What strikes me a bit about that solo stretch is just how much of what Fleetio still runs on today was figured out during those early trial and error months. Important lesson for founders , think first, don’t just build right away. So when you look back at that period of really experimenting your way into the business, pricing, positioning, how you’d reach a market that didn’t know that software even existed, what’s the lesson that stuck with you most about how you actually figure things out when there’s no one there to tell you the answer?

Tony Summerville: I think one of the, constraints that, just being me for a while was just to [00:19:00] try and, stay focused on a very fast learning loop, and using data, pretty early. And then always looking for ways to kinda automate things. The concept of leverage was just always top of mind to me. So how do I do something once and have it be levered, at least two times or three times or infinite number of times? I, And I was always balancing that to some degree being an entrepreneur there’s not oftentimes the answer in data about what you should do. You have to trust your gut instincts you have to have confidence in your own judgment, and you have to be willing to be wrong. We have made a lot of mistakes and corrected for them, starting in the very early days. You just try to try and figure out are we heading in the right direction or not, and you make little changes oftentimes very subtle. And ultimately, you have to have a mentality of nobody’s gonna tell you what to do. You’re an entrepreneur, you gotta go start building towards, what you think is gonna be a viable solution and a viable market. But then [00:20:00] you are trying to use data to help you understand if you’re heading in the right direction. So it’s like this two-brain thing that you’re balancing. Are we pioneering enough? Are we trusting our gut instinct, moving super fast, and willing to just take risk, constantly? But at the same time too, we’re not just in pure cowboy mode all the time. The other half is being structured. And I think you should probably never really outgrow that. But then you need to have a structured way of deciding was my idea, was the thesis right? And if it is, keep going. If it isn’t, figure out something else

Ian Hathaway: Fleetio bootstrapped for about four years before raising any outside capital. You’ve talked about that period in terms of capital efficiency and being head down, but you’ve also been candid that early fundraising attempts were difficult, And that at some point you felt like it was more productive just to keep building rather than wait for investors to come around. By 2016, the business was growing strongly, and a [00:21:00] Birmingham-based mentor helped lead your first outside round, which was a 750K angel investment. That allowed you to hire a head of revenue for the first time in the company’s history. So if you look back on those early years, how much of Fleetio’s bootstrap DNA was a deliberate strategic choice versus how much was just born out of necessity? And then secondly, how do you feel like that DNA shaped what the company would ultimately become?

Tony Summerville: It was certainly like a fundamental thing that’s driven, the entire identity of the company. And, it’s just so part of the DNA of business. there is no right or wrong way. There’s clearly so many successful businesses or at least software companies that raised a lot of capital, very early on, call it even at the idea phase that went on to great success. But, again, kinda going back to my roots and just growing up around dad’s company and other small and medium-sized companies. had the mentality of build some value first. That’s the number one thing. Like why does the company [00:22:00] exist and how is it actually driving enough value to enough people to where, it’s self-sustainable? I wanted to build something big. And I think my ambition got bigger as the company got bigger and I realized that the potential was even higher than maybe I originally thought. But maybe the entrepreneur in me, I don’t like to depend on other people per se. Like I’m a pretty self-dependent person in a lot of ways. Let’s go build something that we make it or don’t because of our abilities to build and serve our customers, not because we were able to convince somebody to give us money. And so I think looking back, it’s kinda easier to say, I think I felt that. But it was also like it was gonna be a big, challenge to go raise capital at that time. I mean, this was 2012, 2013, the, the venture capital industry was a fraction of what it is today globally and certainly in places like Birmingham it was, basically nonexistent. It was more of a necessity, but I think it, it forced a lot of the right habits and way of thinking about things and keeping the most important thing, the most [00:23:00] important thing, building a business that serves, a collection of people that are willing to pay you money for it. What I saw, in others that I didn’t necessarily agree was, the most fruitful use of time was like to constantly be fundraising, looking for some silver bullet, some investor that’s gonna give you money and, oftentimes validate your idea, because they gave you money. But that’s just the wrong kind of validation. You still have to go build a great business. And that’s the hard part, and that’s what I always just focused on. And then, it’s funny how it works out when you do that and you start to build a good business, people will throw money at you. It’s not hard to raise money once you have established something. And it’s like all those calories you burn just trying to go and raise capital on an idea, again, not saying it’s the absolute wrong way, but it’s putting a lot more emphasis on what are you gonna do? What’s the mission? How are we driving, a great ROI for our customers? How are we getting more customers in a repeatable way? Good distribution channels. Those are the things that consume most of my thinking every day. Because those things started to work, [00:24:00] it was very easy to raise capital.

Ian Hathaway: I wanna double-click on a couple things you said because I there’s an important aspect of the cultural DNA of your company embedded in that. You said keeping the most important thing the most important thing, and you were talking about, at a company level, driving enough value to enough people that the business could self-sustain. Maybe you didn’t write those values down, but you were living them, and I can point to one example in your company’s history, a pivotal moment which I think exemplifies this. Making this tough call, you were building a second product called Fleetio Drive, a smartphone tool that ran in the background scoring drivers. It had traction, but it never really hit the revenue expectations. It was a support nightmare, and it pulled focus away from the core platform. But it was doing enough to provide a defensible excuse for keeping it going, right? What ultimately surfaced the decision to kill [00:25:00] it was something, a culture, a practice you had built into the company early, which was these quarterly strategic off-sites where the leadership team would write pre-read briefs, stare at the metrics, and just be honest with each other about what was happening in the business. You’ve described that cadence as the heartbeat of your company. But here’s what I keep coming back to with this example. You started Fleetio alone in your house, doing every job yourself, which is a lonely way to build. But the off-site that surfaced this, glaring problem in the company was the opposite of that. So I’m curious about those two halves, What does it actually feel like from the inside to kill something that’s half working? And how do you go from being a founder who had no choice but to decide everything alone to then deliberately building a team and a culture and a process that you could trust to make the hard [00:26:00] calls along with you?

Tony Summerville: Going all the way back to square one, which like you said, for about a year it was literally just me, and then for the second year it was just me and another guy named Matt. It was a very small business for a long time. And I think, part of my own self-evolution was growing as a leader and leading others and bringing people kinda into the tent to help make strategic decisions. I would say, my style and definitely a strong suit of mine in building a company from scratch is just being confident enough to make hard decisions. And listen, I was wrong and changed things a lot where I was, pretty confident that I was right and then I ended up being wrong. Three or four years in, we started doing those, quarterly offsites. and I certainly did not want to be ever perceived as or actually making big decisions in a vacuum. And whether or not it was me ultimately making a lot of the decisions, I still wanted to riff with people and have some debate about stuff. I think good ideas come from debate. And that’s where too, I think I had to learn over the years of maybe conveying my thoughts last versus first because as the founder, [00:27:00] oftentimes my words are gonna carry more weight. And again I’m not perfect at this today. I still get overly excited and kind of throw up a bunch of stuff that, I should’ve been more patient with my thoughts. But at the end of the day, I, I cared deeply about building a culture of people who , exemplified our core values and ultimately like they’re here because they’re excellent and they’re humble and they have all these amazing qualities and I wanted their opinions. Even if you didn’t agree with the decision that we made, you saw how I thought about it, you saw how we got to a final decision and, people could buy into it. It wasn’t just ever totally mandated down. But there is still this culture of we’re being thoughtful about everything that we’re doing. Let’s move fast, but let’s be thoughtful and let’s try to, make the best decision that we can implement it, and then decide later if that was not a great decision, we’ll change it. And so specifically with the Fleetio Drive thing, it was like, classic trying to do too much at once. I saw this wave of mobile phones are now like super computers in our pockets and, a big challenge and a big part of the fleet management [00:28:00] industry was like GPS tracking. You physically had to go install a device in every single vehicle to track it. And even then it doesn’t really know who’s driving. It’s just like the vehicle’s on and it’s moving in this direction and so on and so forth. And, I became convinced. I was like, “What if we could just use these cell phones and it detects when you’re driving and it detects, the sort of safety aspects and it could see where it was going and all that kind of stuff?” I was probably overly confident that could work really well. And it was like E-exactly what you described, Ian. It It had customers and it had a lot of interest, and even some really big companies that were like safety focused, but it wasn’t a blowout success. Where You’re just like, man, it’s consuming a lot of time and energy. You gotta focus on scaling the business at that point and I sort of got a little bit starry-eyed with the next thing we’re gonna build and meanwhile the thing that we had built and was growing, for probably a year or two just didn’t get as much attention as I should have been giving it. And all those things came to fruition in these discussions, in these quarterly offsites and some of the data. And then ultimately it wasn’t a hard decision to kill it because we had been [00:29:00] talking about it for a while and then at one offsite we gave ourselves by the next offsite which is three months away, we need to have seen this. Got pretty objective about it. By the time we got to that one we hadn’t seen it and it’s like, all right it’s done. We’re gonna, kill it. But now we gotta work through like we had customers. We couldn’t just shut it off tomorrow. That became a nine-month unwinding it process that still took time too.

Ian Hathaway: Turning off revenue, even if it’s bad revenue, is one of the biggest challenges for any founder or CEO. But you did it. Hard choice at the time, but ultimately it was the right choice. Company continues growing. By twenty twenty-three, Fleetio is more than two hundred employees, customers in over eighty countries. You just closed a big Series C round, hundred and forty-five million dollars. In that same month, after twelve years as founder and CEO, you decided to step down and hand day-to-day leadership to John Meechan, moving yourself to the executive chairman role. That’s a decision almost nobody can make for you, The [00:30:00] company can tell you a lot of things, but whether the founder should still be the CEO is, probably one of the loneliest calls you can make. Flash forward a couple years later, in March , twenty twenty-five, the company raised over four hundred and fifty million dollars in a Series D, made an acquisition of AutoIntegrate with the combined valuation of the company at one point five billion dollars, a chapter that happened with you as chairman, not as CEO. How did you come to know the difference between what Fleetio needed from you as its founder and what it needed from you as its CEO? And then now, watching it reach a scale like it has from the chairman seat, looking forward, what feels most unfinished to you? What are you most looking ahead towards?

Tony Summerville: I think in 2022 especially, I was starting to get pretty burned out. I think the job of the CEO is the job that changes the most. If you just look back over course of 2012 to 2022, that 10-year horizon, what [00:31:00] the company needed me to do changed almost monthly. My work requirements changed dramatically. And I think, what I realized was we had this great business. It’s highly valuable, profitable, and, and doing really well by all accounts. But I think I was realizing that what made me a great entrepreneur I was having to constantly learn how to be a great CEO. frankly, I was at a point where I was considering just selling the business and/or... we’ve always had a lot of strategic potential buyers being in a large industry basically the automotive industry. So we’ve had a lot of really big partners, a lot of big strategic interest over the years. I definitely spent a little bit more time kinda talking to those types of folks and also to some of the large private equity groups to sell a portion of the business. And in 2022, what I really spent a lot of time thinking about was am I done? done? Like I wanna sell this thing and, be, hands off and gone after a year? Or is there still a lot more of the Fleetio story to tell? [00:32:00] Even that word Fleetio, like I vividly remember looking for domain names. Ended up on fleet.io, but I was like in our industry, fleet.io is people think they’re getting scammed or something. But I was like, Fleetio, that’s a fun word, so And I remember like having that conversation, with my wife Brittany in our kitchen. I was like: All right. How does this sound if you were calling in? “Thanks for calling Fleetio. How can...” Th- those are like the sort of fun, fond memories that, every entrepreneur can look back to and remember the really early days of like where things came from. And so as I was sitting there and I was like, I think the Fleetio story has a lot more to be told, but I was like: I don’t know if I the right person to run the day-to-day. I, I started to understand that better was just I spent a lot of time kinda outside the proverbial Fleetio walls talking to not just customers but, other entrepreneurs, CEOs, anybody that I could pepper with questions. And then also like we started hiring more seasoned folks that were coming in from bigger companies. And that was in 2022. Our now CEO, John Meacham, came on as our COO. Started working with him very closely. [00:33:00] And what I started to realize was there are people that can run this company and scale it better than I can. I’m humble enough to realize what I’m good at and what I’m not great at and what I, want to do every day and what the job requires. When you get to hundreds of employees, it’s a totally different ballgame than when you’re like 10, 20, even 50 or 100 employees. so I thought a lot about that. ultimately I told, Jeremiah who leads the firm Elephant, and “Hey I think I’m ready to take a step back and not be CEO, but I wanna fully sell the business.” that was a shock to him by all accounts, the business is thriving, I seem like I’m doing a great job, but I just knew it was the right move and, I also wanted to see the company, grow into what it can become. If you sell a company to a much larger mega company, it doesn’t take a long time, maybe a year, maybe five years, for it to just kinda dissipate into thin air, it just happens. That’s just part of the life cycle of companies. And I just wasn’t ready for Fleetio to just become a part of some other larger company And so, I told Jeremiah in that conversation that there’s a lot [00:34:00] of large private equity groups that are interested. Those folks usually have a stable of But I told him, I was like, “I think John Meachen can be an excellent CEO.” and fast-forward a few more months Jeremiah and his team agreed, and they were, convicted and had seen Fleetio’s growth since 2020 when they first invested and saw the potential of what we could do. Ultimately they came with an offer to, buy more of the company from me. And also again we did a large tender offer to our employees and let them sell some shares. We added some more cash to the balance sheet for sure too. And we had a lot of conversations with John. I flew to Austin and took him to dinner and told intentions of stepping down, he could be a great CEO. He was floored and shocked and it was unexpected. And he decided that he was ready for the challenge and wanted to take it on. Been three years now since, I took a step back into the chairman role. I pinch myself most days that it’s all worked out this well. We’re way bigger than we were back then. There’s always little bumps and things like that, but the business is thriving. We’re doing [00:35:00] incredible things. We’re still Fleetio. We’re still this independent company. We still have the same culture. It’s just scaled and it’s evolved. But I couldn’t be more proud of how things have gone. And, for me, it’s taken some work just to find the right sort of balance of where I insert myself, I’m still the founder of the business. I’ll always know more about the history than anybody. But it’s been so awesome to witness John just really thrive as the CEO and come into his own and build his exec team and just take the business to what I knew it could become and even bigger than I thought it could become. And there’s, no end in sight. So it’s been a fun journey.

Ian Hathaway: It’s a great story. To make the decision you made. It’s not easy. Many founders choose to not make it that easy, right? But you did, and it’s working out. I’m happy for you. I’d like to switch gears if we could. Quickly, I wanna talk about Birmingham, Big theme on this show is what it takes to succeed entrepreneurial ecosystems outside the traditional tech hubs. Obviously, your story speaks directly to that. But what’s [00:36:00] also interesting is that a lot of our guests have made the case that the constraints of building in a less mature ecosystem actually made their companies stronger, more resilient, more creative. That what’s perceived as a weakness in these ecosystems actually over the long term turns out to be strengths including Segun Oyelana, who is your, friend and neighbor in Birmingham. And, some of thinking is clearly visible in how you built Fleetio. So I guess I just wanna hear it from you in your own words. What has building in Birmingham actually been like for you? The real advantages, the real disadvantages, and how much of how you built Fleetio do you think was shaped specifically by where you built it?

Tony Summerville: This one goes back to timing as well. I think one of the things back in 2011, 2012, I had a real conviction that you could build a great business anywhere. I was at Daxko, which was a large success. It was a, pretty much [00:37:00] Birmingham-based business that had maybe a couple of like, remote or distributed sales team members, but everybody was in the office each and every day. And we had some incredibly talented people there. Birmingham’s a bigger city than maybe people realize because when you count all the municipalities around it, it’s l- well over a million people roughly in the area. Companies are a collection of human beings that are aligned hopefully on a mission and vision, and they bring their skill sets and talents to achieve that mission and vision. Shegun and others shared the same mentality. And we were all at this place called the Innovation Depot. It’s the perfect storm and a good way us all trying to build great companies out of Birmingham, knowing that the talent pool here is, limited. Shagan and I shared a lot of the same conviction. And then we started to do it, and we had, learnings we could share with each other about how to build and, attract talent and build a culture that everybody feels like they’re still a part of a great company and a great team, even if everybody isn’t all in the same place at the same time. I think the Birmingham [00:38:00] connection was always, and still is very strong. We’re proudly headquartered here. We have an amazing office. and we always had this like hybrid, culture where we always had a relatively high percentage of distributed team members, starting with the third employee, George, who’s still our CTO today. Once he came on board, we were 33% distributed. But over the years we were very intentional. George, when he first started, he came and joined Matt and I for the first probably week or two in our closet-size office in the Innovation Depot. And for years, I mean, all those first, distributed employees, really up until COVID, you would come and spend your first week in the office in Birmingham. And we always had a lot of our sales team in, in Birmingham. We built out certain departments and roles here. But we’d always bring people here early and often to be a part of the team and get the physical, aspects of being around one another. What we learned, and I think what a lot of people learned, is if you balance the right like, yes, people need to be together, and yes, there’s a lot of creative work that [00:39:00] is so much easier when you’re in person, but then there’s a lot of just work that happens each and every day. No matter what kind of company you’re in and what sort of job you have, especially in knowledge work. And there is a lot of value in just having people be distributed and being able to focus, create a comfortable environment wherever they are. But if you can create a great culture with, that’s a hybrid of virtual and in-person and team members, then you get to hire the best people. Like you get this talent pool that’s, infinite. And that’s such an incredible way, I think to build a company. And I think, Fleetio, Shagun’s business, plenty of others that saw that opportunity ahead of others and leaned into it and built intentional sort of hybrid cultures. There’s a reason I think we’ve all had outsized success.

Ian Hathaway: That’s a theme that has appeared on this show multiple times about how do you build, how do you scale in a less mature ecosystem? So I, I wanna ask kinda one last major question here, which is, y- look, Tony, you grew up watching your father build a business, spent your summers [00:40:00] stocking supplies in a warehouse, and built Fleetio from an idea into a billion-dollar platform from a place most people would not have bet on. And now you’re putting your time, your money, and your credibility into making sure the next founder from an overlooked place gets a real shot. So if you could imagine, 20 years from now, looking back on all of it, what do you hope you’ll have proven about what’s possible for solo founders, for founders building something lasting for a customer base that the rest of the industry has overlooked, and about scaling a platform in a place that most VCs would never consider?

Tony Summerville: I, I’ve always loved that phrase, if you can see it, you can be it. Human beings are oftentimes, either intentionally or, even subconsciously inspired by others that they can witness do something. And for me, I think I certainly have benefited from learning about and [00:41:00] witnessing others, achieve success. And to me it’s not just about the business success. Like I’ve always gravitated towards others that their whole self, their entire way that they carry themselves, the way that they treat others the way that they treat their families, treat everybody around them and also have, success and take risks and see things through. And for me I love Birmingham. I can’t imagine having done this in another place. I have, two sons that are now entering the, teenage years soon and first and foremost always try to be a role model for them. A- and then, for others there’s plenty of great talented entrepreneurs here in Birmingham and in other places. We care deeply about this ecosystem and always try to be an objective investor. I’m a capitalist at the end of the day. I want to see, investment dollars go into something that can drive value and a return. And so when we’re looking at, startup investments, that’s certainly part of it. But we try to have a not just, ability to invest in the early stage companies and I know you know some of the, folks in and around the Birmingham [00:42:00] ecosystem that, that we’ve gotten involved with. But, I think it’s fun to see others on the same journey or a similar journey that I’ve been on. And, you know, the one thing I think that I’m pretty confident in is that there’s no perfect answer. There’s no silver bullet that’s gonna solve everything and also there’s so many other aspects to success than just the business side. But what I definitely enjoy is being able to share my story, a- and thank you for hosting me here today, doing it, on a more individual basis, especially with local folks that we wanna see be successful too. And just helping them think bigger, think about, the opportunity set that they have. Being able to challenge people, but, from a place of love and respect and making sure that they’re thinking about all aspects of what they’re trying to accomplish. when I look back, hopefully success to me would be that as my sons get older and, certainly I want them to figure out what’s right for them as far as where they go to school, where they end up in their careers. There’s a lot of us that are in Birmingham that love it here and want to see our [00:43:00] future economy continue to, grow and thrive, and that means, more jobs more opportunities for people to have great careers here, more restaurants, more things to do. And I think at the end of the day that just takes more and more entrepreneurs whether you’re building the next tech company or you’re gonna start a great restaurant or bar or do something kinda off the beaten path. and I just love supporting and being, the biggest cheerleader for entrepreneurs, especially in, , where I live

Ian Hathaway: Well Said. Birmingham is a fantastic place. The ecosystem is strong. The people who have had kind of the breakout successes in the Birmingham tech ecosystem are all relatively young and very engaged in building the ecosystem for future generations that they might have a easier time than they had. I will triple click on the restaurant vibe. The biggest challenge when I come to Birmingham is deciding where to eat because there’s so many great restaurants. And hopefully I have a chance to do that here in a [00:44:00] few weeks. So that’s a great way to end. But before I let you go we like to finish with a segment called Beyond the Bio. These are just some quick hit, questions that let us step away from the resume and dig into what makes you, you. Sound okay?

Tony Summerville: Let’s do it.

Ian Hathaway: All right. What’s a quick piece of advice from a mentor that stuck with you throughout your journey?

Tony Summerville: Had some good advice from a couple of different folks that have just reiterated how you make people feel is what you leave them with, and whether that’s a conversation or more broadly, how you make people feel is probably most important

Ian Hathaway: No one remembers what you do, they remember how you made them feel. Who is an unsung hero in your life and what has been the impact they’ve had on you?

Tony Summerville: Beyond just being an incredible wife, my, my wife Brittany has been joined at the hip with me, proverbially for this entire journey. She supported me and this, taking the leap. And, she in her own right, successful more on the, customer service side of things. And still to this day, just enjoy [00:45:00] her advice and discussion around, all things Fleetio over the years. And now, in the phase that we’re in, just being able to invest and even, on the philanthropic side she’s just such a, a great partner for me over the years.

Ian Hathaway: Who’s someone in the Birmingham startup community who doesn’t get enough credit and deserves a shout-out?

Tony Summerville: He recently did a podcast that I thought was great. But Jared Weinstein is a spectacularly successful individual that grew up here in Birmingham and had an incredible career both working very closely for George W. Bush and then essentially co-founding Thrive Capital. And now he’s on kind of his next act. But he has his, fingertips on an enormous amount of things in Birmingham and is a real just incredible driver of the community, but really is pretty under the radar considering his accomplishments and his stature.

Ian Hathaway: You’re the second Birmingham founder to come on this show and the second to name Jared for this exact question. Tell us something most [00:46:00] people don’t know about you. Something outside of work, could be a hobby, a favorite travel spot, a guilty pleasure, or maybe even a hidden talent.

Tony Summerville: Most people know that I hate onions. If you’re around me and we ever eat I cannot stand onions. I’m the annoying person that always asks for no onions on everything every time we go out. But luckily my wife is the same way so we bonded when we were dating on the no onion thing.

Ian Hathaway: Oh, that’s amazing. I was not expecting that. Okay. What are one or two songs you’d like to add to our Spotify Founders playlist? Something that fuels your workday or has maybe inspired you on your journey as an entrepreneur

Tony Summerville: I’ve listened to so many things over the years as I was building Fleetio in different phases of life. I’m still probably just like an indie rock, person, things like The Strokes and maybe even some electronic indie rock like Management.

Ian Hathaway: That’s great.

Tony Summerville: I I know I’m getting old though because I used to not really like country music. My dad always liked it, and he’d have it in the car, and I just, “Ugh, I just don’t...” [00:47:00] But now I’ve I listen to a lot more country than I did back in my earlier days. Big Chris Stapleton fan

Ian Hathaway: Oh, yeah. My favorite Star-Spangled Banner from the Super Bowl.

Tony Summerville: So good. So good

Ian Hathaway: What’s a book you’d recommend? Maybe something that’s been especially valuable in your own journey or one that you think every first-time founder should read as they’re getting started

Tony Summerville: My favorite business relevant book is “Shoe Dog,” the Phil Knight about Nike. I’ve read it multiple times, listened to it. It’s a great audiobook if that’s more of your flavor. That one is really good. Another book that I keep a lot of copies of and I give out to a lot of the founders that we invest in is Output Management,” which is the Andy Grove book. A lot of people recommend that one. It’s popular in the tech communities, but a lot of people haven’t read it.

Ian Hathaway: We give that same book out.

Tony Summerville: That one’s just good. It’s short. It just... it puts you in a mindset. And then probably the third book that I just find myself recommending for all walks of life and all different categories of future career opportunities is just [00:48:00] old school Dale Carnegie, “How to Win Friends and Influence People.”

Ian Hathaway: Yes

Tony Summerville: books like that, they’re pretty timeless. if you can bake in some of those habits out of those books no matter what you do in life, it’s gonna make you more successful.

Ian Hathaway: Okay, last question. If you could give one piece of advice to someone who’s about to start their first company today, particularly someone who’s maybe a bit of an outsider, what would it be?

Tony Summerville: Well One, I would just say start. I think there’s so many people that I meet that want to start something. And it kinda gets back to that regret minimization framework. Think if you really feel convicted to do something, like start a business, whether it’s a tech company or, a restaurant or whatever there’s never gonna be a red carpet that gets rolled out and invites you to this perfect, situation. There might be some better timing situations than others, but for me personally really good framework for choosing to take action has been that. And then I think if you’re starting a company today I would say spend time thinking. So few people, I get the sense, have given a lot of thought to the question what do [00:49:00] you want? What do you want this business to be? in five years, what do you want your life to look like? What do you want your day-to-day to look like? What do you hope the business looks like? Decide what you want. I think if you can see it, you can be it, and sometimes seeing it is the vision aspect of what do you want to achieve? What do you want your life to look like in five years? And give that some thought.

Ian Hathaway: Yeah, sometimes those simple questions we don’t have answers for. And I like the evolution of this regret minimization framework. At least in my mind, I’m walking away with, would you rather suffer from the pain of action or the pain of regret? so we’ll end there. This was an awesome conversation, Tony. Thank you so much for joining us. I cannot wait to share this episode with our listeners.

Tony Summerville: Thank you, Ian. Thanks for having me. Enjoyed it.

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big thank you to Tony Summerville for joining us and sharing his fascinating story. What stays with me isn’t the one point five billion dollar valuation. It’s how much of Fleetio was already written in [00:50:00] a Huntsville warehouse with a teen watching his dad go through the books on a Sunday. Tony refused the shortcut everyone else was chasing. No silver bullet investor, no validation borrowed from a term sheet. Just months of conversations before a line of code was written, , a whiteboard at an early customer’s office that told him the problem was real, and the patience to let a good business earn its own capital. And he built it in Birmingham proudly, deliberately proving a billion-dollar company doesn’t need a coastal zip code, just talent and someone willing to bet on a place most VCs would overlook. Underneath that discipline is the humility to admit years later, that the founder who built the thing might not be the one to lead its next phase, and to step back, not because Fleetio needed less of him, but because it needed more of something else. Now, he’s pouring that same belief back into the next generation of Birmingham founders. So take his advice. Start. Decide what you actually [00:51:00] want, and remember that when you build something real, the money will find you. If you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn at outsiderincpod. You can also follow me on X at Ian Hathaway. Outsider Inc. is produced by Spellbinder Media. We’ll be back soon with another fascinating Outsider conversation. Until then, thank you so much for listening, and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features Mitchell Green, co-founder and managing partner of Lead Edge Capital — a growth equity firm managing around nine billion dollars, and one of the more unconventional investors you’ll come across.

His résumé looks the Silicon Valley part: Williams, Wharton, Bessemer, and an LP list that reads like a Fortune 500 reunion. But he grew up middle-class in Grand Rapids, in a family shaped by manufacturing. His father ran a generations-old family business, and at eighteen, Mitchell was working the factory floor. He had three paper routes going by sixth grade. He skied his way into college, dropped out to start a company, failed at it completely, and talked his way back into school.

The seat that changed everything came through an online job listing. He answered it, got a referral from a mentor, and became one of the first two cold-callers Bessemer ever hired. Two years and tens of thousands of calls later, he had an education you can’t get any other way. When the crisis hit in 2008, he bought a set of investments out of a struggling hedge fund and financed it by passing the hat. One of those early backers eventually told him to stop doing one-off deals and raise a real fund. He did, in 2011. Fifty-two million dollars, anchored by an Alibaba bet most people thought was insane. That one deal returned around a billion dollars.

Fifteen years on, the firm stands out in the industry. Eight criteria filter roughly nine thousand companies a year down to five or seven deals. Lead Edge will get into a company any way it can — lead the round, buy LPs out of a twenty-year-old fund, buy a profitable bootstrapped software business outright. Holding it all up is the thing that makes the firm unique: more than eight hundred operators and executives as LPs, who don’t just cut checks but pick up the phone and open doors. The founders Mitchell writes checks to tend to look like he did — persistent, a little underestimated, carrying a chip. Only about ten percent of the portfolio sits in the Bay Area, and more than half the time Lead Edge is the first institutional money in.

In this episode, we get into what the factory floor taught him about work and money, the failed startup that taught him to connect people, the two years on the phone that taught him you learn what a good company looks like by talking to ten thousand bad ones, how the LP base itself turned into the product, and why — after all of it — the scorecard he actually cares about is friends, family, and doing work he loves. ⤵️

Follow: LinkedIn, Instagram, X, TikTok, YouTube

Episode Highlights

In this clip, Mitchell says plainly what he wants in a founder. He’ll tell you he isn’t the smartest guy around (though I disagree!) — he just outworks people, and he’s looking for the same. Persistence. Fast responses. Gratitude. A chip on the shoulder. The stuff that got him in the door is exactly what he screens for now.

Here, Mitchell runs the whole thing back to one lesson from a company that flopped. He cold-emailed alumni who ignored him, emailed again, got told no a lot, and learned that persistence is most of the game. Then the bigger idea: introduce two people who don’t know each other, watch them become friends, and you’ve got two people in your corner for life. Keep doing it and you wake up with a crowd rooting for you. That’s where the eight-hundred-person LP base comes from.

Next, having just lost one of his own mentors, Mitchell talks about legacy. He’s less interested in being remembered for the returns than for being relentless, passionate, and someone who did what he said he’d do. His take on mentoring is simple. He answers nearly every cold email and tells people to ping him again in six weeks. Ninety percent of them vanish. The two or three a quarter who come back get the coffee, and then a standing invitation to keep coming back.

Later, his read on AI, which cuts against the room. The idea that it means fewer jobs strikes him as comical — he hasn’t met a single person using it to work less, and he thinks we’re headed for more work, not less. His frame is the old one: people overestimate what happens in the near term and underestimate the long term. The categories that matter most, he figures, haven’t been built yet.

Finally, in a clip about looking everywhere for talent, he tells the story of Chris Friedland, who, by Mitchell’s description, is the biggest internet toilet salesman on the planet. He built a multi-billion-dollar plumbing distribution business out of Chico, California, which was, to be clear, the middle of nowhere. Persistent people are everywhere. The world is small. You never know what someone’s going to build.

I’m grateful for this one. What sticks with me isn’t the nine billion in AUM or the Alibaba deal. It’s how ordinary the edge turns out to be. Twenty thousand cold calls. A habit of introducing strangers who’d remember him for it years later. Mitchell built one of the most distinctive firms in the industry by outworking the field and treating generosity like a system he could run. And there’s real discipline sitting under all that motion — he knows his strike zone, and he lets the wild pitches go by.

The part I keep returning to had nothing to do with money. A colleague of fifteen years gone to cancer, and a guy who’s wanted to be rich since he was five telling us the real accounting is friends, family, and doing what you love. Because you might wake up one day and find out you’ve got limited time remaining. Everything that built Lead Edge — the persistence, the connecting, the willingness to turn over rocks looking for something good — is available to anybody who wants to work that way. None of it requires the pedigree his résumé happens to carry. His closing advice was three things: don’t give up, listen to feedback, write the handwritten thank-you note. I’ve been on the receiving end of the last one. He means it.

Mitchell’s Playlist

I always ask guests what's been fueling them. Mitchell listens to everything, and the list proves it — Sabrina Carpenter, Genesis, Michael Jackson, Eric Prydz, Kesha, Kygo, Addison Rae, Bon Jovi, Ed Sheeran, the Grateful Dead. Depends entirely on his mood. The one fixed point: right before he gets in a race car, it's AC/DC, "Highway to Hell," which he happily admits is completely absurd.

Up Next: Tony Summerville

Next week’s guest is Tony Summerville, founder and executive chairman of Fleetio — the fleet management platform he built in Birmingham, Alabama, and grew into a company recently valued north of $1.5 billion. Tony’s story runs back well before Fleetio, to summers spent in his father’s electrical supply business in Huntsville, where he learned how a real operating business works from the inside. That’s a feel most software founders never develop. After Auburn and a stint at a regional bank, he landed at one of Birmingham’s early SaaS companies, then quit in 2011 on a one-year deal with his wife Brittany and a hunch that a big, ignored market was waiting for him. What came next was disciplined customer discovery, capital-efficient growth, some hard product calls, and the slow work of learning to let go. He’s since stepped back from running Fleetio day to day, and he’s now backing Birmingham’s next wave through capital, connections, and mentorship. I’m looking forward to sharing it.

Listen on: Spotify, Apple Podcasts, Amazon Music

Host Ian Hathaway interviews Mitchell Green, founder and managing partner of Lead Edge Capital, about building one of growth equity’s most unconventional firms by looking where others do not. Green traces his Grand Rapids upbringing, early paper routes, factory floor experience, ski racing path to Williams, failed college startup, and the lessons in persistence and networking that shaped his career. After starting at Bessemer as one of the firm’s first cold callers, he learned outbound sourcing, pattern recognition, and the value of connecting people by speaking with thousands of companies. He describes buying investments out of a struggling hedge fund after the financial crisis, raising Lead Edge’s first $52 million fund, the Alibaba investment that helped put the firm on the map, and the operator LP network that became one of Lead Edge’s defining advantages. They cover the firm’s eight investment criteria, its focus on profitable and capital-efficient companies, creative deal structures, investing outside Silicon Valley, the founder traits Green looks for, the AI productivity boom, mentorship, legacy, and the personal intensity behind his work.

Show Notes:

(04:40) Grand Rapids Roots And Factory Floor Lessons

(06:49) Failed Startup And The Power Of Networking

(09:33) Bessemer And The Cold Calling Apprenticeship

(11:45) Learning The Strike Zone

(15:22) Turning LPs Into An Operator Network

(18:24) Persistence As The Founder Edge

(20:48) Finding Builders Outside Silicon Valley

(21:46) The Lead Edge Eight

(23:26) Outbound Sourcing At Scale

(24:19) Creative Deal Structures And Risk Discipline

(29:32) AI, Productivity, And The Long Term

(32:57) Legacy, Mentorship, And Follow-Through

(35:15) Beyond The Bio with Mitchell Green

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Mitchell Green - Co-Founder & Managing Partner, Lead Edge Capital

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Mitchell Green: I look for founders that have grit, came from nothing. It’s EQ, it’s sales skills, it’s persistence. That’s the stuff that matters. People that are , hustlers, dogged, are very responsive. People that respond back to emails or texts really quickly. People that are always on. People that show gratitude. Founders who have chips on their shoulder, who wanna prove the world wrong.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Mitchell Green, co-founder and managing partner of Lead Edge Capital, a growth equity firm managing roughly nine billion dollars, and one of the most unconventional investors of his generation. Mitchell’s story doesn’t start in a boardroom. It starts in Grand Rapids, Michigan. A father running a generations-old family manufacturing company, and a kid juggling three paper routes by sixth grade. At [00:01:00] 18, he was working the factory floor of the family business, an experience that gave him a respect for ordinary work and a perspective on how hard most people’s jobs really are. He skied his way into Williams College, dropped out to start a company, failed completely, and begged his way back in. Then he found the seat that changed everything, Bessemer Venture Partners, where he became one of the first two cold callers the firm ever hired. Two years, tens of thousands of voicemails and emails, and one, essential education. When the financial crisis hit in 2008, Mitchell did something almost nobody would. He bought investments out of a struggling hedge fund, passed the hat among William’s trustees, classmates’ parents, and CEOs he’d once cold-called, and started doing deals on his own. One of his early LPs finally told him to raise a real fund. so in 2011, he did. $52 million anchored by a now legendary investment in Alibaba [00:02:00] that most people thought was crazy. 15 years later, Lead Edge looks like nothing else in the industry. A rigid set of eight criteria that filters nine thousand companies a year down to a handful of deals. A willingness to buy into great companies any way possible, leading rounds, buying LPs out of decades-old funds, outright buyouts of profitable, bootstrapped software businesses the coastal venture world ignores. And the engine underneath it all? More than eight hundred operator and executive LPs who don’t just write checks. They open doors. The Founders Mitchell backs look a lot like he once did. Gritty, persistent, underdogs with chips on their shoulders. People who respond to every email, never stop pushing, and want to prove the world wrong. He doesn’t care where they’re building or what pedigree they carry, and today, only about 10% of the portfolio sits in the Bay Area, and more than half the time, Lead Edge is the first institutional money in. Mitchell was underestimated at nearly every turn [00:03:00] and then built a firm whose entire model is finding the companies and the people most others overlook. In this episode, I want to explore what he sees that the rest of the market misses.

Mitchell, welcome to Outsider Inc.

Mitchell Green: Sure. Thanks for having me in

Ian Hathaway: It’s good to see you again. Thanks for being here. The conventional wisdom in venture is that all the best deals come from certain kinds of networks, certain geographies, certain product categories, certain founder pedigrees. You built a nine billion dollar firm almost ignoring that entirely, finding durable companies before they’re obvious, usually outside the valley. One of the core ideas of this show is that some of the most enduring companies get built by people and in places the market overlooks at first. Your own story fits that pattern as much as any guest we’ve had, so I’d like to start with something philosophical. When everyone’s chasing the obvious and the glamorous, [00:04:00] what lets you look at a blind spot and instead see an opportunity?

Mitchell Green: So I was like a nationally ranked ski racer growing up, and I’m not afraid of taking risks and I’ve never been part of the cool crowd or I’ve definitely never been referred to as cool in my life. Definitely not by my children and definitely not in school. And I believe you gotta look under rocks to find diamonds. By the way I should have done some of the obvious things like SpaceX is probably only gonna cost us not investing there at 30 billion, 50 billion, 100 billion, 200 billion, probably cost us only a billion dollars personally. Sometimes you can be very wrong even when the crowd is right.

Ian Hathaway: Okay, let’s rewind all the way. You grew up in Grand Rapids, Michigan. Your father ran a generations-old family manufacturing company, and you were entrepreneurial early. three paper routes by sixth grade, your mother helped out, and at 18, you went to work on the factory floor of the family business. I have to imagine that you [00:05:00] were probably the only kid at Williams who had ever done that kind of thing. That environment you grew up in, real businesses, real margins, the factory floor, what did it teach you about work, about money, about ownership, maybe even before you had a language for that kind of stuff? And then do you still look for that type of thing in founders today?

Mitchell Green: Yeah, I look for founders that have grit, came from nothing. I only got into Williams ‘cause I could ski race down a hill fast. I mean, The valedictorian from my school in my class and me got in, and I’m pretty sure the counselor was more surprised than I was actually. And oh, by the way, the great thing for me is, I’m not that smart. Going forward, it’s EQ, it’s sales skills, it’s persistence. That’s the stuff that matters. So The honest thing, I think what working on the factory floor actually helped me understand the most is that there’s a lot of people that work in [00:06:00] regular jobs across America, whether they’re bank tellers or working on a factory floor, who because of inflation, which is like the silent killer, their lives are worse today than they were in 2000. On a real dollars basis. And I think that really pisses people off. But I think you just realize no matter how hard a day you think you had, try to go do the same thing repetitively over and over for every day, third shift. Like your job’s not that hard. Your life’s not that hard. it just perspective when you think you’re having like a tough day.

Ian Hathaway: I agree with that perspective. I grew up, outside of Dayton, Ohio. Feel like, as I’ve spent most of my adult life on the coast, having that perspective that a lot of people don’t, has forced me to look at companies and founders in a different way as well. Speaking of founders and that Williams era, I know you actually left school to start a company.

Mitchell Green: I did. Totally failed

Ian Hathaway: Yeah, tell us about that. What did that teach you? What lessons from that [00:07:00] failure are still with you today?

Mitchell Green: Oh, yeah. So it’s funny, when I failed, the chair of the economics department who I had co-founded the company with, Ralph Bradford, said to me, he said “ Mitchell, you’re gonna be so successful, you have no idea. And I’m like, “What are you talking about?” He’s like, Don’t worry, I’m telling you you’re gonna be successful. I’ve been a professor for a long time. I’ve watched tons of students. So what did I learn? I learned networking. I reached out to wealthy alumni. I never met these people. I cold emailed them, and then I cold emailed them again, and they didn’t respond. And like most of the time people would respond. A lot of times they’d say no. But life is a game of persistence, and the more persistent you are, the better. I learned if you connect people together, if you connect person A and person B together, two people that don’t know each other, and then they become friends, those two people will help you for the rest of your life. And if you’re constantly doing that, you basically get a whole large group of people that are like on your side rooting for you. That’s probably like the biggest lesson learned. [00:08:00] I started a software company the whole idea was when you show up at Amazon’s website, they know who you are and they can sell products to you in a one-to-one way. And so if my wife shows up at Amazon and I show up at Amazon, we see two different websites, because they know all the purchasing patterns. When you walk into Neiman Marcus or something like that, if you’re somebody that spends a lot of money there, there’s a salesperson with like a black book, that knows everything about you. I know you have that pink shirt. These black pants We have, you should like try it on.” It’s how they get people that spend a bunch of money to spend more money. And if you get your top 10% of customers to spend 10% more, it drives like 40% or more profits. It’s crazy the amount by just targeting your top customers. But if you walk into Home Depot or Lowe’s or Walmart, they have no idea who you are. But actually they should, because they have all the data on you. And so we built a system, that was going to use a wireless device to basically identify you when you walked into brick-and-mortar stores [00:09:00] so they could market to you in like one-to-one ways. Problem with the whole thing is twofold. One, selling to retail is like really freaking hard. They have really low margins. It’s much easier to sell to biotech and pharma companies or tech companies that have 90% gross margins. Two, we were doing this in 2004, so we were doing it with Palm Pilots and Bluetooth. Like the idea now, you could just actually walk in and geo-fence a store. You actually wouldn’t even need any infrastructure inside the store. but clearly that was not happening. Completely failed.

Ian Hathaway: Well, timing’s everything. Sounds like you learned maybe some markets to stay away from. You actually begged to get back into school. It worked out. After a short stint in banking, you found your way to Bessemer through an online posting, helped by a referral from Pete Wilmot, a Williams alum who mentored you and backed your college startup. At Bessemer, you and Brian Nieder were the first two cold callers the firm ever hired. You spent two years there making an insane [00:10:00] amount of cold calls, voicemails, emails, well into the tens of thousands. So my question is, what did those years on the phone teach you that you couldn’t have gotten from a traditional venture apprenticeship?

Mitchell Green: Bessemer Venture Partners, was a early-stage venture fund, and this was like a Shark Tank firm. Every year, 500 entrepreneurs would walk in the door. They’d back 10 of them a year, move on to the next one. The people that ran that firm were good friends with the people who ran Insight and they would say why has Insight just done this deal in Omaha, Nebraska or Kansas City or St. Louis? Why did we not see it? We’re Bessemer. We have all these like world-class returns.” And what they realized is all that Insight was doing was hiring 22 to 24-year-olds, pounding the phones at the time, leaving voicemails and sending emails. And if the company calls you back, literally hang up the phone. It’s a CEO you call every two days for a month, that’s a CEO you wanna talk to. And so all they were doing was replicating what Summit and TA did. So when we joined Bessemer, they put [00:11:00] us in front of a phone. They’re like, “Listen, you’re our guinea pigs. We have this great track record but we’ve never gone outbound.” So we were their outbound sales org. So when I took the job and I told my dad what I was doing, his literal response to me is, You’re one of these idiots?” And he’s like, “You better figure out how to add value or you look like everyone else.” So what I would do is if I was calling the CEO of a company in Columbus, Ohio, and it turned out it was 25 million in revenue, and then I talked to another company that was like 40 million in revenue in Cleveland, I would connect the two of them together. Be like, “Hey, You guys both run software companies or you both run tech companies. You don’t know each other. You probably deal with the same kinda like challenges in running your business. You should know each other.” So I built relationships with tons of people, and nobody you’d ever introduce to people would get like mad at you. They’d always be like, “Oh, thanks so much.” 98% of the time both people would thank you and be like, “Oh, that’d be great.” What we really learned though, is you know what a good company is by talking to 10,000 bad companies. If you do something enough, if you’re a [00:12:00] professional baseball player, Ted Williams could’ve hit a ball an inch off the ground, and maybe it was the longest home run he ever hit. But if he did that all the time, he wouldn’t be in the Major Leagues very long. And he became one of the, best hitters ever because he just knew in the strike zone where to swing, and it was all about probabilities and statistics.

Ian Hathaway: Good lessons. I wrote down all these things: persistence, finding opportunities where others aren’t looking, looking for ways to provide value to people, and building relationships by connecting people. That phone bank education got tested fast because by 2009, the financial world had come apart. You had moved on from Bessemer to a hedge fund, and that February, the founder of Bazaarvoice called offering you a chance to invest. You scraped together, I don’t know, eight or 10 million from a few dozen people, Williams trustees, CEOs you had cold called, [00:13:00] classmates with wealthy parents. Later, Jim Schneider, Dell’s former CFO and one of those early LPs, told you to stop doing one-off deals and to raise a real fund. So in two thousand ten and eleven, you went out and did that. You raised 52 million, anchored by an Alibaba investment. That deal ended up returning about a billion dollars and put you on the map Talk to me about that time period and the sequence of events.

Mitchell Green: Which by the way, a lot of people then didn’t want to invest in ‘cause they’re like, “it’s China.” it’s gonna be worthless. And so, like who I owe my career to is one, Jeremy Levine for hiring me at Bessemer Venture Partners, gave me the tools and skillset to be able to be a good investor. Two , Scott Booth hired me at the hedge fund seeded by Julian Robertson called Eastern Advisors. He hired me, he saw something in me. A bunch of people had said no, and he hired and gave me the rope and freedom to go do something, and I made a couple private [00:14:00] investments for him. The hedge fund then didn’t do well in ‘08. I bought the investments out of the hedge fund. Most people would’ve just like left, and I was like, “No, no, I’m, I wanna buy these things out.” And I raised the money by literally raising chunks from, like 25 grand from friends to like, 500 grand or a million bucks. And I raised 10 million bucks to start, probably from 100 people, 50 people. Then Bazaarvoice worked. So I owe Brett Hurt, the founder of Bazaarvoice and CEO, built a huge business, took it public. We made great return. And by the way, I started helping the company a bunch. Like, I was making those intros for him, and I had known Brett through cold calling him at Bessemer. That’s where I first met him. It was not a Bessemer company. I just got to know him and made a bunch of intros for him. And so we stayed in touch. He happened to go to Wharton, when he was at campus, one day he like reached out to me and, ‘ I told him I was leaving Bessemer, and so we got together. and I said, “Look, I’m working for this fund.” Any chance we could put a little bit of money in? We don’t need to own 25% of your business.” And we put a little bit of money in at the hedge fund, and then the hedge fund had a bad year, and so we had to get liquidity at the hedge fund. I bought it out, and then I started [00:15:00] helping him a bunch. I’d be like, “Hey, I’m gonna ask our LPs you say you want an intro to Procter & Gamble, well let’s ask the 100 people who are invested with us if anybody anybody at Procter & Gamble.”

