<![CDATA[Vertical]]>https://verticaltech.substack.comhttps://substackcdn.com/image/fetch/$s_!qEpW!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2F82876004-6df6-4bb6-93ad-985e01e5fcc8_370x370.pngVerticalhttps://verticaltech.substack.comSubstackTue, 01 Sep 2026 11:52:01 GMT<![CDATA[What Matters This Week - 08.29.26]]>https://verticaltech.substack.com/p/what-matters-this-week-082926https://verticaltech.substack.com/p/what-matters-this-week-082926Sat, 29 Aug 2026 14:14:23 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“The biggest risk is not taking any risk. In a world that is changing really quickly, the only strategy that is guaranteed to fail is not taking risks.”
— Mark Zuckerberg

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]]><![CDATA[What Matters This Week - 08.22.26]]>https://verticaltech.substack.com/p/what-matters-this-week-082226https://verticaltech.substack.com/p/what-matters-this-week-082226Sat, 22 Aug 2026 13:28:50 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“All progress has resulted from people who took unpopular positions.”
— Adlai Stevenson

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]]><![CDATA[What Matters This Week - 08.15.26]]>https://verticaltech.substack.com/p/what-matters-this-week-081526https://verticaltech.substack.com/p/what-matters-this-week-081526Sat, 15 Aug 2026 14:43:14 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“To ask the proper question is half of knowing"
― Roger Bacon

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]]><![CDATA[The Alpha GP: Ep #1 featuring Dwight Dunton of Bonaventure]]>https://verticaltech.substack.com/p/the-alpha-gp-ep-1-featuring-dwighthttps://verticaltech.substack.com/p/the-alpha-gp-ep-1-featuring-dwightTue, 11 Aug 2026 02:24:57 GMT

Series: The Alpha GP

Show Notes

Summary: A deep dive with Dwight Dunton of Bonaventure.

Special mentions

Transcript

(Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.)

[00:00:00]

Matt Knight: Hey guys, kicking off a new series here around innovative and interesting GPs or deal sponsors. People that are fundless sponsors or have a fund and are investing in property around the US and around the world really, that are doing things in a unique, innovative, or maybe just a paranoid way where they think AI’s gonna take their job.

And so this first one, we’re gonna have Dwight from Bonaventure. He is in the DC area. Their portfolio, I’ll let him tell you about. But we don’t even talk about AI till two-thirds of the way into it. So just know we talk about lots of other stuff. But this is Dwight from Bonaventure talking about their take on innovation and tech strategy.

Hope you enjoy

Matt Knight: All [00:01:00] right, Dwight. Glad to have you here, man. Excited to get to know you a little better and have you on the podcast. Thank you for being here. And I think it’s always smart to start with where’d you come from? What is Bonaventure? How did it get started? How long have you guys been around? Give us the key stats, and then we can start chasing rabbits.

Dwight Dunton: Yeah. Matt, so excited to be here. Thanks for the invitation. Bonaventure got started because we needed to solve a complex real estate problem. Our family was fortunate to own a piece of a building from the 1960s. Our partners became a huge REIT, and they one day in 1999 told us the property was in a C location and needed $5 million of capital improvements just to keep the lights on, and we didn’t have $5 million.

And so that was the birth of Bonaventure, and the rest is history

Matt Knight: What’s

Dwight Dunton: that lead you

Matt Knight: to now? I was gonna say, what’s the portfolio look like

Dwight Dunton: and where- yeah. So that, over the last 25 years, what started off as helping one family, our family, has now grown to [00:02:00] about 500 families who are all trying to build long-term wealth.

We help them. We have five platforms, about 400 employees, $3 billion of assets under management. So it’s go- grown a lot from that humble beginning.

Matt Knight: And you say asset preservation, I think evergreen funds and REITs that are doing dividends. What’s the structure look like? It sounds like it started as a fundless sponsor, but I think you have REITs now.

Walk us through if we were to give you capital, what does

Dwight Dunton: that look like? Yeah. So I think our kind of investment thesis across all of our different products is that housing is broken in the United States, that where people want to live and the ability to produce housing are disconnected. And from there you have the real estate cycle and the economic cycle creating opportunities, and we seize those opportunities through a variety of different wrappers because we understand that each investor needs slightly different things.

So that could be a single asset investment, that could be a development deal, that [00:03:00] could be an OZ fund, it could be, as you mentioned, a perpetual life REIT. We have a REIT that has about $1.3 billion of assets in it. And so again, it’s all about creating alignment around the economic opportunity and helping connect that capital to investors who are building for long-term wealth to afford their long-term dreams.