Ian Hathaway: Sounds like early shades of what has become your most distinctive asset, an LP base of executives who don’t just write checks, but who actually do work. Was that the first time that you kind of thought of this as like, “Hey, these are capital allocators,” but really that you could build an entire firm with this infrastructure of network? Walk me through that arc from passing the hat for capital to deciding that the LP base itself was the product

Mitchell Green: In April of 2008, I’m working for the hedge fund while I’m in business school. The founder of the hedge fund, Scott’s like, “Hey, Mitchell, we’re going to, like, the Vegas Goldman Internet Summit.” I’m like, “What’s that?” He’s like, “Oh, we’re gonna go meet a bunch of, like, public company CEOs and CFOs.” And In one of the meetings I was sitting with like, the CFO of Expedia or Orbitz, I can’t even remember, and at the end of that I went up to the CFO and he’s like, “Yeah, there’s this company you should, like, meet.” I said, “I’m not an [00:16:00] investor, but why you should meet this company.” I remember they did tons of stuff in the travel space, and it was Bazaarvoice. I think probably a week before I’d just seen Brett or something. And I connected them . And I was like, “Wait a second, I could probably use the hedge fund network, the public equities network, to go meet CFOs and make, like, introductions to private companies.” So I pitched that to like, the founder of the hedge fund, and he was like, “Oh, what company do you wanna do it to first?” I’m like, “Well, this company I’ve known forever.” He’s like, “Sure, I’ve done some private stuff.” He had first invested in Alibaba in 2004. So we put some money in from the hedge fund into Bazaarvoice, and I just started helping them a bunch. And then when the hedge fund went south in ‘08, I bought the hedge fund out But then I’m like, “Well, if ABC person’s invested in this company through me in my vehicle, they’re really invested in Bazaarvoice ‘cause it’s the only thing in the vehicle. So I don’t know, like, why don’t I just ask them for help? Hey, Hey, XYZ investors, Bazaarvoice is looking for a CFO. Do you know anybody?’” And so just asked. And I kept asking again. And then after doing a couple SPVs, Jim, the former CFO of Dell, he calls me, he’s like, “Dude, I’ve been [00:17:00] in tons of funds. Nobody ever asks for help the way you do.” And then I’d, like, self-report back on it. I’d be like, “Oh, hey, thanks so much XYZ person for the intro to GE or Procter & Gamble or the NFL Network. We really appreciate it.” And then a month later, they’d signed up as a customer. So it like reinforced it. It was like almost like game theory. And then after doing that second SPV, Jim was like, “Mitchell, like stop screwing around. You should raise a fund. What you’re doing is truly different.” So we raised our first fund, and I called a guy I used to work with, I actually didn’t know him when I was at Bessemer, but when he joined Bessemer, he pinged me and he’s like, “Dude, I just joined. I heard you’re like a machine as an analyst cold calling.” So we got together and I asked him like, “Hey, do you know anybody that would wanna come work with me and start a fund?” Nimay was at Insight and had been there for a couple years and joined. And I was like, Hey, if you’re any good you’ll be a partner at the end of fund one.” So, I owe my career to Scott from the hedge fund, Brett from Bazaarvoice, and Nimay, my first partner. And then in the middle of fund one, I finally convinced my partner Brian, who had been at Bessemer with me. And the three of us have run the IC ever since. [00:18:00] And God bless 15 years of low interest rates and a bull market.

Ian Hathaway: Obviously there’s been key influential people in your life along the way, but really it’s about just out-hustling people. Maybe you’ve been underestimated at times, right? The factory kid at Williams, the bottom bucket analyst, the cold caller, the guy raising a fund that nobody asked for in the rubble of the great financial crisis. A lot of what this podcast is about is founders who built great companies they were overlooked for a variety of reasons. They were building in the wrong city, they were building in the wrong product category, they didn’t have the right networks. But you went out and succeeded anyway through sheer persistence and ingenuity. So is that your biggest advantage? And then secondly, is that something that you specifically look for in founders that other people might walk right past?

Mitchell Green: 100%. Probably the most important thing is persistence that like anybody could take to anything. [00:19:00] There’s lots of smart people in the world. I’m frankly not that smart, but I’ll outwork anybody. And so like what we look for in founders are like people that are persistent, hustlers, dogged, are very responsive. People that respond back to emails or texts really quickly. People that are like always on. People that like show gratitude. We also look for that in employees too. Like people that were college athletes are amazing analysts because, you know, don’t tell me that getting a C or a D on a test is your biggest failure in life. Like, give me a break. Dropping the ball at the Rose Bowl, that’s like a pretty big deal. Missing the Olympics because you got sick the day before, that’s like real adversity. And if you could get good grades, be a world-class athlete in college, those are the type of people we want. Or be an entrepreneur be a world-class musician or whatever, something. Like, just do a couple things and do them really well. But I think we are looking for founders who have chips on their shoulder, who wanna prove the world wrong. My [00:20:00] partner Brian used to call up Travis Kalanick at his old company and like said no to him. him. He’s like, “Travis called me back 10 times trying to convince me to invest over like a six-month or 12-month period after that.” And the other guy was Evan Williams, I think at Odeo, which became, Twitter. He’s like, I had called them, We passed on it, and they refuse to let me say no.” Both of those guys are multi-billionaires. So there is something to this persistence, just never giving up

Ian Hathaway: Well, it’s funny that you point to two Silicon Valley companies because your firm is not really a Silicon Valley firm. Just around 10% or so of your portfolio is based in the Valley, which is pretty low considering that you invest in software. Is that by design or is it something else?

Mitchell Green: We’ll look everywhere. We don’t care. Look, there’s persistent people everywhere. I first met Chris Friedland, biggest internet toilet salesman on the planet. He built a business called Build Improvement Direct, which became [00:21:00] build.com, which was like an online plumbing distribution business, it was in Chico, California, and Chico was in the middle of nowhere, to be clear. He sold it to Ferguson, which is owned by Wolseley, the big plumbing distribution business, and they built it into a multi-billion dollar business. He stayed there for a very long time. LP of mine since my first SPV, and I reached out to him because of a cold call. The world is small. You never know what people will build.

Ian Hathaway: Well, so you talked about what you look for in founders. You hinted at it earlier, you have this eight criteria that is really a filtering mechanism for the types of companies you’ll even take a look at. And then there’s shift that did occur somewhere along the way where you had some successful early stage investments, but primarily it’s now only later stage growth equity and even buyout. Talk to me a little bit about the LeadEdge eight and how the firm has evolved in its investment style over time.

Mitchell Green: So we’ve always had the criteria. [00:22:00] Are you 10 million-plus in revenue? Are you growing 25% a year top-line revenue growth? Do you have 70% gross margins or higher? Are you profitable at the GAAP net income or EBITDA line? Are you recurring revenue? Do you have 90-plus percent gross dollar retention? Do you have any customer over 10% of sales? And are you capital efficient, are your revenues today greater than historical cash burn? And we’re looking for like a one-to-one ratio or better. So are you, 10 million in revenue? Have you burned less than 10 million historically to get there? We’re looking for this like one-to-one ratio. Now, again, we-- if it’s 20 million in revenue, you’ve burned 3 million to get there, we can argue the market size is too small. We can argue that, you’re overpaying. But we can’t argue you got like a bad business. You’re doing something right, you only spent 3 million to get there, and you’re doing 20 million in revenue, and if you have 80% gross margins, like you spent 3 to have 16 in gross profit, pretty good business. And by the way, I think like seven of the eight criteria were the same criteria we had when we launched the fund. We added capital efficiency I think back in like ‘15 or ‘16. It used to be you have to be [00:23:00] 70% growth. But we said, “Look, let’s do 25% growth,” ‘cause we balance out profitability as well. Fast-forward today, we have almost 18 22 to 24-year-olds that cold call companies, on behalf of Lead Edge. And so our team speaks to about 9,000 companies a year. If I said you had to meet all eight criteria, it’d be 1% or 90 companies. To do five to seven deals a year, that’s too small of a pond to fish in. So we say you must meet five. Just pick five, don’t care. That’s about a 10% yield. 9,000 companies get to 900, do diligence on 150 to 175 of them to do five to seven deals a year. And Yeah, I would love it to be higher than 150 to 175, but again, they’re not calling us, we’re calling them or emailing them. And so we take this very flexible approach which is, “Listen, we’re calling the companies. Let’s identify the company, and if the opportunity is to lead a round, or to do the first round since it’s never raised money before, ‘cause it’s [00:24:00] bootstrapped.” who cares if we own 18% of a company or 76% of a company? Probably two-thirds of our deals are minority, a third is control. We’ve never actually put parameters around what those could be. It’s all a random walk. But maybe that’s not the opportunity. We’ll buy LPs out of 20-year-old funds. If you own a fund that owns 30% of a company and I buy out half your LPs out of a 14-year-old fund I just bought 15% of the company. It’s the same thing, it’s just a derivative. We’ve always done these sorts of deals, like funding co-investments, buying out LPs out of old funds, funding continuation vehicles. We were doing this before they were even called CVs. And so it’s all about being creative. Some people describe us as hustlers. I just believe The number of great companies in the world that we want to invest in is not infinite, and you need to be super creative in how to get it. And look, we’re trying to make two to five times our money in three to seven years, and not lose money. I’m not saying there’s anything wrong with the venture power law business, but this is not what we’re in. We’re not trying to make 50Xs, [00:25:00] because if you’re trying to make 50Xs, you’re going to have a bunch of zeros along it. Which is fine, it’s just a completely different way to invest. We’ve had massive misses because we didn’t go beneath the criteria. We’ve also saved ourself a crazy amount of money by not swinging at wild pitches. SpaceX, when we looked at it, met two criteria. Now again, it will cost us billions of dollars of gains, probably tens of billions of dollars of gains. And there’s lots of examples like that. But I could also give you 300 other companies that we didn’t invest in because of having this very, rigid framework. In fund one, we led an investment in Refinery29. It was 7 million of revenue, and we wrote like a $3 million check and bought like 10% of the company or something like that, Today, we would just buy the entire business if it was that small a company, ‘cause, you know, we run a three and a half billion dollar fund, make 20 to 30 investments in it. We just invested in a business , that’ll do 750 million of revenues this year, up from 500, and that business , we wrote a $200 [00:26:00] million check at like a five and a half billion dollar valuation. So we own like 4% of the company or something like that, right? Had we done it originally in fund one with $50 million, we would’ve written a $3 million check and owned 0.0001% of the company. What’s happened is, in fund one we had like 10 investments roughly. Fund six we had 20 investments. So we’ve doubled the number of companies, and I think average ownership’s gone from like 3.5% to 35% or something like that. There you go. That’s how you go from 50 million to two billion.

Ian Hathaway: So the check size, maybe stage evolution, also the type of company has changed. I read somewhere that, you know, around two-thirds of your companies, you’re the first institutional money in

Mitchell Green: I think it’s like 55% Now we’re the first, institutional money. It wasn’t that much different in fund one. it was like a third. By the way, these special sits that we do, like buying LPs out of old funds, I mean, our biggest investment in fund one was buying LPs out of a hedge fund side pocket to get access to Alibaba. Fund four, we bought LPs out of an old fund to get access to Zoom. Unfortunately, we [00:27:00] are pretty stupid ‘cause we sold it before COVID. We made something like three times, our money but we could’ve made 20 times our money. Oops. But it’s always been let’s just find the best companies with the best risk-adjusted rewards and then like, wrap the investment around the company.

Ian Hathaway: You’ve written quarterly letters for 15 plus years, and one of them put forward a framework, the hierarchy of bullshit. It’s this idea that when a founder can’t lead with the strongest proof, they slide down towards softer, more flattering metrics that are less meaningful. You’ve said that thinking came straight out of cold calling thousands of companies and watching the different patterns. What are the tells that still reliably indicate that someone’s dressing up weakness as momentum? And more importantly, has the spin gotten worse in this hot era of AI that we’re currently operating in?

Mitchell Green: We are somewhere in a bubble, whether we are in ‘97 or 2000, I have no clue. But there is a lot of capital [00:28:00] chasing things, and AI is gonna revolutionize the world in ways we can’t even think about. But just remember, in ‘99 and 2000, the word social media would never have been uttered had I been on here with you. It is today a $4 trillion market. Back then, we would’ve debated was eToys and Pets.com and Boo.com and Amazon gonna put out of business Walmart, Home Depot, Lowe’s, Sears, Target, Montgomery Ward, Kmart. What actually happened? A couple of the new guys became gigantic. Most of the new guys failed in gen one. Then the over-levered incumbents busted ‘cause they couldn’t innovate, ‘cause if you’ve got too much debt, you’re dead. And in any period of rapid technological change, if you can’t innovate, your competitors are gonna crush you or new companies are gonna come along. A lot of the incumbents will do just fine. But again, the ones that are over-levered will be in trouble. And so, we are definitely in a bubble time. I think Anthropic is an incredible business. It’s an incredible product. But when I hear that people use open source at one tenth the price [00:29:00] to run inference that scares me. And if I look at how fast Anthropic came onto the scene, could there be something else come along? Could the greatest money printing machine on earth, Google, flex their muscles? The winners today, I think people are just assuming that they will be the winners in five years or 10 years, and it could be very, very different.

Ian Hathaway: Best guess today, how do you think this plays out?

Mitchell Green: It’s gonna revolutionize the world in ways that we can’t even think about. It’s gonna be the world’s greatest productivity boom. I mean, the idea that there’s gonna be less jobs is absolutely comical. I, I’ve yet to meet one person who’s using AI to work less. I think we’re actually gonna be working more. And there’s gonna be incredible businesses that are built that are just now starting or haven’t even started yet.

Ian Hathaway: I think it’s like all those technological revolutions, right?

Mitchell Green: Yeah, you always, you overestimate the near term and you underestimate the long term. One hundred percent. But I think it’s Gonna be an amazing time. You’re already seeing it, like new business creation has gotten faster. But I think people Are gonna create new whole [00:30:00] categories that we’re not even like thinking about right now. I’m not a healthcare investor, but what’s gonna happen in biotech and pharma? it is possible that you get cures to things like Alzheimer’s and cancer and things like that because of advances in technology. I mean, I don’t think the biggest advances in AI are gonna come from call center software. We are literally scratching the surface. You just need to come in like eyes wide open.

Ian Hathaway: I wanna shift gears a little bit to the personal. You’ve built a great life in Santa Barbara with your wife Lisa and your family. You race cars. You’re involved with lots of interesting things and people. But you also travel constantly, you sleep four or five hours a night, and you work all the time. You said that even after everything Lead Edge has become, the score still matters, right? You still wanna win, that that competitiveness has always been inside of you. It’s always been a part of you. I know that you love your work, but what is the cost of maintaining that constant level of [00:31:00] intensity?

Mitchell Green: I don’t see my kids as much as I probably should. But I do see my kids probably a lot more than some other people do in the same positions as me. People would be Like “Oh, you’re on vacation in Italy.” And my wife would be like, “No, no, we’re in Italy. That doesn’t mean he’s on vacation, cause my husband doesn’t know how to take vacation. He schedules calls 12 hours a day. He could be on the racetrack and get out of a race car and 20 minutes later be on a conference call, and get back in a race car and an hour later after a race be on a conference call again.” But I like what I do. I wanted to make a lot of money. I’ve had that goal since I was five years old. I didn’t wanna change the world, I didn’t wanna become president, I just wanted to make a ton of money and have fun doing it. So the most important thing is if you wanna make a ton of money, realize you can do it doing anything. So just pick something and do something that you’re extremely passionate about. ‘ Cause life Is too short. I just had our controller of 15 years at 61 years old with an 11-year-old dropped dead of cancer. [00:32:00] He had it for three years. Like it sucks. He had colon cancer that progressed to liver cancer. What did he do? Like most stubborn men including myself, he probably had symptoms for two and a half years, and they found it was stage four cancer, but he lived for three years after. So guess what? Go to Prenovo, get scanned. Especially if you have the money to do it. Go get a physical every year. But like live life to the fullest, ‘cause you might wake up and find out you have two years to live. I truly believe cherish your friendships, cherish your family, and just do what you love doing, ‘cause I know so many people that work most of their careers and like hate they Go start a company. It’s never too late. Go start a business, become an entrepreneur. Do something you like.

Ian Hathaway: I wanna end on legacy and mentorship. Pete Wilmot backed your college company when it was nothing, and then vouched for you to get that Bessemer seat after it failed. And Lead Edge has basically institutionalized that access and capital and [00:33:00] experience for founders who’d otherwise be overlooked by traditional VC. Jeremy Levine took a bet on you maybe when others wouldn’t have. Scott Booth as well. So did your partners Nimay and Brian. So when you think about legacy, how much of it for you is the returns, the companies, and the success, and how much of it is becoming for someone else what your mentors were for you?

Mitchell Green: It’s a great question And I just had Jerry pass away, so I’ve like thought about this stuff a lot more than I normally would. I wanna be known as like, oh my God, was he a pain in the ass. . oh my God, was he like relentless Did he . like never give up and drive me insane? But like, oh my God, did he care. And was somebody that would’ve done anything for his friends or his family and my God, was he passionate. And truly worked harder than anybody. That’s what I wanna be known for. Somebody who did what they said they were gonna do. so the way I mentor people is People email me, and they’ll be [00:34:00] like, “Hey, I’m starting a fund. I saw you on Invest Like The Best. I saw you on your podcast. I saw you on CNBC.” And I will respond to pretty much every email that I get. Sometimes I’ll do like a 15-minute call with people, but if not, if I’m like, “Look, I’m just super busy the next month,” me in six weeks.” by the way, that gets rid of 90% of the people ‘cause they don’t ping me in six weeks. But if they do ping me in six weeks, I’ll be like, “ Okay, great. let’s set up like a 15-minute call. I spend summers on the East Coast, like ping me if you’re in New York or Long Island.” Or, “ come and see me in September in Santa Barbara. I’d be delighted to have coffee with you for half an hour.” And then if that goes well, I’ll say to the person, “Look, i- in six months, if you wanna come back and have coffee with me again, breakfast, have at it.” I can count the number of people that wanna come and have coffee with quarterly is two to three. They all could’ve done it. Very few people do. By the way, the same thing happens to me. There are a handful of people that I have as mentors that have built huge investment organizations that I regularly still talk to.

Ian Hathaway: That’s a great place to end, Mitchell, but before we go, [00:35:00] we like to finish with a little segment we call Beyond the Bio. These are just some quick-hit questions that let us step away from the resume and dig into what makes you you. So, what’s A quick piece of advice from a mentor that stuck with you throughout your journey?

Mitchell Green: Hire people way smarter than you.

Ian Hathaway: Who’s an unsung hero in your life, and what has been the impact they’ve had on you?

Mitchell Green: Oh, my wife. For sure my wife or my dad. My wife just to, like, keep me very grounded, and to realize my life is a gigantic vacation. Compared to my wife. She’s like, “I’m sorry, do you wanna be home with four children all the time? when’s the last time the hotel in New York screamed at you what was for breakfast?”

Ian Hathaway: Oh, that’s excellent.

Mitchell Green: When I hear People say like, “Oh, my wife doesn’t work,” I’m like, “No, your wife works harder than you do. Moms are the most underappreciated people on planet Earth

Ian Hathaway: Yeah. 100%. well you’ve talked a little bit about racing, skiing. Tell us something else maybe people don’t know about you. Something outside of work, like a hobby, travel spot, guilty pleasure, or maybe even a hidden talent

Mitchell Green: Okay, I’ll tell you something. [00:36:00] If you take me to a bar I’m very shy actually. People will be like, “That’s impossible. That guy’s not shy.” If you took me to a bar and said like, “Go up and talk to somebody,” I wouldn’t do it. and It’s the same as I was at 21 and the same as I was at 15. If I go to a conference, in a room with 100 people, I will go sit in the corner. I’m amazing one-on-one or like two-on-one, like small group. But I still to this day cannot walk up to somebody in real life and start... It’s very hard thing for me to do

Ian Hathaway: What are one or two songs you’d like to add to our Spotify founders playlist? Something you listen to at work, something that kinda motivates you.

Mitchell Green: So I listen to very eclectic music. My playlist includes sabrina Carpenter, Genesis, Michael Jackson, Eric Prydz, Cascadia, Kesha, Kygo Addison Rae, Bon Jovi, Ed Sheeran, Sam Feldt, Grateful Dead. I listen to everything. Depends [00:37:00] the kind of mood . So if I’m about to get into a race car, I love listening to like AC/DC, Highway to Hell”. It’s like totally absurd,

Ian Hathaway: All right, one last question. If You could give one piece of advice to someone who’s about to out on their founder’s journey today, what would it be?

Mitchell Green: Don’t give up. listen to feedback, write handwritten thank you notes.

Ian Hathaway: That’s a great way to end. Mitchell, thank you so much for being here. I really enjoyed this conversation. I hope you did too

Mitchell Green: Thanks for having me on. Appreciate it

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big thank you to Mitchell Green for joining us and sharing his incredible insights. What stays with me from this conversation isn’t the nine billion under management or the legendary Alibaba deal. It’s how unglamorous the edge really is. Twenty thousand voicemails connecting two strangers who’d thank you for the rest of their lives. Mitchell built one of the most distinctive firms in the industry, not by being the smartest guy [00:38:00] in the room, as he would say, but by outworking everyone in it and by turning generosity into infrastructure. And underneath the relentlessness is real discipline, knowing your strike zone and having the patience to let the wild pitches go by. But the moment I keep coming back to is quieter. A friend gone too soon, and a man who’s wanted to make money since he was five telling us the real ledger is friendships, family, and doing what you love because life is too short for anything else. So take Mitchell’s advice. Don’t give up, listen to feedback, and write the handwritten thank you note. I can tell you firsthand, he does if you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn at [00:39:00] outsiderincpod. You can also follow me on X at Ian Hathaway. Outsider Inc. is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation. Until then, thank you so much for listening. And remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features Garrett Langley, founder and CEO of Flock Safety — one of the most consequential and closely watched technology companies in America today.

Flock’s mission is as ambitious as it is provocative: to eliminate crime. The company builds public safety technology — license plate recognition cameras, drones, gunshot detection, and real-time intelligence tools — now used by cities, law enforcement agencies, businesses, schools, and neighborhoods in more than six thousand cities across forty-nine states. Recently valued at $8.4 billion, Flock helps clear, by Garrett’s own estimate, more than a million crimes a year.

But Garrett’s story is also distinctly an Atlanta story. He grew up in a city defined by large institutions — Coca-Cola, Home Depot, UPS, Delta — not by venture-backed startups. As a kid, he assumed everyone just went and got a “real job.” He built his first computer repair business before he could drive, with his mom as his first employee, ferrying him to clients’ houses. After Georgia Tech and two exits north of $200 million before he turned 30 (first as an early employee and then as a founder), he found himself with everything he’d aimed for ahead of schedule and no idea what came next. What pulled him out of that quarter-life crisis wasn’t a product or a market — it was the realization that what he loved was choosing the people he worked with. That insight became Flock.

Then, his own neighborhood got hit by a crew breaking into cars. The police were hopeless, and an engineer’s instinct kicked in. He learned what investigators actually needed was a license plate. So he and his co-founders tore apart old Android phones at a dining room table, soldered on a battery and solar panel, and built the first Flock camera by hand.

In this episode, we get into where that builder’s instinct came from, what early success did and didn’t solve, how Flock survived a near-death Series B that most VCs wouldn’t even take a meeting for, and how Garrett leads through the genuine scrutiny that comes with building in one of the most contested categories in tech — safety, privacy, policing, and civil liberties. ⤵️

Follow: LinkedIn, Instagram, X, TikTok, YouTube

Episode Highlights

In this clip, Garrett makes the case that Flock’s work is ultimately about preserving the American dream. He argues that safety is the precondition for everything else — school, jobs, mobility, the belief you can do better than your parents — and that when a society loses safety, economic development is the next thing to go.

Here, Garrett reframes Atlanta’s disadvantages as advantages. Building far from the Bay Area let Flock get big before anyone noticed, pushed the team toward unique problems instead of crowded ones, and forced them to find “diamonds in the rough” — like the sales hires from Kennesaw State who outworked everyone because they never started six feet ahead.

Next, Garrett talks about work/life balance through the metaphor he and his wife use to survive the hard stretches: it’s all just chapters in a long book. Not every chapter is fun or happy or a success, but if you like the bookends and the characters, it’s a good book. He also admits the optimism his employees see in him is borrowed — he steals it from his wife.

Later, Garrett makes his case against cynicism. He believes everyone has a right to be safe, and his answer to critics is simple: he’s doing something. You can disagree with how, but you can’t just complain from the sidelines. Go run for office, go build a company — but go do it.

Finally, Garrett takes on the trust question head-on. He points to the data — 10,000 missing people returned in a single year, license plate recognition upheld as constitutional in 17 court cases — and argues that when he probes critics who say the technology will be abused, it usually comes down to a deeper distrust of the police themselves. His honest conclusion: if you believe the system is out to get you, then Flock is just a tool that system uses, and that’s a problem he can’t fix.

I’m grateful for this conversation with Garrett. What stays with me isn’t the valuation or the crime stats. It’s the operating system underneath all of it. A kid who’d rather invent a job than mow grass. A founder who figured out — after two exits — that the whole point was control over who he spent his hours with. A CEO who treats culture as a document you write down and re-teach every week, not a feeling you hope survives the next hundred hires. A company that almost died at Series B because Atlanta, hardware, and law enforcement were three strikes nobody wanted to swing at, and grew anyway because the results got too good to ignore.

What I took most from this conversation is the relationship between conviction and action. Garrett carries the weight of a category where half a room might think he’s doing real harm — and his response isn’t to retreat into certainty or to apologize his way out of it. It’s to keep building, to welcome the critics who fight inside the system, and to let democratically elected people draw the hard lines he doesn’t think a company should draw for them. If you take one thing from this episode, let it be the simplest version of his philosophy. Just because a problem is complicated doesn’t mean the solution has to be. Outsiders don’t wait for the problem to feel solvable before they start. They pick the hairiest thing in front of them, get smart people in a room, and go.

Garrett’s Library

During the Beyond the Bio segment, I asked Garrett about a book every first-time founder should read. His answer was a surprising one: study ancient Egypt. His reasoning is that it resets your sense of time. We think of the Romans as ancient history, but the Egyptians predated them by thousands of years — and for a founder fixated on hitting numbers every quarter, sitting with a civilization that endured for millennia is a useful corrective on what “generational” actually means. As a way in, he pointed to a biography of Cleopatra, who took control of the most important civilization of her age at thirteen or fourteen.

Cleopatra: A Life, Pulitzer Prize-winning biographer Stacy Schiff’s 2010 account, is the natural starting point Garrett describes. Schiff returns to the classical sources to separate the historical Cleopatra — a shrewd strategist and ingenious negotiator who ruled Egypt for twenty-two years — from the figure that Shakespeare, Shaw, and Elizabeth Taylor handed down to us. It’s a fast, vivid read into a short and fascinating life, and, as Garrett suggests, a doorway into the much longer arc of Egyptian history: what came before Cleopatra, a thousand years before, two thousand before that, all the way back to the first pharaohs.

Garrett’s Playlist

I also ask guests what songs have fueled them on their journey. Garrett named two, and made the case that a good playlist needs range — some music to make you cry, some to make you smile. His pick for the first: "On Hold" by The xx, the band he's seen live more than any other, going back to a South by Southwest show years ago.

His pick for the second: anything by Olivia Rodrigo, owning his weakness for a great pop song that just makes you happy.

Up Next: Mitchell Green

Next week’s guest is Mitchell Green, co-founder and managing partner of Lead Edge Capital — a growth equity firm with around nine billion dollars under management, built on a very different kind of edge. His résumé reads like he came up on Sand Hill Road: Williams, Wharton, Bessemer, an investor list like a Fortune 500 reunion. But, Mitchell grew up middle-class in Grand Rapids, Michigan, in a family shaped by manufacturing — his father ran a multi-generation business where Mitchell worked the factory floor. He broke into venture through about the least glamorous door there is: answering an online job listing at Bessemer, talking his way in as one of the first two cold-callers ever hired, some 20,000 voicemails into a career. Then he built a firm the industry didn’t quite see coming. Anchored early by a now-legendary Alibaba investment, Lead Edge found success backing software businesses the venture world tends to ignore. He did it powered by a network of 800-plus operators rather than a handful of giant institutions, and today only about ten percent of the portfolio sits in the Bay Area. In the episode, we discuss how Mitchell got where he is despite being underestimated at nearly every turn — and then built a business that goes looking for exactly that, the people and places everyone else overlooks.

Listen on: Spotify, Apple Podcasts, Amazon Music

Host Ian Hathaway interviews Garrett Langley, founder and CEO of Flock Safety, about building public safety technology with a mission to eliminate crime. Langley traces his Atlanta upbringing, his early computer repair business, lessons from his father’s relationship-driven sales approach, and his early career successes, including the acquisitions of Firethorn and Experience. After a post-exit identity crisis, he prioritized building with the right team and launched Flock after neighborhood break-ins revealed law enforcement needed actionable license plate data. He describes early traction, Y Combinator struggles, near-pivot moments, media-driven go-to-market, and a difficult fundraise amid skepticism about Atlanta, hardware, and law enforcement. They cover rapid scaling, new products, privacy and regulation debates, immigration-enforcement concerns, Atlanta ecosystem advantages, the Thriving Cities Fund, explicit culture-building, and the personal support system sustaining his leadership.

Show Notes:

(02:28) Burden of Responsibility

(06:47) Atlanta Roots and Early Hustle

(12:19) Two Big Exits and Crisis

(15:35) Flock Origin Story

(20:59) YC Breakthrough and Media

(23:19) Series B Near Miss

(26:23) Scaling Innovation and Vision

(29:45) Fatherhood and What Matters

(30:36) Safety As A Right

(31:31) Scrutiny And Tradeoffs

(38:13 Building In Atlanta

(40:18) Diamonds In The Rough

(42:13) Thriving Cities Fund

(44:50) Writing Culture Down

(51:12) Legacy And Safe Cities

(53:22) Beyond The Bio with Garrett Langley

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Garrett Langley - Founder & CEO, Flock

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Garrett Langley: In an environment where hundreds of thousands of kids don’t feel safe They’re not gonna go to school, they’re not gonna get a job , they’re not gonna start a company, and so I guess it’s that conviction that if we are successful, everyone has a chance to be prosperous, and it doesn’t matter where you were born. If everyone has that equal level of safety, we all have a chance to dream for what we might be able to do.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Garrett Langley, founder and CEO of Flock Safety, one of the most consequential and closely watched technology companies being built in America today

Flock builds public safety technology, including license plate recognition cameras, drones, gunshot detection, and real-time intelligence tools used by cities, law enforcement agencies, businesses, schools, and neighborhoods across the country Its mission is as ambitious as it [00:01:00] is provocative: to eliminate crime.

Garrett’s story is also a distinctly Atlanta story. He grew up in a city known for institutions like Coca-Cola, Home Depot, UPS, and Delta Airlines, not necessarily as a place where venture-backed startups were the obvious path.

But after Georgia Tech and a career that included two significant exits before he was 30, Garrett found himself searching for work that felt like more than another conventional win. With Flock, he found it.

Today, Flock operates in more than six thousand cities across forty-nine states, was recently valued at eight point four billion dollars, and by Garrett’s own estimate, helped solve or clear more than a million crimes per year

It’s a company that has grown far beyond what many investors thought was possible, in a category that sits at the center of some of the hardest questions in technology: safety, privacy , policing, trust, and civil liberties. In this conversation, we’ll talk about how Garrett discovered entrepreneurship, what early [00:02:00] success did and did not solve for him, and how Flock grew from solving local problems into a national public safety platform. We’ll get into the realities of building hardware and software for one of the most scrutinized categories in tech, the weight of the responsibility that comes with that scale, and what it means to build a company of this magnitude from Atlanta.

Garrett, welcome to Outsider Inc

Garrett Langley: thanks for having me. It’s good to see you

Ian Hathaway: Thank you for being here.

It’s, great to see you as well. I’m excited to get into the full story of your journey in a moment, but I’d like to kick things off on a more philosophical note first. Most founders are driven by ambition or a sense of purpose, this thing they wanna build, this problem they wanna solve, and I know that’s true for you too, but you’ve also described running Flock as something different.

You said at times it doesn’t feel like an honor so much as a burden and a responsibility. And when you think about what Flock [00:03:00] has become, technology that communities and law enforcement agencies in thousands of cities now depend on every day, that framing makes a lot of sense. So I wanna start there.

What does it feel like to carry that kind of responsibility rather than simply being driven by it?

Garrett Langley: really good question, and I the thing that I try to focus on, and we talk about internally as well. It is a privilege and a choice. I choose every day to take that burden on and so do my colleagues. We’ve got two thousand or so people at the company, and they could go work at a SaaS company that helps salespeople close more deals.

There’s nothing wrong with that. It’s just the consequences are close to zero for screwing that up. And there are certain people in this world, and I guess I put myself in that bucket, who just... That’s not enough. It’s not enough. I want to have a bigger impact on people’s lives. I want to have a bigger impact on my kids’ lives, on my [00:04:00] community, and I think some people, when they have that calling, they choose to run for office, And you look at some of the most successful political figures in our history, and they weren’t career-long politicians. They were people that had this burning desire to do more than maybe you and I have wanted to do in terms of impact and influence. I just happen to have it agree with electrical engineering.

Technology is my avenue to that impact. But I think to your point there are plenty of days when you go, “Man, is this worth it?” To have this many people not like what you do for a living. And I spend a lot of time with elected officials, and they deal with the same consequences. Think about like, being a governor or being a mayor of a small, medium, large city, and that’s not a long-term livelihood.

So you’re doing it most likely because you actually want to help people. And if you think about the most successful mayor in [00:05:00] America today is Mayor Lurie. He had the highest approval rating. He’s in the low seventies. That means if he went and met four people, one of them still thinks he’s garbage.

And if you think about the average mayor is in the fifties, best case, forties. That means if you walk into a room and half the room thinks you’re doing a horrible job. That’s crazy, right? When you were a founder, imagine if half of your company thought you were a horrible CEO.

How would you be motivated to go to work? The only way you could be motivated is if you actually believe what you’re doing is good for the world.

Ian Hathaway: Yeah.

Garrett Langley: That’s how I feel about it, at the bottom of my gut, of my heart, I believe that everyone has a right to be safe, and I don’t think it should be a privilege.

I think everyone should have the same level of safety in America, and a lot of people disagree with, how I’m doing it, and my big pushback is I’m doing something, though.” I welcome other people to do other things, but you can’t just complain on the sidelines. gotta go do it.

Go run for office, go build a company, too. it’s a consequential topic because it impacts [00:06:00] millions of people every single day

Ian Hathaway: I appreciate you sharing that perspective. Obviously, if you’re gonna do something impactful in this world, you’re gonna ruffle some feathers. right? It’s interesting you brought up politicians including governors. Actually, the last guest on the show was Governor Jared Polis from Colorado.

Although he was a very successful entrepreneur before the age of 30 , as you were as well he had this through line of public service, studied politics in undergrad and had been on school boards and actually founded a couple charter schools in Colorado before he ran for office.

The through line for you, I see, is this larger sense of responsibility. This mission to improve the world. I think we’re gonna see that as we navigate your journey in this episode. But before we do that, I’d like to go back to the beginning. You grew up in Atlanta Westminster Schools, then Georgia Tech.

The Atlanta you grew up in wasn’t exactly the startup hub that it is today. It was [00:07:00] Coca-Cola, Home Depot, UPS, legacy institutions. You said before that you had no idea people even started companies, that when you were young, you assumed that everyone went to work for someone else, and yet somewhere along the way, you figured it out.

Something sparked. You were just a kid when you started your first computer repair business, and your mom really became your first employee, driving you around to clients’ houses because you weren’t old enough to get there yourself. So before you knew what startups were, where do you think that instinct came from?

That instinct to solve a problem, sell the solution, and turn it into something that people would pay for

Garrett Langley: To your point, right? You look at Atlanta even today, the last IPO of true materiality, which like led to more companies getting started, was ISS in 1999.

The last IPO for Atlanta. Now, there’s been other technology companies that have gone public but not that led to other [00:08:00] ecosystems where you develop this mafia or this new group of entrepreneurs, this new cohort of investors,

so like Atlanta, we still have a long ways to go. But I do think to your point, if you go to a T-ball game and you survey all the parents what they do, you’re right. They work at Coca-Cola, they work at Home Depot. They would work at SunTrust or Wachovia. Like they, they have normal jobs, right?

That’s what most people do. The concept of an entrepreneur was and still is not a common thing, and my assumption was that everyone just got real jobs. go to high school, you go to college, you get a real job. Both of my parents worked pretty much at the same company their entire professional careers.

And I think for me, like early on my brother and I were expected to either play sports or work in the summer, starting in sixth grade. And so I tried the whole like mow people’s grass thing ‘ cause I wasn’t that into sports. Quickly realized didn’t actually like mowing grass [00:09:00] that much.

I don’t wanna mow grasses. don’t wanna babysit. That wasn’t something that was gonna make sense as a 13-year-old but I loved computers. I really loved computers. And what I noticed is that like when I’d go to my friend’s house, their parents would ask me to help fix their computer. Set up a Wi-Fi network, which, back in, was that guess 1999, 2000, that was like a big deal to get Wi-Fi. And had the spark of well, instead of doing this for free for my friend’s parents, what if I just started charging people?

And so a bit of like I had to create my own job to avoid mowing grasses all summer and was fortunate that I liked people, I liked technology and there was quite a bit of demand

for an at-home type service.

Ian Hathaway: well, So this is like a good lesson here, right? You’re following your nose, but you are a product of your environment. What’s going on around you does affect you. I know your parents, both of them, you mentioned were a part of your foundation that, your mom in that literal sense, and your dad, as I understand it, spent his career in field [00:10:00] sales selling industrial rollers.

I know before you’ve talked about how everything you learned about managing customers, managing employees, managing relationships was through him. So I’m curious what you learned by watching him. Was it how he built trust, how he handled rejection, how he stayed close to customers over time? Or what parts of his approach still show up in the way that you lead today?

Garrett Langley: what makes him really unique is he genuinely cares about people. And if you think about the polar opposite of that what’s the most transactional sales experience you’ve had? Maybe buying a car. They know I’m here to buy a car. I know that they’re here to sell me a car.

There’s no relationship that needs to be built. I’m just gonna try to get the best price, and you’re gonna try to sell me the most things that have higher margin. There’s financing and there’s no even space to have a relationship. And, my dad was selling rollers, right?

Literally to keep the factory running. Yet I think he [00:11:00] genuinely cared for people and viewed sales not as a means to make money, but as a means to meet more people. so when your North Star is not I’m just trying to hit my number this quarter, but what a cool thing.

I get paid to meet interesting new people and talk to them and get to know them. I think people can read that. I’m not as far on that spectrum as I wish I was like him, but when I meet customers, when I meet potential employees, I try to channel that genuine sense of what a cool thing that I get paid to meet people.

for me, That’s probably the most interesting thing of what my dad was able to kind of instill in me is this if you don’t approach the relationship from one of genuine curiosity and genuine interest in their life and their goals and their needs, you just wind up looking like a car salesman, and that I think that motif has existed for a long time for a reason.

Ian Hathaway: That’s a great take. I agree. Obviously building my business that way, but also as hosting this platform. This will be our [00:12:00] 28th episode, and I was reluctant to do this, honestly, but I see this as part of my mission is to tell these founder stories, and I just feel so lucky that I get to meet these people, learn about their lives, and then share those highlights through their own words with our listeners.

So can definitely relate to that. And following opportunity. And so right out of high school, you connect with a group of Georgia Tech alumni who had already taken a company public and were starting another one, a mobile commerce startup called Firethorn. You join as their fifth employee, where you essentially get this masterclass upfront, in how to build a company before you ever tried to build one yourself.

That company gets acquired by Qualcomm for over $200 million. Next, you go on to co-found Experience, a mobile platform that let fans upgrade their seats and access VIP experiences at live events. That gets acquired by Cox Enterprises for over $200 million. You’re still in your 20s. [00:13:00] By any measure, you had made it, right?

But you’ve described that as a sort of quarter-life crisis. You hit goals that you’d set for yourself earlier than you had ever expected, and instead of satisfaction, you felt a little bit lost. Now, we have heard this repeatedly from guests on Outsider Inc., this identity crisis that sets in after an exit where suddenly you’re no longer this founder of the company and you’re not quite sure who you are anymore or what you wanna do.

Tell us a little bit about what that moment felt like for you.

Garrett Langley: So I met Tripp and Derek and Ben when I was 18. And my whole vantage was like, I wanna be these guys, right? I wanna start a company and I wanna sell it. And then you do it.

And there is a, a common saying, but I think it rings true, which is if you are so focused on the end goal and cruise past the experience, you’re gonna be kinda bummed out when you get there. And taking for granted [00:14:00] that experience left me at a point to when we were at the conclusion and we no longer owned the company, right?

We had sold the business. I was a free agent. I have no idea what to do with my life now. Do I wanna go do this again? Is that gonna be fun? Will it be fun to literally do the exact same thing for 10 more years? That feels kinda crazy. And went through this very fascinating life discovery of what it is that actually makes one happy.

And interviewed at big companies like a Home Depot and Coca-Cola. Never thought about being an investor, which is kind of interesting. That never crossed my mind. Knew I wanted to work, put my hands on something. And what I wound up realizing was I don’t like sports, but we built a business in sports.

I could care less about financial services, but we built a company, in fintech. What made those businesses fun was the people.

Genuinely loved spending time with the people that we were building the company with. And that was the eureka light bulb, the whole joy for [00:15:00] me of being an entrepreneur is having control over who I get to work with, who I spend, 100 hours a week with.

And so very quickly realized like, yes, I-- It’s not that I want to go start another company, it’s that I wanna have control over who I spend time with, and the only way to do that professionally is actually to start a company. So I called Paige and Matt and was like, “I don’t care what we build. Very open to lots of ideas, but the three of us should build a company together.”

And obviously hindsight’s 20/20 on this one. It was a good team. It was the right people. But that was this aha for me, was realizing that I cared really deeply about people versus product or market.

Ian Hathaway: That carries us into the Flock origin. Your uncle, who you’ve described as a close mentor, basically said, “Don’t go build another dopey business,” think you said that in your own way. wanna do something with meaning, and I wanna do it with the right people. And I like this idea of building something that you’d be proud of to spend maybe the rest of your life on building.

I know that you [00:16:00] tested a bunch of ideas, and then something maybe sort of random happens. Your neighborhood gets hit by an organized crew breaking into cars. You go to the police, they’re basically hopeless and maybe even apathetic to what had happened. But you’re an engineer, and so instead of just accepting that, you start asking why.

You start asking questions. Eventually, you learn what the police really needed was a license plate, something concrete enough for an investigation to move forward. So you and your co-founders go back to your dining room table, tear apart some old Android phones, solder together a battery and solar panel, and essentially start building the first Flock camera by hand. Take us back there from that search for the next business the night your neighborhood got hit, and the moment that you felt compelled to start building something that could help lots of people

Garrett Langley: I think every entrepreneur has their why. And like I [00:17:00] said, my why was the team. And so Paige and Matt and I knew we were gonna do a business together. we had a bunch of ideas. And, Matt is really passionate about music, and so he wanted to do something in music, and I reminded him that, no one actually makes money in music. And Spotify is like the one out of a million startups.

We should pick a market where people spend money. Paige’s father was a orthopedic surgeon, and so we spent a lot of time looking at medical equipment, med tech built some prototypes.

It’s like we had all of these prototypes being developed, right? We did build a music app. We built this physical therapy device. then, out of all of those, to your point, there was this one idea of what if we could build a camera that actually solved crime? And in my experience at Experience, that’s probably maybe should’ve picked a better name for the company we said, “Oh, we’re gonna go build a company focused on sports.” And it took us probably 12 [00:18:00] months from that to a paying customer. And I would call that not that uncommon of finding product market fit. You gotta go understand your customer. Like, There’s plenty of examples, Figma included, where it’s like it just takes a long time in that kind of journey and customer discovery.

But at Flock, we had this idea. I have the email that I sent to Matt and Paige framed in my office: idea for neighborhood safety. we built that, and we had our first paying customer the same day. From the idea that I sent that email, we cold called, got a paying customer, and then about two months later, we had our first success from a product perspective.

We had our first arrest. And in hindsight I try to tell other entrepreneurs that I meet, as someone who has started three companies now, that is not normal.” It is normally really painful , to go find repeatable revenue. And Gary Tan, who was my first institutional investor he made the joke like, “Man, you have product market fit for the world.”

Everyone wants to be safe And you’ve built a product that actually makes people safer. TAM’s not our problem. Like I know we got a lot of [00:19:00] other problems in this business. I don’t think TAM is the problem. We did not wanna be a hardware company.

We did not wanna be in public. Like we didn’t want any of this. But the idea made so much sense because if you think about it, every existing product related to safety is focused on you as an individual But when your neighbor’s home gets broken into, your sense of safety goes down. Yet every single safety product was for your home, your apartment, your self, when the actual problem was a community problem.

And so I think the secret that we held quite closely was realizing that you needed to move way past the house. You needed to move to the neighborhood. You needed to move to the city. You had to make the impact there. Because in an environment where safety solutions are only built for the individual, safety has been a privilege, not a right. Because if you can afford a gate, you buy it. If you can afford a security guard, you buy it. Those are [00:20:00] privileges. And our whole thesis was if you focus on the community, it becomes an equalizer. Everyone has the same level of safety, and ideally, it’s a very high level. And that gets my blood pumping pretty fast, that is something worth building

Ian Hathaway: Well, I wanna double click on that and especially, something worth building. When we started out, you said privilege and choice. You just referenced privilege. I wanna talk about a choice you made, I heard the stories about that initial customer, DeKalb County detective calls you up, you went on the five o’clock news, like what an amazing way to reach customers

Garrett Langley: people should use local news more often. It’s a really good channel.

Ian Hathaway: free media, right? free advertising. But it’s a difference to go from, “Hey, we helped solve a crime,” and, “Hey, we have, potentially some early customers and a unique way of reaching people.” There’s a big leap between that and deciding to go build a scalable solution around this problem.

So what made you so sure, that this was a leap worth taking?

Garrett Langley: We wound [00:21:00] up doing Y Combinator, and when we got into Y Combinator, we had one paying customer. We did not have a crime solved. So we were at, let’s call it 3,000 of ARR, and I think we had this goal of we wanna get $300,000 of ARR or something. YC does a good job of pushing you to see how hard you can go in 90 days. And nothing was working. The camera didn’t really work that well. It kinda worked, but none of us had built a consumer-grade electronic before.

hadn’t touched a circuit board in more than a decade. Matt had never done firmware, and he was trying to do all this stuff on firmware on the edge, and this is before AI was a thing. This is back when we called it machine learning.

He’d never done that. So the camera wasn’t really working.

Paige and I were outbounding all these neighborhoods and man, was that first customer just a total fluke. The week before demo day, we had gotten to twenty one thousand dollars of ARR. So we had, let’s call it five customers. And I was like, “Maybe we should pivot the company. Maybe we should do [00:22:00] consumer. This isn’t working, guys.” And To your point, that week we solved our first crime We go on the 5 o’clock news and it starts to work. And I’ll never forget, we were debating how are we gonna raise money for this company, because I knew that if we were gonna build a successful company, we were gonna have to raise hundreds of millions of dollars, right?

If you look at every other hardware company before us, you don’t do it on ten million dollars, and like , you’re also not gonna raise $100 in Atlanta. That’s not happening. There isn’t a single investor in Atlanta that’s gonna underwrite spending hundreds of millions of dollars on a single company.

It’s just like that’s not the market that I live in. So no, it wasn’t obvious. We were like days away from just totally pivoting the company. We were gonna be embarrassed going into demo day with such little traction, no real product success. We had very little to show for ourselves and then got very lucky that when we needed it most, we had that success.

We had a very unique go-to-market motion that people didn’t believe was gonna work and scale, and we were like the 5 o’clock [00:23:00] news is on every night in every city in America.” And now, we’re Covered in the media, probably a couple hundred times a day. That is still our dominant channel.

Ian Hathaway: Yeah, for better or worse, right?

Garrett Langley: Exactly. Yeah.

Ian Hathaway: So things weren’t working, then they started working. You caught a break. ARR is climbing. From a few thousand to seven million in recurring revenue in just a short amount of time. Then you’re going out to raise your Series B and face another setback.

Most VCs won’t even take a meeting with you. Too many strikes against you, right? Atlanta, hardware, law enforcement, no thanks. And you’re down to just a few months of runway. Employees who believed in you enough to leave great jobs are counting on you, and only a couple people inside of the company knew how close you were to the edge.

That experience feels quintessentially outsider to me, knowing that you’re building something important while much of the market can’t [00:24:00] see it yet or won’t validate it. So just walk us through how dark it actually got for you during that time period and how Flock survived.

Garrett Langley: It’s funny because we have such selective memories. I’ve deleted that entire chapter out of my normal brain. I only remember the good stuff.

And I’m thankful to have a very supporting wife who reminds me of the bad stuff, because when I have a bad day, she’ll be like was it as bad as that day?” I’m like that’s a good point. No, it wasn’t that bad.” So no, but it was pretty scary, right? I had made a bet the company type decision to enter into the law enforcement market, which, is not a market that VCs have crowded.