Matt Knight: One of the things I’ve heard about you from our mutual friend Eric, is you have this ability to think from first principles. Like just because something was done one way doesn’t mean we have to do it that way. And so I’ve, one, I’m curious if you think of yourself and your firm that way, and then two, if so, give us an example of that, something that kind of other people may not do or just take for granted that you guys have reimagined.

Dwight Dunton: Yeah. I think that’s a good description, but I don’t know that it started off that way. It was simply, I didn’t have any real estate experience when I started the firm, which is crazy to be 25 years old and buy a 378 unit apartment complex, convince Fannie Mae to lend me, I think it was 17 million, and let me start a property [00:04:00] management company.

So I, I had no perspective on this is how we do it or you can’t do that because I had no experience. And we brought that forward, which is we challenged everything. When somebody says, “You can’t do that,” we’d really step back and ask why and really get to the root of it, and have found that so many industry conventions were brought about for one good reason, but then have been misapplied for years and years.

And so for instance, we became one of the largest borrowers with HUD, and we would go to conferences and people say, “Why would you waste time with HUD? It takes so long.” It takes slightly longer, doesn’t take so long, and if you run it concurrently with your zoning and entitlements and getting your plans done and your permits, it actually adds no time whatsoever.

And so the end result is most people have avoided HUD because it, quote, “takes too long.” We found it’s about the same amount of time, but we got these amazing outcomes, which are loans that have l- are gonna last for 40 years. [00:05:00] We reduced our interest rate risk. We had no personal guarantees. And so that’s a, just a simple example of we challenged the convention conventional wisdom of everybody that, quote, “knows what they’re doing in development” and said, “Avoid HUD at all costs.”

Matt Knight: Yeah, I don’t think you know this about me. My first job out of college was lending HUD money, doing the 223and 221(4). So I was-

Dwight Dunton: Ah.

Matt Knight: I was baffled like you, where it’s like, “Look how cheap these rates are. Look at the amortization.” These are... This is great debt, and people are like, “Eh.” Yeah.

Dwight Dunton: Well-

Matt Knight: “Okay, whatever you want.”

Dwight Dunton: And so I... Good for you. You get it. I think what I discovered, because I’m like, people are fairly rational. It seems overly convenient to say it’s too hard. What I figured out was that most people’s business plan in multifamily development is they build buildings, collect fees, and they collect lottery tickets, and those lottery tickets take the form of promotes, and the key is to scratch it off as quickly as possible to see if it has value.

If it doesn’t, you move on to the next deal. [00:06:00] And HUD is not compatible with that because there’s the prepayment penalty for 10 years. And so if you’re in the business of collecting fees and lottery tickets, HUD is definitely not the ideal choice. And and that sounds really self-serving to say that to an LP of why you said, I won’t do a HUD loan,” but it sounds way more convenient to an LP to go, “Hey it just takes too long,” versus, “It’s not in the pr- the sponsor’s economic best interest.”

That’s what I discovered as to why people have just continued to throw out this misunderstanding that it, quote, “takes too long.”

Matt Knight: Yeah. I think that’s fair. And I think there’s another example you guys have of first principles where you were looking at tenants and their experience with internet service providers, and you guys have built something around that, correct?

Dwight Dunton: Yeah. That is a great example. So I was walking one of our properties and, I walk behind the buildings, through the buildings. I wanna see everything. I just don’t want the tour that the staff has decided to prepare for the CEO ‘cause our staff [00:07:00] is awesome, and there’s always something that can be improved, and I wanna help discover that ‘cause they’re there every day, and they might miss something.

So one day I was walking at one of our properties, and I saw the side of the building with all of these wires hanging out of this box that was, like, had the door bent off. You couldn’t even close it. And I was like, “Is that our cable box?” And they’re like, “Yeah, the cable contractor comes to hook up and disconnect internet, and then they don’t bring the key back, and then they leave it open, and then some kids open it, and then they rip all the wires out, and all the internet goes down.”

And I was like haven’t you asked them to stop doing that?” ‘Cause it ultimately is bad for the internet service provider, which was usually a cable company or a large telecommunications provider. They’re like, “We have, but you know what? They just don’t care,” is what it seems like. And that was the moment where I said, “Enough,” because I had poor experience at my home.

Everyone I know has waited for that three-hour window and not had the technician show up, and I was like, “There must be a better way.” So I [00:08:00] spent about a year saying, “How do I find that better way?” And there was a lot of internet service providers that provide internet service in a multi-family environment.

Huge improvement to what the incumbent, monopoly had, but still left a lot to be desired. So we finally said, “We’re gonna have to build this ourselves if we really wanna get the best experience for our residents, the best experience for the property staff, and provide the best value to our building,” because, if you look at it, there’s two values to the building.

One is these internet service providers make a ton of money. If you pull apart Verizons or AT&T or Comcast and look at how much money they are making and minting, the gross margin on internet, high-speed internet is through the roof, which then makes you wonder how can they not give better service if they’re making so much money?”

The other benefit to a building is the Internet of Things just continues to grow, and you need to own your network. So we basically invented that solution. [00:09:00] It’s called Internet Subway, and it has done everything we hoped for and more. It’s effortless for our residents. Our property staff feels empowered to give answers versus saying, “I’ll wait on hold with you when we call India,” to get something resolved with one of the regular telecom providers.

And the last thing is the building value that accrues to owners. I think our program has added about $100 million of building value through increased NOI to the properties that have deployed it, and we’re just getting started.

Matt Knight: Got it. As you’re- have you built that muscle for vertically integrating building things that help your tenants, how does that trickle down to property management, asset management, construction management?

Is all that in-house? Do you have third parties? Does it depend on- Yeah ... the asset and the geography? How do you think about that now having built something that was ancillary to your main business?

Dwight Dunton: That’s a great question. We don’t desire to be vertically integrated for vertical integration [00:10:00] sake.

W- we do it as a last resort when it’s a critical factor to ensuring that we can deliver the outcomes that we promised our investors and our residents when we started the project, even though the world serves curve balls all the time. And so when we’ve been in the construction business and the architecture business, it was really about how do we get the repeatable mousetrap so that we can build the best buildings and continue to drive efficiencies.

The property management business, there are a lot of great property management companies out there, but we’d like to do it the way that works for us and our investors and our residents versus being forced to contort to whatever that property management company’s approach is. And that has turned into a business where we provide great property management services, assuming you’re an owner that wants it the way we do it.

If you want it some other way, we’re not the right person to do that. There’s plenty of other management companies who [00:11:00] will do it your way or force you to do it their way. But we’re, we’ve focused on building the mousetrap that really drives value creation.

Matt Knight: Sure. Yeah, I guess that gets me to thinking of your tenants and none of us make any money until a tenant signs a lease, right?

Yeah. And I think what I’d be curious, with your different geography and the structures you have behind your deals and the different types of properties you own and manage, have there been any interesting through lines with tenants always want more convenience, or they’ll only pay a certain dollars per square foot?

Or, I’ve heard people say the trope about Class B and C doesn’t like tech as much as Class A. I’ve heard that’s not true. Anything like that you’ve seen across your portfolio that, Beza said, like everybody always wants things faster. Is there anything like that you found is a truism as you’re thinking about being tenant focused and thinking about innovative ways to serve them like you did with Internet Subway?

Dwight Dunton: Yeah. What I’ve found is everybody wants to move up the continuum of shelter towards community and belonging. And [00:12:00] so everything that we can do to deliver that experience for the resident, largely in the form of services, Helps move people up that continuum because you wanna be connected in this society where we all have had more access to each other, and yet we’re lonelier.

And so how do we use our buildings to cr- foster that sense of community? And what that usually takes the form of is a and oftentimes a piece of technology that frees our people on site to deliver that experience. Because if they’re busy, doing I’m gonna show my age, TPS reports from Office Space- Oh, heck yeah

where they’re locked away in, the manager’s locked away in their office just doing report after report. We found that three or four man days every single month were devoted to reporting. And we’ve got a company-wide AI initiative that’s all about providing more efficiency, not to reduce headcount, but to empower the h- the people we have to deliver that one thing that only human beings can deliver, which is that [00:13:00] personal relationship.

And so that’s really the driving focus around our technology, is about efficiency so that we can deliver that community connection to our residents

Matt Knight: Yeah. You don’t want Lumbergh coming by your office asking about TPS reports. But- ... I’m curious, when you think about that, ‘cause th- that’s like another false narrative that I think is important to touch on, is “AI’s taking jobs.”

Not really. If you do it right, it’s helping people do different jobs. And so I’m curious what that looks like and if you guys have set priorities, and I guess we have to talk about AI if we’re talking about innovation or they won’t publish us. But if you’re looking at AI priorities, is it taking things off of your onsite staff’s plate and saying, “I want the people on staff knowing first names and hand-delivering packages,” and I like self-guided tours, but not everybody wants those.

Let’s have some humans there, right? Yeah. Is it things like that, or how do you think about prioritization, I guess is what I’m getting at?

Dwight Dunton: So we’re, we have a huge initiative. There’s so much activity going around. But if I boil it all down in the [00:14:00] property management side, the very first thing that we’re doing is telling everybody, “Do these five things today.”