The last company to go public in that space was back in 2005. This is now, 2020. No one thought government was a good market. No one thought Atlanta was a good market, hardware was a good market. Our growth was really strong, and that was probably the weirdest part to me is, we had gone from one million to seven million of ARR in a single year.

Nowadays maybe that’s not [00:25:00] fast, but that was really fast at the time. And it’s no one liked the company. It was not fun. Paige and I sat down in our office. We shared an office at the time and just pulled up a spreadsheet and we’re like, “We have to dramatically change burn.

We need to cut staff, we need to stop everything that’s not working, and just like really narrow the focus.” But I do think when companies go through that type of shock, when you do get to the other side, you tend to be a lot stronger. It’s not fun to think about, but I also think this is why who you work with matters so much.

Because man, it was tough, but doing it with someone other than Paige and Matt would’ve been a million times worse. ‘Cause at least I knew the three of us were gonna figure it out. Like worst case, we go back to just three of us in a garage, But we didn’t. It took us probably a year to bounce back.

We cut staff pretty dramatically. But I kept traveling and selling. This guy Bailey kept doing the same. And eventually, like the results got too good for people to ignore. So we were able to [00:26:00] kinda keep growth going despite the setbacks. And eventually, we were able to get our Series C done and start to really go after the market that I knew we could.

So it just kinda took a year off the company’s, where I thought we could’ve been. So in hindsight, it’s not that bad

Ian Hathaway: I think if you have a good team and family and friends of support and you just keep going, You can get to the other side. You did. Obviously, Flock is a dramatically different company today from the one that almost ran out of money. Tens of thousands of cameras across the country serving thousands of cities, a million crimes cleared a year. I know you’re very specific on saying crimes cleared rather than crimes solved. Drones arriving on scene faster than a patrol car ever could, and a new product called Nova that knits together law enforcement records with public data in ways that would have seemed like science fiction not too long ago.

And going along with that, an eight point four billion dollar valuation with what you [00:27:00] described as, a hundred billion of opportunities still to go. So my question is, what does it actually take to keep innovating at that pace while also scaling a company of this size? And maybe what part of the future roadmap excites you the most right now?

Garrett Langley: One of our early employees, who’s One of our first engineers, he had asked me the question not too long ago, “ It must be kind of fun now. Like, we’re like a bigger company. We have more people.

We have more resources. You’ve probably taken like a step back, right?” And I was like, “John I feel like I’m working harder than ever.” every single time we decide to launch a new product, enter a new market, the expectations just go up. The pressure just goes up. Maybe it gets easier at some point, but it seems to me that things actually just get harder and your goals just get bigger.

for me, The thing that’s continued to be the grounding truth is the support network that I’m very privileged to [00:28:00] have between my family, my coworkers, our investors. And I think for me, I got , this conviction that if we’re successful, this is gonna sound way bigger than maybe I should say the American dream will continue. And I know that sounds crazy, but let me provide an alternative version of history. In an environment where hundreds of thousands of kids don’t feel safe They’re not gonna go to school, they’re not gonna get a job, they’re not gonna start a company, they’re not gonna progress their livelihood above their parents.

And that is effectively the beauty of what makes America a great place , to live, is that there’s this core belief that you can do better than your parents. You can live a bigger, fuller life. And if you look at other countries that have failed to maintain that, safety is one of the first things that goes.

Because once you lose safety, you lose that economic development, you lose that thought of mobility, because you’re just worried about freaking being [00:29:00] safe. And that’s a lot more important than whether you have a job or whether the job is better than your parents or worse than your parents or whether you’re providing for your family.

And so I guess it’s that conviction that if we are successful, everyone has a chance to be prosperous, and it doesn’t matter where you were born. Like whether you’re in one part of a city or another, one city or the other, if everyone has that equal level of safety, we all have a chance to dream for what we might be able to do.

So I know that sounds a little bit crazy, but that’s actually the conviction I have, and it’s what allows me to keep going every day. And like we’re 10 years in, and I can see another 10 years ahead of me, and I have a roadmap for the things I wanna go build, and it’s exciting. It’s It’s a really, really fun space to be in.

Ian Hathaway: Don’t think that’s crazy at all. I really appreciate That perspective. There’s something you said in particular about providing your kids a better life. I’m a father of three. I know you are as well. I heard you give an interview recently as a quick sidebar about you love making breakfast for your kids every day and that [00:30:00] sort of thing, and that’s also my job.

I do the morning routine and take my kids to school, and I never miss that. But I grew up pretty modest in rural Ohio kind of place that got leveled by globalization, and I feel like I’m often defining a better life as material means. But you’re saying it in a way that I haven’t really put at the front of my mind, which is maybe giving a better life is keeping people safe.

‘Cause if you can’t be safe, then you have nothing else.

Garrett Langley: your point, I also grew up with very modest means, but I never felt unsafe .

Ian Hathaway: Yeah, same

Garrett Langley: The sad reality is that there are many cities in this country, many kids who grow up, and that’s not their reality.

And I think when I look at a lot of the people who disagree with what I do, they grew up like you and me. Safety was never a concern, and it is still not a concern, and that’s not who I’m building for. We’re building for the communities where safety is a problem, and it’s a real, [00:31:00] acute problem.

And I think about parts of Atlanta where I live, it’s pretty normal that there’s a homicide every single weekend. That’s horrible. That shouldn’t be the case. That should not be normal and okay.

Ian Hathaway: This is almost hard to say that, I feel like we’ve normalized violence in this country to the point where my wife and I, We were living overseas. We came back to the country during COVID, and the number one concern, most people don’t believe me when I say this, the number one thing we talked about moving home was fear of safety for our kids.

Garrett Langley: Yep

Ian Hathaway: I do wanna double-click on something. You said people who don’t agree with you. You’ve had the success, But your growth has come with a lot of scrutiny. ACLU has been vocal.

Some cities have canceled contracts. There’s lawsuits. The use of Flock by immigration enforcement agencies has alarmed some people, and you’ve pushed back hard including in an email that several police chiefs publicly criticized.

But you’ve also acknowledged that this work does raise genuinely hard questions, right? We hinted at it already [00:32:00] in this episode. One example you’ve given in particular is camera placement. If a city has a limited budget, do you put cameras where crime data says they will be most effective, or do you spread them out evenly which is cleaner and more democratic, but maybe less effective?

So how do you lead through this tension? How do you hold the line on your principles when the pressure to maximize effectiveness is constant, the criticism is coming from many directions, and some of it, though not all of it, might be legitimate?

Garrett Langley: The first thing you have to do is you have to bucket the people who disagree with us into two broad buckets, Look at the group like ACLU a ton of respect for them ‘ they challenge us, they push us to be a better company, and they do it in the constructs of the democratic system that has worked for the last couple hundred years.

We spar with them at the legislative level. but what we agree on, though, is that everyone deserves to be [00:33:00] safe and that regulation in this space is actually the most important thing. And now we disagree on some of the nuances of that regulation. For instance, we agree as two different entities that this data should not live forever. It should have a expiration period. We think it should be around 30 days. My customers think it should be a year. ACLU thinks it should be maybe a couple hours or a couple days. But we’re on the same wavelength that this data should exist, and it just has to have an expiration period.

And what we’re gonna do is we’re gonna let the people who were democratically elected to represent their constituents make the final call. It should be somewhere between a couple days and a year. And it is perfectly okay if that’s different by every city, every county, and every state ‘cause that’s actually how our government works in America. So we disagree on some of the nuance, but we agree that people should be safe, and we agree that regulation is good. And so we welcome and support regulation in every single state. I think this year alone, we’ve had nine new bills passed. We like some more than others, but we like all of them more than no regulation.

I like that. The group that I struggle with [00:34:00] is the group that just says Flock should not exist And I’m like, “Okay, what is your alternative solution to the problem? Or do you not agree there’s a problem?” And that part is the part that I just, I have a hard time reconciling because I just don’t think that’s a very American approach.

Last year alone, we helped return over 10,000 missing peoples. It’s adults, seniors, kids. You can’t debate that. I show you the data. So we’re clearly doing something.

And the ACLU’s point is “Let’s do it better.” And I’m like, “Cool, great.” But the group that just vandalizes the camera you’re now breaking the law. That part I don’t have a lot of like energy for relative to , my good colleagues at the ACLU

Ian Hathaway: So then maybe, in a productive way, what would you say that your critics misunderstand the most, and what is it that you would want to say to them here today?

Garrett Langley: This has been tested in court, uneducated critics would say, “Oh, this is a violation of the Constitution.” And you’re welcome to have that as a personal [00:35:00] opinion, but again, we have a judicial system that’s worked for a long time, and in 17 cases alone in the last two years, the implementation of license plate recognition has proved to be fully constitutional. That’s one. I think the second is that there’s this belief that we can’t give law enforcement this powerful technology. They’ll abuse it. And I go, “Man you’re willing to give this person a gun, but you don’t wanna give them a camera that reads a license plate?”

What it gets down to though is just a lack of trust . And so when I’ve like really spent time probing these people, it eventually gets down to let me ask you a question.

Do you believe the police chief of your town serves your best interest?” And they’re like, “No.” I’m like, “Okay. Well then, your, problem’s actually not with me. Your problem is with the system. Your problem is with law enforcement in general, and particularly the police chief and the agency that you are supported by, and I actually can’t fix that.”

If you grew up thinking the police are out to get you, the [00:36:00] current system is out to get you, yeah I’m an extension of that then. I am a tool they will use, but that’s it. the last thing that I would just hit on is, and this is tough, We believe as a company it’s not our job to write laws.

It’s not our job to pick which laws we think are good and bad. And so for me on a personal level, there are plenty of laws in Georgia that I disagree with, But I vote for a governor, I vote for a lieutenant governor, I vote for attorney general to decide what laws are enforced, what laws are written, and what laws are removed.

I don’t think it’s Flock’s job to articulate like, “Oh, we don’t like that one. We like this one.” And so when the topic of immigration enforcement comes up, I’m like, “Guys, the company has no opinion on this.” If the state of Texas wants to enforce immigration, they might use Flock, but they’re gonna go enforce immigration no matter what Flock does.

And that’s the state of Texas’ choice, That’s the city’s choice. And it’s tough, right? It’s really tough for my employees to work at a company where they’re like, “Oh I, I don’t like that law, [00:37:00] but our, technology is used to enforce it.”

But we can’t make that our problem as a company. We need to let the system that’s worked continue working to refine what as a society we deem illegal or legal.

Ian Hathaway: Seems like, people are mistrusting a tool, but really they’re mistrusting the people who are using it, and those are generally elected officials with accountability to public, it’s not about, demonizing a tool, it’s about electing the right people, having a system of accountability where the use of these tools reflect what the public wants.

Garrett Langley: I think what I’ve realized is people have predisposed positions, beliefs about society, about trust, about the government, and they’re just looking for information to validate that hypothesis.

They’re not actually looking for information to inform themselves about what’s reality. And I get it. That’s what the internet has made so easy is to find a group of people that have the same beliefs [00:38:00] as you, and all you hear is the same thing echoing. And it’s hard to figure out what the truth is in that case.

Ian Hathaway: I know it’s tough. I know you’ve been in the news a lot lately, and I appreciate your perspective. Thank you for sharing it with us. I’d like to switch gears if we could. I wanna talk about your hometown.

You’ve been very intentional about not just building in Atlanta, but actively trying to strengthen the founder community there. You’ve talked about the camaraderie that’s developed among the city’s, tech founders, the work to convince talented people at the big institutions that it’s okay to leave those companies and start out on the entrepreneurial path.

You’ve deliberately kept Flock in Atlanta, saying it would be disingenuous for you to build the company somewhere else. numerous guests on this show have described the constraints imposed on building big tech companies in these less mature ecosystems. But perhaps [00:39:00] surprising potentially is that it’s what made these companies better, More resilient, creative, and innovative, that perceived weaknesses are actually the strengths. So I’m curious, has that been true for you? What have been the advantages or disadvantages of building in Atlanta?

Garrett Langley: probably the biggest benefit is how big we could get before anyone knew we existed. we didn’t really have a competitor until we were probably 100 million of ARR. If you’re in a place like the Bay Area or New York, Word’s just gonna get out that th-this company’s ripping, and someone’s gonna be like, could probably do that.”

so I think that’s one. I think the other big advantage is I think if you live in a city like San Francisco or New York, you tend to just like circle around the popular problems.

And I think it’s really hard to find unique problems. And I would say like crime is a pretty unique one.

So you don’t wind up building products for startups. You wind up building products for really big companies. That’s all we have as a customer base here, right? [00:40:00] You’re gonna go figure out what are Home Depot’s and Coke’s and UPS’s problems, Fiserv problems, and NCR problems, not insert our startup.

So I think are the two biggest positives. I think the negatives are, probably quite obvious, being like access to capital, access to talent. But on the flip side, I was having lunch with the founder of Stripe, John Collison. And we were talking about recruiting, and I was like, what are some of the things you’ve learned over the years?”

And he’s Garrett, the biggest mistake we made we really only recruited from Stanford for like the first five years. And we realized there’s some really smart people that didn’t go to Stanford.” And I’m like, “ Huh.” Because in the Valley they talk about this, like you have to find these people before they’re discovered, right?

You have to find these people at the bottom of their intercept with a steep slope. And I guess the positive way to spin that for a place like Atlanta is everyone looks like that? no one has an assumption... Like, early on, we hired a ton of our sales team from Kennesaw State.

And people were like, “Why are you hiring them from Georgia Tech?” And I’m [00:41:00] like, “Have you ever met someone from Kennesaw State? They’re incredibly smart. They’re working their tail off because they went to Kennesaw State, they didn’t start their career six feet ahead.

And they actually have a really good sales program. So we hired a lot of kids from there, 21 years old, right out of college. Knew how to sell. They wanted to sell. They worked their butts off. And I think about our first two sales reps, they were with me for five years at the company.

They would have never gotten a job at a, pick your Silicon Valley thing because they went to just a college that no one would’ve ever heard of in California. But when you’re in Atlanta, You’re like, “Oh, Kennesaw State’s great. SCAD’s great. Georgia State’s great.” that feels like a negative when you’re trying to build a company and recruiting. But then you meet, these special people. Like I think about our first sales leader we hired. Helped us take the company from 5 million of ARR to over 500 million of ARR. You know how rare it is for a sales leader to do that, it never happens.

And you look at this guy’s resume and you go, “That guy’s not gonna do it.” it’s like apparently he could.

I’ll put that in the middle of a little bit of a negative, a little bit of a positive. Because all you have is diamonds in the rough

Ian Hathaway: I agree with [00:42:00] that. it’s proven out over and over. If you actually look at the data, there are a lot more successful tech companies outside of the Bay Area than inside of it. They just don’t have the household brand name associated with it. Sticking with Atlanta, beyond Flock you launched the Thriving Cities Fund.

You’re putting ten million into small Atlanta businesses, all rooted in this belief that jobs are the bedrock of safe communities. Totally agree. For founders, who’ve come up outside the traditional hubs, giving back to the ecosystem that shaped them seems to come pretty naturally. It’s something that people talk a lot about on this show.

It’s a continuing theme. So what are you trying to change about the opportunity structure in Atlanta for founders, for small business owners, and for the next generation of people who might otherwise assume, as you once did, that what you do is you just go get a job instead of starting a company a company?

Garrett Langley: you think about where Flock sits [00:43:00] today , we’re right in the middle of, let’s call it the crime epidemic. And then we’re in the middle of the process, by the time Flock’s involved, a crime has already occurred, which is bad.

That means there is both a criminal and a victim. I don’t believe people are evil. I think ninety-nine point nine percent of criminals are good people that have made bad decisions. We would like to make sure that the case gets cleared, but we would prefer crime never happened in the first place. Our goal is not to just solve every crime.

Our goal is to eliminate it from happening. And so to do that, you have to go to the start and say why does someone choose to be a criminal?” And they choose to do that because they need this way to make money. They believe they will get away with it, and it is a profitable venture. So we focus on those two things and say we need to create jobs then that are more profitable and safer.”

And so when I look at Thriving Cities, it stemmed from one of the programs we have in Atlanta is this program called the AT Promise [00:44:00] Centers. It’s a really good idea. It’s done really good work for the city. And the thing I’d point out is what they provide is exactly what we’re trying to do through Thriving Cities, which is more jobs.

So that when you’re thirteen, you’re 15, you’re 18, and you’re making decisions about your life, there is one standing in front of you that says, “You can go get a good job that pays well, that provides stability.” But if you don’t see that, you believe your only choice is crime. I will steal. I’ll break into cars. And so, yeah, it’s something that’s like really important to us. I’m a capitalist. I think economic development is the engine that drives our society. You can’t do that if you’re not safe. But once you are safe, that’s, I think, how you stay safe.

Ian Hathaway: Totally agree. And I love the action that you’re taking to make a difference across that broader spectrum. I wanna ask one more question about your leadership not just in the ecosystem, but within your company. I know that you’ve been very open about culture, how [00:45:00] you lead the company, detail-oriented, hands-on. I know your co-founder, Paige, worked on cultural norms, with Ben Horowitz, wrote, one of my favorite books of all time on culture, which is What You Do Is Who You Are. talked about that numerous times on the show. Every new hire gets a 90-day plan instead of a job description.

Just a very unique way of setting culture and beginning that experience for new employees. So for founders in our audience who are starting to scale, what have you learned about making culture explicit before the company gets big enough to potentially distort it?

Garrett Langley: When I was having this conversation with Ben, we were probably 100 people, and they had just invested in the business, and we were adding a lot of people, and he had asked me like, “How’s the culture at Flock?” And I was like, “Oh, Ben, it’s really good.”

And he’s like, “Great. Can you send it to me?” I was like, “No, I can’t send it to you. It’s like a feeling. You gotta feel what it’s like to work at Flock.” And he’s like, “That’s actually not [00:46:00] true. It means you have a very weak culture.” And his point was not that it necessarily has to be weak, but that, that means that the nucleus of this energy is you and Paige The bigger you get, the weaker that’s actually gonna be because the employees are four layers from you, five layers from you, more than one, which means it decays really fast. So the absence of a written document means that you as an individual are the only source of culture, and that’s actually not gonna work. And that was, like, tough to hear because I thought I’d built a pretty cool company at the time.

Andreessen Horowitz had just invested, oh my gosh, and Ben’s like, “No, man, your culture sounds not good.” so we wrote it down and took it to heart. And even to this day, every week, Paige and I walk our new employees through those cultural norms and what it means to be at Flock.

And the whole point we make is that our culture is not good or bad. We don’t believe in yelling at Flock. I can think of a lot of really good companies where yelling is quite normal, and that’s okay. We just don’t yell. We have all these things About what we [00:47:00] believe to be true or to be good at Flock, but we remind people, “ This doesn’t have to be for you but this is how we work.

And every single employee sits through the exact same meeting, signs the exact same cultural norms, and agrees that they will continue to be a shepherder of this culture. And that means actually the energy goes throughout the entire organization. And so we have a lot of beliefs that we think work really well for us.

I don’t think they work everywhere. Like if you look at my executive team, three-quarters of them have been with me since we were sub one million ARR.

That’s really rare. I think every VC I’ve ever talked to is like, “You gotta upgrade your exec team every 18 months.” And I just, I haven’t

And I think there’s a lot that we do different, and I think some of it maybe makes us a better company and some of it makes us a worser company.

But the thing that I remind our team is every one of you will probably go on to work at another company. I’m not hireable, so I gotta go make sure we’re building a company that I love.”

And then I gotta hope That there’s enough other people in this world that like the way [00:48:00] that I like to work, that they wanna come work here. And so we’ve kept a pretty tight, focused culture in that regard.

And while I’m very receptive to feedback and we evolve the culture for sure, what it never leaves from is a place that Paige and I are really proud to work at

Ian Hathaway: Speaking of people being around you for a long period of time, you built a pretty intentional support system around the realities of running a high-growth company. A lot of it seems, designed to protect your family life from the stress of that job. I know you’ve said that the biggest risk to success as a CEO isn’t the business, it’s your personal life causing an outsized amount of stress.

Your wife, Megan, has been a constant through all of this. after your experience at Experience you were figuring out what was next , playing a lot of golf, and she encouraged you to go back to building because you’re a builder. On the other hand, she said she also can see when something stressful is going on at work [00:49:00] because you don’t sleep and you’re not a lot of fun to be around.

So on that personal note, what does she see in you that your employees and investors might not get to have a window into? And when you look honestly at what it takes to build a company at the scale of Flock with the critics with the breadth of activity, how have you tried to keep that ambition for the company from taking more from your family than it gives back?

Garrett Langley: I’ll maybe answer the last question first and then go backwards. I think in moments in time, and maybe we’re in one of those right now, the company takes way more than it gives back. Nowhere near a balance. And the way my wife and I try to rationalize that is it’s just chapters in a long book. not every chapter is gonna be fun, not every chapter is gonna be happy, not every chapter is gonna be a success. But as long as you like the bookends and you enjoy the characters, it’s gonna be a really good book. so [00:50:00] we try not to get too bogged down on what one individual chapter feels like.

And there are plenty of chapters, like to your description of the series B, that’s not a chapter that I plan to go reread very often. But she was there with me through it, and she was the one saying y- you will be fine. We will finish this chapter, and you will like the next chapter.” And I think more than anything, she continues to kinda be that eternal optimist that if I work hard enough, if I believe in what I’m doing, the good guys will win in the long run.

So to go to your original question, I think if you were to survey my average employee base, they would probably articulate that they think I have this endless fountain of optimism. And what I think that they would not understand is that actually stems from my wife. She has what feels like an eternal optimism , for me and what I can accomplish, and that’s actually where I’m stealing it from.

‘Cause I go through my highs and lows, but she’s the one who kinda keeps me balanced and [00:51:00] focused

Ian Hathaway: That’s a nice testament. Thankfully, I feel the same about my wife. I know it’s not easy for anyone. And I know you still got a lot of building, a lot of work to do. But I do kinda wanna end asking about legacy, which seems especially important in this case. The company you’re building from home in Atlanta, it’s now valued at over eight billion dollars.

We’ve talked about the impact. We’ve talked about the numbers. But I don’t really get a sense that’s why you’re in it. So when it’s all said and done, when your kids are old enough to really understand what you’ve built and why you’ve built it, what do you hope that Flock will have proven about safety, about Atlanta, and about what’s possible when you build something that actually matters?

Garrett Langley: If we fast-forward some number of years, like five, seven, three on the optimistic side, there will be these cities. [00:52:00] We call them safe cities. And crime will be something talked about like fax machines, where yeah, that, that made sense. That kind of existed.

But no one really talks about it anymore And what I hope they will take away from that is when I’m criticized by some people, they’re like, “Oh you’ve simplified the problem too much. Technology can’t actually fix this problem. Technology isn’t enough. You can’t just solve crime.

That’s not how it works.” And those are people that also have no plan either to fix it, and they argue that the thing is just too big. And what I hope In our success we’re able to show is that just because a problem is complicated doesn’t mean the solution has to be complicated. And you look at some of the things facing this country today, crime being one of them We can devise simple solutions.

It doesn’t have to be complicated. It can use common sense. And I think if that is what my kids learn, maybe other people learn, that you can pick the [00:53:00] hairiest of societal problems, think about it really hard, get a smart group of people together and commit a decade plus of their life to fixing it, and it can work.

And if we can build that level of optimism, I think we can look at all the problems we face as a community and start knocking them off one by one.

Ian Hathaway: That’s a great sentiment. It’s a nice way to end. We’re almost out of time, but before I let you go we like to finish with a little segment we call Beyond the Bio, which is just some quick hit questions to go beyond the resume and just dig into what makes you. Sound okay?

Garrett Langley: Yep

Ian Hathaway: Okay . What’s a quick piece of advice from a mentor that stuck with you throughout your journey?

Garrett Langley: Team first

Ian Hathaway: Who is an unsung hero in your life and what has been the impact they’ve had on you?

Garrett Langley: my brother, he forces me to have fun. Without him I would never have fun.

Ian Hathaway: That’s great. haven’t heard that one before. Who’s someone in the [00:54:00] Atlanta startup community who doesn’t get enough credit and deserves a shout-out from you?

Garrett Langley: Oh, okay. Good guy. Scott Voigt runs a company called FullStory. OG, been around a long time. A dear friend and someone I leaned on really heavily the first few years of Flock

Ian Hathaway: Tell us something most people don’t know about you, something outside of work. Could be a hobby, a favorite travel spot, a guilty pleasure, or maybe even a hidden talent

Garrett Langley: During COVID, I went vegan for a full year. And I can share, I looked the exact same. I felt better. It was a lot more work, a whole lot more work. But I feel quite strongly That our current food system is killing us and we need to rethink the food we put in our bodies.

Ian Hathaway: So you’re still Vegan?

Garrett Langley: no, I went back

because I was like, “This takes too much time.” I went back to all the bad stuff ‘cause it was too much work to be vegan, but I did it for a year.

Ian Hathaway: I feel like it would be too hard for me to give up pizza. That’s my guilty pleasure maybe.

Garrett Langley: Cheese is so good

Ian Hathaway: [00:55:00] yeah. What are one or two songs you’d like to add to our Spotify founders playlist? Something that fuels your workday or has inspired you on your journey as an entrepreneur

Garrett Langley: Oh man, The XX, On Hold. It’s a really good one. I’ve always loved The XX. I saw them for the first time ever at South by Southwest in Austin many, many years ago, and that’s probably the band I’ve seen the most live. And then this is gonna be, i’m a sucker for like a good pop song. I think every single song that Olivia Rodrigo makes is just like great. Some music makes you cry, some music makes you smile. You kinda gotta have both in your playlist

Ian Hathaway: Great. We’re gonna add those. What about a book you’d recommend? Maybe something that has been especially valuable on your journey, or maybe one that you think every first-time founder should read as they’re getting started

Garrett Langley: There’s a handful that are worth reading, but it’s worth studying ancient Egypt, and it’s not intuitive why. One of the things that are actually really fascinating, but what I think is more important [00:56:00] is it gives you a new sense for time. ‘ Cause you think about the ancient Egyptians , they existed for thousands of years before the Romans. And we think of Romans as that’s ancient history , right? That’s 2,000 years ago. The Egyptians were there 5,000 years before them. And so when you’re a founder, right?

You’re like, “Man, I gotta e-every day, I gotta hit my numbers every quarter, every year.” And you think about “Oh, I wanna build this generational company.” America’s not even that old. America’s a couple hundred years old. So you start to understand what were they doing?

Why were they so successful? How could they survive so long as this dominant society?

So I think that’s like a really understudied, underread ancient history, and I’ve read a bunch of books on it and I think it’s a ton of fun.

Ian Hathaway: I hadn’t thought of that perspective. Is there like a specific one that would be the best to kind of dig in on that subject?

Garrett Langley: So there’s a really good biography on Cleopatra as a starting point. it’s a fun read because Cleopatra had a fascinating life in her short span on this earth. [00:57:00] But it does delve into a bit of the history of Egypt, and if you find that book interesting, you’ll naturally jump to what was it like before Cleopatra, a thousand years before, two thousand years before?

What was the first pharaoh like? What was that evolution into pharaohs, into treating them like god-like figures? There’s so much to learn and it spans thousands of years.

Ian Hathaway: It’s amazing. Great one. All right, last question. If you could give one piece of advice to someone who’s about to start their first company, particularly someone who’s maybe a bit of an outsider, what would it be?

Garrett Langley: At the end of the day, you’ll build a company that no one can ignore. And so don’t worry about where you’re based. Don’t worry about the ecosystem. Don’t worry about investors, because eventually you’ll build a company and they will all come to you

Ian Hathaway: I can’t think of a better way to end, Garrett. Thank you so much for sharing your time today, your wisdom. I cannot wait to share this episode with our listeners

Garrett Langley: Awesome. Thanks

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big thank you to Garrett Langley for joining us and sharing his journey and wisdom. What stays [00:58:00] with me most from this conversation isn’t the eight point four billion dollar valuation or the six thousand cities or even the million crimes cleared a year.

It’s the framing. Garrett doesn’t talk about Flock as an honor. He talks about it as a burden he chooses to carry every day alongside two thousand people who could be building something far easier There’s something deeply inspiring in that. He built in Atlanta because leaving would have been disingenuous.

He went into a market that nearly every investor told him was a mistake, hardware, government, law enforcement, and got within weeks of running out of money before the results got too good to ignore . And underneath all of it is a conviction most founders never have to articulate , that safety isn’t a privilege, it’s a right, and without it, the whole American promise of doing better than your parents quietly falls apart For the outsiders listening, don’t worry about where you’re based or who’s writing checks.

Build something [00:59:00] no one can ignore, and eventually they’ll come to you.

If you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn at outsiderincpod. You can also follow me on X at IanHathaway.

Outsider Inc. is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation. Until then, thank you so much for listening, and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. is Part Two of The Outsider Playbook. Part One was about getting in the door: how being underestimated builds hunger, how constraints force discipline, and how the outsider’s toolkit of bootstrapping, hustle, and resilience becomes a competitive advantage. This one picks up after you’ve actually built something. Because once you’ve proven the doubters wrong and scaled against the odds, the challenge doesn’t disappear. It becomes even more difficult.

The guests on this show built from places venture tends to overlook, and they kept building long after the headline exit. Kyle Porter grew SalesLoft into a $2 billion category leader with culture at the center. Dug Song borrowed the rituals that defined Duo Security from a Jewish deli down the street before selling to Cisco for $2.35 billion. Scott Dorsey turned a feeling into a culture called “Orange” that still draws a thousand people to reunions a decade after the $2.5 billion Salesforce exit. Gail Goodman built Constant Contact over 17 years, took it public, sold it for $1.1 billion — and woke up feeling like something had died. Jewel Burks Solomon sold Partpic to Amazon and couldn’t get out of bed. And many more.

Different industries, different decades, different geographies — but the same hard-won lessons keep emerging once the building is done. This episode pulls them into three threads.

The first is culture — not the perks and parties, but the operating system that makes execution possible under pressure. The values people share, the behaviors that get rewarded, the rituals that let culture survive when the founder isn’t in every room. The thing competitors can’t copy because it has to be earned.

The second is the identity crisis most founders never see coming. When you’ve poured everything you are into what you’re building, the company’s wins become your wins and its struggles become your struggles. So what happens at the exit, the transition, the failure — when the thing that proved who you were starts changing form, and you have to answer the question you’ve been avoiding: when it’s no longer my company, who am I?

The third is what you do with success once you have it. Take your winnings and move on, or pay it forward in ways that don’t just help individual founders but actually shift the landscape — the catalytic capital, the studios, the success stories that make the next outsider’s pitch a little easier to believe.

The bigger idea underneath all of it is that the real goal was never just proving the doubters wrong or building one breakout company from an unlikely place. It’s changing the odds for everyone who comes next — until the unlikely place stops seeming so unlikely, and the question shifts from “can you really build that from there?” to “what else are we missing?” ⤵️

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Episode Highlights

Here are some highlights from the show. In this first clip, Kyle Porter, Wade Foster, Shegun Otulana, Dug Song, and Scott Dorsey explain why culture isn’t a perk you earn later — it’s the operating system that makes execution possible under pressure. Whether you reverse-engineer it from who thrives, anchor it in shared values, or borrow rituals like appreciations from a Jewish deli down the street, the work is the same: turning what you believe into something repeatable that survives growth — and, in ExactTarget’s case, outlives the company by more than a decade.

In this next clip, Jewel Burks Solomon, Gail Goodman, Sean O’Sullivan, Jimena Pardo, and Melodie van der Baan get into the identity crisis most founders never see coming. The exit that’s supposed to feel like a victory feels like a death. The failure that feels like a personal verdict. The years of obsession that quietly blend the company into the self until you’re left asking who you are once it’s no longer yours. The throughline: you are neither as good as your best company nor as bad as your worst — you are not a hat, you are a person.

In this next clip, Brad Feld, Dug Song, Jewel Burks Solomon, Hernán Kazah, and Jon Lensing talk about the multiplier — what happens when hard-earned experience becomes infrastructure for the next founder. You put energy into the flywheel without knowing what you’ll get back. You become the friends-and-family money for founders whose families don’t have it. You become the investor you wish you’d had. One founder succeeds, then helps ten more, those ten help a hundred, and eventually what young people aspire to changes — and the unlikely place stops seeming so unlikely.

In this final clip, David Cohen, Gail Goodman, and Jimena Pardo make the case that the real goal was never one breakout company — it was expanding who gets to participate at all. Startup communities are more powerful than any company inside them. Helping an underrepresented entrepreneur go from “I don’t know where to start” to a business that survives. Breaking the capital barrier so the next great company isn’t limited by where its founder was born. It’s ecosystem-building as the endgame, not the afterthought.

I’m grateful for every guest who trusted this show with the harder parts of their story — not the headline exits, but what came after. What sticks with me from pulling Part Two together isn’t the wins. It’s the honesty about the cost. Kyle treating culture as the one thing he could actually control. Dug starting every meeting with appreciations he learned from a deli. Gail writing her “all the things I effed up” memo at the end of a $1.1 billion exit because she felt like something had died. Jewel making a big deposit and not being able to get out of bed. Sean counting the founders he’s known who didn’t survive the failure. Melodie reminding herself she’s a person, not a hat. Different chapters. Same lesson underneath: the thing you build will try to become who you are, and the work is refusing to let it.

What I took most from putting this together is that the Outsider Playbook doesn’t end at success — it evolves. Building something that lasts means building a culture that survives when you leave the room. Surviving that success means holding onto an identity the company can’t take with it. And earning that success means doing something most founders never get to: turning your hardest chapter into someone else’s head start. That’s the part that moved me most. Dug being the friends-and-family money for founders whose families don’t have it. Shegun generating his own gravity in Birmingham. Jewel becoming the investor she wished she’d had. Jon inspiring the next twenty companies out of Iowa. None of it automatic. None of it owed. If you take one thing from this episode, let it be this: the goal was never just to prove the map was wrong. It was to redraw it — so the next founder from the unlikely place gets a little more evidence, a little more permission, and a few more doors already cracked open.

Up Next: Garrett Langley

Next week we’re back to founder conversations, with one of the most consequential and closely watched companies being built in America today. Garrett Langley is the founder and CEO of Flock Safety, which builds public safety technology — license plate recognition cameras, drones, gunshot detection, real-time intelligence — used by cities, police departments, schools, businesses, and neighborhoods across the country. Its mission is as ambitious as it is provocative: to eliminate crime. Garrett’s is a distinctly Atlanta story. He grew up in a city known for Coca-Cola, Home Depot, UPS, and Delta — not as an obvious launchpad for venture-backed startups. But after Georgia Tech and two exits before he turned thirty, he went looking for work that felt like more than another conventional win, and found it. Today Flock operates in more than 6,000 cities across 49 states, was recently valued at $8.4 billion, and by Garrett’s own estimate helps solve or clear over a million crimes a year. It also sits at the center of some of the hardest questions in technology — safety, privacy, policing, trust, and civil liberties. We get into how he discovered entrepreneurship, what early success did and didn’t solve, how Flock grew from a local fix into a national platform, and what it means to carry that kind of responsibility while building it from Atlanta.

Listen on: Spotify, Apple Podcasts, Amazon Music

Host Ian Hathaway continues The Outsider Playbook by pulling the next set of patterns that show up after outsiders have already proven they can build. Part 2 is about what lasts: culture that can operate without the founder in every room, the rituals that turn values into behavior, and the hard identity work that hits when the company changes shape or you step away. Along the way, Ian connects lessons from Kyle Porter, David Cohen, Dug Song, Scott Dorsey, Shegun Otulana, Gail Goodman, Jewel Burks Solomon, Jimena Pardo, Melodie van der Baan, Brad Feld, Linda Rottenberg, and others on hiring and standards, “better not bigger” discipline, post-exit emotional reality, separating the role from the person, and how success compounds when founders pay it forward and invest energy into their communities.

Show Notes:

(03:05) Culture as the operating system, not a “nice to have”

(06:00) Why culture must be reinforced through rituals as you scale

(07:00) “Appreciations” and making excellence visible and repeatable

(09:00) Orange culture: turning values into a shared identity that survives scale

(12:00) “Better not bigger” and resisting growth that erodes standards

(18:00) The emotional reality after a win: rumination, grief, and getting it on the page

(24:00) Founder identity fusion: when the role becomes the person

(26:00) You are not a hat: separating who you are from what you do

(30:00) The post-exit gap between the headline and how it actually feels

(33:00) Give First flywheels and putting energy in without a defined return

(36:00) Generating belief: building gravity when the world is not watching

(41:00) Startup communities as the durable force, more powerful than any one company

(45:00) The ecosystem multiplier: turning one win into infrastructure for the next wave

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Kyle Porter, Salesloft; Wade Foster, Zapier; Shegun Otulana, TheraNest, Harmony Venture Labs; Dug Song, Duo Security; Scott Dorsey, ExactTarget, High Alpha; David Cohen, Techstars; Gail Goodman, Constant Contact; Jewel Burks Solomon, PartPic, Collab Capital; Sean O’Sullivan, MapInfo, SOSV; Melodie van der Baan, Max Retail; Jimena Pardo, Carrot, Hi Ventures; Jason Seats, Slicehost, Techstars; Brad Feld, Foundry, Techstars; Linda Rottenberg, Endeavor; Jon Lensing, OpenLoop; Hernan Kazah, Mercado Libre, Kaszek

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Kyle Porter: I think all companies should have an answer to the question, why do we exist?

Gail Goodman: Business is a team sport that you learn by doing.

Dug Song: It’s not about who’s right, but what’s right.

David Cohen: Bigger isn’t better, better is better.

Jason Seats: I was actually feeling kind of lost

Jimena Pardo: if I’m not Pime from Carrot, who am I now?”

Jewel Burks Solomon: you’re supposed to be happy and you are devastated. What is that about?

Melodie van der Baan: You are already more valuable right now than anything you will ever do or accomplish.

Brad Feld: keep putting energy in. All of a sudden the flywheel starts to turn.

Linda Rottenberg: If you’re an outsider, tell your story.

Shegun Otulana: You can’t wait for the spotlight to shine on you. You have to generate belief.

Ian Hathaway: Welcome back to Outsider Inc. I’m your host, Ian Hathaway.

In our last episode, we started talking about the outsider playbook. Things every outsider founder knows in their bones: how being underestimated builds hunger, how constraint forces systematic thinking, and how the outsider toolkit of [00:01:00] bootstrapping, hustle, and resilience aren’t just survival skills, they’re competitive advantages that can only be forged through experience.

Today, we’re continuing that conversation because once you’ve actually built something, once you’ve proven the doubters wrong and scaled against the odds, the challenge doesn’t disappear. It transforms into something harder.

Now, you need a culture that can sustain itself when you’re no longer in every room. The kind that shows up in who people hire, what they reward, how they make decisions without you, how they treat customers when no one’s watching, and how they show up for each other when things go sideways.

Then there’s an identity crisis most founders don’t see coming. You’ve spent years, maybe decades, pouring everything you are into what you’re building. The company’s wins are your wins. Its struggles are your struggles. . And then one day, whether it’s an exit, a transition, or just the natural evolution of scale, you have to answer a question you’ve been avoiding. When it’s no longer my company Who am I?

And if you’re fortunate enough to succeed, you face an even deeper [00:02:00] question. What do you do with that success? Do you take your winnings and move on, or do you pay it forward in ways that don’t just help individual founders, but actually shift the landscape for everyone who comes next?

Because here’s what we’ve learned from 25 conversations with outsider founders, investors, and ecosystem builders. The real goal was never just proving the doubters wrong. It was never just building one breakout company from an unlikely place.

The goal is turning their stories into validation, proof that makes the next outsider’s pitch a little easier to believe, infrastructure that makes their path a little less lonely, capital that flows to places it never reached before, and ultimately, an ecosystem where being an outsider stops being a liability and starts being recognized for what it actually is, a competitive advantage.

The foundation for all of it starts with something most founders treat as an afterthought until it’s too late, the intentional work of building culture.

Most founders treat culture as something you think about after product market fit, after the first big customer, after the series A. After the urgent [00:03:00] stuff is handled.

But ask any founder who’s built something that lasted, and they’ll tell you differently. When you’re building far from the center, when talent is scarce and capital is scarcer, culture isn’t optional. It’s often the only sustainable advantage you have.

Just take it from Kyle Porter, the founder and former CEO of SalesLoft, who built the company into a category-defining sales engagement platform worth over two billion dollars.

Kyle Porter: I think all companies should have an answer to the question, why do we exist? And if what you’re doing today is not fulfilling the answer to that question, then you’ve gotta go some other direction.

No matter what, I wanna run a business with culture at the center of everything. As a founder, the values that I have and that we have as a company is something I have total control over. And there’s not a lot you have total control over, but that’s one thing.

Ian Hathaway: You can’t control the conditions you’re building in. You don’t control the market, the timing, the competition, or whether the fundraising environment turns against you.

But you do control the kind of company you’re trying to build inside those conditions. What you value, what you [00:04:00] reward, how decisions get made, how people treat each other when the plan changes.

That’s the first mature lesson in this part of the outsider playbook. Culture is not a perk you earn later. It’s the operating system that makes execution possible under pressure.

But here’s the question: How do you actually build it?

For some founders, culture starts by paying attention. You watch who thrives, study how they work, and reverse engineer the traits that make them successful. Wade Foster, CEO of Zapier, sees it that way.

Wade Foster: you’re gonna wanna have a way of thinking about what makes somebody particularly great at your company, you know, when you get your first early employees, you’re probably gonna notice some of these folks, you’re just like, “This just wasn’t a fit.” Maybe it’s your fault, maybe it’s their fault, probably a little bit of both.

But You really wanna pay attention to the ones that are, like, really awesome, and you start to, reverse engineer what is it about the way they show up at work? What is it about the way they interact with you and the rest of the team that makes that such a great experience? And then you can start to back into a set of things in your rubric that you go hire for. And these are [00:05:00] things that are gonna be agnostic of skill set.

you know, Look at how Facebook runs its company: move fast and break things. And you contrast that with Apple , “Hey, we’re gonna measure twice and cut once.” Two very opposing ways of thinking about it. Two incredible companies, both have been amazingly successful, but you couldn’t have two more different ways of working. And so I think you kinda have to establish those things and how those work for you. Otherwise, you’re gonna get pulled apart at the seams amongst this team that you’re building, because the way in which folks approach work will be too different.

Ian Hathaway: You hire, you watch, you identify patterns, then you turn those patterns into principles.

But one of the easiest mistakes founders make is confusing culture with the visible stuff, the parties, the perks, the things that look like culture from the outside. Real culture is deeper than that. It’s the values people share, the behaviors that get rewarded, a shared perspective of what it looks like to do the work the right way.

Shegun Otulana, who built TheraNest from Birmingham, Alabama into a billion-dollar company, didn’t have money for the Silicon Valley version of culture, and that forced him to get clear about what [00:06:00] culture really meant.

Shegun Otulana: For us, culture never meant keg parties or things like that because we didn’t have the funds to do Culture for us meant really alignment of values, doing whatever we had to do to make the customer happy. Culture meant since we’re not all in the same room, you have to be able to exercise good judgment, and here are the rules and the guardrails for exercising the good judgment, now go run with it. Culture meant move fast, and we rewarded that. And culture also meant learn and share.

The place where I would say we didn’t do a good enough job as we got bigger was we didn’t ritualize enough of those things. Because the way you reinforce culture is through storytelling and ritualization. My own individual interactions with people was a lot of what sustained the culture in the early days, but that is not going to scale,

Ian Hathaway: That’s the trap. Early culture is relational. People know the founder. They hear the stories. They [00:07:00] watch the decisions. They absorb the values through proximity.

But scale creates distance, And if you don’t turn the founder’s instincts into rituals, stories, and operating principles, Then culture becomes dependent on access to the founder. The people close to you get it. Everyone else is guessing.

So whether you’re reverse engineering culture from who succeeds, or defining it from what you value, eventually you have to do the same thing. Make it real. Make it repeatable. Make it survive when you’re not in the room.

And that means building rituals.

Dug Song, who co-founded Duo Security in Ann Arbor, Michigan, and sold it to Cisco for two point three five billion dollars, borrowed some of Duo’s most important cultural habits from an unlikely source, \

Dug Song: we took as many lessons from Zingerman’s, a Jewish deli down the street from us, and a lot of these things were like the basic kind of rituals and operational behaviors. We had open book finance. Everyone in Duo knew all of our spend and our revenue numbers, all this stuff.

Another thing we took from them that I think is also sort of very Midwestern is this ritual of appreciations. For every team meeting we started or ended with three to five [00:08:00] minutes of thanking each other for the specific things other team members do that made the team successful. And that really is what I think drove a lot of the, the success in learning our business,

We did that in a way that elevated and standardized excellence. You sort of got to understand quickly how people were successful, and other people would model it. everyone did it together, and we all learned together.

It’s not about who’s right, but what’s right. To really be an effective team, we have to go out of our way to help each other be successful. By defining kind of our culture, we defined our behavior and that ultimately led to our results.

Ian Hathaway: Appreciations weren’t just feel-good moments. They were a feedback system. They showed the company what excellence looked like. They helped people understand which behaviors actually moved the business forward. But more than that, they turned culture from an idea into a practice.

“Help each other be successful” sounds good on a value slide, but when every team meeting includes people naming the specific ways their teammates help them win, the value becomes visible. It becomes repeatable, part of how the company learns.

That’s the power of ritual. It takes the thing you say you believe and turns it into [00:09:00] something people actually do. Dug Song shows how culture becomes behavior. And Scott Dorsey from ExactTarget shows what can happen when those behaviors become something even bigger, a shared identity.

ExactTarget’s two point five billion dollar acquisition by Salesforce gets the headlines, but its legacy wasn’t the exit. It was the culture the company built along the way, a culture so distinctive that employees, customers, and partners could feel it.

Eventually, they gave that feeling a name.

Scott Dorsey: along our journey, we felt like we were building something special. We had a strong, kinda tight-knit culture and partners and customers and employees would really feel it. But we didn’t have a great way to describe it, and our CMO, Tim Kopp, came up with really the brilliant idea of kinda creating a brand framework or an identity for our culture called Orange or Be Orange. Turned out to be one of the best moves we ever made because it, brought color and identity to a feeling that all of us had. And when we were going through our real surge of hiring and doing acquisitions and opening offices all around the world, it became the thread that knitted all of [00:10:00] us together.

Employee onboarding became called Officially Orange, and any hire all around the world, you’d fly to Indianapolis, go through two weeks of training, and really get kind of indoctrinated into our team and our culture. We started investing in leadership development, and that became Leading Orange.

And what I really, really loved about Orange is that we didn’t mandate too strong of a narrative or language around what the culture meant. We really left it open for everyone’s individual interpretation, and I think you know you have a powerful culture when people feel it, experience it, and kinda describe it in their own words.

Ian Hathaway: That’s the difference between a slogan and a shared identity.

ExactTarget didn’t start with a corporate framework. It started with a feeling The work was to give that feeling language, rituals, and a meaning so it could survive growth.

And unsurprisingly, it did.

Scott Dorsey: I would say our culture still lives on today, over a decade longer than when the company even existed. We have a Facebook group called Orange Crush with a couple thousand members, and people are posting several times a week photos, pictures, career updates, life changes. We had a 10-year reunion where [00:11:00] we threw a party here in Indianapolis. We had over 1,000 people attend the reunion, many flying in from all over the world just to reconnect with, friends and kinda relive that Orange culture where people felt such a strong connection to one another, what we built, and then to see that live on in a number of different ways is really, really rewarding.

Ian Hathaway: A thousand people. Flying in from all over the world. Ten years after the acquisition. For a culture, not a company.

That’s what durable culture looks like. But culture isn’t only how you behave when things are working. It’s also what pulls you back when growth starts to pull you off course.

Because success creates its own kind of pressure. More markets, more partners, more opportunities, more reasons to stretch beyond the principles that made the company work in the first place. And when that happens, culture becomes a compass. It reminds you what you’re actually optimizing for and helps you recognize the difference between real growth and drift.

David Cohen, who co-founded Techstars and helped build one of the most influential startup accelerators in the world, put that into practice when [00:12:00] he recently returned to the CEO role.

David Cohen: there was so much pull going on for us to be in so many places. In some of those places we had to say, “Yeah, this isn’t working. It’s not the right market for us.” Wrong people or, just doesn’t work culturally with how we do things. When I came back almost two years ago now as CEO, I did so with a set of recommitments. One of them was bigger isn’t better, better is better. We’re very careful now about where we’re expanding to, the companies we’re investing in. There’s been a real return to that focus on quality and just better being better.

Ian Hathaway: Bigger isn’t better. Better is better. That’s culture as discipline. Because growth pressure always pulls you toward more. More markets, more programs, more opportunities, more reasons to stretch beyond what you know how to do well.

David’s recommitment was about resisting that pull, getting back to the right markets, the right people, and the standards that made Techstars work in the first place.

And when culture really works, when you stay true to it, something remarkable happens. Future leaders emerge from your company [00:13:00] carrying those principles with them. Day-to-day conflicts get resolved through process, not emotion, and the team moves as one.

Gail Goodman built that kind of discipline into Constant Contact, the email marketing platform she grew over seventeen years, took public, and ultimately led to a one point one billion dollar acquisition.

Gail Goodman: business is a team sport that you learn by doing. Something that shaped me early, mostly by seeing really bad CEOs, I worked for a few, I did see some horrible dysfunction. The biggest thing I saw was just wasted resource because of lack of alignment. One group is going that way, the other group is going this way. When you’re small, in particular, you have such limited resources and such a short runway to the next fundraise. If you’re not rowing in the same direction, you spin the boat around.

The internal culture at Constant Contact, really got the best out of people. We created a place where we challenged each other, we had healthy conflict, but in the [00:14:00] end we were super aligned. I’ve spawned more than 10 CEOs out of Constant Contact, and they’ve taken these operating principles, executive team alignment, the giving and receiving of feedback, customer first, and they’ve brought them to other companies.

We had a whole methodology for how we ran as a team that resolved stuff. So many places leave things messy and unresolved and they don’t close issues or there’s a debate and executive A didn’t agree with the answer, and he goes running back to his team and says, “We’re doing B, but I didn’t like it.” That was a fireable offense at Constant Contact. We disagree, we have the debate, and when we make a decision, we line up and we execute like hell.

Ian Hathaway: Disagree and commit, not as a platitude, as an operating principle with real consequences. Healthy conflict, then total alignment. That’s culture as execution.

And that’s the outsider advantage when it comes to culture. When you’re building beyond the hubs, when you can’t just throw money at problems, when retention matters [00:15:00] because talent is scarce, you’re forced to build culture that actually works.

Your competitors can copy your product. They can poach your talent. They can outspend your go-to-market. They can copy the visible stuff, the rituals, the language, the playbook.

But the real culture lives underneath all of that. In the trust people have built, in the stories they share, in the standards they hold each other to, in the feeling that work belongs to all of them.

And that can’t be copied. It has to be earned.

But there’s a cost to building something that meaningful, because founders don’t create culture from a distance. They put themselves into it, their values, their instincts, their relationships, their sense of what matters. Over time, the company starts to carry pieces of them.

And that can be beautiful. It’s how a company becomes more than a product, more than a cap table, more than a job.

But it also creates the next challenge: what happens when the thing you built starts becoming inseparable from who you are?

For outsider founders, that question cuts even deeper because the company is rarely just a company. It’s the proof.

Proof that the doubters were wrong. Proof [00:16:00] that the overlooked market had power. Proof that the person who didn’t fit the mold belonged in the room all along.

That proof can carry you through years of scarcity, rejection, and pressure. But once the company becomes proof, it can also become a trap. Because what happens when the thing that proved who you were starts changing form?

What happens when you get the outcome you were fighting for, and instead of feeling free, you feel untethered?

Jewel Burks Solomon built Partpic, pioneered computer vision technology for industrial parts, and sold the company to Amazon. From the outside, it looked like the dream ending. The breakthrough technology, the acquisition, the proof that all the sacrifice had been worth it.

And at first, that’s how it felt.

Jewel Burks Solomon: Yeah, it felt so strange to experience at the time. I mean, it was. It was a big deposit into my account, and literally not be able to get out of the bed because I was so sad. It just didn’t match. It’s like you’re supposed to be happy. This thing that you have been working really hard for, you have [00:17:00] sacrificed a lot, you have postponed a lot in your life for this moment, and you are devastated. What is that about?

Ian Hathaway: We celebrate the deal because it’s easy to measure, but we rarely make space for the quieter part, the grief, the disorientation, the work of rebuilding identity and direction once the transaction is over.

Gail Goodman experienced that when Constant Contact was acquired. Seventeen years building a company at a one point one billion dollar exit, and instead of feeling victorious, she felt like something had died.

Gail Goodman: It was really hard, and it was weird because everybody was congratulating me, and I felt like something had died. It was the end. You know, ‘cause It didn’t feel like a victory to me. I kept waking up in the middle of the night with woulda, coulda, shoulda. If I had done this, might it have gone differently?

I should have been thrilled, and I was lost, angry, pissed at myself, pissed at a few of my leaders who didn’t do things I wanted them to do, who I thought were to [00:18:00] blame. Just generally grumpy. finally I decided I need to get it out of me. So I sat down and wrote the all the things I effed up memo. I just really needed to get it out.

Ian Hathaway: From the outside, an exit reads like a victory lap. From the inside, it can feel like loss, a sudden silence where the work used to be. The calendar clears, the fight ends, and the identity that organized your days for years suddenly has nowhere to go.

And then the mind starts replaying everything. Woulda, coulda, shoulda. Every mistake, every decision

for Gail, the way through started by getting it out of her head and onto a page. The all the things I effed up memo, the lessons learned, the deliberate pause.

But the deeper pattern is this: when the business and the self are fused, a company transition doesn’t just feel professional, it feels personal. And if a successful exit can trigger that kind of identity crisis, failure can cut even deeper.

Sean O’Sullivan founded MapInfo, took it public, and later built SOSV into one of the [00:19:00] world’s leading venture firms. But his second venture after MapInfo burned through millions and fell apart. The team fractured, and when it failed, Sean didn’t just lose money. He lost his sense of who he was.

Sean O’Sullivan: the wake-up call to me was like, “Hey, you’re a failure. You don’t know what you’re doing. You couldn’t keep it together. You couldn’t get the team to function well. There was too much divisiveness.” And it really challenged me. I got very depressed about the situation, and frankly, I thought I was a failure.

And that is a thing when I counsel and mentor startups these days, is to sort of separate the business from the personal. We have backed, about 1,200 companies, probably about 3,000 different founders, and there have been, I’d say three or four founders who have had their companies fail and then committed suicide after that.

I felt that guilt and that sense of responsibility to the people that I had committed to building the [00:20:00] business when the company failed. And there’s no question I was responsible for it. I was the CEO of the company but on the other hand, you have to basically just recognize the business is incorporated for a good reason. It is separate from the individuals that are trying their hardest to build, a meaningful company. And so the failure is something you have to try in every way to prevent, but, if it happens, that’s just part of the game and you have to get over it

I think it’s helpful to even think about it from the viewpoint of sports. You’re out there, you’re leaving blood on the field., But you know what? You win a game, you lose a game, it’s okay. Just try your damnedest to play the game as best you can, and really just not fully identifying your success or failure with the company’s failure. And frankly, the company’s success. You’re neither as good as your best company that you start and that you run, and as bad as the worst company that you start and you run.

Ian Hathaway: You’re neither as good as your best company nor as bad as your worst one. That’s the line to hold [00:21:00] onto.

Because Sean isn’t saying founders should take less responsibility. He says the opposite. He was the CEO. He felt responsible. He made commitments to people. He knew the failure mattered.

But responsibility is not the same as identity. A company can fail without making the founder a failure, and a company can succeed without making the founder whole.

That distinction sounds obvious from the outside, but inside the pressure of building, when your name, reputation, investors, employees, family, and purpose are all wrapped up in the outcome, it can be almost impossible to feel.

And that’s why Sean’s warning lands so heavily When founders have no separation between the business and the self, the stakes can become dangerously personal. Not for everyone, not every time, but often enough that Sean now treats that separation as something founders need to learn before they need it.

Because failure is hard enough, but when the business and the self are fused, failure doesn’t just mean this didn’t work. It starts to mean [00:22:00] I didn’t work. And that is a dangerous place for any founder to live.

So the question becomes, how do you hold the obsession without losing the person underneath it? Because the answer cannot be care less. Great founders care too much. They think about the problem in the shower, in the car, at the airport, in the middle of the night.

The question is not how to eliminate obsession. The question is how to keep that obsession from becoming your entire identity.

Melodie van der Baan, founder and CEO of Max Retail, was given a frame that helped her understand the difference.

Melodie van der Baan: You are already more valuable right now than anything you will ever do or accomplish. And if you can receive that as a founder, you need to know your self-worth, and you need to know who you are outside of what you build. But you also need such a deep-rooted passion for the problem you solve that nothing will veer you off course. Who am I? What is my value? i’m Melodie. I have a hat that is a founder. I have a hat that is a mother. I have a hat that is a wife, a [00:23:00] hat that is friend.” But take off all the hats, I am me, okay? And no one can take that away from me. And that is the first thing you need to win at this game, because you gotta be able to take your hats off and be you every day at some point. You can’t keep the hats on all the time. It is not sustainable. And you are not a hat, you are a person.

Ian Hathaway: You are not a hat. Simple to say, harder to live.

Because the hat gets rewarded. The hat gets introduced on stage. The hat raises capital. The hat gets written about. The hat gets congratulated when the company wins and blamed when it struggles.

Founder, CEO, visionary, operator, builder, outsider, success story. Those hats can become so familiar that you start mistaking them for the person underneath it.

Melodie’s point is not that founders should be less passionate. It’s the opposite. But you also need an identity strong enough to survive taking the hat off.

That’s the paradox. You need enough obsession to survive the mission, but enough separation to survive yourself.

Jimena Pardo, also known as [00:24:00] Pime, lived that paradox. She co-founded Carrot, Mexico’s first car-sharing startup, becoming a mobility expert and one of Mexico’s most visible founders.

Then she stepped away.

Jimena Pardo: I think it happens so many times to entrepreneurs. When you go all in into a project, and on some days when you’re with your family, you keep talking about it, and they see you, step up from dinner to take a call and make another call, and on holidays to plug in, et cetera.

You get obsessed in what you’re building, and truly, I think that’s the way a founder should be. But it comes with a big, big price. I started to be, Pime from Carrot.

You start to blend your personality to what you do and suddenly I was the mobility expert and the female founder image, and so much exposure. And when I took the decision to leave Carrot, I did have this identity problem as, “ Well, if I’m not Pime from Carrot, who am I now?”

Ian Hathaway: [00:25:00] That’s the hidden cost of going all in. The company can start to swallow the person. The role becomes the identity, and stepping away can feel like losing the version of yourself the work created.

Jimena’s answer wasn’t to care less, it was to separate what she built from who she was, so the next chapter didn’t become a free fall.

Jimena Pardo: the internal work you have to do is that it’s not the position you played, it’s who you are internally, and that’s the only way to solve it. If you’re a founder, you probably go into so many lifetimes. You will become a serial founder, you will change jobs. You will have so many phases, but if you have your inside strengthened, you’ll be very suited to be successful in each one of them, and with your family and friends, also provide a better you because you know who you are. What I’ve learned is that I, I will always do everything I do with as much passion as I can. But at the end, it’s about who you are internally.

Ian Hathaway: Jimena is arriving at the same truth Melodie named, [00:26:00] but from the other side of the experience. Melodie said, “You’re not the hat.” Jimena is showing what happens when the hat has become part of your name, Pime from Carrot.

So the lesson isn’t less passion, it isn’t less ambition, it isn’t less commitment. It’s knowing that the position you’re playing is not the person you are.

Because the position will change, the company will change, the work will change, and sometimes the hardest part isn’t leaving the old role, It’s realizing the old role no longer fits before you know what comes next.

Jason Seats, who co-founded Slicehost and sold it to Rackspace, felt a different version of that. For a while, he stayed inside Rackspace, but then his life changed. His daughter was born. He took paternity leave, and when he came back, the office felt different.

Jason Seats: I started asking these questions like, “Oh, is this where I really wanna be?” And I just had one day where I was moping around the hallway, and this guy, he saw me and he’s like, “Look, you don’t look like you feel good, man. You wanna sit down and talk?” He’s like, “You’re not thinking about quitting, are you?” And I told him that I was not thinking about quitting, but now that you mention it, that [00:27:00] is exactly what I need to do.

Ian Hathaway: Sometimes the identity shift arrives before the plan does. You know the old role no longer fits. You know the company doesn’t need you in the same way.

But knowing what you’re done with is not the same as knowing what you’re moving toward.

Jason Seats: what I didn’t have a plan for was what I was going to do next. And so I spent probably close to a year trying to promote various hobbies into full-time occupations and kind of flailing at it. And I was actually feeling kind of lost in a weird way because I just didn’t know what to do with myself, and my identity was so coupled to what I had spent my time doing over the past five years.

Ian Hathaway: A year of flailing, trying to promote hobbies into full-time occupations, trying to fill the space the company used to occupy. That’s not laziness. It’s not lack of imagination. It’s identity lag. The old role has ended, but the new self has not formed yet.

And in that gap, founders often try to recreate the feeling of what they had instead of discovering what this new season is actually asking of them.

Kyle [00:28:00] Porter, who we heard from earlier about building culture at Salesloft, tried to avoid that trap from the beginning For Kyle, the safeguard was not detachment. He cared deeply about SalesLoft. He poured himself into it for more than a decade.

But he refused to let the company become the whole story of his life.

Kyle Porter: there’s two common pitfalls that founders explain. One, you hear people say being a founder is a lonely road. And the other, a lot of times you hear people say that, as a founder, you really wrap your identity up in your business and your role. I recommend anyone listening to this that you don’t do either of those two things.

The story of Kyle Porter doesn’t end with SalesLoft. That came through Bob Lewis, my CEO coach, quite frankly, when he said the words, “Kyle, you’re a holy, righteous, blameless child of the living God.” And I heard that and I go, “Well, that’s something I could tie my identity to that can never be taken away.” I could tie my identity to being a great dad. That could be taken away. I could tie my identity to being a great husband. That could be taken away. so many things, But when I tied it to that, I think that that was the beginning of something really special for me.

Ian Hathaway: when founders [00:29:00] struggle, it’s often in the same two places: isolation and identity. One is about trying to carry the whole thing alone. The other is about letting the role become the only place your self-worth lives.

Kyle is pointing to a more durable foundation, something underneath the company that stays intact when the role changes. For him, that foundation was faith. For someone else, it might be family, service, craft, community, or a deeper sense of personal worth.

The point is not which answer you choose. The point is having an answer the company cannot grant and cannot revoke. Because if the business becomes the only container for your purpose, every transition feels like a collapse.

The way through is remembering the company was never the whole story. It may have been the clearest expression of your values, your creativity, your ambition, your commitment to a place, a problem, or a community, but those things don’t disappear when the role changes. You carry them forward.

And for many founders, that’s what turns a hard ending into a meaningful next chapter. not recreating what was, [00:30:00] but using what you learned to build what comes next. That’s exactly what started to happen for Jewel Burks Solomon.

Jewel Burks Solomon: And what I landed on was I need to share with people what I learned. And so I kind of put out a post, if there are any founders who wanna talk about what they’re working on, I’m available. So I started to turn outward to heal. And mostly to make sure that other people didn’t repeat some of the mistakes that I made. And that’s really what started me on the journey to become an investor. Because once I started having those coffee meetings, I began to get really excited about the companies and the founders that I was meeting with, and I was like, oh, I have a little extra change right now. I can, I could write some checks.

That’s really how I got into investing initially.

Ian Hathaway: That’s the shift. Jewel’s depression after the exit led her towards sharing her story, angel investing, and eventually the purpose of helping more underrepresented founders access capital.

Gail’s grief after Constant Contact eventually turned into reflection, mentoring, and [00:31:00] helping other entrepreneurs build the lessons she had earned the hard way.

Sean’s failure became part of what he now teaches founders, including the importance of separating the business from the self before the pressure becomes unbearable.

And Jason Seats’ year of flailing after Slicehost eventually led him somewhere unexpected. Not to another company of his own, but to helping other founders build theirs.

Different stories, different outcomes, same pattern. The next chapter is not always another company. Sometimes it’s a wider purpose, a way to take what you learned, what you built, what you survived, and make it useful beyond your own role.

That may be the real answer to the founder identity crisis. You don’t stop caring about the company. You don’t pretend it didn’t matter. It mattered because you put yourself into it.

But you are not only what you built, you are also what you carry forward from it.

And for many outsider founders, that becomes the final piece of the playbook: mentoring, investing, coaching, building institutions, Turning hard-earned experience into leverage for others.

creating the infrastructure they wish they had [00:32:00] when they were starting out.

That’s when the outsider playbook expands beyond the individual founder and becomes something bigger, an ecosystem.

and the question becomes, how do you build one?

How do you actually create the conditions that make it easier for the next founder to believe, begin, survive, and scale?

The answer across these conversations is that ecosystems don’t get built by extracting value. They get built by putting energy in without knowing what you’ll get back.

Brad Feld, co-founder of Foundry Group and Techstars, has a name for that philosophy: give first.

Brad Feld: It was trying to underscore how to get a positive feedback loop going in a startup community. Non-transactionally, they do not know what they’re going to get back. They don’t define upfront what they’re going to receive, but they’re willing to make the investment of energy, time, whatever the resource mix is, and they’re willing to stay with it, keep putting energy in. And , If you get enough of that happening, all of a sudden the [00:33:00] flywheel starts to turn and stuff starts to happen, and things start to emerge out of the startup community.

It, It’s not generosity, it’s not altruism, it’s not charity. It’s that you’re just willing to engage and see where it goes and not have to have a defined outcome, and to do that consistently as a way of being, which then leads to a bunch of other stuff.

Ian Hathaway: Give first, not as a transaction, as a way of being.

You put energy into the system without defining what you’ll receive. And if enough people do that, the flywheel starts to turn. Things emerge, connections form, trust builds, introductions happen, capital starts to move.

That’s how ecosystems actually get built. But there’s another crucial piece. Because before someone can give, they first have to believe it’s possible for someone like them to succeed. Give first creates the behavior. Storytelling creates the permission.

Linda Rottenberg, who co-founded Endeavor to support high-impact entrepreneurs in emerging markets, calls this the permission [00:34:00] effect.

Linda Rottenberg: if you’re an outsider, tell your story. Because if you’re different, you’re gonna give permission to somebody else who can say, “Okay, if Daniela can do it, I can too.” And that is hugely important.

Ian Hathaway: If you’re different, tell your story because your success gives permission. It tells the next outsider this path exists. This is available to you. You don’t have to fit the mold to build something that matters.

But permission alone isn’t enough. The next founder also needs someone who will believe in them before the market does, someone who will take the first risk.

That’s the role Bob Compton played for Scott Dorsey and ExactTarget.

Scott Dorsey: Bob was an incredible coach and mentor to us over the years, but he really gave us kind of the first big break on raising capital and giving us a chance to really start scaling the company. Bob would often ask us. “If you’re successful with ExactTarget, what would you want to do next?” And I would always say, “I wanna be you.” I wanna find a way to support young entrepreneurs and put capital into their companies and provide coaching and support, and really give them a chance to build something special. So Bob was an incredible [00:35:00] role model and a real difference maker for us. And I think whenever you look at tech ecosystems that are really thriving, they have a lot of Bob Comptons.

Ian Hathaway: Thriving ecosystems typically have a Bob Compton, people who lend credibility when everyone else still sees risk, people who believe before the market does.

But not every founder has access to a Bob Compton. Not every community has accumulated the wealth, the networks, or the experience to provide that early support. That’s the access gap Dug Song has been working to close in Michigan.

Dug Song: We try to be the catalytic capital, taking the risks on other people that a lot of the other big foundations won’t. we’re trying to be the friends and family money for a lot of founders here whose friends and family don’t have money And so we started some things like the Michigan Founders Fund, a peer network of 150 founders of high tech, high growth businesses here on the angel and venture sort of journey, and when you see those founders, taking risks, personally, on behalf of their customers or their communities, we have to wrap around those people and protect them, and we have to support them. That’s how progress happens in our community.

Ian Hathaway: That’s the access gap in the most [00:36:00] basic form. The traditional startup story assumes there’s someone nearby who can take that first risk, a parent, a former boss, a wealthy connection. But in many communities, that bridge doesn’t exist yet.

So Dug is building the bridge, not just with checks, but with networks, visibility, and support systems that help founders get started and keep going.

After TheraNest, Shegun Otulana looked around Birmingham, Alabama, and saw a city with talent and opportunity, but without the gravitational pull that more established startup hubs take for granted.

Shegun Otulana: So after TheraNest and Therapy Brands, I didn’t wanna just build one more company. I wanted to actually build a system that could launch many companies. Cities like Birmingham, they have a ton of opportunity. But they suffer from attention deficit, right? The world isn’t watching. You can’t wait for the spotlight to shine on you. You have to generate your own gravity. You have to generate belief.

Ian Hathaway: In places the world overlooks, you can’t wait to be discovered. You have to [00:37:00] create momentum yourself. Build belief yourself. Put infrastructure in place that helps more founders get started and get better faster.

That’s what Shegun is describing, hard-won experience turned into a repeatable system, a place where talent can learn, collaborate, and keep building even when attention is scarce.

And that kind of ecosystem work is bigger than venture-backed tech. It also shows up in small businesses that create jobs, strengthen a community, and expand what feels possible locally.

When Gail Goodman was building Constant Contact, she fell in love with small businesses. After her exit, she turned her energy toward helping underrepresented entrepreneurs start Main Street businesses.

Gail Goodman: I want to help people realize the dream of small business ownership, and I have found and am now working with a nonprofit called Entrepreneurship For All, where we help underrepresented entrepreneurs, people who have an idea and don’t know where to start. We do it exceptionally well. Three years in, 70% of our entrepreneurs are still in business. That is eight points better than the [00:38:00] national average, and these are economically challenged folks who would normally fall below that. We now are able to deliver this program nationwide. I want that to be my legacy.

Ian Hathaway: That’s ecosystem building at ground level, not just producing unicorns, but expanding who gets to participate in entrepreneurship at all. Helping someone with an idea believe there is a real path from, “ I don’t know where to start,” to, “ This can become a business.”

And once that path exists, the next question is capital. Who gets backed? Who gets believed? What kind of investor does a founder meet when they finally get in the room?

Jewel Burks Solomon lived that. After selling Partpic to Amazon, she could have walked away. Instead, she became an angel investor, then co-founded Colab Capital to back underrepresented founders at scale.

Jewel Burks Solomon: my mission at Collab was really born out of my experience as a founder. I had a really difficult time as a founder raising capital. I had really challenging experiences with investors. And I made a vow to myself while I was still building my company, that if I [00:39:00] ever got on the other side of building that business, that I would become the investor that I wish I had.

Ian Hathaway: A lot of ecosystem work starts with a personal gap. You go through the hard version, then build the support you didn’t have, so the next founder doesn’t have to do it alone. That’s how experience turns into infrastructure.

John Lensing, co-founder and CEO of OpenLoop in Iowa, sees his role the same way.

Jon Lensing: You need to have more people that wanna contribute, that wanna build a company there, because those success stories provide the inspiration for the next layer down. If I can inspire the next 20 companies that come out of the University of Iowa by telling my story, and then maybe one day help fund some of those, and then they can rely on the experience of what OpenLoop went through, then they’re in a much better spot than we were. They already have a leg up.

Ian Hathaway: That’s how the multiplier starts. One founder succeeds, then helps 10 more. Those 10 help 100. The playbook spreads. Capital starts to move. The network strengthens The culture shifts.

And eventually, what [00:40:00] young people aspire to changes. Hernan Kazah saw that shift happen in Latin America.

Hernan Kazah: When we started, all graduates were aspiring to get a job. And today they look up to joining a startup or starting a startup. And I think that shifting mentality is a very positive one.

Ian Hathaway: That shifting mentality is the long game. The first generation has to prove it’s possible.  The next generation grows up assuming it’s possible.

That’s how a place changes. Not all at once, not because one company exists, but because success leaves behind more than wealth. It leaves behind talent, confidence, capital, mentors, and a new default setting in the culture.

The question stops being, can someone from here build a company like that? And starts becoming, why not me?

But cultural shift needs champions. It needs people who make it their mission to grow the infrastructure the next generation requires. Jimena Pardo, who we heard from earlier, is doing exactly that.

Jimena Pardo: I want to break the capital barrier to our regions. I want every founder in Latin America to have the [00:41:00] opportunity to build as in the US. I want them to have the resources, so they won’t be limited by capital for testing their products. And whenever we do that, the next e-commerce, the next health tech, the next prop tech, the next ed tech will come, not specifically from Latin America, but also from Southeast Asia, from Africa, from all around the world.

Ian Hathaway: That’s the global version of the same playbook. The goal is not just to celebrate founders from overlooked places after they beat the odds. It’s to change the odds. To make sure the next great company is not limited by where the founder was born, who they know, or whether their region already has a mature capital stack.

And that brings us to the final lesson David Cohen learned when he returned to lead Techstars: the community matters more than any single company.

David Cohen: The startup communities we operate in are way, way more powerful than we are as a company, and we need to continue to incentivize and reward them for being partners in what we do.

Ian Hathaway: The startup communities are more powerful than the [00:42:00] company. That may be the final lesson of the outsider playbook. The mistake is treating a startup community like a distribution channel. Another market to enter, another place to extract from, another logo on the map.

David is pointing to something deeper. The local network is the force.  Any platform is only a guest inside of it. If you want durable impact, you don’t extract from that community. You invest in it. Reward it. Build with it.

Because communities outlast companies. They’re where founder lessons get recycled into shared advantage.

A single success story says, look what they built. A movement says, look what they’re building made possible.

And that brings us back to the belief at the center of this show. Great entrepreneurs can come from anywhere. After 25 conversations, that still feels true.

But it also feels incomplete, because the lesson isn’t just that outsiders can build great companies, it’s that the very things that make them outsiders, the underestimation, the constraints, the distance from traditional centers of power, can become [00:43:00] part of how they build.

Not automatically. Being underestimated doesn’t magically become an advantage, neither does scarcity or constraint. Sometimes those things just make the work harder.

But for the founders who make it through, those pressures leave behind a playbook. Conviction before validation, focus before abundance, creativity before resources, customer discipline before scale, resilience before traction.

And if the company works, the playbook becomes more than a founder’s survival toolkit. It becomes culture. It becomes how the team makes decisions, handles pressure, serves customers, and carries the work forward. That’s why the company can become so hard to separate from the founder. You put so much of yourself into it that eventually you have to ask what still belongs to you when the role changes.

But the playbook is yours.

It’s what you carry forward to the next founder, the next check, the next mentor session, the next institution, the next ecosystem. Because you know what it felt like to build without one.

And [00:44:00] that’s the turn. Outsider founders don’t just prove the map was wrong They redraw it for the next person. The next founder gets a little more evidence, a little more language, a little more capital, a little more permission, a few more doors already cracked open.

And if enough founders do that, the story changes. The unlikely place stops seeming so unlikely. The overlooked market stops seeming so invisible. The outsider stops sounding like an exception.

And eventually, the question changes. Not, “Can you really build from there?” But, “ What else are we missing?” That’s the outsider’s playbook.

if you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn @outsiderincpod. You can also follow me on X @IanHathaway.

Outsider Inc. Is produced by Spellbinder Media. We’ll be back [00:45:00] soon with another fascinating outsider conversation. Until then, thank you so much for listening, and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. is different. After 25 conversations with founders, investors, and ecosystem builders who’ve succeeded from unlikely places, I started noticing the same patterns showing up across wildly different stories. So instead of another interview, we’re stepping back to ask what we’re actually learning. This is Part One of The Outsider Playbook.

The guests we’ve featured on this show have built from places the traditional venture world tends to overlook. Hernán Kazah built a $100 billion company from Argentina when everyone said Latin America would never work for tech. Wade Foster built a $5 billion company from central Missouri with just $1.3 million in outside capital. Shegun Otulana came to Birmingham, Alabama, from Lagos at 18 years old and built a billion-dollar company. Linda Rottenberg literally helped add the word “entrepreneur” to the Spanish and Portuguese dictionaries because it didn’t exist. Scott Dorsey turned Indianapolis into a tech powerhouse, culminating in a $2.5 billion exit to Salesforce. Jewel Burks Solomon built novel computer vision technology in Atlanta and sold it to Amazon. And many more.

Different industries, different decades, different geographies — but a lot of the same hard-won lessons keep emerging. This episode pulls them together into three threads.

The first is what being underestimated actually does to you. Not the version of that story you’ve heard before, but the operational reality of walking into rooms where people have already decided you’re not going to make it. The hunger it builds. The freedom it creates. The work ethic it forges.

The second is why constraints tend to be features rather than bugs. Smaller markets force scale. Limited capital forces discipline. Missing infrastructure forces founders to build more of the stack. And the lived pain of operating far from the center of things creates customer understanding insiders can’t fake.

The third is the toolkit every outsider ends up developing, whether they planned to or not — bootstrapping with almost nothing, hustling to acquire customers one phone call at a time, and the kind of resilience that only comes from getting knocked down enough times to realize you don’t actually die of failure.

The bigger idea underneath all of it is that the outsider advantage isn’t really about overcoming disadvantage. It’s about running a different operating system — one that’s been stress-tested in ways the insider path never is. Part Two will pick up where this leaves off, covering culture, identity, and what it means to pay it forward. ⤵️.

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Episode Highlights

Here are some highlights from the show. In this first clip, Jewel Burks Solomon, Gail Goodman, Linda Rottenberg, Shegun Otulana, and Wade Foster share what being underestimated actually feels like from the inside. It’s not a one-time hurdle to clear — it’s the operating environment outsider founders live inside, and the thing that ends up forging the muscle insiders never have to build.

In this next clip, Shegun Otulana, Hernán Kazah, Jon Lensing, Dug Song, Scott Dorsey, and Willy Schlacks make the case that constraint isn’t something to overcome — it’s something to build from. Small markets force scale, capital scarcity forces discipline, missing infrastructure forces you to own more of the stack, and lived pain creates customer understanding insiders can’t fake.

In this next clip, Michael Praeger, Dug Song, Jason Seats, Jon Lensing, and Guillaume de Zwirek get into the toolkit every outsider founder ends up building — picking one customer and one problem, executing without the resources you’d ideally have, doing the legal work out of a library book, handwriting 300 letters to land one signup, and removing the exit ramp so retreat isn’t an option. The tactics are different, but the throughline is the same: resourcefulness is what you reach for when nothing else is available.

In this final clip, Melodie van der Baan, Brad Feld, Chris Schroeder, Isaac Saldana, and Hernán Kazah talk about the resilience that gets you through the part of the journey nobody warns you about. Failure stops being terrifying once you’ve lived through it. Being wrong starts to feel like information instead of identity. And the irrational commitment to keep going — even when the company looks like it’s failing — is what separates the founders who make it out of the death valleys from the ones who don’t.

I’m grateful for every guest who has come on this show and shared their story. What sticks with me after pulling 25 episodes together isn’t any single anecdote — it’s how consistent the underlying machinery is. Hernán building a payment system because Latin America didn’t have one. Wade pre-selling Zapier before the product existed. Isaac trading sleep for time at nineteen and finding the startup easier than the life that came before it. Melodie learning her industry one phone call at a time, mistake by mistake. Jewel watching investors write “alleged” four times about facts that were plainly true. Linda walking into a room with 40% of Mexico’s GDP and telling them to feed the little fish instead of eating them. Brad gnawing on an untoasted bagel and getting back up anyway. Different stories. Same operating system underneath.

What I took most from putting this together is that the outsider advantage isn’t a consolation prize. It’s not the version of success you settle for when Silicon Valley doesn’t return your call. It’s a fundamentally different way of building — one that produces founders who know how to scale without a safety net, sell without a brand, raise without a network, and keep going when the validators say it isn’t working. Being underestimated builds hunger. Constraint forces creativity. The toolkit gets sharpened through use. And the resilience that comes out the other side isn’t something you can buy or shortcut your way into. If you take one thing from this episode, let it be this: the patterns you’re seeing in your own journey — the doubt, the scarcity, the grind, the slow build — aren’t bugs. They’re the operating system. And it’s been stress-tested in ways the insider path never is.

Up Next: The Outsider Playbook Part 2

Next week we close it out with Part Two of The Outsider Playbook. If Part One was about how outsiders get started — the hunger, the constraint, the toolkit — Part Two is about what happens once you've actually built something. Because the challenge doesn't go away when the company starts working. It transforms. Now you need a culture that holds together when you're not in every room. You face an identity crisis most founders don't see coming, when the company's wins have been your wins for so long that you have to ask who you are once it's no longer yours. And if you're fortunate enough to succeed, you have to decide what to do with that success — take the winnings and move on, or pay it forward in ways that shift the landscape for the next outsider. The real goal was never just proving the doubters wrong. It was turning these stories into validation — capital that flows to places it didn’t reach before, and an ecosystem where being an outsider stops being a liability and starts being recognized as the competitive advantage it actually is.

Listen on: Spotify, Apple Podcasts, Amazon Music

Host Ian Hathaway marks 25 episodes of Outsider Inc. by stepping back to synthesize an emerging “outsider playbook” from founders, investors, and ecosystem builders succeeding outside traditional venture hubs. The episode focuses on underestimation and constraint as structural advantages: being dismissed builds hunger and calluses; small markets force repeatable systems and early scaling; capital scarcity creates discipline and focus; missing infrastructure pushes founders to build more comprehensive, defensible solutions; and lived customer pain produces deeper insight. Stories include Mercado Libre’s rise from Argentina amid skepticism, Zapier’s Central Missouri origins, SendGrid’s work-ethic forged by hardship, investors doubting Partpic even amid an Amazon offer, and lessons from ExactTarget, EquipmentShare, OpenLoop, Duo Security, DoubleClick, and others on bootstrapping, resilience, learning from being wrong, and “failure is not an option.”

Show Notes:

(02:14) Being Underestimated

(05:29) Proving Yourself Twice

(11:34) Constraint as Advantage

(12:11) Small Markets Scale Faster

(15:11) Capital Scarcity Discipline

(17:10) Missing Infrastructure Moats

(20:42) Outsider Toolkit Basics

(21:08) Bootstrapping and Optionality

(24:19) Focus and Early Revenue

(26:21) Hustle and Customer Grind

(28:04) Resilience Through Failure

(30:34) Gatekeepers and Being Early

(32:15) Learning From Being Wrong

(33:59) Irrational Commitment

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guests: Hernan Kazah, Mercado Libre, Kaszek; Wade Foster, Zapier; Isaac Saldana, SendGrid; Jewel Burks Solomon, PartPic, Collab Capital; Shegun Otulana, TheraNest, Harmony Venture Labs; Linda Rottenberg, Endeavor; Gail Goodman, Constant Contact; Willy Schlacks, EquipmentShare; Scott Dorsey, ExactTarget, High Alpha; Jon Lensing, OpenLoop; Dug Song, Duo Security; Jason Seats, Slicehost, Techstars; Sean O’Sullivan, MapInfo, SOSV; Guillaume de Zwirek, Artera; Michael Praeger, AvidXchange; Melodie van der Baan, Max Retail; Brad Feld, Foundry, Techstars; Kevin O’Connor, DoubleClick, Graphiq, ScOp; Chris Schroeder, Startup Rising, HealthCentral, Next Billion Capital Partners; Jared Polis, Governor of Colorado; AIS; Blue Mountain; Proflowers; Techstars

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Dug Song: Entrepreneurship is really the art of executing without all the resources needed.

Linda Rottenberg: I can say things that are unexpected, partly because they didn’t fit me into a mold.

Brad Feld: they can’t kill you and they can’t eat you.

Shegun Otulana: constraints lead to creativity.

Jon Lensing: pressure builds diamonds.

Melodie van der Baan: I learned this industry one phone call at a time, one mistake at a time.

Michael Praeger: Don’t try to boil the ocean.

Chris Schroeder: one of the most powerful things you can do is have almost a wonder or amazement in being wrong.

Kevin O’Connor: And so our theory became this is inevitable.

Hernan Kazah: Failure is not an option.

Ian Hathaway: Welcome to Outsider Inc. I’m your host, Ian Hathaway. After 25 episodes and 25 extraordinary conversations, I believe that we’re building something special here. A community of founders, investors, and ecosystem builders who’ve succeeded from unlikely places.

Hernan Kazah, who built a $100 billion company from Argentina when everyone said Latin America would never work for tech. Brad Feld, whose give first [00:01:00] philosophy is now powering ecosystems worldwide. Jared Polis, who went from internet entrepreneur to governor of Colorado. Linda Rotenberg, who literally had to create the word entrepreneur in Spanish and Portuguese because it didn’t exist. Wade Foster, based in central Missouri, who built a $5 billion company on just $1.3 million raised. Scott Dorsey, who turned Indianapolis into a tech powerhouse with ExactTarget’s $2.5 billion exit to Salesforce.

And so many more, from Argentina to Birmingham, from Detroit to Dubai, we’ve talked to people building, investing, and succeeding in places the traditional venture world overlooks.

Somewhere around episode 15, I started noticing the patterns. Similar insights kept emerging from wildly different contexts. The same advantages kept showing up in the most unlikely places. The same necessary toolkit kept appearing in completely different hands.

So we’re doing something different. Over the next two episodes, we’re stepping back after 25 conversations to [00:02:00] ask, what are we learning? What’s the outsider playbook that’s emerging from this community?

For the entrepreneurs just getting started or dreaming of your next company, if you’ve ever felt underestimated, under-resourced, or outside the traditional centers of power, this is for you.

Let’s start with something every outsider knows: being underestimated.

There’s this moment that every outsider founder has experienced. Someone looks at you, your geography, your background, your resources, your age, your accent, and you can see it in their eyes. They’ve already decided this isn’t going to work.

Hernan Kazah, who built Mercado Libre into a $100 billion company, felt it when he and Marcos Galperin were trying to get started in Argentina in the late 1990s.

Hernan Kazah: we were totally, totally convinced that what was starting to happen in the US with the internet and with the Amazons and the eBays of the time was going to happen in Latin America. And everyone would say, “No, in Latin America, the internet will not work,” or going directly into the [00:03:00] specifics of Mercado Libre’s business model, they would say, “People will never, ever trade with strangers,” and those kind of things.

In Latin America, you need a higher level of trust. We knew that what we were building was very compelling and it was going to work. We knew it was going to be difficult, we knew we were going to have competition, we knew it was going to take time, but were very convinced about it.

So there was lots of conviction about that.

Ian Hathaway: Everyone said no. The internet won’t work there. People won’t trade with strangers. Latin America needs a higher level of trust. But Hernan and Marcos had conviction anyway. They knew it would be difficult, knew there would be competition, knew it would take time. They built it anyway.

The geographic dismissal, you’re in the wrong place, shows up everywhere. Wade Foster, who launched Zapier out of a Central Missouri startup weekend and built it into a $5 billion company, grew up with a different version of it. Not people telling him it wouldn’t work, but something he’d internalized before anyone even had to say it.

Wade Foster: coming from Missouri, there’s these whole things in my mind where I’m like, “Oh, that’s for other people. Other people do [00:04:00] that. Rocket scientists do that. Geniuses do that. That’s not for me.”

And then you kinda get to go experience it and you go, that “actually, that’s not so hard. I think I could do that.” And you start to realize, you sort of have been artificially constraining what’s possible in your head.

Ian Hathaway: that mindset, that’s for other people, might be the most damaging form of underestimation because you do it to yourself. Wade had to physically spend time around the insiders of Silicon Valley to realize they weren’t any more special than he was, that he could do what they were doing too.

Isaac Saldana, co-founder and CEO of SendGrid, which he took public and then sold to Twilio for $2 billion, Faced real constraints, and not just mental ones. Born in the US, moved to Mexico at five, came back at 14 not speaking English well, married at 19 with two kids, working two jobs while going to school full-time.

Isaac Saldana: What I traded at that time is health and sleep. I traded that for time. Eat whatever you can as fast as possible and try not to sleep.

So what that did [00:05:00] to me is that when it was time to do a startup, it was more like, “Oh, I got this. It’s not as hard as when I was 19.” That time when I was in college, it gave me so much work ethic that now it just feels that it’s much easier compared to that time.

Ian Hathaway: Think about that calibration. Most people think startups are impossibly hard. Isaac thought his startup was easy compared to being 19. Two jobs, a family, no sleep, trading health for time. Work ethic forged by constraint.

But there’s another layer to this. It’s not just the work you do, it’s that people don’t believe the work you’ve already done. Jewel Burks Solomon founded Partpic, built novel computer technology, and ultimately sold the company to Amazon. But along the way to that successful outcome, investors still questioned the facts.

Jewel Burks Solomon: I so vividly remember investors simply not believing me. One of the stories I share is that I had an opportunity to read an investment memo that was written about Partpic, and in the memo, the word alleged was [00:06:00] used four different times to describe things that were very obviously true. The funniest one, this was an investor that we were talking to towards the end of our journey, and we had already received an offer, Amazon was circling around, and the investor wrote as sort of the closing part of the memo that Partpic has allegedly received an offer to be acquired by Amazon. Just the facts of what was happening at the time, they didn’t believe. That I think, was really indicative of what my life and career looked like, honestly, probably to this day, in terms of always having to prove something, always being second-guessed.

Ian Hathaway: Alleged, not speculation, not rumor. They’d received a documented acquisition offer from Amazon. But when you’re an outsider founder, it’s easy to be second-guessed. You’re always proving something.

Segun Otulana, who came from Lagos, Nigeria, to Birmingham, Alabama, at 18 and built a billion-dollar company, knew he’d face that questioning, that constant need to prove himself his entire [00:07:00] career.

Shegun Otulana: Obviously, moving from Lagos to Birmingham, Alabama has its transitions, in terms of people understanding you and dealing with preconceived ideas of what it meant to come from Nigeria. In some cases, it worked for you. In some cases, it worked against you, and you learn, and you adapt over time.

Ian Hathaway: Segun showed up authentically and filtered fast. The wrong people left, the right people stayed.

Linda Rottenberg, founder of Endeavor, which has supported nearly 3,000 high-impact entrepreneurs globally, encountered underestimation at a systemic level. When she started working in Latin America in the late 1990s, she discovered the infrastructure for entrepreneurship didn’t just need to be built. The language itself was missing.

Linda Rottenberg: my driver has an engineering degree. And so I’m like, Oh my God, why aren’t you a...” and I couldn’t think of the word for entrepreneur. And he informs me after back and forth, there is no word for entrepreneur at that point in Spanish. Empresario meant you had government connections, one of the oligarchs of business. And I thought, wow, [00:08:00] no wonder no one’s starting their companies. They can’t even tell their parents what it is they wanna do. There’s talent in these markets. There’s capital in these markets. There is no trust. But in about 2004, in Brazil, the editor of the Brazilian-Portuguese dictionary, called up our team and said they were adding the words “empreendedor” and “empreendedorismo”—entrepreneur and entrepreneurship—into the lexicon. So we went from not having a word to having words.

Ian Hathaway: You literally couldn’t tell your parents you wanted to be an entrepreneur because there was no word for it. Linda had to help create the vocabulary before she could do the work.

And being the unexpected person in the room, the one who clearly doesn’t belong by traditional standards, actually gave her a different kind of power.

Linda Rottenberg: I remember walking into Mexico, and literally it was me and probably 40% of Mexico’s GDP with like 10 people in the room and, I had to convince them to take a bet on Endeavor. I can say things that are unexpected, partly because they didn’t fit me into a mold. I could say things like, “Well, you’re the [00:09:00] big fish, and entrepreneurship is about little fish growing, so why don’t you think instead about eating the little fish, feeding the little fish?” They didn’t know what to make of me, but they knew that I had a story, that we had done some things that were real in places like Argentina, and at that point Brazil. And so they’re like, “All right. This sounds a little bit off, but we’re gonna go with it.” And in fact, then a decade later, the headline was, “Big Fish Feeding the Little Fish.”

Ian Hathaway: When you’re already the outsider, when they already think you don’t belong, you have nothing to lose by saying the unexpected thing. You can challenge the most powerful people in the room. Tell them to feed the little fish instead of eating them, because the conventional approach was never going to work for you anyway.

And sometimes that directness, that willingness to say what insiders won’t, is exactly what breaks through.

Of course, being the unexpected person in high-stakes rooms is one thing, but the underestimation doesn’t stop once you’ve proven yourself. Even after you’ve built something significant, even after you’ve earned your place, you can still walk into a room and have people assume you’re not someone worth [00:10:00] their time.

Gail Goodman built Constant Contact over 20 years, took it public, and grew it into a $1.1 billion business. But even after all that success, she still felt like an outsider.

Gail Goodman: I certainly felt like an outsider raising venture capital. I was a first-time CEO, and I was, female, 40. I’d go to these, networking events in Boston, and I’d look like everybody’s mother.

I walk up to these two women and I’m like, “Hi, You guys founders? What are your businesses?” And you could see they were like we need to go find somebody important to talk to. An hour later, I’m on the stage telling the story.” One of these women runs up to me afterwards and says, “ I had no idea who you were.”

Ian Hathaway: Gail had already built a massive company, and she still got snubbed at networking events. But being outside the system, it builds muscle, work ethic, hunger, the ability to see opportunities others miss, the freedom to say unexpected things, the calluses to keep going when people doubt you. Those skills don’t just come to anyone who wants them. They have to be fought for. And in order [00:11:00] to win that fight, you have to develop them. Willie Schlacks, the grassroots entrepreneur who took EquipmentShare from humble beginnings in rural Missouri to a category-defining platform on the Nasdaq, says a so-called normal upbringing might just prevent you from developing those skills in the first place.

Willy Schlacks: I think if I had grown up in what we would call normal, it’d be quite a struggle. The biggest struggle to humans in this day and age is a moderately middle class or wealthy, easy upbringing. That’s something I’d find challenging to surmount

Ian Hathaway: When you don’t face constraints, you don’t build the muscle. When everything comes easy, you don’t develop the hunger. So what if we stop thinking of constraint as a liability? What if being far from Silicon Valley, having limited capital, operating in overlooked markets, what if those aren’t disadvantages at all? What if constraint itself is a competitive advantage?

I’m talking about the constraints every outsider founder knows. Geographic, you’re building in a small market, far from capital and talent. Financial, you’re raising a tenth of what Bay Area companies raise. Market, the infrastructure you need doesn’t [00:12:00] exist where you’re building. Talent, you can’t recruit the people you need locally.

But what if these aren’t just obstacles? What if they’re forcing functions that lead founders to create new pathways they wouldn’t have considered otherwise?

Before Scott Dorsey co-founded ExactTarget and scaled it for more than a decade, selling it to Salesforce for $2.5 billion, most pundits doubted a big software company could be built in a place like Indianapolis. But they didn’t understand something that Scott did.

Scott Dorsey: a lot of benefits that come from building companies in a smaller community. I don’t know that Exact Target would’ve made much of a dent in San Francisco or Chicago, but in a smaller market like Indianapolis, you can feel the impact, and that’s very motivating.

Ian Hathaway: In San Francisco, ExactTarget would have disappeared into the noise. In Indianapolis, the company mattered to the city. The constraint of a smaller market created something you can’t manufacture in a major hub.

Willy Schlaks experienced the same constraint with EquipmentShare, but in a different way. He was building an equipment rental and technology company out of a small market in [00:13:00] Central Missouri. That forced something critical.

Willy Schlacks: it enabled us developing scalable process and scale far quicker than we would’ve if we were in a low constraint environment. Say we decided, Hey, New York’s great, or Southern Florida or whatever. Those markets are so big that we wouldn’t have had to really figure out scale and remote,

‘Cause our ambitions were global. So a big part of what is underappreciated when you have a brick-and-mortar aspect to your business is store number two. if that’s just next door, you’re not really doing scale. You have to figure out all your systems and process for scaling people and hiring.

When you’re not there to solve the problem, how does the business continue on? How does culture emerge that’s far beyond and impactful than you as an individual?

Very quickly, we had to expand outside of the known. And if you look at what we achieved, scaling in the industry, nobody in the history had ever done that. Now, it’s not because we were rocket scientists. It’s simply because we had this constraint of small market, and we had an ambition of the whole industry. The constraint of having a small market was a huge advantage because we were forced to figure [00:14:00] out scale very early.

Ian Hathaway: That constraint forced them to figure out remote operations, systematized processes, and culture that works when founders aren’t in the room. Not because they were brilliant. Because Missouri gave them no choice. Store number two couldn’t be next door. It had to work remotely. That constraint forced operational innovation nobody else in their industry had solved.

Staying in the Midwest, Jon Lensing co-founded OpenLoop, a telehealth infrastructure platform recently valued at over a billion dollars. He and his co-founder made a deliberate choice to stay and build in Des Moines, Iowa, to live inside the same constraints their customers were facing.

Jon Lensing: we started the company, my co-founder and I, in the state of Iowa ‘cause he’s from Missouri, I’m from Iowa. We wanted to do something to give back to the Midwest. We contemplated moving to San Francisco. New York was calling to us as well, but firmly believed in our roots, and that’s the reason why we started it. We wanted to address a lot of the accessibility issues for rural America, and that just happened to be where we were from. And so it made sense to live in the middle of the pain while we were trying to build solution [00:15:00] for it

Ian Hathaway: Living in the middle of the pain, being far from major medical centers, watching patients drive hours for basic care. That geographic constraint gave them the understanding their San Francisco competitors could never have. But Jon experienced another constraint that shaped how they built: capital scarcity. Des Moines isn’t exactly the center of venture capital.

Jon Lensing: I think capital constraints put some very realistic pressure on companies, and that pressure builds diamonds. It’s like when you back a dog into a corner, they’re gonna fight like hell to get out of it, right? The same is true in our DNA, and I think the way our strategy has evolved, the way the business has evolved, you could view it as a series of some really significant pivots, but then a bunch of more micro pivots along the way.

Some people might call it chasing opportunity. I would say it was calculated opportunity risk-taking. And if you don’t have that external pressure on the business to generate the revenue, generate the impact, generate the traction that you need to build a sustainable company, you end up wasting a ton [00:16:00] of venture capital dollars on your initial singular mindset,

and so that capital constraint, I think provided a world of benefit

Ian Hathaway: Pressure builds diamonds. Capital constraint forced them to learn fast, pivot when needed, find what actually worked instead of pouring money into the wrong product. The scarcity became the impetus for finding product-market fit.

Doug Song co-founded Duo Security in Ann Arbor, Michigan, and sold it to Cisco for $2.35 billion. He saw the same thing Jon did. Capital scarcity creates discipline But Doug went further. He argued that constraint isn’t just helpful, it’s essential because removing it creates larger problems.

Dug Song: there’s a discipline that really drives. ‘Cause you have to focus on what matters. When you’re flush with cash and someone else’s cash particularly, you know, you end up sort of spending like drunken sailors ‘cause there’s just no feedback mechanism around this and there’s no more internal locus of accountability. It’s just very easy to go and then spread it around like peanut butter. All the kind of [00:17:00] trivial kind of many things that you could do instead of really focusing on the few things that actually are moving the needle for you.

Ian Hathaway: You spend like drunken sailors because there’s no internal accountability forcing you to focus.

But sometimes the constraint isn’t what you don’t have, it’s what doesn’t even exist where you’re building. When Hernan and Marcos started Mercado Libre in Latin America, they couldn’t just plug into existing infrastructure the way eBay did in the US. The infrastructure simply wasn’t there.

Hernan Kazah: in particular, when you go to solving a problem, you identify one problem and you wanna fill that gap, but then you realize that on the way to filling in that gap, there are many other gaps that appear because the infrastructure is not there.

So you need to be much more comprehensive in your solution.

The first version of Mercado Libre, didn’t have a payments mechanism. And then, hey, people are trading things, but, it’d be much easier if we could also solve the payment challenge. And if you were in the US, eBay had PayPal and there were other mechanisms to pay for the item you were buying. Now to Latin [00:18:00] Americans, you need to start building lots of things around that solution that you’re building for it to work. So that’s a challenge. You need to have a much more open mind, be willing to address problems that you think maybe are not yours. But if you don’t solve them, and nobody solves them, then you cannot really provide the solution where you’re trying to build. But at the same time, if you end up doing that, maybe your model ends up being more resilient, more defensible, because you own not only that particular solution, but also the ecosystem that serves that solution.

Ian Hathaway: The missing infrastructure forced them to build comprehensive, vertically integrated solutions. In the US, you focus on one thing and plug into existing infrastructure. In Latin America, if you don’t build it yourself, it doesn’t exist. That constraint forced them to own the entire ecosystem, and owning the ecosystem created a moat their competitors couldn’t replicate. Mercado Libre is worth a hundred billion dollars today. The constraint became the defensibility.

Here’s the pattern that emerges again and again. Constraint doesn’t just force you to do [00:19:00] things differently. It forces you to learn what actually works. Shegun Otulana experienced this firsthand in Birmingham.

Shegun Otulana: constraints lead to creativity. You doing a job within the constraints of being a one-man band helps you think about efficiencies within that job that you can then pass on to the next person. I didn’t have any resources, but I knew the bigger challenge was not the ability to build the software. I could build the software. It was my ability to sell the software and market the software that would be my biggest problem. So what I did was I found a really great engineer, because I knew what a great engineer would look like, and I passed on a lot of the engineering work. I really started focusing on how do I become somebody who will drive traffic into the website and do marketing. When I now got a little bit of funding, we knew exactly where to put the money from a marketing standpoint to significantly drive growth, because I had been [00:20:00] doing the marketing work. So when October came around and we ended up raising a seed round, we knew this works, this didn’t work, this works, this didn’t work. Let’s double down on what works.

Ian Hathaway: Early on, Shegun had no choice but to become the growth engine himself. That season turned guesswork into instinct and instinct into a repeatable playbook. When resources finally unlocked, he could move with speed and confidence because the fundamentals were already proven.

A smaller home base forces repeatable systems. Limited capital forces focus and discipline. Gaps in the environment force founders to build more of the stack. And lived pain creates a kind of customer understanding you cannot fake.

These aren’t just hurdles, they’re advantages your competitors can’t replicate.

Knowing this is one thing. Actually executing on it every day is another. Because if you’re an outsider, you don’t just think differently, you operate differently.

It requires a specific toolkit: the ability to bootstrap with almost nothing, the hustle to acquire customers creatively, the scrappiness to solve problems resourcefully, [00:21:00] and the resilience to keep going when others would quit. These aren’t just traits, they’re survival mechanisms that outsiders are forced to adopt early.

Dug Song, who we heard from earlier, co-founder of Duo Security, raised just $14 million and scaled to $100 million in ARR before the exit to Cisco. He has a one-sentence definition of what entrepreneurship actually is.

Dug Song: Entrepreneurship is really the art of executing without all the resources needed. You don’t have to starve, but maintain optionality. Right-size the business for your learning

Ian Hathaway: You can’t wait until you have everything you need, because you never will. Figure out how to execute anyway.

Jason Seats co-founded Slicehost in the mid-2000s, one of the first cloud hosting platforms, and bootstrapped the company to millions in annual recurring revenue within just two years, eventually leading to an eight-figure acquisition by Rackspace. When he started Slicehost, he and his co-founder didn’t even hire a lawyer.

Jason Seats: we went to the library and got a book, “The NOLO Book Series.” NOLO stands for no lawyer. And it Tells you what to do. [00:22:00] So we formed the business and handled everything ourselves, and it cost $50.

It’s a little bit like “Good Will Hunting.” Get the Harvard education for $2.50 in late fees.

Ian Hathaway: That’s one way to bootstrap. You figure it out as you go.

Sean O’Sullivan also had to bootstrap. He founded MapInfo in 1986, took it public, and later went on to found SOSV, one of the world’s leading hardware and deep tech-focused venture firms that’s backed over 1,000 companies. from a family of nine kids, raised modestly in upstate New York. And MapInfo began with the help of his eight siblings, each chipping in what they could.

Sean O’Sullivan: We basically bootstrapped the business. We didn’t really need that much venture capital. I have eight brothers and sisters. They all invested $1,000 each, and my sister invested $5,000. Several years later, that $5,000 was worth over a million dollars after we went public. We raised, I think, $75,000 was our first friends and family round, and we were nearly profitable with that.

I think we raised a total of $300,000 before we were profitable and never looked [00:23:00] back.

Ian Hathaway: When your first backers are family, you treat every dollar like it matters. That kind of accountability forces focus, discipline, and a path to real profitability instead of fundraising as a crutch.

Guillaume de Zwirek knows this pressure intimately. Gui founded Artera, formerly known as WellHealth, a patient communications platform that’s grown to serve nearly 1,000 health systems and federal agencies, and processing 3 billion patient interactions per year. Gui scaled the company to over $100 million in revenue while taking inspiration from an unlikely story.

Guillaume de Zwirek: there’s a story that I reference often, it’s about a Spanish conquistador who has a small fleet of men who’s going to colonize some place. He lands on shore, his men are getting off the ship and he says, “Burn the ships.”

And they’re like, “But sir, if we burn the ships, how are we gonna go back? How are we gonna retreat?” And he goes, “There is no retreat. Burn the ships.” Remove any way that you could fall back to something. When I started this company, I quit my job, I had some life savings, and then I got [00:24:00] 10 friends to give me $20,000 each. You talk about burning the ships, there is no going back when your friends’ hard-earned capital is in your business. There is no other outcome than success.

Ian Hathaway: When you remove the exit ramp, you show up differently. With your own savings and your friends’ money on the line, commitment stops being a mindset and becomes the operating system.

But commitment alone isn’t enough. You need resourcefulness, the ability to get creative when conventional paths are closed. Michael Praeger is the co-founder and CEO of AvidXchange, a fintech company he built in Charlotte, North Carolina over more than two decades. He took the company public in 2021 in a deal that produced nearly $5 billion in exit value. Today, AvidXchange has over 1,600 employees and processes more than $200 billion in annual payments. But Michael didn’t get there by trying to do everything at once.

Michael Praeger: one of the things that, I kind of learned, previously to starting AvidXchange related to getting a business off the ground is around the concept of starting kind of small and being really [00:25:00] good at solving one problem for one set of constituents. And I think one of the things that in my coaching with other entrepreneurs that a lot of companies struggle with is day one, they try to boil the ocean and they try to do too much for too many people rather than being really good at one very specific thing.

I would say, don’t try to boil the ocean. Start by solving a very specific problem in a really good way, for a single customer.

Ian Hathaway: Start narrow enough that you can win. Pick one customer, one pain point, and build something so good it becomes the foundation for everything that comes next.

Wade Foster, who we heard from earlier, CEO of Zapier, took the principle of focused validation and made it even more rigorous. If you really wanna know who has the problem, see if they’ll pay for the solution before it exists.

Wade Foster: I just wanted somebody to cut some amount of money. The 100 bucks was totally arbitrary. And so the first 10 or so folks did it that way, and then eventually we switched over to a more self-serve model where people could pay us five bucks to get in for the lifetime of the beta. That was the [00:26:00] path up until we eventually launched. We certainly felt like if we made it free or didn’t ask for money, we would just get a bunch of tire kickers, and that feedback might be different from the people who really had the problem.

Ian Hathaway: Charging early customers filters signal from noise. The people who pay are the ones who actually feel the problem, and their feedback is the only feedback that matters when you’re deciding what to build.

John Lensing, co-founder of OpenLoop, wasn’t working from a sleek startup office in the beginning. He was working from a cafe inside of a grocery store, sending hundreds of letters just to find the first customer.

Jon Lensing: Christian and I were handwriting letters, 300 of them to be exact. Went and bought all the stamps, sat there for hours just getting our initial cohort of doctors to sign up. I mean, we bought like a $20 mailing list off of some like list site that gave us the physicians in Iowa. We got zero responses, but we had one person sign up . Then we got our first office. It was a sublet within a larger office, but our office was 10 feet by 10 feet, and we had a mini fridge and an old Bunn coffee pot from my parents, and [00:27:00] we felt like we made it.

Ian Hathaway: When you’re bootstrapping from zero, that’s what customer acquisition looks like: inefficient, manual, relentless.

Melodie van der Baan is the founder and CEO of Max Retail, a venture-backed platform now serving over 2,000 retailers across all 50 US states. But before that, she went bankrupt at age 21, lost everything in the housing crash, and drove a sprinter van 36 weeks a year selling designer clothes to boutiques. She had to hustle, learning her entire industry one cold call at a time.

Melodie van der Baan: I said, “I’m Melodie from DBC Showroom. I will place your brand into stores for a commission.” So they gave me the samples, and I did not know what I was doing, Ian, but I knew I could pick up the phone. And so I just started calling. “Oh, it’s Melodie calling from such and such.” And they’d say, “What are the price points?” I’d say, “Let me call you back.” Hang up, go look up what a price point was, made the next call. “Melodie calling from so and so. Price points are 69 to 129 wholesale.” They’d say, “What are the deliveries?” And I’d say, “ I’ll call you back.” And I learned this industry one phone call at a time, [00:28:00] one mistake at a time.

Ian Hathaway: When you have nothing else, resourcefulness is everything.

But hustle has a half-life The scrappy tactics that get you from zero to one, the pre-selling, the handwritten letters, the cold calls, eventually take a toll, and you start questioning whether this is actually going anywhere.

That’s when you need resilience, the ability to absorb the doubt, the setbacks, the slow progress, and keep going anyway.

Melodie discovered what she was made of at 21 when everything collapsed, and it’s what kept her going long enough to get to everything that came later.

Melodie van der Baan: I think the gift that I was given that many never receive is realizing that it’s okay to fail, and you don’t die of failure, Ian. And so by 21, I had already thought I gained so much and lost so much, and it was fine. And that just really built me from there on out to keep trying. And it’s funny because if you look at my personality assessment from the predictive index, it says, “Undaunted by failure.”

Ian Hathaway: Failure stops being [00:29:00] terrifying once you’ve lived through it and you’re still standing. When that lesson lands early, it rewires your relationship with risk and turns “What if I fail?” into “ What if I try?”

Even legendary figures like Brad Feld needed that lesson. Brad is an accomplished author and co-founder of Techstars and Foundry Group. His give-first philosophy has reshaped how startup ecosystems around the world operate. But during the dot-com crash in 2000, when one of his portfolio companies was imploding, Brad woke up one morning and couldn’t even bring himself to toast a bagel.

Brad Feld: I really was not motivated. You have those mornings where your engine doesn’t get started. So I’m drinking my cup of coffee. I’m gnawing on a bagel that I haven’t even bothered to put in the toaster because I’m just so despondent. Most of the way I feel that morning is I just don’t wanna fucking do anything. I don’t wanna go out the door. I know what’s in front of me. I know that there’s a bunch of stuff that I gotta deal with, and I’m certain that there’s a bunch of stuff I don’t know about that’s crappy that’s gonna come at [00:30:00] me because every day was just like another pile of new bad. And so Len, came in the kitchen, and I remember him sort of stopping and looking at me and saying, “ Brad, they can’t kill you and they can’t eat you.” The hard stuff is hard. It’s no fun. I’m not happy about it. lot of times it’s really emotionally, stressing in many different ways. But it’s just stuff. Deal with it.

Ian Hathaway: Brad’s story is a reminder that most days are not life or death. They’re just hard. Once you can separate catastrophic from difficult, you get your agency back, and you just keep moving.

But there’s another kind of resilience, the kind you need when the most powerful people in your industry look you in the eye and tell you your entire premise is wrong. When the validators, the ones who are supposed to know, dismiss what you’re building as irrelevant.

Kevin O’Connor co-founded DoubleClick in New York in the mid-1990s . The company later sold to Google for $3.1 billion in what many consider one of the most important acquisitions in Google’s history. His company spawned the [00:31:00] term Silicon Alley, which branded New York’s emerging tech scene as a counterweight to Silicon Valley. But in the early days, he was trying to convince the old media companies to sell advertising on the internet, and one of those meetings was with Michael Bloomberg.

Kevin O’Connor: I didn’t really know who Mike Bloomberg was, and I was trying to get them to have us sell their advertising on the internet. And the guy’s looking at me, he’s like, “We totally get it. We believe you. Internet’s great, but, you know, Mike just doesn’t really believe in the internet.” They’re like, “Will you talk to Mike?” I’m like, “Yeah, I’ll talk to Mike.” What the hell? I don’t know who the guy is. So I’m talking to Mike and I said, “Mike, the internet’s gonna be big. Everyone’s gonna be using the internet.” And he looks at me and he goes, “I’m a fucking mogul, and I don’t use the internet.” And so I started laughing ‘cause I’ve never heard anyone use the word mogul other than discussing Genghis Khan. And Mike Bloomberg’s got that great sort of hang dog face, and he’s not laughing at all. But that was what we ran into. And so our theory became this is inevitable. The old guys running these media companies are gonna die one day. And it all played out. The people that grew up with the internet and [00:32:00] didn’t know anything different eventually took over all these companies.

Ian Hathaway: One of the most powerful media moguls in the world looked at him and said the internet doesn’t matter because he doesn’t use it. Kevin kept building anyway. He understood that being dismissed by gatekeepers doesn’t mean you’re wrong. It might just mean you’re early.

But what about when you’re actually wrong? When it’s not a gatekeeper’s skepticism, but your own miscalculation. When you ship the wrong product, choose the wrong market, hire the wrong person, make the strategic bet that fails. External doubt you can ignore. Your own failures, those you have to absorb.

Isaac Saldana, co-founder former CEO of SendGrid, who we heard from earlier, understands that failure isn’t the end of the journey. It’s only a stop along the way.

Isaac Saldana: if you’re a basketball player, if you don’t make a basket, then what do you do? Well, you just try to play the game longer so that you can make more baskets. And so I think founders should be okay with failing because that’s just part of the process. I’ve seen very, very smart people with funding not succeed. We see that all the time with even very experienced founders. It doesn’t define who you are, the [00:33:00] outcome, but we do get better over time.

Ian Hathaway: You miss a shot, you take another one. The game isn’t over until you stop playing.

Chris Schroeder takes that idea even further. Chris founded HealthCentral, which he grew to over 15 million monthly users and led to a successful exit. later co-founded Next Billion Ventures to invest in emerging markets and wrote the influential book, “Startup Rising,” about entrepreneurship in the Arab world. And Chris believes the real shift happens when you stop treating failure as something to avoid and start seeing it as the only path to getting things right.

Chris Schroeder: you learn, I think quite early in life if you’re paying attention, we don’t want to be wrong, and so we do everything we can to prove that we’re right. When you get knocked down a rut, you start to realize that one of the most powerful things you can do is have almost a wonder or amazement in being wrong because it helps you to get it righter

Ian Hathaway: Getting better starts with getting comfortable being wrong. Chris is pointing to a kind of humility you only learn through repetition, where mistakes stop feeling like identity and start feeling like information. Once you make the shift, you course-correct faster and keep moving.

Ultimately, it’s [00:34:00] about refusing to let failure be the final outcome. And maybe Hernan Kazah actually put it best.

Hernan Kazah: the most important thing is, that irrational commitment that will make them stay involved and work hard when it looks like you’re failing. Because at all companies at some point think that they’re going to fail. We experienced that ourselves with Mercado Libre several times, and you only go through those death valleys if you really believe that failure is not an option.

Ian Hathaway: We started this episode asking what we’ve learned from 25 conversations with outsider founders, and here’s what I keep coming back to: the outsider advantage isn’t just real, it’s structural.

It’s not about overcoming disadvantages. It’s about realizing you’re running a different operating system. One that’s been stress-tested in ways the insider’s path never is.

Being underestimated builds hunger. Geographic constraint forces systematic scale. Capital scarcity creates discipline. Missing infrastructure forces comprehensive solutions. Bootstrapping teaches resourcefulness. Hustle validates what [00:35:00] actually works. Resilience turns failure into data.

These aren’t just compensatory skills, things you develop to make up for what you lack. They’re competitive skills. The kinds that hardwire advantages your well-funded, well-connected competitors can’t match because they were never forced to learn them.

And here’s the deeper insight: The learning never ends. When you’re forged by constraint and built through struggle, you don’t coast. You keep challenging yourself to grow.

Serial entrepreneur Jared Polis, who co-founded Techstars and currently serves as Colorado’s governor, put it like this:

Jared Polis: look, showing up and trying is a big part of it. And I always say, you wanna be in the deep end just paddling above to keep your head above the water, right? You don’t want it to be just so easy you’re like standing in the shallow end. You always wanna be struggling and learning.

Ian Hathaway: Jared is describing a builder mindset that chooses the hard reps early, because that is where skills compound and confidence becomes real. That’s what builds the outsider advantage.

But that’s only half the playbook, because once you’ve built something, once you’ve proven the doubters wrong and scaled [00:36:00] against the odds, a whole new set of challenges emerges. How do you build the culture that actually scales and sustains your values? How do you separate your identity from your company when everything you are is tied to what you’ve built? And finally, maybe most importantly, what do you do to pay it forward in ways that actually multiply? Ways that build the infrastructure so the next generation of outsiders doesn’t have to start from zero.

That’s part two. We’ll be back with it soon.

Outsider Inc. Video Highlight Thumbnail(3): If you want more from Outsider Inc., don’t forget to subscribe to the platform at outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. on YouTube, Instagram, TikTok, and LinkedIn at outsiderincpod. You can also follow me on X at Ian Hathaway.

Outsider Inc. is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation. Until then, thank you so much for listening, and remember, great entrepreneurs can come from [00:37:00] anywhere. See you next time.

​

The latest episode of Outsider, Inc. features Jared Polis, a serial entrepreneur-turned-political leader who has spent his career operating outside conventional boundaries. His career redefined what success looks like in both business and government, and he’s doing it right now as the sitting Governor of Colorado.

Jared’s path has never followed the traditional script. Before the age of 30, he had built and exited three companies for more than a billion dollars in combined value — including BlueMountain.com, an early internet breakout in digital greeting cards, and ProFlowers, which reshaped the online flower delivery industry. Soon after, he co-founded Techstars, the global startup accelerator that’s now backed thousands of companies and helped redefine how mentorship and community can materially change a founder’s trajectory.

But even as he was building companies and supporting other founders, he was being drawn into public service. He studied politics at Princeton, served on the Colorado State Board of Education, and ran for U.S. Congress in 2008. That campaign marked a turning point, not just professionally, but personally. Jared came out publicly during that race, at a time when being openly gay was still considered a political liability. Colorado elected him anyway, making him the first openly gay non-incumbent ever elected to Congress.

He went on to serve five terms and, in 2018, returned to Colorado to run for governor — and won. With that victory, he became the first openly gay man elected governor in U.S. history. But beyond the historic nature of his election, what’s most interesting is how he’s approached the role itself. Jared leads more like a builder than a traditional politician; focused on execution, systems, and outcomes, applying entrepreneurial principles to government in ways that challenge how things have always been done.

In this episode, we get into the early experiences that shaped his entrepreneurial instincts, what he saw in the earliest days of Techstars that made him commit instantaneously, and how being an outsider in multiple dimensions has shaped the way he leads. We dig into how founder principles do and don’t translate inside government, and where he sees the biggest opportunities to build that have an impact now and in the future. ⤵️

Follow: LinkedIn, Instagram, X, TikTok, YouTube

Episode Highlights

In this clip, Jared looks back on his three exits before 30 — AIS, BlueMountain.com, and ProFlowers — and admits the disintermediation pattern wasn't something he saw at the time. He walks through how AIS started with $5,000 split between three college friends, and how ProFlowers ultimately became the most literal disintermediation play of the three.

Here, Jared explains how he used his startup background to push back on policies that frustrated him as an entrepreneur — chief among them, the accredited investor rule. He argues the net worth threshold is arbitrary and a poor proxy for sophistication, and floats the idea of replacing it with a certification test so anyone who can demonstrate the knowledge can participate.

Later, when asked what advice he’d give an outsider about to start their founder journey, Jared pushes back on the premise — no founder is an insider when they’re starting out. His advice: jump in, learn as you go, hold tight to the vision, and stay flexible on how you actually get there.

Finally, Jared makes the counterintuitive point that Congress felt natural to him as an entrepreneur because the job is fundamentally about selling — pitching ideas, adding co-sponsors, working the floor. The governorship was the harder adjustment, since he’d never run anything close to the size of a 32,000-person operation, and he suspects big-company CEOs would actually struggle more in a legislative body than founders do.

I’m super grateful for this conversation with Governor Polis. What sticks with me isn’t the exits, the historic firsts, or the legislative record. It’s the operating system underneath all of it. A kid who spoke up at city council at eleven. A seventeen-year-old trading privatization vouchers on the floor in Moscow. A founder with a billion dollars in exits before thirty. A congressman who worked the floor like a pitch meeting, adding co-sponsors the way a founder adds customers. A governor who ran cabinet hiring like an executive search and seven years later still has most of his original team in place. The through line is that Jared has never really separated building from governing. Identify the leverage point, recruit the right people, ship the work, measure the outcome. The labels change. The instinct doesn’t.

What I took most from this conversation is how understated that kind of consistency really is. Showing up as your full self when the safer move is to hide. Choosing the deep end on purpose — keeping your head just above water because that’s where the learning happens. Treating policy the way a good founder treats product: with conviction on the vision, flexibility on the implementation. If you take one thing from this episode, let it be Jared’s parting line. There’s no such thing as being an insider when you’re starting out. Outsiders don’t wait for permission to build. They just jump in. The water, as he put it, is fine.

Jared’s Library

During the Beyond the Bio segment, I asked Jared about his favorite book and, in particular, something he recommends to aspiring founders. He named one.

Atlas Shrugged, Ayn Rand's classic 1957 novel imagines an America buckling under government overreach, where the country's top industrialists and inventors quietly vanish one by one. Railroad executive Dagny Taggart and steel magnate Hank Rearden try to keep things running as the economy unravels, eventually discovering that a man named John Galt has convinced the world's producers to go on strike and retreat to a hidden valley. Galt's marathon radio speech near the end lays out Rand's case for rational self-interest and laissez-faire capitalism as the only moral foundation for society. The book has been a touchstone for libertarians and entrepreneurs ever since, and a lightning rod for everyone else.

Jared’s Playlist

I also ask guests what are one or two songs that have inspired them on their journey. Jared shared a vast array of musical styles that have inspired him, but he named two specific songs: “The Kid” by Cry Cry Cry, and “Wild Montana Skies” by John Denver.

Up Next: The Outsider Playbook

Next week is a special one — Part One of The Outsider Playbook. After 25 episodes, I started noticing the same patterns showing up across wildly different conversations. Founders building from Argentina, central Missouri, Lagos by way of Birmingham, Des Moines, Detroit. Different industries, different decades, different backgrounds — but a lot of the same hard-won lessons. So we’re stepping back to pull it all together. Part One digs into three threads: what being underestimated actually does to you, why constraint tends to be a feature rather than a bug, and the toolkit every outsider ends up developing whether they planned to or not — bootstrapping, hustling, and the kind of resilience that only comes from getting knocked down a few times. The bigger idea underneath it all is that the outsider advantage isn’t really about overcoming disadvantage. It’s about running a different operating system — one that’s been stress-tested in ways the insider path never is.

Listen on: Spotify, Apple Podcasts, Amazon Music

In this episode of Outsider Inc., host Ian Hathaway sits down with Colorado Governor Jared Polis, a serial entrepreneur and Techstars co-founder who has spent his career blending founder instincts with public service. Jared shares how he built and exited multiple tech companies early, including BlueMountain and ProFlowers, and what those years taught him about capital, timing, and learning by doing. They also unpack how a founder mindset translates inside government, why Congress felt more like entrepreneurship than executive leadership, and how Jared approached policy like a builder. Along the way, Jared discusses accredited investor reform, why wealth is a poor proxy for competence, and the practical systems thinking behind Colorado’s biggest moves, from universal preschool and insulin price caps to Bitcoin tax payments and criminal justice reform. The conversation is a rare look at what happens when a repeat founder brings startup operating principles into politics, and what outsiders can learn from it.

Show Notes:

(03:00) Early work ethic, risk tolerance, and learning in the deep end

(07:00) Three exits before 30 and the pattern behind them

(10:00) Co-founding Techstars and the early days of backing founders

(14:00) Building and scaling ProFlowers and disintermediating the supply chain

(16:00) Running for Congress and stepping into public service

(20:00) Why Congress felt like entrepreneurship, not CEO leadership

(22:00) Founder mindset in policy and the push to rethink “qualified investors”

(23:00) Outcomes as governor, universal preschool, insulin caps, pardons, and more

(19:00) Bitcoin for taxes and treating government like a system you can improve

(32:00) Advice for first-time founders and why every new founder is an outsider

(34:00) Beyond the Bio: Jared Polis

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Jared Polis, Governor of Colorado; AIS; Blue Mountain; Proflowers; Techstars

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Jared Polis: [00:00:00] Congress was actually very comfortable for me as an entrepreneur. I have an idea. I’m like selling people on it. I’m pitching them on it. I’m getting to add their name as a co-sponsor. I’m working the floor. I’ve always been interested in policy, love policy, but like the kind of selling part and legislative part was much more like being an entrepreneur than being a big CEO.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Jared Polis, a serial entrepreneur turned political leader who spent his career operating outside conventional boundaries, redefining what success looks like in both business and in government. And he’s doing it right now as the sitting governor of Colorado.

Jared’s path has never followed the traditional script. Before the age of 30, he had already built three companies for more than a billion dollars in exit value, including blue mountain.com, in early internet breakout and digital greeting cards and pro flowers, which reshaped the online flower delivery industry.

Soon after he [00:01:00] co-founded Techstars, the global startup accelerator that’s now backed thousands of companies worldwide and helped redefine how mentorship and community can materially change a founder’s trajectory. But even as he was building companies and supporting other founders. He was also being drawn into public service, studying politics at Princeton, serving on the Colorado State Board of Education, and eventually running for US Congress in 2008.

That campaign marked a turning point, not just professionally, but personally. Jared came out publicly during that race at a time when being openly gay was still considered a major political liability. Colorado, a state that had been dubbed the hate state just 16 years earlier after Amendment two. Tried to strip away L-G-B-T-Q protections, elected him anyway, making him the first openly gay, non-incumbent ever elected to Congress.

He went on to serve five terms and in 2018 he came back to Colorado to run for governor and won becoming the first openly gay man elected to governor in US History. [00:02:00] But beyond the historic nature of his election, what’s most interesting is how he’s approached the role itself. Jared leads more like a builder than a traditional politician focused on execution systems outcomes, and applying entrepreneurial principles to government in ways that challenge how things have always been done.

I’m excited to dive into the early experiences that shaped Jared’s entrepreneurial instincts. What he saw in the earliest days of Techstars that made him commit instantaneously and how being an outsider in multiple dimensions has shaped the way he leads. We’ll get into how founder principles do and do not translate inside government and where he sees the biggest opportunities to build that have an impact now and in the future.

Governor Polis, welcome to Outsider, Inc.

Jared Polis: Great to see you. Ian.

Ian Hathaway: Thank you so much for being here. I wanna start at the beginning. Your parents are a remarkable origin story on their own. A Princeton PhD who gave up theoretical physics to become a watercolor artist and a poet who became one of the bestselling greeting card writers in America.

Together. [00:03:00] They built Blue Mountain Arts out of a pickup truck, traveling the country, selling posters before growing to dozens of employees. They describe themselves as hippies, and you grew up in the middle of all that, literally traveling to trade shows as a baby, watching your grandmother work, trade show floors and heels for 12 hour days.

Then at age 11 on your own initiative and without your parents’ involvement, you went to San Diego City Council to stop a condo development in a canyon where you played. You spoke at that meeting for about 10 minutes and actually helped change the outcome of the vote. The mayor even credited your speech.

The summer before you started Princeton at age 17, you took the money you’d earn from running a scrap metal arbitrage business out of the government surplus auctions in high school and used it to fly to Moscow where you spent two months as a floor trader on the Moscow commodities exchange.

post-Soviet Russia, early days of capitalism, often the only American on the floor. Most 17 year olds were surfing or [00:04:00] lifeguarding, but not you. When you zoom out on all of that, the family, you grew up in the Canyon speech at 11, the Moscow trading floor at 17. How do you trace the line between those early experiences and who you became as a builder, and was there a moment early on where you first understood that you could actually change the outcome of a situation just by showing up?

Jared Polis: You really did your homework, Ian. That’s great. Look, showing up and trying is a big part of it, and I always say you want to be in the deep end, just paddling above to keep your head above the water, right? You don’t want it to be just so easy. You’re like standing in the shallow end. You always wanna be struggling and learning.

So, yeah, in, in high school I traded scrap metal. These were sealed bid auctions from Department of Defense, and I would figure out what I would get for something about how much it would cost to get there, do sealed bids, and when I got it, I would arrange logistics and trucking mostly, you know, helmets and shell casings, things like that.

And then back to when I went to Moscow, it was a very exciting and hopeful [00:05:00] time. Obviously it worked out terribly for the people of Russia, but this was the time when. Communism had ended. There was a bright future, and the underlying commodity that was being traded were actually privatization vouchers.

It was, and always is interesting to me, how do you privatize a state on economy? They issued every citizen a privatization voucher. Now they had to be aggregated because in practice you can’t have a million citizens showing up with one voucher. So there was a market in these, they were 20, 30 bucks each at the time.

And then they also traded cement. But I didn’t trade cement. I just traded the privatization vouchers and you know how a floor on Chicago Board of Trade or something, I don’t know what they cost, like millions of dollars. Right. To get to the floor. It was equivalent of about a 25 cent admission price daily to be a trader there.

So the barrier to entry was low. You just had to fill out the paperwork and pay about a quarter to be a trader. So that was a lot of fun and great experience. Trans scrap metal, great experience. And then growing up, you mentioned my parents business. Small greedy card company was about 40 people, but it’s a very niche kind of love and poetry look.

People know the look, my mother writes the poetry, my dad does the artwork. And I grew up going to trade shows. My grandmother was sales [00:06:00] manager, so I grew up working and setting up booths the day before the trade show. These are gift shows, book shows, stationary show, all over Texas, New York, Chicago. So that’s what, you know, kind of my job as a 14, 15, 16-year-old in summer was.

And then you, you’re up in the booth usually with my grandmother, with a local commissioned sales rep for three days. You know, writing down greeting card orders that stores would take. So that was also very exciting.

Ian Hathaway: From early on there was this sense of industriousness, this sense of adventure. You finished high school in three years, you said it would have felt like a waste of time to stay another year.

You got accepted into Princeton at age 16, founded an internet service provider out of your dorm room freshman year, selling it for $23 million by age 23. Then you converted your parents’ greeting card business into Blue mountain.com, turning it into one of the most traffic sites on the internet before selling it to at and t for $780 million right before the.com bubble burst.

Then [00:07:00] you went and did it again with Pro Flowers, a direct from grower online flower delivery company that went public and sold for $477 million in 2005. Three exits over a billion dollars combined all before the age of 30. What you pulled off at such a young age is extraordinary by any measure. But I guess zooming out a bit, when you look at those three companies together, ais s Blue mountain.com, ProFlowers, there’s a pattern.

They’re all disintermediation plays. They all scale through network effects and the timing on all three is almost uncanny at that time. Were you thinking in that framework, or does the pattern only become clear in retrospect?

Jared Polis: It definitely only becomes clear in hindsight. In fact, as you were talking, it’s the first time people made me think of a IS as a disintermediation play, but in a sense it is.

We bought T one lease line access, sold dial up. Internet accounts and and lower speed lease line accounts? No. The thought processes on that was much simpler. Obviously, somebody who’s entrepreneurial, two friends I met through mutual friends at Princeton. They were both at U of I at the [00:08:00] time. Josh and Mike.

We kind of just were talking about what can we do without much money. We didn’t have capital, right? We had maybe between us, I think $5,000 or something. So like, what can you do? We said, you know, this internet thing is pretty cool. We as college students get to use it. It hadn’t gone mainstream yet. We actually thought the initial target market for internet accounts, if you will.

Unix based. This is before graphical Worldwide web. There was something called links, which was interface, but generally speaking, you had to be somewhat familiar with Unix. But you know, pine and and Mail were the two programs you used to read your mail. But in any event, I think that when college students graduate, many of them would want to pay 20 bucks a month to like keep.

An internet account. ‘cause at that point the colleges would kind of terminate it. There were sort of gateways to the internet from like the big commercial providers, A OL, CompuServe, prodigy. But then you had a weird looking account, you know, how do you get kind of a regular account even with your own domain?

And so that we thought was the target market, right? And it was a market. We certainly had those, but we quickly moved more into kind of where the money is, which it turns out is not. People have just graduated college, and it’s generally more on the business end. And when we sold the [00:09:00] company to a company called Exodus, which was doing a roll up, 98, I believe we started at 93, sold it in I think 98.

We were basically a third or third, a third, a third dial up internet access, a third commercial high speed corporate connectivity, and a third kind of web development, consulting services and hosting. Exodus paid us mostly based on the. Hosting and consulting piece. But yeah, that’s that story. In retrospect, the biggest disintermediation play was obviously pro flowers.

We literally disintermediated the supply chain rather than flowers, going from a grower to a wholesaler to retailer, to out on the delivery van. We worked directly with the growers importers, utilizing people like FedEx and UPS to get’em the point of delivery. So fun business

Ian Hathaway: continuing on your entrepreneurial journey, especially in Boulder, Colorado, and the startup community there.

Brad Feld, of course, has been on this show and he told us about the moment that Techstars was really born. He steps out of a meeting with David Cohen for the first time after David had pitched Brad on the idea of Techstars. [00:10:00] Brad calls you and says, I’m putting 50 K into this thing called Techstars, and your answer to his telling was something like, I’m in for 50 K.

What is it? It’s an amazing story that. To me is so fitting as a founding story for Techstars, given its cultural DNA of Giving first and a community orientation. Going back to that moment, what were you actually trusting that you were committing to that idea so fast, and maybe what’s the lesson that others can take away from that example?

Jared Polis: So going back to that moment in time, I was actively doing Pro Flowers. I was probably chairman of their board at that time. We’d have to look at the exact year. I had exited a IS exited Blue mountain.com. I don’t think Pro Flowers was public yet. It went public in oh three, so it was probably a little bit after it was a publicly traded company.

So I was excited by startup ecosystem. I think that the initial pitch was, we wanna do something like a startup accelerator here in Boulder. And I said, count me in. I was actively involved with and looking at a number of other startups. Some did well and some didn’t. I didn’t wanna be a, a manager [00:11:00] of a fund, but I wanted to kind of look for fun things that were also had a lot of upside and get a little involved to medium involved as a model.

I didn’t really plan to go back into like a day-to-day operating capacity where I could just do one thing, like CEO of a medium sized company. So. Tracking startups in accelerator Boulder was very exciting to me. I knew Brad for a number of years at that point. I met him in 96, so I probably knew him a decade or or eight or nine years.

I did not know David, but Brad vouch for him, met with him later on. Super excited and really excited by the concept. At that point, it wasn’t necessarily thought of as a scalable concept, as you know. It was like, we’re doing this in Boulder, right? We’re gonna bring people to Boulder. We’re gonna have fun with these companies.

Obviously later on, scalable, many cities, perhaps too many. You know, resized and, and hopefully pivoting. But at that time, very much let’s do something special here in Boulder.

Ian Hathaway: It’s interesting you mentioned that you wanted to get involved, you didn’t wanna run a fund, but you wanted to scale your activities more in Boulder.

That’s exactly the reason that David has given for his initial motivation, which, you know, he had just gotten out of an exit and wasn’t really satisfied with the engagement model from angel investing. [00:12:00] It was sort of write a check and move on. And so it’s interesting that you share that.

Jared Polis: Yeah, and that was very much the meeting of minds.

I was very excited about that level and picking the 10 companies the first few years and very, very hands-on. It was a lot of fun. As people that I met in those first few Techstars classes, I still keep in touch with.

Ian Hathaway: Well, that tradition still lives on today. It’s what drew me in. I was a Techstars mentor for five years before I became an employee.

I’ve been out of Techstars as an employee for four years and I’m still mentoring, so it lives on to this day. Jumping ahead. Techstars goes on to back thousands of companies worldwide, but what it really pioneered was this philosophy, the idea that mentorship and community, if done deliberately, can materially change outcomes for founders.

And you were mentoring actively, especially early on, including during your 2008 Congressional campaign finishing campaign events late at night and going straight into mentoring companies afterwards. That’s a big commitment of time and energy, not [00:13:00] just capital. What did you understand early on about what founders actually need that goes beyond capital, particularly for founders who, like you were building tech companies far from Silicon Valley, and maybe secondly was your experience as a founder and motivating factor for wanting to help the next generation of entrepreneurs coming up behind you.

Jared Polis: So I had founded businesses both with and without partners and, and a ISI had two very much coequal partners. Three of us ProFlowers I founded on my own. We brought in executive leadership, but for me the innovation was distribution technology. We innovated, patented. It was great. It is kind of fun. I’ll explain this to you, but basically these flower growers were pretty low tech, and so at the time, my value proposition to them was.

We are going to literally give you a fax machine and we will fax you the dynamically generated FedEx label and the card and the packing list all in one perforated form. And then all you have to do is assemble that and ship it off, and they come every day at three or four. So it was really [00:14:00] a solution that worked with.

Folks that maybe didn’t even have computers. We were among FedEx’s, I think the very first to do a dynamically generated shipping label through T-C-P-I-P. No, nobody had done that before. We were their pilot, which was really cool. I actually went to Tennessee and met with Fred Smith. That’s how important this was at the time.

It was a really cool meeting and they were like, okay, we’re gonna pilot this with you, and we were the first to do that. We didn’t even require that the growers had pc, so that was my innovation, but I realized we had to acquire customers. This was not an innovation, but we quickly had to become experts in customer acquisition, pricing and models, and I had to bring in that expertise of cost of customer acquisition, lifetime cost of customer, how do you do it across different channels to build on this proprietary advantage that we created that allowed it to be sold.

I didn’t really answer your question there, but through that experience I kinda learned how do you access different expertise, right? Okay, great. Your supply chain solution fine. How do you access expertise on selling through different channels or through marketing or finance if you’re gonna be doing some kind of a raise in stack?

So that was for me as a founder, what I wanted to [00:15:00] help other founders with, and wasn’t always me providing direct expertise. It was more how do we connect people to people who’ve been there and done that in areas. So the founder might not realize that they need to get to know very well in addition to their core competency for their innovation.

And

Ian Hathaway: sometimes you don’t know where that answer’s gonna come from. I think that’s one of the magical things about the Techstars mentorship model is that you bring lots of mentors together. Some of them might on paper feel like the perfect fit for a specific company, but others may have some hidden networks that wouldn’t be clear from a resume that’s actually the right person you needed to meet.

And so I think there’s a good lesson in innovation there that it’s really a numbers game and you just gotta take a lot of at bats.

Jared Polis: Yeah, and Colorado is a good size. It’s just very accessible. I mean, through, you know, an introduction, a one-on-one, you can meet with anybody and everybody, as you know. So you can usually access that expertise across different sectors when you need it.

And just you talk to people and sometimes that results in board of advisors or even more.

Ian Hathaway: And so continuing in 2008 on that. First Congressional campaign of yours to be US Congressman in Colorado. [00:16:00] You decided to come out publicly during that campaign. Colorado had been called the hate state just 16 years earlier when Amendment two was a statewide ballot measure to constitutionally strip anti-discrimination protections for L-G-B-T-Q people passing with 53% of the vote in Colorado.

The Supreme Court struck it down in 1996 and then 12 years after. The Supreme Court struck that decision down. You’re running in that same state as an openly gay candidate for Congress. That decision has a parallel to something a lot of founders face, something we’ve talked about on this show before, which is whether they should bring their full self into a high stakes situation where being different might work against them.

Whether that’s pitching investors, hiring a team, or building in public. When you decided to come out during that race, what made you decide that showing up as your full authentic self was the right decision? And maybe what did you learn on the other side [00:17:00] of that decision about yourself and about the public You hoped to lead?

Jared Polis: Well, so I was obviously out to my family. I had a boyfriend, he’s now my husband. But what was awkward at that moment in time, it’s probably even still true, is that there needed to be some like public acknowledgement. Otherwise, maybe somebody would’ve asked me at some point and I would’ve said yes, but you wanna do it on your own terms.

‘cause it had never like appeared in print. It had never like been public. So it was a really. Awkward thing, and that was the reason. It was more just, okay, obviously at some point this’ll come out. I mean, I’m not, I wasn’t like super closeted per se. It wasn’t official. Maybe people whispered or some knew, but how do you do it on your own terms?

And that would be the same for any corporate messaging announcement is, yeah, you always wanna do things on your own terms, right? This wasn’t bad news, it wasn’t good news, it was just kind of news that was material, I suppose, to some people. But how do you go about presenting material news in your own way?

And owning it, rather than just sort of, it randomly coming to you in some way where it could be portrayed as something negative. But I do think it’s important to bring your full [00:18:00] self. Another story is when I was raising capital for some of these companies, part of it worked to my advantage, being young.

I was like, you know, 23, 25 pitch deck for the internet. That’s who people wanted to invest in. If you were 55 or my age, now I’m 50. At that time you were not expected to know the internet. If you were 50, there was kind of reverse age discrimination. So I was the right age at the right time to kind of say, oh yeah, here’s a young guy who knows the internet.

This is who we wanna back.

Ian Hathaway: You raise a good point. I think it’s still an issue today. What people don’t realize is actually even amongst high growth entrepreneurs, even venture backed entrepreneurs, the average age of a successful outcome, the founder is around early to mid forties. That time of founding, but that’s a great point.

Age discrimination in tech is a real thing. Sticking with your time in government, you came into Congress with a background that almost no one else had. You built companies, you co-founded an accelerator. Manage real organizations with real outcomes, and you clearly brought a different operating philosophy.

You were the only Democrat in the Liberty [00:19:00] Caucus. You wrote a paper on privatizing the postal service you called Atlas Shrugged, a great book. You were the first representative to accept Bitcoin donations. This all made fellow Democrats nervous. That’s a very different operating system than how the government typically works, especially the legislative branch.

What did you learn about where that way of thinking like a builder, like an entrepreneur, actually moves the needle inside government in an effective way and where it just runs into a wall.

Jared Polis: Let me also give a little context. So while I was doing entrepreneurship in the 2001 to 2007 timeframe pre Congress, I also was involved with education in a entrepreneurial way.

I started two charter schools, and then I was a chairman of both For a while. I actually came in and ran one as superintendent for a year or two. That’s what I would’ve kept doing for a while had I not run for Congress. So I was really an entrepreneur in that kind of nonprofit sector with the charter schools and doing some philanthropic work.

Congress was actually very [00:20:00] comfortable for me as an entrepreneur. I probably had to grow into some of the skillset to be an effective governor ‘cause I had never run anything large, but Congress, there’s 4 35 of ‘em, as I used to say, was someone to be an entrepreneur. I have an idea, I’m like selling people on it.

I’m pitching them on and I’m getting to add their name as a co-sponsor. I’m working the floor. Knowing policy is something that’s a hobby. I’ve always been interested in policy, love policy, but like the kind of selling part and legislative. Was much more like being an entrepreneur than being a big CEO. I think the big CEOs who have some running things going into a legislative body hard adjustment for them.

And maybe you talked to some, maybe some enjoyed it, some didn’t, but it would be a very, very, very different thing. It’s a lot more similar to being an entrepreneur than it is to running something large. When you went a legislative.

Ian Hathaway: So your effectiveness in Congress then maybe bridging these idea of Techstars giving first, right.

Help someone without the expectation of receiving something in return. Was that a way for you to build bridges and build relationships and ultimately build coalitions to get things done? Or is that just like a [00:21:00] completely naive way to think about how to operate inside the halls of congress?

Jared Polis: I’d say I put time into the personal relationships like you do as an entrepreneur too, and the members appreciated that.

I had many good friends and trusted friends on both sides of the aisle. So when I wanted to work on something, I was able to get bipartisan folks to hear us out and get us on. So I did put time and effort into that. It’s an interesting way to talk about it, but I think understanding. That people like to attack Congress, attack politicians.

I get that. But by and large, these are dedicated people who care deeply about the country. I mean, it’s a ton of work. Most of ‘em would be making more money with a much easier lifestyle for what they weren’t doing this. So you gotta respect them. They’re there to make a difference, not not every single one, but the vast majority.

And so you really kind of get point, Hey, what got you into this? What do you care about? And try to form that basic values discussion and go from there on different policies.

Ian Hathaway: That’s been actually my experience as well. I’ve been involved with this organization called The Center for American Entrepreneurship, which is advocating for entrepreneur friendly policies in DC until last year was on the [00:22:00] board.

Wendy Lee, a mutual friend of ours, also serves on that board. We go to DC every year and I meet with members of the house in the Senate and what I tell people. Is that everyone’s really normal and we talk about really serious things, and all we’re focused on is getting things done. It’s nothing like the television spectacle, and so to me that’s encouraging in a way that maybe most folks don’t get to see.

Jared Polis: Sometimes I was able to use my startup sector knowledge and policy advocacy a number of different times, but one that comes to mind is having the concept of color qualified investors always irritated the heck outta me. I thought it was ridiculous that just because you weren’t super wealthy. You weren’t allowed to invest.

And I also said, just ‘cause you have a lot of money doesn’t mean you’re smart. I mean, there’s plenty of people that got a lot of money and they aren’t any more sophisticated than somebody who’s 25 years old and worth a hundred thousand dollars. So having this arbitrary like net worth validation for qualified investor was just something that irritated me.

So I kept trying to pound away at that from the day I got there and maybe replace it with a. Tests people take to get certified rather than a net worth thing. So [00:23:00] it was interesting to be a startup congressman. I worked on a number of tech issues. I formed an entrepreneurship caucus with Darryl Isa, a Republican.

He’s actually still there. He was an entrepreneur as well. So there were a handful of us, maybe 10, 12 of us that had that in our background.

Ian Hathaway: After five terms in Congress, you came back to Colorado and ran for governor, which is a fundamentally different job. You’re not voting on things, you’re running something, a large organization with real accountability and outcomes that you can actually measure.

And by that standard, the list of what you’ve gotten done is striking. You abolish the death penalty and commuted every death row sentence you pardoned. Over a thousand marijuana convictions. You launched free Universal preschool and all day kindergarten. You kept insulin prices. You eliminated state taxes on Social Security for seniors.

You made Colorado the first state to let residents pay taxes in Bitcoin. You signed abortion protections and gender affirming care into law. You signed the free range parenting bill before you were [00:24:00] governor. You founded two charter schools, as we just discussed, the New America School for Immigrant Youth who’d aged out of the traditional system and the Academy of Urban Learning for homeless teenagers.

Through the Jared Polis Foundation, you put thousands of refurbished computers into Colorado schools at a time when most kids in underserved communities didn’t have access to one. That’s not a legislative record, that’s an operating record. So I want to ask. How do you actually think about governance? Is running a state closer to running a company than most people expect?

Is that just a cliche? And where does that analogy break down?

Jared Polis: So, I had not run a large company when I came into state government. To me, the largest company that I had. And I wasn’t running it at the time as CEO, it was pro Flowers and at the time we sold it, it had 250 people. Right. And so to me, as an entrepreneur, 250 people was huge, right?

Like that’s, you know, I was not a big company guy. Like, oh yes, we have 8,000 employees in 16 different cities, right? But when I came into governor, we had 32,000 employees [00:25:00] roughly for the city of Colorado. So the first thing I had to do over two months was basically recruit my cabinet. We’d open applications for every cabinet position.

‘cause the way the government works, state government, it’s more like a conglomerate. We have different operational units. I had to hire the guy that runs Department of Corrections in our prisons. I had to hire the person that runs Department of Transportation and fixes our roads. I mean, we do very different things across state government.

We run colleges. We keep prisoners. We fix potholes. We license different professions. We monitor air quality. So 19 different cabinet positions. And I was experienced, I had some experience with hiring executives, right? I had done executive searches, not just my companies, I’d been on boards of others and been part of that, brought in high level executives, usually C-E-O-C-F-O.

So that was familiar to me and I was very proud of the fact that we had great tenure. In fact, here we are. Seven years later, and I’d have looked at the numbers, but I think about 70% of my original cabinet is still in place, which is huge for a governor. There’s usually a lot more turnover than that, certainly more than half.

We have great people. They’re really the ones that [00:26:00] run their divisions well, and as I said, when I was facing reelection, which I won by almost 20 points, I told my cabinet, I said, I’m here because your work excelling in your areas. People are happy with the work we’re doing, and that reflects on me and my reelection.

Ian Hathaway: You’ve been intentional throughout your career about. Not leading with identity, but you’ve also made a lot of history, so it’s natural that that becomes a part of the story. At the same time, you’re a father, you’re a husband, you’re someone who plays League of Legends to wind down at night, given those real personal responsibilities and human desires.

How do you stay grounded in who you are as a person outside of that role of Governor, Congressman, or CEO? And what are some tips that entrepreneurs out there listening can learn from your example?

Jared Polis: I think it’s obviously not only possible, but important that if you have a high power job, you also have a personal life.

I mean, for me, it’s having two kids, right? Which I didn’t when I first started. When I got elected to Congress, I didn’t. But we have two kids. One’s a teenager, another’s, almost a teenager, so [00:27:00] they’re middle school and high school. And it’s fun to spend a lot of time with them growing up. And obviously when you’re in a high power position, you never know.

You might get called or texted at any hour or day or night. You try to deal with it quickly, but it is important to have that balance. It’s hard in Congress in particular because of the travel and the job, right. Just so people don’t understand the, which Congress people do. They basically fly to DC every three to four days.

And then back home for three to four days. So your family could try to live in dc they could try to live home, but they’re basically, you’ll be with ‘em half the time, and that’s a sacrifice that members of Congress make. It’s also one of the reasons there’s fewer younger members of Congress. It’s very hard when you have young kids to do that and respect those who do.

As governor, obviously I’m able to be home pretty much every night. Our state’s a big state, and very rarely, three or four times a year, I might have to spend a night in some corner of our state, but generally speaking, home every night.

Ian Hathaway: Well, maybe just double clicking on that. Being a parent and having a demanding role, I have a demanding job.

My wife has a demanding job, but I view the role of Father as the most important job that I have. How has being a father made you better at all of these different [00:28:00] roles?

Jared Polis: It’s definitely helped me view the work I do in, in education more from that consumer lens. It’s always how I viewed it, but I also kind of came to it more from like, okay, do you have a thriving economy?

We need to make sure we have people with the skills to power the private sector. And that’s great. And it’s high level. Yeah. But it’s also about individual learners and, uh, how many kids do you have, Ian?

Ian Hathaway: I have three boys.

Jared Polis: You have three and I have two. And and you probably experienced this too, they’re very different.

Like my kids are different learning styles. They’re just totally different and every kid’s different. Right. And, and that’s why the challenge we have in our schools, in our workforce preparation programs is how do you meet the individualized learning needs of every kid, right? Diversity of learning styles, opportunities, outcomes that they seek.

Empowering parents and kids with information to make good choices. Colorado has open enrollment, school choice, a wide variety of different schools. But making that work for people. Certainly my experience as a parent help connect the dots. Obviously, I still believe we have to be competitive in the private sector.

We have to make sure we have kids graduate with the skills they need to power our economic success. Of course, ‘cause [00:29:00] everybody’s kid needs to work in, you know, an economic powerhouse and a rising tide. Obviously loose all boats, but there’s a lot more to it than that.

Ian Hathaway: I love the way you answered that. I grew up in Ohio, but I live in Santa Barbara, California, not the cheapest housing market in the country by any means.

And it’s interesting, most people say, I hope I can have enough wealth so that if my kids, when they get older, if they ever want to come back here, I can buy them a house or help them buy a house. And the way I think about it is, how can I help create a job for them to bring them a magnet back? And, and as you said, as governor, you’re thinking, how can I keep my state vibrant so that my kids will want to stay here so that they will have.

Opportunities.

Jared Polis: Yeah. Especially because the economy is information and skill-based. Do we have things like natural resources and ag land and are those top areas? Of course. But the bulk of our economy is what people have up here in our state. So it’s really about will we be competitive and human capital?

Will we be competitive and growing our own and attracting the best and brightest and hardest working people from across the country and across the world [00:30:00] to choose to deploy their talents here in Colorado and here in the United States.

Ian Hathaway: Well, Colorado is famously a magnet for talent growing more so every year comes with it, some growing pains, but it’s a problem of abundance that I’m glad you’re solving.

Speaking of your time as governor, your term limited this year, and we’ll be out as governor at 51 years old when your term expires next January. George Will, the conservative columnist once wrote that you’re someone the country is hungry for, and it’s hard to disagree with that. When you look at the moment we’re in right now, people are exhausted by polarization and the noise just seems to keep getting louder.

Leadership at the national level feels increasingly disconnected from solving the problems that people care about most, but you’ve proven that you can lead differently with thoughtfulness. The unconventional approaches and actual results being accountable to the public. So I have to ask, given where the country is right now and what [00:31:00] you’ve been able to do, is there any reason why you shouldn’t run for president?

Jared Polis: Well, it’s a very unpleasant experience to run for president. You probably heard that. I actually enjoyed running for Congress. My first race for Congress was a lot of door to door. It was fun for me every day. I went door to door five, six days a week, basically five to 8:00 PM in summer, four to six in winter.

So just meeting people talking. I enjoyed that. I was like in encyclopedia salesperson. You know, running for president, we’ve made that horrifically unpleasant. And then we wonder why no sane person wants to do it. It’s because it’s kind of a horrific thing. As I said, if the whole country begged me to do it, maybe I’d do it for a few years, but I don’t wanna run.

‘cause it’s really just horrific. I mean, it’s just two years outta your life and. And you know, just be honest, at the end of the day, probably a one or 2% chance of winning, which is great. It’s higher than you, right, Ian? Right. I have a one or chance, but I mean, you know, to invest when I have a lot I can be doing to say I’m gonna put two years of my life on something that, I mean, when you do a startup, you [00:32:00] realize the odds are against you, but they’re better than one or 2% right.

Ian Hathaway: I guess you have to start somewhere and if the whole country needs to beg you, maybe I’ll be the first. So hopefully we can get you to consider that. Maybe my last major question for you, you’ll have spent the better part of two and a half decades in public life by the time you leave Office State Board of Education, five terms in Congress, two terms as governor.

The historic first will always be attached to your name. First openly gay man, elected governor, first sitting governor in a same-sex marriage, first Jewish governor of Colorado. But those are designations that describe what you are, not what you’ve built. And when I think about what you’ve actually built, the New America School.

The Academy of Urban Learning, which you started even before Congress for kids who had fallen completely through the cracks. The Jared Polis Foundation, putting thousands of computers into schools that didn’t have them co-founding Techstars and mentoring companies on weeknights during a congressional campaign, abolishing the death penalty, universal [00:33:00] preschool, the ecosystem of entrepreneurs and founders you’ve tried to cultivate at the state level.

That’s a lot. Not to mention your insanely successful business career as a teenager and a young man. Looking back on all of that, putting the labels aside, the accomplishments, what are you most proud of? Not necessarily the history making moments, but the thing that you actually set out to build.

Jared Polis: Well, as you said, I’ll be 51 I guess when I’m done, which it helps me feel young to know that both of the candidates to be my successor will be older when they start being governor than when I finish being governor.

So I’m a little in heartened by that. It’ll be fun to see what comes next. I obviously love business and entrepreneurship and be nice to be able to spend more time with my family and those sorts of things, and we’ll figure out what comes next.

Ian Hathaway: Okay, so we’re almost out of time, but here on Outsider Inc.

We like to finish with a segment called Beyond the Bio. These are just some quick hit questions that let us step away from your resume and get to know you a little bit [00:34:00] better.

Jared Polis: Okay?

Ian Hathaway: All right. What’s a quick piece of advice from a mentor that has stuck with you on your journey?

Jared Polis: Just work hard every day at every task.

Ian Hathaway: Who is an unsung hero in your life and what has been the impact they’ve had on you?

Jared Polis: My parents obviously have been a great support network and, and just wonderful people

Ian Hathaway: who is someone in the Boulder or Colorado entrepreneurship community who doesn’t get enough credit and deserves a shout out from you.

Jared Polis: Good question. Obviously Brad does deserve the credit he get, but he, he’s not somebody that is unsung by any means. I would say. You know who ran, he ran Texas for, while David Brown probably is a little bit more unsung and he is teaching entrepreneurship at cu, I’ve guest lectured in his class and. Great guy and he’s a little bit more low key than some of the others, but deserve a lot of the credit.

Ian Hathaway: Great call. Tell us something most people don’t know about you. Something outside of work could be a hobby, a favorite travel spot, a guilty pleasure, or maybe even a hidden talent.

Jared Polis: It’s probably won’t surprise too many people, but I enjoy skiing with the kids. Don’t make it up a lot as [00:35:00] governor, but maybe five, six days a year.

So enjoy skiing.

Ian Hathaway: Yeah. Gotta support that Local tourism economy. What are one or two songs you’d like to add to our Spotify founder’s playlist? Something that maybe fuels your workday or has inspired you on your journey as an entrepreneur?

Jared Polis: These have to be. Short answer, Ian, that’s hard. I don’t know. In our family, my husband picks all the music and he plays it.

Luckily we have similar tastes, so Sarah Brightman, Barbara Streisand from Modern Stuff. Love Lady Gaga, but favorite songs that inspire entrepreneurship. I’m gonna go with The Kid. I by Cry. Cry Cry. And Montana Skies by John Denver. Those are two that always inspire.

Ian Hathaway: Oh wow. John Denver. Amazing. Those

Jared Polis: are both, you’ll have to look them up and you’ll have to add them to your lists.

Ian Hathaway: Okay, we will, I know this one is maybe even more difficult, but a book you might recommend, you know, maybe something that has been especially valuable to you on your journey, or maybe something that every first time founder should read as they’re getting started.

Jared Polis: Well, I would always recommend Atlas Rug by Anne Rand for sure.

That’s one of my favorite [00:36:00] books. In terms of what else I read, I, I usually pick an author and I just read through like all their works. Agatha Christie is one that I’ve read through all of her works. It’s just fun and easy reading.

Ian Hathaway: Yeah. Or the correct answer was The Startup Community Way by Brad Feld and Ian Hathaway Startup Community

Jared Polis: Way by Brad Feld and Ian Hathaway non-fiction category.

Ian Hathaway: Oh man. Well, it depends which ecosystem you’re in. Sometimes that might be fiction, but, uh, so, okay, so last question. If you could give one piece of advice to someone who’s about to start their founder’s journey, particularly someone who’s a bit of an outsider, what would it be?

Jared Polis: There’s no such thing as being an insider, as a founder, starting your journey.

So just do it. Jump in the water’s fine, and you just gotta learn as you do it and keep that vision, that powerful vision, that founder’s vision, and be ready to pivot on how to implement and make it work.

Ian Hathaway: That’s an inspiring way to end. Governor Jared Polis, thank you so much for joining us today, sharing your wisdom, your time.

I cannot wait to share this episode with our [00:37:00] listeners.

Jared Polis: Thank you, Ian. Take care.

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big thank you to Governor Jared Polis for joining us and sharing his remarkable journey. What stands out about Jared isn’t just the exits, the historic first or the legislative record.

It’s the operating system underneath it all. A kid who spoke up at a city council at 11, a 17-year-old trading privatization vouchers in Moscow, a founder with a billion dollars in exits before 30, a congressman who worked the floor, like a pitch meeting, a governor who ran cabinet hiring like an executive search.

The through line is that Jared has never really separated building from governing. Identify the leverage point, recruit the right people, ship the work, measure the outcome. The labels change, the instinct doesn’t. What I took most from this conversation is how understated that kind of consistency really is.

Showing up as your full self when the safer move is to hide. Choosing the deep end on purpose treating policy, the way a good [00:38:00] founder treats a product. Jared’s career is a reminder that outsiders don’t wait for permission to build. They just jump in. The water as he put it, is fine. If you want more from outsider, inc, don’t forget to subscribe to the platform@outsiderinc.substack.com.

It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. On YouTube, Instagram, TikTok, and LinkedIn at Outsider Inc. Pod. You can also follow me on X at Ian Hathaway Outsider Inc. Is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation.

Until then, thank you so much for listening and remember great entrepreneurs. Can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features Chris Schroeder — entrepreneur, investor, and author who’s spent the last fifteen years chasing a question most people in his position never bothered to ask.

Chris built an impressive career. Harvard. Two presidential campaigns. A State Department tour under James Baker. Wall Street, private equity, and then CEO and Publisher of WashingtonPost.com. He co-founded HealthCentral, backed by Sequoia, Carlyle, and Barry Diller’s IAC, grew it to over 15 million monthly users, and reached a successful exit. The next move was his to pick.

But in November 2010, he went to a startup gathering in Dubai, and something broke open. He realized he’d been living inside his own narrative bias, missing an entire generation of founders building across the Middle East, Asia, and Latin America. Instead of chalking it up as an interesting experience, he followed the thread.

That journey became Startup Rising, the first book on entrepreneurship in the Arab world — built on more than a dozen trips to the region and conversations with 150+ founders, investors, and operators. Chris went on to co-found Next Billion Ventures and backed exits like Careem’s $3.2 billion sale to Uber.

But the credentials aren’t really the point. What makes Chris different is that he actually goes. Millions of miles logged to places most investors don’t think about, asking better questions than the people who stayed home.

In this episode, we get into where the curiosity came from, why he walked away from the obvious path, and what fifteen years on the road has taught him about where the next great companies are actually being built. ⤵️

Follow: LinkedIn, Instagram, X, TikTok, YouTube

Episode Highlights

Chris unpacks the power of being wrong. He illustrates this point with two bookend moments he experienced that made him permanently suspicious of expertise. From experts dismissing the fall of the Berlin Wall weeks before it happened, to others who missed the Arab Spring weeks before it erupted, he makes the case that real insight lives closer to the ground than most people think.

Next, Chris recounts a meeting where entrepreneurs from Latin America, Africa, and Asia told him the Chinese tech community understood them in a way Silicon Valley never has. What follows is a sharp take on why American investors keep missing the mark in emerging markets and what actually shows up in the room when rising markets talk to each other without the American playbook front and center.

And here, Chris lands on one of the hardest-won lessons of his career: if you understand the incentive structure, you can predict with near certainty how people will behave. I pick up the thread with a question I put to founders all the time — do you actually know how your ideal customer earns their Christmas bonus? The answer to that question provides more insight into who buys your product than you might think.

Finally, Chris makes the case that being on the ground is a completely different exercise than consuming information from a distance, because you see behaviors, talk to cab drivers, and catch the 11pm conversations over beers that you'd never get on Zoom. This gives him a more complete picture of what’s happening in the places he’s trying to better understand.

I’m super grateful for this conversation with Chris. What sticks with me about this conversation isn’t just Chris’s resume. It’s what he did in Dubai in 2010 — walking away from a path that was basically paved for him to go chase questions most people in his seat never think to ask.

He traded certainty for curiosity, expertise for exploration, and the last fifteen years have pretty clearly vindicated the call. The story lands not because of the miles logged or the deals backed, but because of the posture underneath it all. Chris has built a career on a simple idea: the most powerful move isn’t saying what you know — it’s owning what you don’t. Humility isn’t soft. It’s exploration. Being wrong isn’t a failure; it’s usually the first honest step toward getting it right-er.

If you take one thing from this episode, let it be this. The best investors, builders, and operators aren’t the ones with the cleanest answers. They’re the ones still asking sharper questions than everyone else in the room. Go. Get on the ground. Push on your own narrative bias. Don’t let the real story pass you by while you’re deferring the hard questions to a third cappuccino. The next great founder or market is almost certainly taking shape somewhere you haven’t thought to look — and the only way to find it is to show up.

Chris’s Library

During our conversation, Chris and I discussed his love of books, and his audacious goal of reading 150 new books each year. He called out a handful by name in the episode. Brief summaries and links to a few of them are below.

Startup Rising. Chris Schroeder’s on-the-ground report from a startup scene most Americans didn’t know existed. After more than a dozen trips to the Middle East and 150+ conversations with founders, investors, and operators, he came back with a simple argument: a generation of young builders across the Arab world — phones in hand, “why not us?” on their minds — was quietly reshaping what was possible in places most Western investors had dismissed. Marc Andreessen wrote the foreword and called it a potentially trillion-dollar question hiding in plain sight. This is a great book on understanding entrepreneurial ecosystems generally, and the Middle East specifically. It made my visits to the region more enjoyable and productive. I highly recommend it to anyone doing business in the region.

The Hard Thing About Hard Things. The honest version of the job of a tech CEO. Famed venture capitalist and former entrepreneur Ben Horowitz writes about the stuff nobody brags about on Twitter — laying off people you love, firing a friend, demoting a loyal exec, keeping your own head on straight when the whole thing is on fire. A lot of it comes from running Opsware through the dot-com crash and eventually selling to HP. Less a business book than a survival manual for founders in the thick of it. This is one of the first books I read on startups and was floored by how different it was from the others (and aligned with my experience working at my first company).

What You Do Is Who You Are. Another Ben Horowitz gem. His core argument is that culture isn’t your values deck or your all-hands slides — it’s what people actually do when you’re not in the room. He makes the case through four unlikely stories: Toussaint Louverture and the Haitian Revolution, samurai Japan, Genghis Khan, and the prison code of Shaka Senghor. The takeaway: culture is built through behavior, and you end up with the one you actually design, whether you meant to or not. This is one of my all-time favorite books on any subject and I recommend it to founders all the time, particularly new CEO’s who are slowly realizing that culture is destiny.

I Deliver Parcels in Beijing. A Chinese gig worker spends eight years bouncing through 18 different jobs — parcel courier, warehouse floor, convenience store, you name it — and writes about all of it. It started as a blog, went viral, and became a book. What makes it great isn’t the big picture; it’s the small stuff. The pace, the ridiculous rules (the no-bathroom-break thing is real), the quiet negotiations workers make with 996 culture and the expectations their parents still carry. Funny, sharp, sometimes gutting. It’s the China you don’t get from the experts.

Chris’s Playlist

I also ask guests what are one or two songs that has inspired them on their journey. Chris shared a vast array of musical styles that have inspired him — from Bach (which he wrote Startup Rising to) to Jazz to Korean hip-hop (he called out the artist Lee Young-ji specifically) to Quincy Jones to Kendrick Lamar. He named one specific song, Rakim’s “Paid In Full”. Chris described Rakim as a personal hero.

Up Next: Jared Polis

Tune in next week with Jared Polis — serial entrepreneur, political leader, and the sitting Governor of Colorado. Before he turned 30, Jared already built and exited three companies for over a billion dollars combined, including BlueMountain.com and ProFlowers. He went on to co-found Techstars, which has backed thousands of companies and changed how a generation of founders thinks about mentorship and community. But public service kept tugging at him. In 2008, he ran for Congress, came out during the race, and won — becoming the first openly gay non-incumbent ever elected to the U.S. House. Ten years later, he came home to Colorado and won the governor’s office, becoming the first openly gay man elected governor in US history. What makes his story interesting isn’t just the firsts. It’s how he actually does the job — more like a builder than a politician, focused on execution, systems, and outcomes. In this episode, we dig into where his entrepreneurial instincts came from, what he saw in the earliest days of Techstars that made him go all in, and where founder principles do — and do not — translate inside government.

Listen on: Spotify, Apple Podcasts, Amazon Music

In this episode of Outsider Inc., host Ian Hathaway sits down with Chris Schroeder, entrepreneur, investor, Co-Founder of Next Billion Ventures, and author of Startup Rising, to explore what American entrepreneurs and investors miss when they overlook the rest of the world. Chris reflects on a career spanning politics, media, venture-backed startups, and global investing, and shares how a 2010 trip to Dubai reshaped his thinking about entrepreneurship, emerging markets, and the future of innovation. They discuss the power of asking better questions, why humility matters more than certainty, what Silicon Valley often gets wrong about founders in other regions, and how time spent on the ground in places like the Middle East, Southeast Asia, Latin America, and China reveals patterns most people never see. Chris also shares lessons from building and selling HealthCentral, writing Startup Rising, investing through Next Billion Ventures, and why the best founders stay focused on real problems, not prestige.

Show Notes:

(03:00) Why asking better questions matters more than having all the answers

(05:00) The wonder of being wrong and learning through humility

(09:00) Family history, immigration, and the entrepreneurial mindset

(14:20) Politics, transactional relationships, and the long game of trust

(20:10) Building inside the Washington Post during digital disruption

(27:45) The HealthCentral thesis and why community can save lives

(33:10) The Dubai trip that changed Chris Schroeder’s life

(38:00) Writing Startup Rising and seeing what others missed in the Middle East

(41:30) Why global founders need to be understood on their own terms

(50:45) What Chris learns by getting on the ground in China

(55:20) The questions American entrepreneurs and investors should be asking now

(58:45) The danger of “third cappuccino syndrome” and losing focus on what matters

(1:00:00) Beyond the Bio: Chris Schroeder

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Chris Schroeder, Next Billion Ventures; Author of Startup Rising; former CEO, HealthCentral

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Chris Schroeder: [00:00:00] I will never have the depth of many of the people who have lived and have been a part of the cultures that I’m blessed to go to. But I can take a swath of interesting things and make connections and ask unusual questions that then are instructive to new kinds of answers. Overall, I can bring in an analogy they hadn’t thought about.

I can pull them out of their inbox and have them think about something they had not thought about before, and I think there’s a superpower in that.

Ian Hathaway: Welcome to another episode of Outsider e. I’m your host, Ian Hathaway. Today’s guest is Chris Schroeder, entrepreneur, venture investor and author who spent the last decade and a half challenging one of the biggest blind spots in global entrepreneurship.

What originated with Italian grandparents at Ellis Island? Chris built an extraordinary career, Harvard. Two presidential campaigns, a state department tour under James Baker, wall Street, private equity, CEO, and publisher of Washington post.com. [00:01:00] And finally, co-founder of Health Central, a community health platform backed by Sequoia, Carlisle and Barry Diller’s, IAC, which he grew to over 15 million monthly users and led to a successful exit.

But in November, 2010, at a startup gathering in Dubai, something shifted. He realized he’d been trapped in his own narrative bias, completely blind to the massive wave of entrepreneurship, taking shape across the Middle East, Asia and Latin America. With an insider’s track seemingly laid out ahead of him.

Chris chose a different path. That awakening led to Startup Rising, the first book on startups in the Arab world, the product of more than a dozen trips to the Middle East. In interviews with over 150 entrepreneurs, investors, and global tech leaders across the region. Mark Andreesen wrote The Forward, Chris, since co-founded Next Billion Ventures, backed exits like Kareem’s, $3.2 billion sale to Uber, and now chairs the German Marshall Fund.

But more than those credentials, Chris has actually been on the ground repeatedly [00:02:00] logging millions of flight miles to visit places. Most investors never think about asking better questions, determined to see what others miss from the heights of American politics, media finance, and technology, to the streets of Cairo, Shanghai in Sao Paulo, Chris’s perspective is one that American entrepreneurs and investors desperately need right now.

Today we trace the full arc of his journey where his curiosity came from, what it took to turn toward the places others overlooked, and what 15 plus years on the road has actually taught him. Chris, welcome to Outsider,

Chris Schroeder: Inc. Ian, it’s always wonderful to be with you. Thanks for including me.

Ian Hathaway: I wanna start somewhere personal.

When I was getting ready to launch this show, I asked one person for advice about how to be a great interviewer, and that person was you. Your advice was simple just to be myself. I’ll never forget it because at the time, I guess I was looking for something tactical or more specific, but I feel like what you gave me was far more valuable.

I came to you [00:03:00] specifically with that question because I consider you to be one of the best interviewers and moderators anywhere. You ask great questions, but more than that, you actually prefer it. You lean into asking questions rather than declaring expertise, which is interesting to me because I also see you as one of the sharpest and most knowledgeable people I know on a range of different topics.

I say all of this not as flattery, but as genuine observation that I think can be learned from. So with all of that in mind, you said. That the only thing you know for sure that you’ve achieved is that you ask better questions now than you did in the past. What’s the power of the question over the answer?

Chris Schroeder: You know, it’s a wonderful question that at one level I have difficulty answering because it’s been, I think, part of my nature. My mother thought I was a pain in the ass in my questioning, and so there’s a dynamic of it, but I think there is a more concrete answer, and it comes [00:04:00] under not only a sense of aspiring to have humility, but humility bred on a many, many humiliations.

You learn, I think, quite early in life if you’re paying attention, we don’t want to be wrong, and so we do everything we can to prove that we’re right. When you get knocked out a lot, you start to realize that one of the most powerful things you can do is have almost a wonder or amazement in being wrong because it helps you to get it right or.

And I had two sort of bookends of experience that made me very suspect about expertise. And it does not mean that expertise is not a thing or it’s not important, but it is been an exercise in humility. Again, when I was a kid, you’d mentioned, you know, I was like 22 years old and I worked in for Baker at the State Department at this time where the Berlin Wall fell and Nelson Man LOE was released.

It was a very formative experience for me, and I’ll never forget having some of the best of the best experts on Europe and Germany, say for all intents and purposes that the Berlin Wall will not fall and Germany will not unite anytime in the next 10 years, even though there were a lot of trends happening that people will remember from history.

I got a [00:05:00] lot of that in October of 1989 and two weeks later the Berlin Wall fell and a year later, Germany’s Unified, 20 years later, and I was in the Middle East and at a startup gathering in Egypt ever. I just had been in Damascus looking at entrepreneurs there and I was sitting with a couple of very senior American government officials, some very senior.

Egyptian business people. Very sophisticated, very smart. And there were a couple of young entrepreneurs there. This was just the time when the president of Tunisia had left Tunisia and the country changed dramatically. And the question at hand was, could this happen with Egypt? And the experts, the older people there kind of patted me on the head and said, um, nah, it could never happen here.

It’s a totally different country. The armies are different. Personalities are different. And I turned to the kids, you know, the entrepreneurs 26, 27 years old, and they gave, what I was later told was an extremely Egyptian answer. They were very courteous to their elders. They were like, oh, no, no, no. They know more.

And I, they have PhDs and everything else. And they paused and smiled at me and said, but I don’t see why we’re that different. And those [00:06:00] two young people, of course, were in career square two days later and 18 days after that Mubarak was gone. And so I think the, it’s a anecdotal way and book-ended way of saying that if you really, really pay attention.

You realize that predicting the future is a fool’s err, and that expertise is a never ending, uh, development and experience. And the only way to get better and better at sort of piecing it together worlds as an investor, as a citizen, is to embrace humility, to embrace wonder, and being wrong and realizing in the end, the best you’ll probably end up is asking better and better questions in service of whatever you care about

Ian Hathaway: to embrace this philosophy that underpins all that For you, this wonder of being wrong, was this something that’s been with you from the beginning?

And then maybe what are things that people can practically do to release this fear of humiliation, of saying the wrong thing, of looking stupid and embracing that wonder of being wrong.

Chris Schroeder: I learned pretty early on that if I could make people laugh, they embrace the whole kind of [00:07:00] circumstance, and so a little bit of self-deprecating humor when you screwed up and to kind of roll with it, you would get kind of a buy-in around you.

To this day, there are times when I’m dealing with someone and they’re pissing me off and my ego kicks in and I wanna prove them. I’m right. You never lose it. So I think it’s just part of human instinct and there’s actually tremendous value in it. But if your North Star is, in some respects, it’s almost a question or a word that’s always in my mind when I’m processing information, whether it’s War Now in the Middle East, or it’s a entrepreneur who’s pitching something and trying to convince me that they have a mode against ai, I almost have this voice in my head that says, well, maybe.

Now let’s unpack it. And I will tell you that I ran Washington post.com in sort of an era where this was one of the core values of the institution. I think it’s changed in the news world a lot and to be surrounded by reporters who were serious reporters. It’s not like they didn’t have ego, but they were fanatical about getting the story that was their North star.

And I think that also trained me to have a sense of persistence, but also first [00:08:00] things you hear may not be the stuff that will guide you most clearly. But in the end, we’re human beings and we have egos and we want to be right. And it’s a voice in our head that says, well, maybe let me pause and upon what evidence is that true?

And you can go from there. The great legendary editor from the Washington Post was a guy named Ben Bradley, who’s sort of a legend. He used to have this wonderful line. So you’d say something to him and he’d look at you and say, interesting, comma, if true. And I think interesting if true has been something that’s remained with me as a guy who built businesses as a investor and a lot of stuff that I do in the policy worlds now.

Ian Hathaway: Oh, I love that. I’ve got some new material. Now, what I like to say often to founders and definitely myself on a daily basis is, do you want to be right or do you want to be successful?

Chris Schroeder: I mean, the little secrets you and I know people would rather be Right. And that’s a tell you learn something in that.

Ian Hathaway: Yeah, unfortunately. So I feel like too much of the world is consumed with being right, rather than being successful. [00:09:00] We’ll dig into that more in a little bit, but I’d actually like to go back to the beginning for you. You were born in Manhattan’s Lower East Side, but grew up outside the city in the Westchester suburb of Scarsdale.

Chris Schroeder: Yeah.

Ian Hathaway: Your grandparents were all immigrants who came to this country with very little classic, you know, Ellis Island story, which really became an American dream for you. I know. You visited your ancestral origin a couple years ago, tracing your family’s footsteps in a small town in the Basili Kata region in southern Italy.

Why did you go there and what did that experience do for you?

Chris Schroeder: I’ve always been extremely interested by history overall, not in some academic intellectual sense, but in an understanding of what are the things that built us to where we are today. To give a context, I wish we can see the world and it’s very interesting to me ‘cause I’ll talk to people in Silicon Valley, like, I don’t care about history and it’s all about the future and everything else.

I’m like, you know, you played basketball when you had your ass kicked last week. Did you not learn from [00:10:00] that ass kicking and bring it to the next game? But it is a sense of trying to understand why we are where we are, what is the context to it? What are some lessons about leadership or things that have worked or not worked?

Where are the rabbit holes that people before me have gotten themselves into and not been able to pull themselves out? And can I keep that in mind without being too overly wedded to it? My family was a typical Ellis Island family from a hundred years ago, and my swath came from Central Italy and then Bocato, which was just breathtakingly poor at that time.

They also came from Naples from sort of middle class, so it was a Southern Italian story. So we found this little town my grandfather’s family was. The irony is it’s as beautiful a hill town now, as you would see in Tuscan. Yeah. And so you were kinda looking around like, grandpa, you should have stayed here.

It’s not so bad. But what really hits you in a sense of the humility is the nearest town was like 10 miles away and 10 miles away a hundred years ago is, uh, univers away. And the idea that this guy at 19 years old, his father and his wife of 17 years old, looked to each other, [00:11:00] walking around this town, I was walking around.

It looked pretty much as it must have then, and looked to each other and said, I have a great idea. Let’s leave it all. And they made the decision to go 10 miles to the next town and then 30 miles to a port and somehow or rather figure out how to get to New York City. It is a reminder. One, what I come from and a reminder of why I think I admire so much, that sense of in your teeth, I’m gonna solve a problem, whatever it takes.

That has been very helpful to me as I’ve been helping mentoring entrepreneurs.

Ian Hathaway: It’s a great story, and the very act of immigrating to a new country is an entrepreneurial act. To no surprise, immigrants in the United States are twice as likely to found companies as native born, partly out of necessity.

But I think it’s also part of that DNA of someone who’s willing to strike it out on their own, start new things. Your parents as well? They were both lawyers, but really, if you dig deeper, they were social entrepreneurs. Your father went to the first concert, Leonard Bernstein had ever conducted [00:12:00] and eventually founded an organization called Education Through Music because he was horrified that the arts programs were being cut from New York City schools.

Your mother who went to law school at age 18 as one of just two women in her class. She spent 50 years building the CareMore Center for Music and the arts. The family ethos was if you see a problem, fix it, not something that was necessarily discussed explicitly, but something that was just lived. How much of your curiosity and your instinct to ask questions like, what do you need?

How can I be of help? Two questions that you always ask me every time we talk. How much of that comes from directly watching their example?

Chris Schroeder: I think a lot came from their example. My mother’s father also served in government under LaGuardia in the city of New York, and there was always, uh, ethic that was implicit as much as explicit that if you, as you said, see a problem, you’re gonna fix it and not just talk about it or sit on the sidelines overall.

But it [00:13:00] was heavily implicit. They did not sit us down and say one day, go fix things. It really was observing when they took on things as they did, because it’s interesting to think of them as social entrepreneurs who spent much of their lives as attorneys, which is not normally thought of as a entrepreneurial venture, and I think in some odd ways seeing what their parents had been through.

Certainly the depression weight on them. World War II was a part of them. I think that they were this balance between the, also the immigrant value that you become a lawyer, engineer, doctor, or whatever it is, which was in their environment, but also saying, look, we’ve got some stuff and with that stuff we should fix things.

But I can’t remember a single time where we had a conversation about it. It was merely that you just kind of understood it and you unpacked it and you find something that you cared about. My father has always adored music, was raised very much in that tradition, but he could not stand because to him the data was crystal clear that schools that had good arts and music programs, kids performance in that school academically and in test scores, the R Square was like nine two, and yet these are the first places getting cut.

And so he came up [00:14:00] with this idea of education through music so that they could help fund arts programs and have kids exposed to music as a way not only to enjoy that in and of itself, but to build some additional musculature that was very valued. It became very large. It’s a problem that we may never be solved, but he certainly contributed a tremendous verse.

Ian Hathaway: Discovering problems, highlighting their existence and doing something about it feels like that’s what you’ve spent most of your career doing. So switching gears a bit on that, something that I don’t really get a chance to discuss on this show, the DC policy world, I spent time working in the DC policy arena during my career, so I have a bit of a window into that.

You of course, did as well during and after college. You worked inside of the Bush presidential campaigns, and then at the State Department you worked under legendary diplomats like James Baker and Robert Zeek mentors who undoubtedly had a huge imprint on you as well. But that world also taught you about something else.

It taught you about transactional relationships, people who were your best friend [00:15:00] until you left office. I’m curious what impact that realization had on you, particularly since. The world of entrepreneurship and ecosystems that we’re both operating in and thriving in today is famously the exact opposite of transactional thinking.

Chris Schroeder: I don’t wanna be overly sanctimonious about this. If we’re in business, there’s a transactional element to we do. We try to sell something and we try to convince someone. You pitch a venture capitalist, there’s a transaction to that, and so I don’t wanna blanket it. It’s problematic. But what I learned starting in those days as a kid, and I’ve seen it among the best that I’ve dealt with in the business world since, is that there’s a real distinction between people who come to you solely for the transaction short term, and if you don’t deliver it, they move on.

And someone who wants to engage with shared interest and shared outcomes of interest with a view that this could be a lifetime engagement, and it’s not always a lifetime engagement, but the nature of it is great. I know a lot of people in the policy world and globally and, and certainly in the business venture capital and [00:16:00] VC worlds, and I can almost tell within 10 minutes why somebody’s meeting with me and I know that they’re trying to get to somebody or they want my money, or whatever it is.

That kind of stuff. And there are other people where it’s the beginning of an engagement of understanding in a almost of service way. What are we trying to do here and what are we gonna be doing over time? And maybe this time there will be a transaction, but if not, there will be another transaction another day.

And we should just be under that kind of level of connectivity, under the thesis of good people, knowing good people, a lot more great outcomes come, whether they’re monetary or structural or just impact as we define it. And it was very, very clear to me very early on that the best people I saw were not hyperly transactional.

And in fact. When they got reputations of being about the transaction, they may succeed. Right? This is staggering to me how some people who I thought may not succeed end up doing very well because they’re so good at the transaction. They go, go, go, go. But they’re known for who they are and they’re not liked, and people don’t necessarily want to do business with them.

[00:17:00] Whereas there are these people who have just become legends and have done amazing things, and they really have that balance down, I think, in a very powerful way, and that inspired me, I think a great deal.

Ian Hathaway: So I think what you’re saying is it’s not just that you want to engage with people through a mechanism of a relationship rather than purely transactional.

It is in fact that in most of these cases, in these industries, I point out the example of tech and entrepreneurship, which I think is inherently collaborative, but even in politics, it can come back to bite you unless you’re truly exceptional. It’s not just about personal taste over the long term. In most contacts, it’s a better way to get where you want to be.

Chris Schroeder: I had a great sales executive in my life who mentored me a lot of times when I had sales problems and companies I invested in. We’d have this conversation, it sounds almost pedantic in its obviousness, but he would say to me, don’t ever forget. People wanna buy from people that they wanna buy from. I think the fundamental construct that [00:18:00] let’s figure out if there are win-wins together and let’s kind of go at it, does not mean that we’re not transactional does not mean that we don’t wanna make a lot of money.

It doesn’t mean that I may wanna beat you from time to time, but it’s a arc. Of understanding. And I will say, you touched on this and you and I have talked about it a lot because not only has it been exciting, I think one of the really better things one can say about Silicon Valley and American entrepreneurship writ large, but I think you and I have seen it replicate in other markets of the world.

It’s extraordinary, the generosity of time that entrepreneurs show to each other and the best of the venture capitalists show. And they’re not looking for an immediate hit because of that. I mean, they may realize that someday it could work out into something else, but it’s almost a cultural instinct. We will all get each other through this absolutely ridiculous and and absurd thing called entrepreneurship that we all know 90% of them are gonna go to zero.

And we’ve all felt it and we’ve all been there, so let’s lock arms. And that is a magnificent, and I think very genuine thing that often gets lost when people like to point fingers. They miss, I think what you articulated so well,

Ian Hathaway: one of the things you were describing there [00:19:00] reminds me of Annaly Ian’s famous collaborative competition framework.

You were on a podcast with her and Brad Feld. I’ve listened to that numerous times. I love that framework that really, it’s this collaborative competition. It’s not that we’re not competing against each other, it’s that we’re putting the cause, the mission of advance above even our own short-term interests at times.

And that’s what keeps the ecosystem vibrant and sustaining.

Chris Schroeder: It’s so interesting because the best entrepreneurs, you and I know are also killers. They are steely focused. They wanna win. You can slow ‘em down. You cannot stop ‘em. You. When we think about the super builders that you and I know, and we’ve been fortunate enough to fund a few of them, it’s not a hundred percent, but a lot of ‘em, I don’t really want to hang out with.

I don’t think I would’ve liked Henry Ford a whole lot. I don’t think I would’ve liked JP Morgan a whole lot. But the fact of the matter is, they built a lot with their tenacity and their killer instinct and transaction. But if you were to look at the arc of it overall and the kind of life you wanna live and the success you can still build, I still defer [00:20:00] to the things that you and I have just been sharing.

Ian Hathaway: Departing from your time in politics. You went to business school back at Harvard, where you went to undergrad, then into banking, private equity, corporate leadership. You became CEO of a company called Legislate, a B2B platform covering federal and state legislation, which you ultimately sold to the Washington Post in 1999 after working to bring the company into the online world.

I should also mention somewhere in all of that you had a successful DJ business that things were going great until they weren’t. On the back of the Legislate sale, you were tapped to become CEO and Publisher of Washington Post Newsweek Interactive at the age of 35. An enormous job at a relatively young age, a truly transformational time for the media business as it faced the tidal wave of the digital age.

First, set the scene a little bit for what it was like to build a digital media company at during the [00:21:00] time of the.com boom, when things were moving so quickly. And then secondly, what was the core lesson of trying to build something entrepreneurial inside of such a large storied institution?

Chris Schroeder: It’s amazing.

I think back 15 years ago, we got it to 30 million. Seemed like very big numbers and they seemed like nothing today, but they were big numbers at the time, and there were a lot of things that we experimented on that was making a case, which leads to your question, which is that there was going to be a significant paradigm shift in the way people engaged with information.

We were one of the first partners with Google, so we had a frontline understanding of how people behaved when they had the ability to find what they want, when and how they wanted to find it, how people wanna share information, how people aggregated truth. The idea that you go to one destination to know how the world works and evaporated before I even got there.

So you had all these dynamics, but when you think about those dynamics as I just rattled them off the top of my head, every one of those was a threat to the paradigm of the legacy business. The legacy business was based on the idea that you are a monopoly as a business. If you’re at the Washington Post [00:22:00] and you had a this juggernaut monopoly, local news and information sector, advertisers had no choice but to come to you, and now all of a sudden we’re in a world where I used to do this in meetings with the newspapers.

I’d show every section of newspaper and rattle off 20 competitors of every subsection of that thing to wake them up, that it was gonna be a very different paradigm. And while I think I was right on the substance of what was happening, that doesn’t mean that people loved you for it. And there were a lot of people who wanted to understand it and they were incredible co-authors.

And there were a lot of people who I think in many respects, either one wanted to squash it, or two, which one executive said to me at, actually at Time Warner at the time, he said, I know all this stuff is happening. I just want it to happen after I retire. It’s amazing to me that, ‘cause we had this flurry of new startups maybe, uh, 5, 7, 8 years ago, and you had Vox and you had, uh, Buzzfeed and all that, and everyone said that’s it.

Like the traditional news is over. And in point of fact, almost all of them are dead. And traditional news people are struggling for a whole host of reasons and a lot of things that have happening [00:23:00] with the diaspora of information. But I think you asked about lessons. One is change happens slower than you think.

Often. Not always, but I can’t tell you the number of VCs at the time who said, you know, newspapers and news will be dead in three years. And that did not play out that way. But the second thing in a way was a personality thing, because I sort of lucked into this role and I love the news and I’m very interested by it.

It was a huge consumer buy it. I thought it was important and I thought we could make it into a very big business. But when I began to observe. These structural ankle weights and the shuttle diplomacy that you described before, I actually most importantly learned something about myself. We see intrapreneurs a lot, and on occasion, people who are very successful in a large organization with a large balance sheet and so on, who do pretty well there, kind of should stay there.

Being an entrepreneur is just subsequently, subsequently different than being an intrapreneur. And I looked at myself in the mirror and said, I wanna build my own things and I have a lot of ideas and theses now how to do it, and I cannot be in that position. So when I broke off with some folks to do the [00:24:00] Health Central thing, I remember a board member from the Washington Post pulled me aside and said, what are you doing?

Are you crazy? The odds of this are very low and what are you doing? And I said to him, look, it may not work, but I’ve been dying to do this. I’ve had it in my teeth for years. I was an entrepreneurial kid. I’m gonna do this and there’s no going back. And I said, more importantly, no matter whatever goes wrong.

No one is ever gonna say to me, don’t do that because you might hurt print advertising. And he just cracked up. I mean, he got it right away. And to be an intrapreneur means a willingness and a personality type to navigate legacy that has a very different set of values and incentives. And if you are of that nature, you should do it.

And, and I think many large organizations, truly now in the AI world, we’re gonna find themselves very threatened, will need that kind of capability, instinct. Barry Diller would never have lasted a second. Mark Zuckerberg would not have lasted a second pick whatever, great entrepreneur, you know, they would not have lasted a second in that environment at that time.

By the way, I think Diller learned that because Diller did rise within very big [00:25:00] media companies, and when he did IAC, he could have very well have taken over another studio yet again. And he’s like, I don’t want that. I wanna build something that was never there before. And it’s a different musculature and it’s a different mindset.

And I would add, by the way, my first year as an outright entrepreneur was probably the shittiest year of my career in terms of my own performance. I realized that I had to up my game in a very different way. It wasn’t work ethic. I always worked 80 hours a week. It was mindset and getting out of me, the DNA of legacy.

That made me have some better success eventually,

Ian Hathaway: especially in this era of ai. I think understanding the inner mechanizations of legacy industries is going to be particularly valuable and important. A couple episodes ago we had Aeron Kaza, who’s one of the co-founders of Merta Libre. He talked about how his time at Proctor and Gamble, he was a brand manager working in marketing before Stanford Business School, before Mercado Libre.

He felt very [00:26:00] constrained in that environment, but then when it came time to scale Mercado Libre, he actually started leaning on some of those very processes that annoyed him as a young man. Are there ways, perhaps surprising ways that now you look back on it, or times when your experience in that role actually helped you as an entrepreneur?

Chris Schroeder: No question. That at a certain level of scale, you understand. There are things that need to be done operationally, accountability and so on, which are very important. But I will say at the same time, it is much better in a way to understand the importance of that at scale, but to make sure you’re doing it in the most efficacious and often new ways.

The thing which doesn’t change as much, I think, is that a leadership level, meaning I don’t think people change that much. I wish I understood this at 30 the way that I understood it. At 50, if you understand the incentive structure you put in place, in almost any operational organization, you could pretty much predict with 95% certainty how people are gonna behave.

[00:27:00] So the idea of that learning in a large enterprise of how in the end, I watched lots of people do things that actually at one level made no sense to me. But then when you understood the incentive structure, they made perfect sense. Understanding that mindset and being a realist about what motivates people and where they will behave to incentive, what is the kind of talent you want or not.

I want, I don’t have any question that some of the more established. Stuff reminded me of that.

Ian Hathaway: The incentives one is a powerful learning. There’s something that I ask entrepreneurs all the time, which is, do you know how your, your ICP, your ideal customer gets their Christmas bonus? It’s a simple question that they almost never have the answer to, but it ultimately, you’re selling to a person who has incentives that may be different from the organization and certainly different from yours.

Give all the credit in the world to my partner, Jonathan, for, for seeding me with that thought. Shifting gears, you leave the post and you join an investor group along with legendary investors like Mike Moritz at Sequoia Capital, Alan Spoon at Polaris Venture Partners, Carlisle [00:28:00] Group, Alan and Company, and eventually Barry Diller’s, IAC to acquire and essentially rebuild from scratch a company called Health Central where you or the CEO and Founder.

I know that thesis for Health Central was personal for you, and you had seen how these online communities of people going through the same thing, were helping save each other’s lives. It’s very clear your why, but it had to be a big adjustment for you. What was it like going from leading the company that we just talked about with this household name recognition, but with a lot of unwanted structure for you to then being the CEO of this company that most people had never heard of before?

Chris Schroeder: We inherited a few assets of which Health Central was one, and we elevated the brand, so we weren’t trying to relaunch it ‘cause we had a very different thesis. But what became very clear to me was the world did not need another WebMD, an encyclopedia of Health. They had very precise questions with very precise ideas of what they wanted to be.

And one, we should be delivering to those needs at scale. And two, that one of the most foundational needs that I learned in [00:29:00] the personal experience that you talked about is that if you can talk to someone who’s like you, going through what you went through and what they did worked. Then you were gonna absolutely replicate it and technology would allow that experience to scale in a way.

For me, it was the ultimate definition of empowerment. When I see someone like me do something that works and I do, it is an act of empowerment. And so I said, there’s no way how WebMD is gonna do this. These other sort of encyclopedias health weren’t gonna do it. Harvard had their own website. There’s a cacophony of information.

In many respects, I think I, I underestimated. But we realized that if we could start matching people, it could be very powerful. And the second thing that was very specific about that was the journey was not about let’s get anybody with breast cancer to a site. The thesis was, if I have an illness, what I want is someone who looks like me, acts like me, is in my background.

And the questions I’m asking are not yet. One more question about different kinds of drugs or treatment, though that’s a part of it. It’s like when do I [00:30:00] tell my children? Or do I tell my children, or I’m gonna go talk to my parents? Do I tell my parents this? By the way, I need some time off from work. I’m afraid I’m gonna lose my job.

How do I think about it? And it was only when you talk to people who had been there that those rich conversations became so profound. And so that’s what we tried to organize at scale. And there was a business model to it. It was very, very clear to me that if we could get the right advertising message, you would literally say, I’m someone who is struggling with this condition, whatever it was, and then all of a sudden, all I’m seeing are ads that are related to what I’m thinking about.

Those ads were no longer an interruptive annoyance. They in fact, were content. And because of that, we were able to charge much higher CPMs and it performed well.

Ian Hathaway: The company achieved its mission, it saved lives. Right. You’ve talked about that you grew to over 15 million monthly users, integrated five acquisitions, and ultimately you sold the company to Remedy Health in late 2011.

What went into the decision to sell the company [00:31:00] then, and when you stepped away from something that you had spent seven years building, particularly something that was so personal to you, so mission oriented, I can hear it in your voice about how valuable that innovative construct that you introduced about how people can engage with information and content around something that is threatening their lives.

What did it actually feel like for you to let go of the company? At that time,

Chris Schroeder: we had been building for about a year and a half different strategies about. How to accelerate the growth. We got very close to acquiring a very large enterprise. That would’ve changed the dynamics of the company very well. We actually had discussions about a merger with another enterprise that we would’ve split things pretty evenly and had a great CEO would’ve come in.

I could have been chairman and there was plenty of debate in the company, let’s go it alone ‘cause we’re actually, the trajectory is good. And all of a sudden we met an unbelievable CEO, just amazing guy who really understood our vision, who was working for this company called Remedy Health, that had a tremendous data and [00:32:00] traditional content, and it was a perfect fit.

And after negotiating it and going through both personal intellectual exercises that made an offer that was by far and away the best offer of how to think about building for the future. I think by that time in that process, my mental outlook was what’s best for this enterprise going forward. But I really felt that at that time in the competitive environment, one, we needed better scale, faster.

And secondly, we got an offer that was a great offer and that we all looked at each other and I said that was the right thing. But then all of a sudden, you know, the emails got smaller and the phone calls became less. And you start realizing, well, all right, now it’s time to do something else. There is, um, aour in it, but the morning was subjugated to this was a very good outcome for the enterprise and for a lot of people.

And now let’s see what we can do next.

Ian Hathaway: Speaking of that, I’m excited to get to what I think may have gotten you out of that morning period. Up to this point, you had an impressive track record, Harvard State Department, Washington Post Sequoia backed [00:33:00] founder with Mike Moritz On your board, you had a clear pathway to stay inside of that world.

I mean, who knows? You maybe even could have been an investment partner at Sequoia, but instead in November, 2010. Before the acquisition, you go to Dubai. You said that at the time you weren’t super thrilled about that trip. In fact, you were giving a keynote speech that wasn’t exactly relevant to what you were doing, but within a few hours, your life changes completely.

There were thousands of young entrepreneurs, another 3000 on the waiting list. You realize that you’ve been maybe stuck in your own narrative bias and missed this movement entirely. Walk us through that experience. What happened to you there in Dubai that changed your life in the span of just two hours?

Chris Schroeder: There was a dull roar to that particular event in Dubai because like every kind of gringo, CEO at that time, I outsourced technology to every emerging market. You can mention from [00:34:00] Argentina to Sri Lanka, right? Because it’s very easy to get high quality, great engineering at a fraction of the cost by doing so.

But unlike I think a lot of my gringo sisters and brothers, I actually visited some of my partners. And when you got on the ground, you realized almost instantly, and and Hernan would be an example of this in Mercado Libre, these people did not wanna spend their lives selling cheap engineering to people like me.

They had in their teeth. All these problems they knew that had already been solved elsewhere and could not understand why they weren’t being solved in their backyards. Mercado Libre is a perfect example of this, which is really why at the end of the day, Amazon may come here, they may not, but quite frankly, who’s better to create the Amazon of Latin America than us?

And even in the Middle East, at that point, there was not an Arabic email. And so all these young generation who were very well aware of what the internet was doing in English, and all the juggernaut activity that had begun with Microsoft and beyond in Silicon Valley began to ask this central question, why not us?

And then there was a second question, which is if everyone has a [00:35:00] supercomputer in their pocket, which was gradually happen. That meant one talent is everywhere and now you could unleash it. And two, I can deliver new services that leapfrog the traditional ones or the ones that never existed at all. And I just saw these conversations over and over again.

Anyway, in parallel of this, friends of mine who are really leaders in the tech ecosystem in the Middle East, in the Arab world, I mean, everyone knew about Israel and some amazing companies that came from there. No one, no one in America thought anything like this was happening in Egypt or Jordan or Lebanon or whatever.

Certainly not in the Gulf. In those days, Saudi Arabia was completely locked off and the UAE just looked too expensive to do something like this. And most Americans that if you ask them about the Middle East. Their answer would’ve been about ISIS or terrorism and so on. And I remember someone saying to me, he said, there are maybe 30,000 ISIS and maybe 150,000 people support ‘em, and the region is 350 million.

Wouldn’t you like to know what other people are doing in the meantime? And it woke me up so that when they had this conference, the [00:36:00] first major gathering of startups in the Arab Middle East, I was curious and I wanted to do it and I had no bandwidth to do it. ‘cause we were in the process of having sale discussions, everything else.

And they pretty much said, as a friend, would I do it? And you’re not wrong in what you said because within two hours I had been rewired of being there because it was 3000 young people who did not wanna talk about any of the geopolitical stuff. They could not have given a damn about any politician talking about anything.

They were incredibly sophisticated and creative about the problems they were solving. They knew exactly what they were. They asked me better questions than sometimes I got from people here. They had different problems than I would normally see in Silicon Valley. And it was very, very clear to me that this question of when the world has massive access to supercomputing, the whole idea of business, the whole idea of society, the whole idea of innovation, the whole idea of unleashing talent was gonna become completely different.

Than anything that happened in my year. And so at that time, I did have opportunities to work [00:37:00] in venture capital and particularly EIR. ‘cause I thought I’d go and build another company from scratch. But I got sucked in more and more to this question because I thought if I could understand this question better, I’m gonna understand something that most people don’t.

And this is where the world is going. And I should start focusing my time. So the lens became the Arab Middle East. But of course what I saw there, I eventually saw very quickly in Southeast Asia, Latin America, and China’s Exhibit a China was all of this on steroids. I mean, nothing drives me crazier. When Americans then and now talk about these places as copycats, they miss that these companies had familiar themes to successful Western companies, but they had certain clarity about things that were cultural, technological language, how people behave, how they use money, what their experience base was.

Last mile logistics that was gonna give them incredible innovation edge. In the companies they made and the journey just went from there.

Ian Hathaway: You got sucked in. Ultimately, it culminates in [00:38:00] you writing this book, startup Rising, which was the first book on startups in the Arab world. I know you made more than a dozen trips to the region.

Chris Schroeder: Yeah, a lot more.

Ian Hathaway: Yeah. Interviewed hundreds of entrepreneurs in the region from all across the region.

Chris Schroeder: Yeah.

Ian Hathaway: It’s a great book. I’ve read it more than once. There were lots of amazing nuggets in it. I think about this term, I learned from that book, wasta that you introduced, at least into my life. I apply it in lots of contexts.

Wasta is not just a Middle Eastern thing. It applies in lots of different pockets of society.

Chris Schroeder: Yeah. I’m in Washington, DC like the ultimate wasta city.

Ian Hathaway: Yeah. So Wasta, for those who don’t know, is really about this notion that you can’t get ahead unless you’re connected into the right networks, which is true in lots of different places we just discussed.

But really the success stories that were coming outta the Middle East just prove that it’s not just about knowing the nuts and bolts of building a product company and scaling. It’s the inspiration, the fact that, oh, this could be true for me [00:39:00] if that person can do it. So can I. Just tell us a little bit about the book coming together and what the initial reception was.

When you came back and explained to people what you were seeing, what was the reaction? Were people skeptical? Did they think that you were onto something or did they think you were a little bit crazy?

Chris Schroeder: I think a little bit of all of the above. I mean, why would you write a book at all? I had not written a book before.

I had blogged a lot and I had written magazine articles in Wall Street Journal and stuff like that, and very often it was in service of me clarifying my head. I realized. That is I process a lot of information. If you distill your thinking to 750 words, it’s hard to bullshit yourself, right? You need to really get to the essence of what you’re trying to say.

And the idea of writing a book was that what I observed seems so big and so important and such a case study of this bigger question that selfishly, if I spent a year going back and forth and reporting it, I would organize my thoughts and then it became clear to me if I did that it would be not just a series of articles, which I did do at that time [00:40:00] for a bunch of different groups.

Kara Swisher and others recruited me to write pieces about what I saw. Well, I wrote it. Those pieces became part of the outline of what was a book. And obviously Andreessen wrote the introduction because he was not making any predictions. But even said in the forward, this could be a trillion dollar question that needs to be looked at in a different way.

So I think when I came back, first of all, anyone. Who I met in Silicon Valley or even here who either came from the Middle East or came from a rising market, uh, they felt like I was preaching to the converted. They understood it. They knew it. They just couldn’t believe. No one was really focusing on it, but a whole swath of people.

But it wasn’t just Washington. It was like it’s a waste of time. Like there’s no way on earth this is real. I remember a top journalist at the Washington Post who published a op-ed that I wrote from one of those trips. Initially, his first reaction is, I’ve covered the Middle East for 20 years. There’s no way this is real.

And I just walked him through it and I reported him, I’m not a Middle East expert. I’m literally telling you what I saw and how technology is changing dynamics. And he took it and became a big supporter of it. [00:41:00] So it was a journey I think, of education and pushback. Some people embrace and some people just didn’t.

And I think the old narratives die hard.

Ian Hathaway: That was more than a decade and a half ago. Since then, you haven’t stopped. If anything, you are accelerating this curiosity of yours about entrepreneurship and innovation around the world. Next billion ventures, investment committees across the Middle East and Southeast Asia, the German Marshall Fund.

You fly hundreds of thousands of miles a year and you’ve backed exits like Kareem’s, $3.2 billion sale to Uber. I consider you someone who is extremely knowledgeable about the global tech ecosystem, and yet as we sort of just discussed, like the label you’ve chosen for yourself is not expert or authority.

You’ve called yourself an In-N-Out gringo, a gringo, CEO, the first person to say that no matter how many trips you take or how many books you read, you still don’t know enough. I think that’s real humility in an era where I wish more people [00:42:00] had that level of humility. Most people with your stature and experience might not do that.

They lean the other way, but you keep reminding yourself of what you don’t know your desire to question rather than tell. How do you think that’s improved the work you do in your life? More so than people who have decided that they’ve already figured it out?

Chris Schroeder: I must say there are many people in my life and career who would not describe me as humble, and I make many mistakes in my arrogance on a regular basis.

It’s more of an exercise in humiliation. It’s a beautiful thing of being my age, and you’re younger, but the difference between being 22 and 52 is you’ve been knocked around and you can either make a choice that you get knocked around and you wanna get off the field, or you get knocked around and therefore you’ve seen it all before and you have all the answers.

Or you can say, I got knocked around so I’m smarter, and now let me go dig through it. Having said that, I am deeply humbled when I go on the ground the minute I start thinking I’m getting a handle, particularly on a place. But the thing that you’ve done a lot, Brad Feld has done a lot and I’ve tried to replicate you guys in a way, [00:43:00] is that, well, I will never have the depth.

Of many of the people who have lived and have been a part of the cultures that I’m blessed to go to. I have a very unique pattern recognition by putting together trends of things in the intersection, firstly of different kinds of countries and seeing how different stages look at. I also think I have a tremendous amount of depth by also understanding how the intersection of technology, business, and policymaking has never been greater before, and that is also instructive.

I am not a great public servant. I am not the deepest person on China. I sure as hell can’t stand toe to toe with some of the greatest of Chinese expertise, but I can take a swath of interesting things and make connections and ask unusual questions that then are instructive to new kinds of answers.

Overall, I’ve also brought comfort in understanding that I will never understand with real depth. What other people have in the areas where they’ve been either focused on, they live, they come from, but I can bring on obvious connections. And often [00:44:00] the questions I ask are not only helpful in my curiosity or helping me refine thesis ‘cause I come from a different lens.

I’m very helpful to other entrepreneurs. I can bring in an analogy they hadn’t thought about. I can pull them out of their inbox and have them think about something they had not thought about before. And I think there’s a superpower in that. It’s just a different musculature that has its own value.

Ian Hathaway: I feel like you bring this journalistic lens into so much that you do.

I know your background with Washington Post was business, but it is a journalistic company. Mike Moritz, who was on your board at Health Central, famously a journalist.

Chris Schroeder: Michael and I used to talk about this. He actually was not officially on the board, but honestly he was as accessible and helpful as if he were on the board.

I learned unbelievable amounts of things from him. But early on when we were knowing each other and I did write periodically thoughtful pieces to help clear my head, he turned to me once and said, look, you’ve gotta make a choice here. I understand that this writing is service of your action, but do you wanna be a writer or do you want to build?

And I said, I wanna build, but I gotta tell you my [00:45:00] bullshit detector is in the writing. And he smiled and he said, I get it. I get it. But it was a good pushback and it was a reminder. You can sort of convince yourself the things that you do are in service. And lo and behold, as you know very well, great entrepreneurship is an exercise in focus.

And you gotta be careful of what’s serving what in the different ways you approach problem solving or question asking

Ian Hathaway: a hundred percent. Switching gears a little bit, also building on another journalist friend of yours from Jerusalem gave you this term that I know you enjoy. The third cappuccino syndrome.

Yeah. I wanna ask you, can you tell us about what is the third cappuccino syndrome, and more importantly, are we in a third cappuccino moment right now?

Chris Schroeder: She would argue that that is an element of human nature, that we’re always in the risk of a third cappuccino. And it, of course, you and I could now rattle off examples of why this is true today.

And the essence of it is how easy it is for us, all of us, to get spun up about something and then [00:46:00] get comfortable in the environment and move on. And I think in many respects, that very human instinct is on steroids now in the world of social media and AI because. It’s very, very easy to get spun up and to get value at saying, I tweeted X, or I put whatever it is on Instagram and therefore I’ve done my duty and hurrah.

And then two weeks later, nobody’s talking about a thing. And the definition of entrepreneurship is persistence in many ways. You can’t just sort of show up and say, I made a statement and move on. And yet there is a desire among a lot of us to do that. She’s a magnificent journalist and she’s taught me a lot about that.

Written amazing books also. And this first experience hit her when she was covering Jerusalem, probably would’ve been 2006 when there were attacks going on. She said, it just hit me very, very clearly that war could be here not far away. And then you go look, and the cafes are filled and the restaurants are filled, and people want their third cappuccino.

It’s like a very natural human instinct to do it. The [00:47:00] upside of it is it gives us a sense of survivability and appreciation that when things are uncertain, we can still grab onto something that we enjoy and love. But the bad thing is, what I alluded to before is that there’s a complacency in it. There is a substitution.

Of enjoyment and moving on quickly to the next thing and not the persistence that big and thorny problems require. I can remember being in Italy years ago, and there’d be all these headlines about Berlusconi taking over and making the country more fascist. And you’d go, and literally in Luca, you’d go into Florence.

The cafeterias are filled and the restaurants are great, and the energy is great, and I totally get the instinct and share the instinct for that third cappuccino, but I think there’s a real cautionary notice of that. It’s true in entrepreneurship, and I think it’s absolutely true in our willingness to stand up for things that we believe in, in any element of society.

Ian Hathaway: You once told a story about an endeavor meeting where a dozen or so entrepreneurs from Latin America, Africa, and Asia, sat down with their Chinese counterparts, and afterwards they told you, look, [00:48:00] the Chinese tech community understands us so much better than the American tech community does. Because when the American show up, they tell us how to be like Silicon Valley companies.

But when the Chinese see us, they expect us to be great Indonesian entrepreneurs, or Brazilian entrepreneurs, or Nigerian entrepreneurs. So from your perspective, what does it actually mean to engage founders on their own terms and why does Silicon Valley keep getting this wrong?

Chris Schroeder: This story, which was a very profound story.

Crystallized many experiences I had. You described it perfectly well. These were growth stage companies, all FinTech companies. Some of them had hit very large, multi hundred million dollar revenue bases and were on a good trajectory, many of whom were coming from regions in Southeast Asia and Africa and Latin America, where 80% of the population ever been banked before.

And literally we’re now learning about what it was like to do financial transactions on a phone. So it’s sort of an extraordinary thing. And what you realize generally speaking is that when you sit with an entrepreneur from Jakarta or from Cairo [00:49:00] or from Sao Paulo and they are trying to solve a similar problem, it is amazing how they share.

Very clear questions that you would never hear in Silicon Valley. So for example, you would hear literally 80% of my country has never been banked before. How do I educate people about what it means to bank and to move money and that kind of stuff? How do you navigate last mile logistics where in many parts of my country there are actually no addresses, but I need to think about how do you do that?

Regulations changing all the time. Politics is changing all the time. How do I think about this? I mean, all of a sudden there’s like a list of questions that have unique cultural and political and language differences, but are striking not only similar, but they are questions that almost invariably would never come up in Silicon Valley Venture Capital meeting.

And so here I am in Hong Jo with Ant and Alibaba. They’re some of the most senior people there with these great companies. And I literally just sat back and watched. Because this was a conversation of rising market to rising market. And China, of [00:50:00] course, 15 years earlier was an emerging market too. So they spoke the language perfectly.

They completely understood the questions that were being asked. And I watched literally one conversation form with four major regions of the world where 80% of that conversation would never have been included in a pitch in New York City or Silicon Valley. And it just hit me. There’s tremendous opportunity in that.

But there’s also a lot of shared learning. And that, needless to say, people in a place like China had a knowledge base and an understanding that was gonna serve them very, very well in a world where, you know, 80% of humanity was being unleashed by a supercomputer. And yes, the entrepreneurs love to gimme shit about this.

And I must say to you, it was two Mexican entrepreneurs who really gave me the gringo lecture about how much the Chinese were smarter than anyone they ever met in Silicon Valley, solely because of this thing. And they were funny about it, but they weren’t wrong.

Ian Hathaway: Speaking on China. I remember a couple years ago you spent a significant amount of time in China.

You wrote extensively about this on [00:51:00] Substack. Those were highly engaging articles. I recommend anyone out listening to read those. You mentioned before we started recording that you’re going back to China again soon.

Chris Schroeder: Yeah.

Ian Hathaway: What is it that you learn by being on the ground in a place like China? What question is it that you’re most hoping you can answer on this upcoming trip?

Chris Schroeder: I think the difference being on the ground and not on the ground is night and day. I have friends in Silicon Valley and elsewhere who are more than happy not to travel that much, and they aggregate incredible amount of information. They’re very informed in the world. But the fact of the matter is when you’re on the ground, you can watch behaviors and you walk into stores and you talk to cab drivers and you talk to translators who have 11-year-old children.

How they’re thinking about ai it, it is a very different exercise. I will tell you at 10 or 11 o’clock at night, entrepreneurs have a few beers. You have a very different conversation than you’d ever have on Zoom, and it’s just unbelievably refreshing and helps me reframe things. There are two fundamental things which I [00:52:00] absolutely optimize for in understanding where our world is going for whatever time I have left in the world and they are AI and China.

I don’t think there are gonna be any two issues that I could name that will have greater significant impact in the way the world will function holistically going forward. And some of those will be threats and some of those will be opportunities. And we have no idea what leadership will be like in five years.

But to me they are the most central historical shifts. And in fact, in the case of ai, I think we are wrestling with something that has no precedence. This is not some new to technology. This is a capability that allows us to think in ways that were simply never possible before. In the case of China, this is the first time in American history since World War II, where we have to deal toe to toe with an extraordinary, powerful, not only country with capability, but a culture of many thousands of years.

We have to ask ourselves, what does it mean to coexist and are there opportunities to co-author? And if not, we still have to default on coexistence. I could spend [00:53:00] every traveling day. Of my life between now and the next, whatever years I have left. And I will still not have a drop in a bucket of understanding a place like China.

But I think it is incredibly worthy for people to get on the ground because I think you see things differently. You understand things differently. You have a sense of how people view you there, and that gives you room to maneuver. And I think we’re living in a world now, whether it’s in technology or business or geopolitical, where there’s tremendous amount of instability and uncertainty, and at the same time, unbelievable opportunity to do things that you and I could not have fantasized about five years ago to say to ourselves, are we jumping down simple answers in complex areas?

Are we deferring the complex questions of a third cappuccino or are we doing the work? It takes to help to be proactive and intentional in building the world as it’s coming. And I have found being on the ground is very powerful. So to your specific question, I try on the trips to China, I’ll always go to Beijing and Shanghai and hung Zou and places [00:54:00] like that because they’re very much in the sweet spot.

I do not invest in China. I will not be investing in China, though of course, China looms large in the markets. You and I care so much about. I also am trying to get out of the, what I’ll call the gringo corridor and see other parts of China. On this last trip, I went to Shian, which is a second tier city, obviously has tremendous history, but I also have friends there who really walked me around.

And we talked about day-to-day life in Shian a little bit. I went to Nanjing, ‘cause history means a great deal to me, and it was a very, very significant cultural moment of horror in what happened in World War II there. So I wanted to understand that. Do our young people still thinking about that? You know, it gives me a different lens on it.

This trip, I’m gonna go to Sichuan and I’m gonna go to Chung Du and to Chung King. There will be business people I meet that will be interesting and what have you. But you know, most Americans don’t realize that these are like, these are cities of 30 million people and I wanna see something that’s outside of the corridor where I’m usually most comfortable and kind of watch.

The worst case scenario is I’m gonna see [00:55:00] interesting stuff and eat very well. But I have found in every trip that I go to, I come out thinking significantly differently than I felt going in.

Ian Hathaway: I wanna end where we began with this idea of asking the right questions. ‘cause right now there’s something I’m wrestling with internally.

You mentioned AI and China being the defining moments of the day, but I’m thinking about the country that you and I are both in right now as we are recording this. We’re genuinely in a strange moment for America’s role in the world, including for America’s relationship with the global entrepreneurship community.

We’re at war with Iran. Our relationships with traditional allies, longstanding relationships are strained. The Chinese tech community, as you described it, understands emerging markets founders better than we do. I’ve seen it firsthand in Latin America, Asia and Eastern Europe, and yet this is also the country that defined.

High tech entrepreneurship, right? That produced the most transformative technology [00:56:00] companies in history and really invented the social and cultural blueprint for how to create an environment for innovation and entrepreneurship to sustain, to thrive. So given everything that you’ve seen on the ground in so many places, being an American, but really a, a citizen of the world, what are the questions that American entrepreneurs and investors should be asking right now that almost nobody is asking?

Chris Schroeder: It’s such a powerful question. There are many situational elements of it, but I would tell you a couple of things. One is an environment and uncertain times with things changing as rapidly as they are, and with technology compounding it in many ways, one of the biggest things to do is breathe and say maybe and ask questions.

The act of being able to breathe and to ask the question and now have tools available to say, is this actually true? Do we really have evidence of this? Or are we acting as if we have evidence of this is an incredible one opportunity. It also has been something [00:57:00] psychologically helpful to me, this ability to sort of say, is this true?

Is it possibly true? But we don’t know yet, so let’s breathe. Is it helpful to me, even if it is true, is I think a tremendous opportunity that not just entrepreneurs, but all of us can bring to bear in a system that right now that rewards political polarization on each side and not a lot of latitude and freedom to be able to pause and breathe.

And ask those questions. And I think it also compels us through incentive to be very short-term focused and the ability to sort of say things are the way they are now. And I must say, Ian, I think there are a lot of cards on the table now that have been laying on the table for years. We may not have wanted to look at them for what they are, but I think the rise of China, there’s a lot that we hadn’t really thought about before.

The idea that 90% of Europe’s energy would come from one country, everyone kind of knew it but didn’t look at it. The idea that all of us wake up with 95% of our chips and the most advanced chips coming from one island, I mean, we have this ability. To ask questions [00:58:00] that have been brewing and are not just of the last year or 18 months, but have come to roost in a way that’s very important.

That approach, I think, can be very powerful, whether we’re thinking about politics as society, but is a very, very similar approach to the companies that you build. Because I think a lot of times, and I see this a lot, not just internationally, but very much in American entrepreneurs, is they have all the buzzwords down, but they’re not actually telling me a problem that they will solve over time for which they have a sustainable moat to do so.

And there’s a first principles element in everything I’ve just talked about that I think each of us individually can bring to bear. Not only in the questions that we ask, but the way we think about and frame them.

Ian Hathaway: It’s a great perspective. I’m definitely concerned. I feel like in so many ways we are on our sixth cappuccino, not really dealing with the fundamental issues in front of us.

Too busy being enraged.

Chris Schroeder: It’s real. I’m with you, cat Rapon to hopeful elements that come from the same space and they’re not enough to counter your worry and my worry, [00:59:00] I hope nothing I’ve said does not suggest that I’m not concerned about where these moments can go, because I tend to be a very hopeful man in the vlo haval sense.

But I also know that enough of a historian to know how things can go in other ways. But I gotta tell you something. My youngest works for SpaceX, and when you tour SpaceX. It’s hard to articulate how moving that experience is. Again, this does nothing to do with personalities. It has to do with being a mile long facility where people from all walks of life are building things that you and I could not have fantasized about in high school and college.

And it’s moving and it’s a reminder. And I’m sure you watched, and I know I was glued and literally teared up watching the launch of the first human craft going to the moon. Maybe it’s a version of the third cappuccino, but I don’t think so. I think this is a reminder to us that there’s so much actually that we can do, and the craziness that we’re dealing with and the things that people wanna focus on, what is problematic about ai, we will cure cancer with this thing.

And so it is a good reminder, I [01:00:00] think, to me, as something of a counterbalance, knowing full well that if you counterbalance too much, all of a sudden you’re on your third cappuccino. So we have to be alert and attending. To the worry that you and I, I think, share in many ways and remind ourselves of the unbelievable things that we do at big scales like going to the moon.

But also you and I could probably rattle off right now if we had more time, 10 human beings we saw this week who are doing such impactful things for their communities or for their families, and that’s very powerful. And not to be lost track.

Ian Hathaway: That’s a very optimistic way to wrap the conversation. I agree with that wholeheartedly.

But before I let you go here on Outsider Inc. We like to finish with a little segment called Beyond the Bio. These are just some quick hit, quick answer questions that go beyond your resume and let us dig into you. Sound okay?

Chris Schroeder: Sure. Great.

Ian Hathaway: Alright, let’s do it. What’s a quick piece of advice from a mentor that stuck with you throughout your journey?

Chris Schroeder: God, I’ve gotten so many of them overall, but I think Harold Tanner reminded me [01:01:00] often. About the long-term power of relationship building in many ways. He was the first guy many years ago who really showed me an action, indeed, the difference between transaction and, and long-term relationship engagement.

Ian Hathaway: Well, I can see you’ve embodied that throughout your life and career. Who is an unsung hero in your life and what has been the impact they’ve had on you?

Chris Schroeder: Yeah, I think people often will talk about older people as unsung heroes and all. But my kids are my unsung heroes. They have very different drummers.

They have done things in very, very different ways and have different passions. They’ve taught me unbelievable things about those passions, and they’re circumspect. They are humble, they’re incredibly funny and self-effacing, and they’re reminders to me to stay focused on things that matter in the way that we can be helpful to each other.

Ian Hathaway: Who’s someone in your local startup community or in your broader network who doesn’t get enough credit and deserves a shout out from you? [01:02:00]

Chris Schroeder: Man, there’s just so many courageous entrepreneurs. I really can’t single them out. I like you. I talk to three entrepreneurs probably a day. 80% of them blow me away and what they do and the courage, I would say that there are several that have stuck to their guns in places of impossible calamity.

Sometimes in the Middle East and Syria. Refugees who I’ve met in other parts of the world, I have that perseverance. You can slow me down, but you can’t stop me. And this is the opportunity for me to build something helpful in a moment. I have a special place in my heart for them.

Ian Hathaway: Tell us something most people don’t know about you.

Something outside of work could be a hobby, favorite travel spot, a guilty pleasure, or maybe even a hidden talent.

Chris Schroeder: I’m not sure I got that much in talent, but you touched on something parenthetically that surprised people generally speaking, which was earlier than you suggested in high school and college.

I was in fact a dj. If people think that I was the cool thing that we think of DJs today, I want you to think of the greater New York City area of weddings and bar mitzvahs. ‘cause that was kind [01:03:00] of it.

Ian Hathaway: Oh, that’s great. Well, building off of that, what are one or two songs you’d like to add to our Spotify founders playlist?

Maybe something that fuels your workday or it has inspired you on your journey as an entrepreneur.

Chris Schroeder: I am a fanatic of music and I like many things overall. I wrote my book to Bach and I love jazz and have dear friends who have shared that. And I love a lot of the current music now, particularly in areas of hip hop.

And I will tell you that I think some of the most interesting hip hop storytelling and flow is coming from Asia and particularly Korea. Lee Young G is one example of it. But I will tell you that through Ben Horowitz, who has created this incredible thing called Paid in Full, he has built an enterprise that has helped give economic support to the kind of the founders of the hip hop generation.

People that I think a lot of kids don’t know anymore. Quincy Jones did this for jazz artists. ‘cause you know, many of the geniuses who built jazz in the forties and fifties, sixties ended up homeless. No one remembered them and whatever this has happened. With the pioneers of [01:04:00] rap and hip hop in the seventies, eighties, and even nineties.

And so when I listened to someone like Rakim who, or people my age will remember, but a lot of kids don’t. It’s poetry. I mean his, his word and flow is poetry. In fact, he was very inspired by jazz saxophone and tried to replicate that in his flow. And there’s not a great rapper today, chancellor, rapper, or Kendrick, who would not tell you Rakeem was foundational to who they are.

And so folks like that, their music is incredibly inspiring to me. Then your entrepreneurs would love one of the epic songs of Rakeem who’s paid in full, and so you can play that one.

Ian Hathaway: All right, we’ll add it. I know you are an insanely voracious reader, so this question is almost impossible, but let’s give it a shot.

What’s a book you’d recommend, maybe something that’s been especially valuable to you on your journey, or one you think every first time founder should read as they’re getting started?

Chris Schroeder: I read over a hundred books a year, and my goal is 150, which I didn’t quite hit last year, but I’ve tried to do. Look, I mean, there’s a tactical answer to your question from an A founder perspective, Ben [01:05:00] Horowitz’s books, both of his books on culture and the hard things were unbelievable.

Our friend and hero, Brad Feld has written amazing books. You’ve written amazing book about entrepreneurial ecosystems and also kind of a handbook of how to think about things, which I think are very powerful. But I really think in the end. That the best books, quote unquote, to help entrepreneurs are in history and biography, and to understand perseverance and how people think and how human behavior is, and also to try to aspire to get more of a bottom up view of where the world is going.

So very concretely, in preparation for my last trip to China. Late last year in November, I read, I dunno, 25 books on China. And most of ‘em were very good. A couple of them were exceptional. But the one that jumped out was a book I deliver parcels in Beijing. And the book was written by a Chinese gig worker who had a blog for many years that got fanatically valued in China.

And he turned it into a book and literally he had like 18 jobs in eight years and he was literally delivering parcels, but he also worked on warehouse floors. The book is extremely [01:06:00] poignant in that it talks about how hard that work is and the expectations of not being able to go to the bathroom and other things.

It’s very funny. There were stories that were hilarious, but it was an incredible reflection about how I think about work. Like, do I wanna be 9, 9, 6? My parents want me to be an engineer. I don’t wanna do that. You know, everyone says the young guy should be 9, 9 6, which is the Chinese way of working very hard.

I don’t want that. You know, maybe my gig life for all of its problems. Fits the kind of life I wanna live or does it this incredibly poignant view, not from China experts telling you about China and economy, but what are real people on the ground navigating? I just couldn’t get enough of it. It was a brilliant, brilliant book and it changed me in many ways.

Ian Hathaway: That sounds incredible. I’m gonna check that out. I also agree with you obviously Brad Feld, amazing writer, Ben Horowitz. I love his book. What You Do is Who you Are. Even the statement, the book is amazing. The stories in that book are incredible, but just that statement is something I try to think about often and history, right?

So the book I try to read every day [01:07:00] is Meditations by Marcus Re, Marcus o.

Chris Schroeder: Good for, I no surprise that you say that. I swear to you that what a wonderful thing because if every entrepreneur had that on their end table, they’re, they should not take their foot off the pedal one iota, but they’d be more circumspect about what their day brings.

Ian Hathaway: Fantastic book. Okay, so last question, Chris, if you could give one piece of advice to someone who’s about to start their first company today, particularly someone who’s a bit of an outsider, what would it be?

Chris Schroeder: You need to have a problem that you wanna solve it in your teeth. You can’t imagine not solving the problem or grab the opportunity that you want.

And in parallel with that, you know more about that problem and activity. Than almost anyone around you and never, ever be intimidated by money. I can’t tell you the number of entrepreneurs who go meet venture capitalists will come to me like, well, the guy’s rich, so he must know something. I don’t know.

If you have a great idea, the money will come, and if you don’t, it may not. But this idea that if you get to meet with Sequoia, then all of your problems are solved and [01:08:00] you’ll be great forever, is a story we tell ourselves in the head that have no bearing on the actual outcome of what you have. Money matters, and having people around you who can shore up your weaknesses can be additive, but there’s a courage in sort of saying, I will not be intimidated by money and I will focus on this thing that I can’t imagine not solving.

Ian Hathaway: That’s a great perspective, certainly a unique one that we’ve had on the show. I can’t think of a better way to end. Chris, thank you so much for being here and sharing your time and wisdom. I’m so excited to share this episode with our listeners.

Chris Schroeder: Honored to be with you and you’re a great friend, so thank you.

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. A big thank you to Chris Schroeder for bringing his curiosity and candor to the conversation. What stays with me most isn’t the impressive resume. It’s the choice Chris made in Dubai to abandon the path he seemed destined for, and instead chased the questions most people don’t ever ask.

He traded certainty for curiosity, expertise for exploration, and spent 15 plus years discovering what [01:09:00] most others. Miss. Chris reminds us that the most powerful position you can take isn’t declaring what you know. It’s admitting what you don’t. That humility isn’t weakness. It’s a superpower that being wrong isn’t failure.

It’s the first stop on the path to getting it right and that the best investors, builders, and leaders aren’t the ones with all the answers. They’re the ones still asking better questions. For outsiders listening, get on the ground. Challenge your narrative bias. Don’t miss what’s actually happening while you’re sipping that third cappuccino.

The next billion dollar insight might be waiting at a place you never thought to look. If you want more from outsider, inc, don’t forget to subscribe to the platform@outsiderinc.substack.com. It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc on YouTube, Instagram, TikTok, and LinkedIn at Outsider Inc.

Pod. You can also follow me on X at Ian Hathaway Outsider, Inc. Is produced by Spell Binder Media. We’ll be back soon with another [01:10:00] fascinating outsider conversation. Until then, thank you so much for listening and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features Willy Schlacks, co-founder and President of EquipmentShare, and one of the most intentional builders we’ve had on the show.

Willy’s story doesn’t begin in a startup hub or around venture capital tables. He grew up in a cloistered environment in rural Missouri — a world with no private property, no personal ownership, and strict control over money and agency. Inside that environment, entrepreneurship didn’t show up as ambition or status-seeking. It showed up as curiosity — a way to engage with the world and learn how things worked. Alongside his brother Jabbok, Willy began building real businesses at a young age, learning through necessity how to pre-sell, reinvest profits, and operate with discipline, long before those ideas were fashionable.

When Willy left that environment in his late twenties, he effectively started over. That reset eventually led to EquipmentShare — a company born not from chasing a hot market, but from lived experience as an operator confronting work that was reactive, chaotic, and disconnected, and deciding it didn’t have to stay that way. What began as a Startup Weekend idea in Missouri grew into a vertically integrated platform spanning technology, equipment, and services — scaling into one of the largest companies in its category, and just weeks ago, going public at a $7 billion valuation.

In this episode, we trace how those experiences shape the way Willy thinks about building — from why constraints matter, to how leadership evolves at scale, to what it means to stay close to the work as the stakes grow. ⤵️

Follow: LinkedIn, Instagram, X, TikTok, YouTube

Episode Highlights

In this first clip, Willy goes straight to the heart of what drives him—the relationship between struggle and creation. He argues that comfort, taken to its extreme, doesn't deliver peace. It delivers boredom. And boredom is the death of everything worth building. The real game, he says, looks more like music—rhythm, dissonance, and movement. The only time it stops is when you're dead. Plenty of time to rest then.

In this next clip, Willy reframes what most people call failure, arguing the word itself is the problem. Mistakes aren't wrong turns; they're just movement. His advice to founders is less about tactics and more about orientation: start with yourself, stay authentic to what you actually feel, and stop applying moral wrappers to the things you chase. The path, he says, begins and ends with you.

And here, Willy answers the question most people around him got wrong — why Missouri instead of Silicon Valley. Most thought it was a foolish choice. His answer is almost disarmingly simple: Missouri was home. But what follows is a deeper argument about the difference between a place you land and a place you manufacture from a checklist — and why only one of them has any real roots to it.

Finally, Willy reflects on the unexpected gift of his unconventional upbringing — it taught him early not to conform. The real obstacle, he says, isn't hardship. It's a comfortable, easy childhood. And it's something he worries about with his own kids.

I’m grateful for my conversation with Willy. He’s one of those rare people who has thought deeply about the relationship between constraint and creation—not as an abstract philosophy, but as something he’s lived from the beginning. From early on, Willy developed a clarity of purpose that I think is almost impossible to manufacture later in life. That’s what makes his story so worth sitting with.

What I took most from this conversation is how countercultural his whole orientation really is. In a world that rewards optimization for comfort—the right city, investors, and network—Willy kept choosing the harder thing. Missouri over Silicon Valley. Constraint over ease. Roots over relocation. And the result isn’t just a $7 billion company. It’s a way of building that has integrity all the way down, because for Willy, it was never about chasing the signal. It was always about the work.

If there’s one thing Willy would want you to take away, it’s this: stop waiting for the conditions to be right. Constraint isn’t the enemy of building—it’s the engine. You don’t need everything to be perfect, you just need the discipline to stay in motion and the belief that the friction is the point. The only thing standing between you and what you want to build is the story you’re telling yourself about why today isn’t the day.

Willy’s Library

During our conversation, Willy called out three books he enjoys, mentioning Range specifically as one that founders should read. He also mentioned his admiration for Henry David Thoreau. But since he didn’t offer a specific Thoreau book, I chose one. Brief summaries and links to all four are below.

Range: Why Generalists Triumph in a Specialized World, by David Epstein. A counterintuitive and thoroughly researched argument that generalists, not specialists, are better positioned to thrive in complex, unpredictable domains. Epstein challenges the “10,000 hours” gospel popularized by Malcolm Gladwell, showing through a wide range of evidence that breadth of experience, late starts, and cross-domain thinking are often significant advantages rather than liabilities. The book draws on examples from sports, science, music, and business to make the case that the most creative and adaptable people are rarely the ones who specialized earliest. For founders — especially those who came to entrepreneurship through an unconventional path — it’s both a vindication and a call to lean further into what makes them different.

Team of Rivals, by Doris Kearns Goodwin. The definitive account of how Abraham Lincoln built his cabinet by deliberately surrounding himself with his most formidable political opponents. Goodwin spent years in the archives reconstructing not just the political history but the interior lives of the men involved, and what emerges is a portrait of leadership that is as much about emotional intelligence and self-awareness as it is about strategy. Lincoln’s ability to absorb criticism, subordinate his ego, and hold together a fractious team under the most extreme conditions imaginable is the throughline. More than a Civil War history, it’s a study in what resilience actually looks like when the stakes are civilizational.

Duel: Alexander Hamilton, Aaron Burr, And The Future Of America, by Thomas Fleming. The story of the famous confrontation between Alexander Hamilton and Aaron Burr, but really a window into the founding era’s raw ambition, rivalry, and moral complexity. Fleming brings both men to life with novelistic detail, tracing the long arc of tension between two of the most brilliant and flawed figures of the early republic. What makes the book so compelling is how fully it captures the human dimensions of the story — the pride, the grievance, the miscalculation — in a way that dry historical accounts rarely manage. For anyone who has ever been drawn to the idea that character is destiny, it’s a hard book to put down.

Walden: Life in the Woods, by Henry David Thoreau. Thoreau’s account of two years living deliberately in the woods outside Concord, Massachusetts, stripping life down to its essentials and paying close attention to what remained. It is part memoir, part philosophy, part provocation — a sustained argument against the kind of busyness and conformity that Thoreau believed kept most people from ever truly living. The prose is dense and rewards patience, but the ideas have a way of staying with you long after you’ve finished. It gave Willy one of his favorite framings: that life pursues us more than we pursue it — that the most meaningful arrivals are the ones we never quite planned for.

Up Next

Tune in next week with Chris Schroeder — entrepreneur, venture investor, and author who spent the last decade and a half challenging one of the biggest blind spots in global entrepreneurship. Chris built an extraordinary career: Harvard, two presidential campaigns, Wall Street, and ultimately CEO of Washington Post online, before co-founding HealthCentral and leading it to a successful exit. The path forward was well-paved. But in November 2010, at a startup gathering in Dubai, something shifted. He realized he'd been completely blind to the massive wave of entrepreneurship taking shape across the Middle East, Asia, and Latin America — and he chose a different path. That awakening led to Startup Rising, the first book on startups in the Arab world, and investments like Careem ($3.2B sale to Uber). In this episode, we trace where his curiosity came from, what it took to turn toward the places others overlooked, and what fifteen-plus years on the ground has actually taught him.

Listen on: Spotify, Apple Podcasts, Amazon Music

In this episode of Outsider Inc., host Ian Hathaway sits down with Willy Schlacks, Co-Founder and President of EquipmentShare, to explore what it really looks like to build a category-defining company outside Silicon Valley. Willy shares how EquipmentShare grew from operator pain in the field into a vertically integrated construction tech platform spanning technology, equipment, and services, and why embracing constraint can be a strategic advantage, not a limitation. They dig into the chaos of jobsite operations, the early decision to take a platform approach, what Willy learned from time inside Y Combinator, and how building from Missouri forced the company to master scale early. Willy also reflects on taking EquipmentShare public at a $7B valuation, building the startup ecosystem through Redbud VC, and what he looks for in founders when the hard part is still ahead.

Show Notes:

(03:00) Why struggle and friction can be an advantage

(10:00) Curiosity, questions, and what “creation” really means

(16:10) Reframing mistakes and failure as fuel

(19:05) The operator pain behind EquipmentShare

(23:00) The jobsite moment that forced the idea into motion

(27:00) Inside Y Combinator and what Willy learned from the Silicon Valley bubble

(29:05) Building from Missouri and the meaning of “home”

(32:45) Constraint as a forcing function for scale, systems, and resilience

(35:25) Going public and what founders misunderstand about the shift

(38:10) Redbud VC and building an ecosystem close to home

(41:10) What Willy looks for in founders when success is still unproven

(46:05) Legacy, ritual, and the long game of creation

(48:00) Beyond the Bio: Willy Schlacks

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Willy Schlacks, Co-Founder & President, EquipmentShare

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

AI-Generated Transcript

Willy Schlacks: [00:00:00] In starting EquipmentShare, I think you still made every mistake in the book. It’d be hard to find a mistake we didn’t make. So I would just encourage people who moved on a path of creation that the way we label these things like mistake and failure or. So wrong. If we could recapture those words so they don’t have a wrongness to it, then they’re very useful.

The most important thing is that your perspective is just deeply grateful to be breathing and creating.

Ian Hathaway: Welcome to another episode of Outsider Inc. I’m your host, Ian Hathaway. Today’s guest is Willy Schlacks, co-founder and president of EquipmentShare, and one of the most intentional builders we’ve had on the show.

Willy’s story doesn’t begin in a startup hub or around venture capital tables. He grew up in a cloistered environment in rural Missouri, a world with no private property, no personal ownership, and strict control over money and [00:01:00] agency. Inside that environment, entrepreneurship didn’t show up as ambition or status seeking, but as a curiosity, a way to engage with the world and learn how things worked.

Alongside his brother, JAIC Willy began building real businesses at a young age, learning through necessity how to pre-sell, reinvest profits, and operate with discipline long before those ideas were fashionable. When Willy left that environment in his late twenties, he entered the capitalist world for the first time and effectively started over.

That reset eventually led to EquipmentShare. A company born not from chasing a hot market, but from lived experience as an operator, confronting work that was reactive, chaotic, and disconnected, and deciding it didn’t have to stay that way. What began as a focus solution grew into a vertically integrated platform spanning technology, equipment, and services, scaling from a startup weekend idea in Missouri into one of the largest companies in its category.

Along the way, Willy made a series of deliberate values-driven choices. Building outside of Silicon Valley, embracing [00:02:00] constraint instead of comfort, choosing venture capital only when the problem demanded it. And just a few weeks ago, taking EquipmentShare public at a $7 billion valuation while retaining long-term stewardship of the company.

In parallel, he’s investing deeply in founders building far from traditional tech centers through Redbud vc, helping shape the kind of ecosystem he believes great founders actually need today. We’ll trace how those experiences shape the way Willy thinks about building from why constraints matter to how leadership evolves at scale, and what it means to stay close to the work as the stakes grow.

Willy, welcome to Outsider, Inc.

Willy Schlacks: Thank you. It’s quite the intro almost seems like we’re done.

Ian Hathaway: Well, you have an amazing story. I’m so excited to have you here while reading and learning about you. A theme that kept surfacing was the importance of struggle. The idea that too much ease can be its own trap, and that meaningful progress often requires friction.[00:03:00]

Most people spend their lives trying to add comfort and remove struggle. You do the opposite. So from your perspective, why do people so often misperceive the value of struggle, and in what ways have you seen it function as an advantage?

Willy Schlacks: Yeah. You’re going to the heart and soul of what it means to be human, which is an interesting topic for this day and age.

I think comfort and struggle. For me, there’s this innate common experience that I observe in myself and other people where we want ease and comfort, but the extreme boredom on the other side of that. Is very apparent. We can certainly observe humans who sort of accept maybe that reactive, here’s comfortable environment, and then I’m forced into uncomfortable.

And if life puts me there, I’m always trying to snap back to comfort. And that’s generally fear driven. But when I look at things that are creative or built or movement, these are the patterns that really get me excited. So my experience of. What is creative? What is [00:04:00] movement? What’s the dance? That’s where it looks a lot more like music and there’s certainly a cadence to it and there’s harmony if we want to use that pattern, but it’s where this human experience suddenly shifts away from a programmatic.

We’re all just doing a similar thing to, we are creators of something in the future. The ability to create that future is something I think we underappreciate, and that’s really what gets me excited about pursuing the North Wind of discomfort versus the couch of, oh yeah, this feels good. Oh yeah, I like it, but I get bored very quickly and I think everybody does.

Everybody wants something more. Instead of life being lived, they find themselves in a bullying lane with the lines up. It’s a fun little game, but there’s just so much more than that. It’s just the expiration that I continue to discover every day, and I enjoy it. The only time things stop is when we’re dead, so I’ll have plenty of time to rest then.

Ian Hathaway: I feel like actually [00:05:00] we have an epidemic in society to avoid discomfort of any kind, avoiding short-term pain at all costs. So to make that idea a little more concrete, I’d love to rewind to the beginning. You grew up in a cloistered, highly structured environment in rural Missouri. One where money ownership and even personal agency worked very differently than how they do in the outside world, at least for most of us.

Can you paint a picture of what daily life was actually like in that environment and how that way shaped how you think about work independence and building.

Willy Schlacks: First off, I feel so much gratitude, like the lens I see just is filled with deeper gratitude. Now, I don’t say that to negate pain or other people’s experiences because when I think about my early life, it was just in this environment that was definitely filled with certain things like fear.

Control. But for [00:06:00] me, I don’t shy away from or label those things as bad. It’s like, no, that’s part of this experience, this environment. Yeah. It was very cloistered. Everything was controlled when I was a kid. Didn’t really know anything outside of that. That was life. Everything was communal. There was no such thing as personal property.

Well, if there were personal property was pretty. Small intangible, like maybe your clothes, but even then, one of the calendars that we had kids was the clothes we would wear every day. And growing up in that, I never thought that that was unusual. Of course, ‘cause you grow up in it, but I didn’t expect to have agency over the clothes I wore.

I just was like, yeah, everybody has a calendar and somebody’s telling you what clothes you wear. It’s just all I knew. And it’s a funny flavor of the culture that I grew up in and I think as a kid. Those experiences that can be very different than as an adult or as a mind. That then starts to question and read and explore thoughts beyond a known environment.

And I really credit my parents for my curiosity and my exploration because there was a very [00:07:00] tight knit worldview that was imposed on us very tight knit with a heavy dose of fear if you didn’t comply with that worldview. But my parents are, were always like, yeah, I mean, this is it. But if you think of something else.

Go explore it. Like they always had that release valve for me and a lot of other folks there didn’t like, that was not an acceptable thought and I took advantage of that and I really explored in my mind and encountered philosophy at a young age, and they sort of banned the public library, which made all the more enticing to go discover books and the rethinks that were.

Banned and wrong and evil. And I think that’s where I also started to explore the concepts of, well what is that? What is this human word of evil? And what is the word good and what was the origination? Now, of course, in the environment I grew up in, there was an extreme rapper of religion around all of that.

And that was an unquestionable thing. You couldn’t question it. ‘cause if you question it, everything sort of crumbles. [00:08:00] And it did teach me, you could never label or consider curiosity as wrong. Curiosity to me is just, I’m like, yes, I’ll be the wind in that sail, whether it’s my kids or people I work with or whatever.

Because I experienced the fear of others when I would be curious. And what I quickly realized is that. Fear is just the caution tape to a question because all they’re doing is saying, Hey, your curiosity, you’re about to step across my caution tape and holy fuck, that’s gonna destroy my world. So please don’t.

So for me, when I would push on questions as a kid, and I really enjoyed it because I suddenly discovered that people would bristle up and it was meaningful to them, and I would push on. Their views of religion or the why of life or what is life, and I didn’t do it in the sense of I was right. I did it with questions and I started to learn that you can discover so much with a question and you had very little to discover if you had [00:09:00] the answer.

And it was those early experiences where I started to at least subconsciously appreciate that being right about things is the most freaking boringest thing on earth. Not knowing is just the adventure that you wanna be on. And as soon as you absorb something and it feels right, like okay, check it back there because it’s no longer interesting and you want to build on it, the theme and the movement of life and where I found as a kid that whether I would sneak off and go to the library and get books and feel guilty about it because it was wrong, but at the same time deep inside myself, start to form and question why is this wrong?

There was a lot of control around, particularly relationships and interactions. If they controlled the clothes we would wear, they probably controlled everything else, as you can imagine. But also to know that it didn’t matter to me, like what I enjoyed as a kid was the things everyone enjoys, you know, friendship and playing and all these other things.

And [00:10:00] I can remember that and taste it and also remember and think about the times where there was fear and darkness and all these other things, and I appreciate the complexity of that.

Ian Hathaway: That’s very fascinating. I wrote this down. Fear is a caution tape to a question. I haven’t heard that one before. You mentioned things you were curious about, books, philosophy, something else was entrepreneurship.

For you, more of a channel for curiosity, more than ambition. Maybe it’s not what you were calling it in your mind, entrepreneurship, but what do you remember about some of those early experiences, tinkering, building businesses? What were you trying to do? Were you trying to access knowledge, freedom, control?

Meaning, what was inspiring you to

Willy Schlacks: be able to create. That was the heart and soul of it. You have a fairly controlled environment, and I think this is true of any human. There’s something inside of us we want to express, we want to build, we want to create something, and whatever that medium is, we’re gonna lean [00:11:00] into it.

But for building businesses, it was creation. We didn’t even think of it as really building a business, even though we were, and I was fairly young when we started some of those efforts, my brother. Was six years older than me, so he was always more responsible and doing the adult things, and I was like literally a kid just coming along for the fun of it.

Now obviously as we both got older, we had some fairly sizable business ventures going on, but the unique aspect of it is we didn’t keep any of the money. ‘cause it all went to this environment and that didn’t bother us. We never thought about it. We wanted to make money. It was like, that’s the thing of whether we’re succeeding or failing.

But actually having the money was meaningless to us. We never had experienced that. There was certainly no driver beyond the fact that it was fuel for the next thing. But yeah, creating was amazing and I loved whatever the medium was. It was incredible. But there was so much risk to this creation of building a business.

Suddenly we would find ourselves outside this environment in a whole new world that we call them the others or whatever. [00:12:00] It’s like, well, these are the people that are outside and they’re paying us money, and so what do they want? And you start to get to ask these questions about making stuff people want and what if the stuff that you make is stuff you enjoy?

And so a lot of our early businesses had flavors of construction and craft and service things and whatnot.

Ian Hathaway: You mentioned going outside. Eventually you did. You left at age 27, which was not just a physical move, but a full reset. You were already married, you already had a child. You’re stepping out into this totally different world.

You mentioned your brother Jaic. He left as well, and along the way, the two of you have built everything together. I’m curious about that partnership. How did it form so early, and why do you think that particular division of trust and responsibility has held up across decades of building companies together?

Willy Schlacks: My brother Jabba, he’s ridiculously high integrity [00:13:00] person for him. It’s a very binary world for me. It’s a very fluid musical world. And so the reason it worked so well though is because we had always had a different perspective of everything, but ultimately a very similar route and a very similar outcome.

So through that understanding, we knew that there was nothing hidden. There was nothing inauthentic about our engagements. Like when you engage with another human who is authentic, it’s magic. You just win the lottery at that moment and you’re like, okay, let’s stay connected for as long as we can, or whatever this experience is gonna give us.

Whatever that relationship might be. It might be a spouse, a sibling, a business partner, whatever. But we’ve all had experience of encountering humans where we discover the inauthenticity and the older we get. I’m like, shit, I don’t wanna spend time with that. So yeah, my brother is so insanely authentic to a core that it made it really easy.

We didn’t even think about it. I [00:14:00] was like, of course. Who else would we. Business with?

Ian Hathaway: Well, it’s not always such an obvious answer. In fact, you know, many people would never do business with family members. But I think it’s a testament to the relationship that the two of you have. One of the components of that has been clear boundaries on responsibilities.

You’ve described in the past having this consistent split where he sort of runs operations and you’re more focused on customer and product. How did you discover that division and does it ever break down?

Willy Schlacks: Oh, it always breaks down. Yeah, it was just leaning into our strengths. I definitely love the ambiguity.

Whatever is ambiguous and unknown. That’s where I love to run to Jaic. He does not quit. He’s ruthless. He’s also a detailed operator. Everything has to be a known quantity in his world. So these two lenses that we had on the world really created strengths for him when it comes to operations and execution.

And then for me, you can have [00:15:00] five things that are all true at once. Like most people would struggle with that, but for me, it’s just an interesting puzzle. But for his world, I would say he has to collapse Those things, like reality has to collapse into something, and he’s much better at that than I am in the operational side of the business because everything does have to collapse into something.

Whereas I’ll sit there with my team and go, well, you know, there’s multiple possibilities. And they’re like, well, what the hell are we supposed to do with that can’t really do tomorrow with, with that type of response. So our strengths is what ultimately led us to handling different parts of the business.

More businesses as we were building them.

Ian Hathaway: Good compliments. That’s important in any business partnership. I want to, of course, get to EquipmentShare in a minute, but before we do that, we’ve kind of hinted that you and JAK have built multiple businesses before EquipmentShare, not tech, not venture. These were real businesses with customers and cash flowing.

You reinvested [00:16:00] profits stayed close to your customers. What were the core operating lessons that were forged during that time period that still shape your decisions today? And then maybe conversely, what lessons did you have to unlearn when you were building at scale?

Willy Schlacks: Yeah, we did some technology things too, like even in that environment we grew up in.

When I was a kid, I first encountered computer programming. I didn’t even know it was computer programming at the time. So we did a bunch of different things, including trying to start a technology company. It then got shut down when they realized what the internet was J it got put on church discipline, but we were always pushing the envelope.

I don’t know how many businesses we started before EquipmentShare, but quite a few in a lot of different domains. What I would say your question though of what did we learn even in starting EquipmentShare. I think we still made every mistake in the book. It’d be hard to find a mistake we didn’t make.

So I would just encourage people who moved on a path of creation that the way we label these things like mistake and failure are just so wrong. [00:17:00] If we could recapture those words so they don’t have a wrongness to it, then they’re very useful. The most important thing is that your perspective is just deeply grateful to be breathing and creating.

Doesn’t matter. If the thing that you did yesterday looks a little dumb compared to the thing you know now, that should be an obvious thing that should be occurring. Just the movement and progress of thought. Because yeah, you’d think after we built all those companies, we’d maybe do less things that people would observe as mistakes.

But no, for us it was learning. It was fun. So if for our advising people that, Hey, based on everything you learn what’s important in business and all this stuff, first and foremost, it’s derivative of you. You can’t escape yourself. If you are not authentic with yourself, you’re gonna be screwed up. This is the barrier.

You are that doorway to something where it just feels so amazing or you have regret in these other types of emotions that are completely unnecessary to live with, completely [00:18:00] unnecessary. It is a choice even when it doesn’t feel like it, it starts with you. I didn’t realize that till much Later on.

Pursue yourself. Give yourself a break too, just because you love money and you wonder if you shouldn’t. Who the flip cares love money because as soon as you get it, you’re gonna wanna love something else. And that’s okay. The way in certain societies we apply a moral wrapper around the things we chase is, is not helpful.

It actually just creates this divergence from the reality of what we feel. So embrace the feelings, embrace the internal knowing, and whatever your future is, it’s gonna be mind blowing versus. The level of control or the conformance that you wanna bring to your life. That’s probably what I am deeply grateful for about my upbringing is that I learned early on to not conform.

I loved being an iconoclast. I think if I had grown up in what we would call normal and it’d be quite a struggle, like the biggest struggle to humans in this day and [00:19:00] age is a moderately middle class or wealthy easy upbringing. That’s something I’d find challenging to surmount, and I worry about that with my kids.

I’m just putting so much barrier in front of ‘em. They’re gonna have to be super humans to get to the other side of it.

Ian Hathaway: That’s great. I agree with that. I wanna switch gears if we could, to EquipmentShare. What eventually became EquipmentShare was not about chasing a market opportunity, but confronting something that you and your brother kept running into over and over again As contractors, job sites were reactive, chaotic, and disconnected.

So what was the moment that you realized this wasn’t just your problem, that it was a systemic issue, a failure across the industry? And then secondly, once you realized this, how did you actually take steps towards solving this problem for other people?

Willy Schlacks: We assume everyone else was more organized than us, but we also could observe that even [00:20:00] that perception of maybe they’re better than we are still was a.

Leap and bounds from any contemplation of an industry moving forward and leveraging this whole digital world that had developed since late 60 seventies. Everything still was incredibly analog within another set of friction and duplication within certain digital realms. The chaos of an industry that has job based, I mean, there’s other job based industries, but nothing at a scale of construction where we have 14 trillion of stuff.

That moves towards a job based environment because a job or a project is a proof of concept. It’s very different than manufacturing or retail or any type of other industry that you sort of refine the same thing over and over again. You still have a lot of challenges in any environment of building a business, but when the outcome is once a proof of concept, like you build the bridge or the building or the tunnel or the house, it’s like, yeah, you’re not gonna do that again.

You sort of have to deconstruct into the things that you will do again. [00:21:00] But the whole digital revolution, what it could enable, and what we believed was that even with all these challenges. In construction and with an industry and humans that could absolutely still build stuff and keep getting better, but it was all analog driven.

The digital side was not helping for the built environment. Now, different for a design phase. When you design something that’s, that can absolutely be translate to largely digital, but the built environment you’re dealing with is physical realm. And if we wanted support. An enhancement from these digital tools, then you had to have a platform approach was our belief.

And because things weren’t wired up like a manufacturing site or a farm or retail. You had to have a platform and primitives in that digital world that could contemplate this crazy, flexible, chaotic movement of goods and services and entities interacting. And was a bit of a macro observation because we could observe and had deep experience in this [00:22:00] industry for decades.

We knew what it felt like to be chaotic, and we also knew that nothing was changing. Even as tools were showing up, we also felt certain severe pain points that felt matic of this problem that could be alleviated if a solution existed, if a platform existed, and one of our most severe points was.

Equipment rental, which is why we started that space. We never started the company with a thought of, this is our domain and this is the end. The day we started a company, or even when we started thinking about it, it was always a macro problem of, well, how big is this entire thing? And we wanted to find our landing pad, but we never constrained the thought to that.

We’ve been thinking about this for our whole lives, but the spark that launched it, we had a bunch of jobs going on and there was one project that was. Ridiculous in its intensity, its schedule, and it was a big, huge utility project, 16 feet underground. And we were connecting live sewer [00:23:00] and water and all this stuff.

And I remember it was freezing cold day. It was raining. J was 16 feet underground doing a live sewer connection, and we couldn’t find the equipment we needed, so we had to go rent some stuff and combine this whole environment where. It was such a specific high intensity urgent thing. We’re constantly sending people to go rent stuff and by the end of it, everything was fine.

It all got figured out like it always did. We were just problem solvers. Didn’t matter what the problem was. It was like, of course we’ll solve the problem, but we could sort of reflect and go we a shit storm literally and figuratively in this case. And I remember at that point I was like. We have to do something like this is so freaking insane.

It was everything from the economics of the rental provider that we were working with to the lack of their organization, to the lack of our organization. Nothing was measurable is what it felt like. So it all required superhuman effort on our part. We felt like that was fairly similar [00:24:00] for most companies we encounter in the industry.

You had some amazing superhuman people that could practically do anything, but if you’re always relying on super humans, can’t we alleviate that somehow? Can’t they progress past being the tip of the spear every single day? There’s a level of excitement around developing a craft and such ability, and I think that’s gonna be more common in the future as we create tools that let humans focus on craft.

Humans wanna be creating. They want a new frontier. They don’t wanna necessarily be doing the repetitive things every single day is, if this problem is solved, let’s not solve it again, type thing. So that next week is when we really got intense about, okay, we’re gonna build something that is solving this problem.

We just had a visceral understanding of the disconnection that was present in our industry.

Ian Hathaway: So early on you understood the pain, but while maybe the vision was clear, you had to find where the real leverage was. So do you remember in those early days, you’ve got the vision, but something is not quite landing.

What [00:25:00] exactly was wrong and where did you learn about where real leverage lived?

Willy Schlacks: I think because we’ve been doing this since we were kids, we didn’t even think about this. Beyond just a subconscious intuitive sense that if you’re gonna do something in this capitalistic environment, you have to ask what do people want and give it to them.

You have to earn the right to creating a better solution. We never even thought about the option of, Hey, let’s build something and raise money. And if it works and people like it, great. And if it doesn’t, that’s fine. We couldn’t even contemplate. How could you not go talk to somebody and they say, Hey, I want this.

You have to do it. We just wanted to do it in a way that had a perspective that would evolve towards alleviating all this chaos that we experienced. So we knew technology would be part of it, but it was just part of it. We never thought about the isolation of build software and leave the dirty works outta people.

Of course, we were gonna shoulder more than our customers. That was just, uh, intuitive, innate, [00:26:00] visceral feeling we had. Now, I would say later on, investors could not. Comprehend why the hell we were shouldering this vertical approach and they were frequently suggesting that we pivot only do software and or get rid of this other chaotic stuff.

But obviously we never did and we couldn’t contemplate those things. I don’t wanna say it’s ‘cause we were smarter or anything. We just happened to go, alright, we got a customer. But guess what? We’re also more interested in solving. A $14 trillion industry problem versus just their one thing. And for us, that was new, which is why we then had to go raise money and go down the path we did

Ian Hathaway: dealing with investors raising money.

One of your earliest experiences with that. You and your brother spent time inside Y Combinator early on, which also meant spending time inside the Silicon Valley way of building and doing things right, the pace, the assumptions about the need for capital growth talent. Why did you decide to go to YC and [00:27:00] what did being in that environment teach you about how companies can be built?

Willy Schlacks: We had never heard of yc. We bumped into Wade from Zapier and he heard what we were building. He was like, you guys should go to yc. And we’re like, well, what is yc? Looked it up online and like, okay, yeah, we’ll give that a shot. Applied and got in. There was no strategic thought to that. And as far as raising money, we had never raised money for businesses before.

We always just built the business with nothing and then use the profits to grow it. That was all we knew. So encountering this world of people will give you money. You really haven’t built something felt very weird and odd, but also it’s like, wow, that’s pretty cool. But we perceived it as sort of taking advantage of the system.

It’s like other people would literally go say something and then raise money on the thing. They said, like, there’s nothing real of that, but people are giving them money. And that felt weird, but that was the bubble we suddenly encountered in San Francisco. I do remember seeing that and just having a [00:28:00] slight moment of, oh, I wonder if we’ve just always been doing it wrong, and maybe that’s really how the world works.

But of course, our gut couldn’t ever escape the raw reality of just building value and doing stuff, so we never really experimented with the fantasy of raising money and the option of failure. I use failure only in the term of when you stop trying, like to raise money from somebody. Then to tell ‘em a year later, Hey, I’ve learned a lot, but your money’s not there.

That’s incomprehensible to me. But I watched a ton of people do that. Like to me, that feels like the couch. It’s just so easy to go, Hey, I’m gonna stop exploring that hard adventure because I’d rather have this couch and that million dollars you gave me. Thank you. I learned a lot. Like, what the fuck? I mean if a founder actually said that, like, okay, now I have a definition of failure, and that’s it.

Ian Hathaway: Yeah,

Willy Schlacks: so that’s what we encounter a lot of in San Francisco, and that [00:29:00] was a bit mind blowing to see people so cavalier about the promise and the facade of as if they are an adventurer. Then they open the door and it’s a little cold outside, and then they close it real quick and go, okay, yeah, let’s end this adventure.

I’m just, ugh.

Ian Hathaway: It’s a very unique and special place. I think a lot of what you’re describing is resurfacing now in the AI boom, but you made a very conscious decision to return home to Missouri. What gave you the conviction? To build EquipmentShare in Missouri rather than staying inside of that Silicon Valley gravity.

I mean, I have to think that many people, or at least some people around you, were discouraging your choice to do that, especially investors. But what gave you the confidence to do it anyway?

Willy Schlacks: Definitely. Most people thought it was a foolish choice, and I don’t discredit them for that at all. ‘cause they’re probably just working off pattern recognition and other things.

The reason we did it is a pretty simple answer though, and it’s simply because it was home. I [00:30:00] love the concept of home because home has different gradients to it, but it has a feeling of constraint. It has a feeling of walls, it has a feeling of ritual. ‘cause even choosing a home, people don’t realize the choice of home is not really ultimately home ‘cause you’re manufacturing something, something that loses a depth and a root to it.

So. The easy answer and the authentic one is it was sho like we never thought about it. And the older I get, the more I. Deeply appreciate the concept of home and not that you can’t move homes either, like, ‘cause I, I left an environment when I was 27 and it’s not like home has to hold you in that sense, like life will move you through it.

But that’s my point is life holds you through whether you find yourself in a stream and then you’re up on a rock or wherever. Life has a way of saying this is it. And you can sort of feel it in your gut and you know when you’re migrating to look for something else. But if you sit down and go, okay, I want good weather, [00:31:00] palm trees, beach, this, that, whatever, and then you go there, that’s the easy couch.

And the people that I observe who do that don’t have the same. Depth and sense of the home feel. Now, it doesn’t mean they can’t enjoy it, but because it is easy, they will get bored. Not that I’m wrong, I like traveling. I like a beach, but I do know that a good seven days into my travel indulgences, I am fucking bored home.

I just cannot imagine like the ritual of when I wake up, my wife and I are awake in the morning and it’s still dark outside, and then we start the fire, then we have coffee. Holy freaking hell. That’s so much more enticing to me than a seven day trip in The Bahamas. Home is just such an underappreciated thing, and I don’t mean that in the sense of a control perspective.

I mean, sometimes life drops you somewhere and you find roots there and it’s great, and sometimes you’re uprooted and then you find roots elsewhere. But it’s like [00:32:00] life chose versus me putting the list down of comforts.

Ian Hathaway: You don’t have to move somewhere for a job or to build a company. You should feel most equipped to build that company where you feel most at home.

Coming back from the Valley, you also made a very conscious choice not to optimize for comfort or abundance, but to keep operating inside of real constraints. Some of that is a function of where you’re building the company. You’ve talked about scarcity, not as attacks or a hindrance, but as a forcing function that actually builds resilience.

Tying this back to the idea of, of struggle as a key ingredient. How did choosing to build in Missouri actually shape how you operated day to day? Where did struggle show up as a strategic advantage rather than just a circumstance?

Willy Schlacks: I think it enabled us developing scalable process and scale far quicker than we would’ve if we were in a low constrained environment.

Say we, we decided, hey, new [00:33:00] York’s great, or, you know, Southern Florida or whatever. Those markets are so big that we wouldn’t have had to really figure out scale and remote ‘cause our ambitions were global. So a big part of what is underappreciated when you have a brick and mortar aspect to your business is store number two.

And if that’s just next door, you’re not really doing scale. Like you have to figure out all your systems and process for scaling people and hiring, and when you’re not there to solve the problem, how does the business continue on? How does culture emerge That’s far beyond and impactful then you as an individual.

Like when I think about my brother in the 16 foot trench doing live sewer, okay, superhuman Great. Guess what? I can’t clone him, put him around. So you have to then develop a culture and a company and process that is sort of starting to replicate not only the operational, but also the technological side of this.

So it was a huge advantage that, you know, our home is not a big market, it is the smallest market we’re in currently. [00:34:00] So very quickly we had to expand outside of the known. And if you look at what we achieved, and I just mean this from a data perspective. Scaling in the industry. Nobody in the history had ever done that.

Scaling like you had constraint of a balance sheet and just quantity of locations. Nobody’s ever done that. Now it’s not because we were a rocket scientist, it’s simply because we had this constraint of small market and we had an ambition of the whole industry. There was no plateau of, oh, okay, if we get to this revenue or we get to this thing, we’re sort of done.

Like even right now, we haven’t remotely approached done. It’s like when you see your destination on the horizon, like you keep driving for six hours is still not closer, 10 hours, that destination is not closer, which is fun because all the stuff that’s around us in our her view is different and exciting.

But I love having a destination that’s so freaking far out that there is no foot off of gas. But yeah, the constraint of having a small market was. [00:35:00] A huge advantage because we were forced to figure out scale very early and did, there’s a lot of lessons and things and tactics that we learned, not because we were so brilliant, but because the vision and our view of what we’re building forced us down that path.

Ian Hathaway: So you mentioned the goal is always in the horizon. You’re never reaching that destination. You’ve had some really big news, let’s call it a milestone, a huge milestone. EquipmentShare. Just became a public company listing on the NASDAQ at a $7 billion valuation. It’s an incredible accomplishment to be celebrated, and I have to think that that moment on the NASDAQ platform was surreal and a defining moment in your life.

But as you said, you’ve been very clear about going public. This is not an exit for you. It’s a tool. You see public markets as faster, cheaper, more transparent way to access capital so that the company can continue growing and [00:36:00] serving customers at scale around the globe. How do you personally think about.

The trade-offs of becoming a public company. And what do you think founders misunderstand about what actually changes and what doesn’t when you cross that line?

Willy Schlacks: We learned a ton through that process. This wasn’t part of the plan, but almost nothing was. So let me just put that out there. Now being public, I think my brother and I enjoyed watching that experience through other people’s eyes, probably more than our own, because.

We felt deeply that the year long effort of work to go public wasn’t that useful to our customers, and that always makes us uncomfortable when we’re doing things that are not useful to customers. In the grand scheme of things, it was necessary and it will absolutely be able to help serve customers. But the actual emotional content of experiencing it was super exciting to see through other people’s eyes, like our family, like having our parents there.

My mom and dad really aren’t. Big city people and having my mom and dad there and my mom [00:37:00] on the podium when we pushed the button, and she had no expectations. She didn’t even freaking know what was going on until she showed up and she was like, oh, what? What are we doing? Oh, this is great. And she was our biggest cheerleader.

And my dad, when we started the company, he was our first driver. It’s a family business type thing. Like there was so much trust and belief in what we did and our deep appreciation for what they did for us, that watching that come together was a really cool moment. The whole year of preparation was less cool, and then the moment after was wonderful because now we’re back to work and we really love that.

It does feel like we’ve got more ability from just a resource perspective to keep the foot on the gas towards that thing in the horizon that hasn’t moved an inch. ‘cause if our goal is this massive industry, we are so early on this effort. There’s no stopping.

Ian Hathaway: Well, speaking of building, which is what you’ve done your whole life alongside of building EquipmentShare, [00:38:00] you’ve also been very intentional about building the startup ecosystem in Missouri.

First, you founded scale, which later became Red Bud vc, investing your time, your capital, and your attention into founders building companies far from the coast. It’s not just a side project for you. It’s deeply tied to how you think about company building and leadership. What was the gap that you saw in the Missouri ecosystem that made you feel like this kind of founder first platform needed to exist, and why do you feel it’s important for you to help to build it locally rather than backing companies far and wide?

Willy Schlacks: We back companies anywhere, like our constraint is, it’s maybe flipped from what most VCs would do. So like most VCs have a, a domain, a region, a focus that’s more outward facing. [00:39:00] We put the constraint on ourself where our constraint is, here’s home, so we’re gonna do it here. Didn’t really think about any other option.

We weren’t trying to create ease for us. And then even raising money, this is an unnecessary constraint, but one we put in ourselves, we’d rather only take money from people that we resonate with. And that is because of some super negative experiences I had with investors. And I’m not saying it’s carp blanche, like I’m met so many good investors and I deeply appreciate our investor base writ large.

However, there are some anecdotes of. Just people that we made a tremendous amount of wealth for that are incredibly antagonistic and intent on our destruction. And that was puzzling to us. And it took me a while to come to reconcile the fact that some humans are a little different, whatever made them different.

Point being that humans don’t change for other people, they change for themself. And if they’re not interested in that, then guess what? They’re not interested in that. So it does matter to me. Where we raise money [00:40:00] from that is constraint. I want to resonate with those folks. So if somebody shows up with a hundred million bucks and there’s not that resonance and there’s a question of that alignment, life’s too short for that.

The outcome is not money. There’s something far more interesting and impactful. Money is really the fuel. We put the constraint on ourselves, but there is no constraint in who we invest in. And for that reason, a lot of our companies are. Now the fact that we are here and there is access to those resources for folks who are in the Midwest is really cool because when I was raising money.

For EquipmentShare. Back in 2015, there just wasn’t an awareness in an ecosystem. So I like the fact that that’s there, but also don’t wanna make a virtue outta that. It’s literally, again, the answer is home. That’s the only reason why I like those constraints. And venture is an amazing source of capital that’s fairly new in the grand scheme of history.

By and large, it’s a very healthy thing for creators who want to create, and I’m, I’m happy to be part of it. [00:41:00] Like I feel very fortunate. Everything else in life. This is fun. I think we’re following the footsteps of a lot of phenomenal people here.

Ian Hathaway: You mentioned creators. I think it comes down to people. I imagine you would agree.

Where the focus at Redbud in evaluating founders and companies is less on pitch decks and traction metrics and polished narratives, and more about the founders, right? Their judgment, their resilience, their capacity to grow their coachability. A lot of venture funds say they do that, but the reality is they default to pattern matching surface signals and social proof consensus, really so.

What did you feel was fundamentally broken about how early stage founders are evaluated? And when you’re meeting founders today, what are the qualities that immediately pull you in?

Willy Schlacks: I don’t know if anything is broken about the overall industry, but I would say that people who deploy capital, the way they deploy capital is reflective of themself.

So a lot [00:42:00] of people do it very successfully, but some people are great at raising money. Then when it comes time to deploy it, what capacity and experiences do they have to really do that, where they’re gonna create a phenomenal return for their investors? So what I felt is that we bring ourselves to the table, and that’s it.

So the abilities and the outcome of what we’ll create, that’s a constraint there. But being an investor, I would say it’s the easiest job on freaking planet Earth. I imagine this is the way actors feel too. Now, it doesn’t mean there aren’t fun challenges, but when I stack it up to all the other jobs I’ve done, like this one’s super easy.

And what that makes me wanna do is lean even more into what is hard. What really can create the outcome that I want, because I feel this obligation as an investor is too easy when it’s my money, when it’s other people’s money, I really lean in more. I like the risk of that because it’s, [00:43:00] it’s actually much harder for me and requires more work and effort and thought.

And attention when it’s other people’s money. So I think the fact that we were able to raise money is what’s really created this maturity in our venture world. I love the pressure of that, but what we look for is pretty challenging because what I know will create phenomenal returns for our investors is if we pick founders who have resilience to a degree that is abnormal and that cannot be tested unless you have time.

So one thing we love is when we have a lot of time with these companies. So our effort, we do a tremendous amount of work to get early into the conversation, even before a founder would ever be thinking about raising money. Now, that’s very hard. We, we do a lot to make that happen, and so I think that’s a whole part of our venture efforts that’s fairly unique.

I don’t see a lot of other venture efforts doing that. They prefer almost to wait for the symptom of success, but what we know is that if you’re waiting for the [00:44:00] symptom of success, your return profile goes down substantially. Now your risk goes down too, potentially. It depends on what people call success, but if you can discover resilience.

These attributes that we know always equal an outcome that’s quite remarkable. If you can discover that early on, you’re, you’re doing phenomenal. So that’s where we keep trying to push the boundary. But fundamentally, what we’re bringing to the table is decades of building companies. So whether it’s assessing the company or just helping them, I’ll put helping in quotes because I don’t really think a good creator, a good founder, needs help.

I literally mean that in the sense that they couldn’t take advice or something. I mean that in the sense that help ultimately sort of steals an experience from ‘em. It steals the learning. And that’s a double-edged sword. So I often find myself telling founders, oh yeah, here’s what I did and all this stuff.

And then I sometimes have to catch myself going, wait, what am I trying to do? Giving them the fast path to success. There’s no such thing. [00:45:00] This is about them, their internal growth. When they’re aligned, awake at night, they’re afraid of something. That’s magic. The only question is, are you gonna fucking quit or pursue it?

Are you gonna start to discover that this adventure can be enjoyed versus, oh my God, this is too stressful and that’s a little cold outside and lemme tell everybody I learned some lessons and that is really hard to surface in a human because everybody is gonna say they have it. So. You’re really approaching the conversation with, okay, I already know you see you have it, and I’m trying to figure out if that’s real.

You’re questioning the very core of what somebody says is true. And you’re going, I’m not sure. I’d love to believe that, but let me dig deeper. Lemme try to suss this out because it’s not the words that are gonna tell me. It’s the other things. And I can’t give up all that now because if founders hear me say it and then they show up, they’re just gonna say the words again.

I don’t have to come up with new tactics.

Ian Hathaway: It’s an amazing lens. We think a lot about this. My partner, Jonathan and I, we’ve kind of used the frame execution risk, like how can we [00:46:00] filter that better? But it’s really, we’re trying to say the same thing. How do you know if people have the. The grit and the ability to overcome these immense challenges.

So look, you’ve spent your life deliberately choosing hard paths, building in constraint, embracing, struggle, staying close to the work. 20 years from now, what do you hope you can look back to and say, that was a job well done.

Willy Schlacks: Couldn’t predict that at all. But the feelings I’m hoping to experience in 20 years are gonna be reflective of a mindset I have at the moment.

So I can’t escape the fact that what has continued to feel deeper and better only grows in magnitude. And that is the ritual I experience with close relationships. The depth of that just gets deeper. That movement of ritual with relationship is, is definitely gonna be the thing and the ability to.

Create on the other side of this, like the medium and the environment, all that, that’s hard to predict 20 years in the future, but the theme of [00:47:00] creation certainly isn’t gonna change, but the people you deal with, that’s where satisfaction structure really set in. And it’s not just the creation because ritual is this flip side of creation.

Ritual says, I’m gonna do the exact same damn thing every single fill in the blank, whether it’s day or whatever the ritual cadence is. But the thing that brings meaning to it is the relationship, whether it’s one with yourself or someone else, and you want to invite people to that. So it’s this beautiful other side of the coin of life where you have part of your life, you just run into the unknown, and then the other part is so known.

But that knowing part of it, the comfort of it, gives you this exploration of things that are below the surface. So I think in 20 years, I hope that the depth of both these sides. I appreciate I’m better at in the sense of like the natural motion of a dancer or a figure skater or whatever. When you see the, the number of reps they get is just so easy, but it doesn’t change the [00:48:00] delight in it because you keep doing it.

You just have such a fluid motion through those things where when you first try it, whether it’s a ritual or creation, it’s pretty awkward. If you get the bug, you don’t stop.

Ian Hathaway: I love all of your visuals. You’re such a visual explainer of things. I can’t think of a better way to end, but before I let you go, we have a little segment called Beyond the Bio.

These are just some quick hit, quick answer questions that kind of let listeners get to know you beyond your resume. Does that sound okay?

Willy Schlacks: Sure.

Ian Hathaway: Okay. What’s a quick piece of advice from a mentor that stuck with you throughout your journey?

Willy Schlacks: All my mentors are bad people in books, so I must caveat with that.

Ian Hathaway: Amazing. The best mentors

Willy Schlacks: like Thoreau, an impression that he was describing how instead of pursuing life, life pursues us. And I love that because we get surprised, it taps us on the shoulder. I’m like, oh shit. I’m where I never thought I would be versus I’m running after the thing that [00:49:00] we think we need to pursue.

Ian Hathaway: Oh, that’s beautiful. Who is an unsung hero in your life and what has been the impact they’ve had on you?

Willy Schlacks: Too many, but this ties closely in with. My person’s in my rituals. My wife is the center of that universal. I’m constantly pursuing her. Like even when I dress in the morning, I’m only thinking about she’s gonna be attracted to this.

I bet. My wife’s name is Caitlin. So many things that I do and I’m excited to do, they’re inextricably linked to me trying to woo her constantly. Like every day it feels like an adventure for me. She has a cafe that is one of her businesses. So part of my ritual most mornings is to. Go by her cafe, and sometimes she’s there early in the morning because she still loves the obsession of creating product.

But I show up and if I’m looking nice and all that, it’s like she has a gravity in my life that I revolve around and hope never to escape from that gravity. Well, and eventually I might get absorbed in it, but yeah, for now, it’s, it’s, uh, something that keeps me [00:50:00] trapped in a good way.

Ian Hathaway: Yeah,

Willy Schlacks: her story is freaking insane too.

Like even that story of that cafe, which. 20 years from now, it’ll just have a life of its own. But yeah, it’s pretty cool.

Ian Hathaway: What’s a strongly held belief you hold today that most people would disagree with?

Willy Schlacks: Take any one of those off the shelf, and I think I’d find an army of folks that would be on the opposite side.

My current one that I think most people would struggle with and disagree with, which I like because I want to evolve this view, is just fundamentally what truth is. And I think most people. Force themselves in a corner where truth has to have some binary meaning to it. Like at the end of the day, something is true or false.

And my view is that we’re still dealing with extracted concepts and that truth is not binary and truth is movement. Now, whenever I bring that up, I always get the classic, well, what about Hitler and what about this? And people very quickly subscribe. Truth and evil and good, and all these same things. [00:51:00] But my belief that truth is motion is probably the opposite of what most people would lean into.

Ian Hathaway: Tell us something most people don’t know about you. Something outside of work could be a hobby, favorite travel spot, a guilty pleasure, or maybe even a hidden talent.

Willy Schlacks: I like being healthy. I like working out and all this stuff, but when I’m lifting weights, the motivation for lifting that weight, I’m like, I’m doing this because I wanna look good, but I think I should be doing it because I wanna feel good at its core.

I’m like, okay, I’m just doing this for pure vanity, but I know there’s a lot of other good reasons to do it. I’m like, if the vanity wasn’t there, would I do it? And I’m not sure I would. I think I am purely vain in this effort because what I really want to do is not lift weights. I want my life to have so much motion and activity to it that I don’t need to lift weights, but it doesn’t.

Like I’m sitting at this desk talking to you and you’re talking to me. Yeah. We’re sort of vegetating at the moment, but [00:52:00] what if we were swinging an anvil? Making some cool sword, like we wouldn’t be lifting weights. I haven’t expressed this before, but since you asked the question, I observe an extreme vanity in this effort of moving this bar and steel around.

That is somewhat humorous to me because I see everybody else saying it’s for other reasons. So I think there’s probably some childhood trauma wrapped up in that that I haven’t deeply explored yet.

Ian Hathaway: What are one or two songs you’d like to add to our Spotify founders playlist? Something that fuels your workday or has inspired you on your journey as an entrepreneur?

Willy Schlacks: Music is deeply impactful to me. Most things in my life, I generally subconsciously associate to music and the pattern of music. Even morality to me is simply music. Not in the literal sense, but from a pattern perspective. As far as songs that are part of entrepreneurial journey, I don’t know. I don’t think any of us appreciate the depth that [00:53:00] harmony and discord and cadence have, and we see it as a thing that’s more entertainment.

We don’t realize that this thing rules at all. The TLDR R is the entrepreneurial side of my. Or building and whatever is not something that, you know, I’ve got my playlist,

Ian Hathaway: I feel like. Then my next question’s gonna open up a whole other can of worms. What’s a book you might recommend to a founder? Maybe something that help you on your journey.

Maybe something that every first time founder should read as they’re getting started. I

Willy Schlacks: think range is a good book for a founder to understand that. Good

Ian Hathaway: book.

Willy Schlacks: Yeah. Don’t sweat it if you’re not the expert. And being the expert is a disadvantage and most founders are not experts, so you know, pat yourself on the back because you’re in the right mindset.

That’s a great one.

Ian Hathaway: Okay, last question. If you could give one piece of advice to someone who’s about to start their first company today, particularly someone who’s maybe a bit of an outsider, what would it be?

Willy Schlacks: Better not be tomorrow, like God damnit, [00:54:00] do it. Because what the hell are you waiting for? And there’s absolutely nothing.

And that would stop you. And if there is, then go find another job. And that’s okay. But if, if you want to do the thing, then do it. Like we just don’t realize the amount of control we have over today. And that’s also all we have. I’m talking to myself here, by the way, too. And, but yeah, if somebody wants to do something, what the fuck?

I mean, why is this a conversation for tomorrow?

Ian Hathaway: Yep. Go get it. Well, speaking of conversations, this was an awesome one, Willy. Thank you so much for being here today, sharing your journey, and your amazing insights. I can’t wait to share this with our listeners.

Willy Schlacks: Thank you. Yeah, it’s been a pleasure to talk and thank you so much for being a storyteller.

Storytellers have. One of the largest impact on my life. So I deeply admire the trade and I’ve never done it, so this is cool when I encounter the folks that do it.

Ian Hathaway: That’s a wrap for today’s episode of Outsider Inc. [00:55:00] A big thank you to Willy Sch Slacks for joining us and sharing his fascinating story.

Willy’s journey is a reminder that constraint isn’t the enemy of building. It’s the engine. No outside ecosystem, no inherited playbook, no comfort to fall back on just the discipline to stay in motion, and the belief that the friction is the point. What lingers for me is how deeply the concept of home permeates through everything he’s built, not as a limitation, but as a root system.

You build better when you’re planted somewhere real. And if there’s one thing Willy would want you to take away, it’s this stop waiting. The only thing standing between you and the thing you want to build. Is the story you’re telling yourself about why today isn’t the day. If you want more from outsider, inc, don’t forget to subscribe to the platform@outsiderinc.substack.com.

It’s packed with highlights from today’s episode and bonus insights you won’t wanna miss. You can follow Outsider Inc. On YouTube, Instagram, [00:56:00] TikTok, and LinkedIn at Outsider Inc. Pod. You can also follow me on X at Ian Hathaway Outsider Inc. Is produced by Spellbinder Media. We’ll be back soon with another fascinating outsider conversation.

Until then, thank you so much for listening and remember, great entrepreneurs can come from anywhere. See you next time.

The latest episode of Outsider, Inc. features David Cohen, the co-founder and CEO of Techstars, serial entrepreneur, and one of the most consequential figures in venture capital and entrepreneurial ecosystems over the last two decades.

Before Techstars, David was a founder himself—building companies, experiencing real wins and real failures, and learning firsthand what early-stage entrepreneurs actually need when the system isn’t designed to help them. Out of that experience came a radically different approach to investing and mentorship—one rooted in trust, long-term thinking, and community, rather than short-term transactions or manufactured hype. What began as a small experiment in Boulder grew into a global network behind companies like DigitalOcean, Zipline, and SendGrid, reshaping how founders are supported in markets that Silicon Valley largely ignored.

Through Techstars Ventures, David was also a first-check investor in Twilio and made one of the largest returns in venture history with a first-round bet on Uber. He recently returned to the CEO role at Techstars at a moment of real change—for founders, for ecosystems, and for the venture industry itself.

In this episode, we trace the full journey—from his earliest companies and influences, to the philosophy behind Techstars, the hard tradeoffs of scale and culture, and the work he believes is still unfinished for the next generation of outsiders. ⤵️

Follow: LinkedIn, Instagram, X, TikTok, YouTube

Episode Highlights

In this first clip, David traces the origin of Techstars to a humbling realization—after selling his first company, the acquirer told him he'd left half the money on the table. That sting pushed him to ask harder questions. What he found was a pattern. The things that worked almost always had experienced people around them. Networks matter. That insight, and a "no" from Paul Graham when David asked to bring Y Combinator to Boulder, set him on a different path—one that became Techstars.

In this next clip, David breaks down his investment framework—team, team, team, market, progress, idea—and why team comes first, second, and third. At the earliest stages, the idea will shift and the market will evolve, but the team is what determines whether founders can feel their way through the dark and stay alive long enough to figure it out. The signal he looks for is intrinsic motivation, where founders are doing it for some reason other than a spreadsheet.

In this clip, David shares the founder trait he thinks the rest of the industry overvalues in founders—experience. At the earliest stages, it can actually be a liability—founders trying to change the world in genuinely new ways don't need to know how everyone else did it before them. In fact, that knowledge can get in the way.

Finally, David gets personal about what the first thirteen years at Techstars cost him—his identity wrapped up in the company, working until three in the morning, traveling too much, a Fitbit chart that told the whole story every time they raised a fund. Coming back as CEO, he committed to doing it differently—exercising, prioritizing family, and building in time for rest. For him, that’s meant padel—a sport he loves enough to have built a five-court club in Boulder, playing almost every day, often in the middle of the afternoon. The lesson he keeps coming back to—you can sprint so hard you lose the marathon. Work-life balance may be a myth, but harmony isn’t.

I’m grateful for my conversation with David. He’s been a mentor to me, and someone whose philosophy has quietly shaped the way I think about this work. David’s story is a reminder that the most durable things in venture aren’t built from pattern-matching; they’re built from relationships, trust, and a genuine commitment to the person across the table. When the ecosystem isn’t there, David didn’t wait for someone else to build it for him. He showed up, gave first, and bet on people before the evidence was in.

What I took most from this conversation is how countercultural that really is. In an industry that rewards speed, scale, and signal, David spent two decades optimizing for something slower and harder to measure—community. Not as a brand, but as a practice. And what he’s modeling right now—returning to lead the organization he built, trading growth for quality, choosing depth over reach—is a kind of discipline that most people only discover after they’ve already lost something important.

If there’s one lesson David leaves us with, it’s this—surround yourself with great people, give before you take, and don’t mistake momentum for progress. And always remember, bigger isn’t better. Better is better.

David’s Library

In the Beyond the Bio segment of each episode, I ask guests a number of quick hit questions that let’s listeners get to know them beyond their resume. One question I ask guests each time is what are one or two books they recommend to entrepreneurs. David named one that he recently came across. And, although we didn’t discuss it in the episode, David co-authored with friend-of-the-pod Brad Feld.

Anyone Builds It, Everyone Dies: a New York Times bestselling alarm bell from Eliezer Yudkowsky, a founding researcher of AI alignment, and Nate Soares of the Machine Intelligence Research Institute, arguing without apology that the race to build artificial superintelligence is not an arms race but a suicide race. The core case is deliberately simple: modern AI systems are grown rather than crafted, their inner workings opaque even to their builders, and a system that genuinely surpasses human intelligence would pursue its own goals with a competence that leaves us no recourse. Critics have called it tendentious and thin on opposing views, and those critiques have merit. But the questions it raises are serious ones the AI industry has not answered to anyone’s satisfaction, and its willingness to call out wishful thinking from prominent figures at the frontier labs gives it a credibility more cautious treatments lack. A direct and accessible statement of the existential risk case yet published. Anyone building companies, allocating capital, or making policy in the age of AI should engage with it.

Do More Faster: a practical field manual disguised as a book, co-authored by Techstars co-founders David Cohen and Brad Feld and built from the ground up out of the hard-won lessons of founders and mentors who actually lived them. The book is structured as a collection of short, direct chapters organized around seven themes: ideas and vision, people, working effectively, product, fundraising, legal structure, and work-life harmony; each is written by founders and mentors from inside the Techstars network, including Tim Ferriss, Eric Ries, and Matt Mullenweg. Cohen and Feld aren’t trying to write the definitive theory of startups. They’re trying to compress the most useful advice into the smallest possible footprint, and hand it to founders who don’t have time to waste. It is refreshingly dense and direct. The book reads like a mentorship session with people who have seen every mistake and want to help you skip the ones that don’t teach you anything. For anyone building at the earliest stages, particularly outside the traditional networks where that kind of mentorship is hardest to find, it remains one of the most honest and useful guides available.

David’s Playlist

I also ask guests what are one or two songs that has inspired them on their journey. David shared what is one of my long-time favorites: Money by Pink Floyd. This song will always remind me of my dad, who gave me my first CD as a young kid—Pink Floyd’s The Dark Side of the Moon, which launched this iconic song.

Up Next

Tune in next week for a conversation with Willy Schlacks, co-founder and president of EquipmentShare, and one of the most intentional builders we've had on the show. Willy grew up in a cloistered environment in rural Missouri with no private property, no personal ownership, and strict control over money and agency. Entrepreneurship showed up not as ambition but as curiosity. When he left in his late twenties and effectively started over, that reset eventually led to EquipmentShare—a company born not from chasing a hot market, but from lived experience as an operator who decided the chaos didn't have to stay that way. What began as a Startup Weekend idea in Missouri scaled into one of the largest vertically integrated platforms in its category, recently taken public at a $7 billion valuation—one of the largest tech exits outside Silicon Valley in recent years. In this episode, we trace how those experiences shaped the way Willy thinks about building—why constraints matter, how leadership evolves at scale, and what it means to stay close to the work as the stakes grow.