Those are the most important things you do. And it differs every day or by property, but when you show up to work and you’re bombarded with all kinds of fires and problems and issues that crop up, you don’t have any time to analyze your business as to what’s important, and so you just get stuck running on the treadmill.

We use AI to synthesize the vast volume of data. There’s never been more data in our business than today, and less information because it is overwhelming. And so we use the AI to synthesize the data, turn it into infor- into information, and then say, “These are actionable.” It is empowering because now the staff doesn’t have to pile through the thousand TPS reports to try to figure out what’s important today.

And what that does is it all of a sudden it frees up and makes ev- gives everyone a bias towards [00:15:00] action, and it is really empowering.

Matt Knight: Have you picked, out of curiosity, an AI partner yet? It seems this week Claude’s better than GPT, and GPT’s better next week, and Gemini was better three weeks ago, and they just constantly are back and forth.

Have you picked someone that you’re building on, or is it more dependent upon the use case?

Dwight Dunton: So we are taking a very different approach, which is we are building our entire AI platform to be LLM agnostic because you’re right, they’re leapfrogging each other every day. And so the key innovation that we have, and we have an AI team, it’s called BIRD, Bonaventure Innovation and Research Department.

But what we’re doing is we’re building company-- a company brain that is a middleware layer that sits between the user and the LLM, so that let’s say today we’re using a lot of Claude. So we’re using Claude. It’s capturing all that context at our layer. But then tomorrow when Gemini or [00:16:00] ChatGPT or maybe Grok finally shows up to the party becomes the best mo- model for what we’re doing, all we do is then point that model to our MCP server and it cap- it has access to all the context that’s come before it.

And so I think that’s the key innovation that a lot of businesses are not yet around, which is you need to have personal brains and company brains to disintermediate lock-in with the LLM providers

Matt Knight: It almost parallels the cloud battles from five years ago, right? Yeah. Are you an Amazon shop? Are you an MC- are you an Azure shop or do you use Google?

And it’s like use all of them. Who cares, right? It’s cloud storage, right? Like they all do the same thing. It seems like AI’s almost becoming the same type of commodity, right?

Dwight Dunton: Yeah. And I think there’s one more risk besides the lock-in. It’s the token cost because, right now tokens are effectively being subsidized because there’s not enough tokens to go around.

People are trying to build market share and so on. If the trend continues, [00:17:00] tokens are gonna become extraordinarily expensive, and you need to be able to shop your model needs around based on the cost of tokens for your workload, and it’s gonna become very difficult if you don’t have the ability to have a piece of middleware in between that can route requests based on the cost of tokens, the complexity of the request and so on to the model.

Matt Knight: Got it. I know we’re low on time, so I’ll just ask the final two questions. And I’m curious- Yeah ... is there anything you’re looking for this year? Anything that listeners can help with or send your way or maybe not send your way? If you don’t want anybody sending you AI stuff, that’s totally fair too.

Dwight Dunton: We’re always looking for ex- extraordinary visionaries that see the future and can start to make it happen today. We are very innovative. We have a team of six people here. And we’re always looking for the right people to add. I’d say the other thing is if you want to have best in class internet services add [00:18:00] value to your residents, your property staff, and most importantly, the building’s balance sheet contact Internet Subway.

It’s the best in class experience.

Matt Knight: Very nice. I really appreciate this. This has been very educational, and I’m very impressed. So congrats on all you guys have done so far, and good luck.

Dwight Dunton: All right. Thanks, Matt.

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]]><![CDATA[What Matters This Week - 08.08.26]]>https://verticaltech.substack.com/p/what-matters-this-week-080826https://verticaltech.substack.com/p/what-matters-this-week-080826Sat, 08 Aug 2026 13:16:52 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“You can reinvent yourself whenever you want.”
— Sahil Bloom

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Source: Visual Capitalist

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]]><![CDATA[What Matters This Week - 08.01.26]]>https://verticaltech.substack.com/p/what-matters-this-week-080126https://verticaltech.substack.com/p/what-matters-this-week-080126Sat, 01 Aug 2026 13:32:47 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“The difficulty lies not so much in developing new ideas as in escaping from old ones.”
— John Maynard Keynes

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Q2’ 2026 Funding Data Update.

  • 108 funding rounds were announced.

  • Globally, $2.964B raised.

  • $8.3M - the median round size, and $30.5M - the average round size.

Source: @ProptechAngelGroup

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]]><![CDATA[Into the FIRE: Ep #6 with Stephanie Gubiotti]]>https://verticaltech.substack.com/p/into-the-fire-ep-6-with-stephaniehttps://verticaltech.substack.com/p/into-the-fire-ep-6-with-stephanieThu, 30 Jul 2026 21:32:55 GMT

Series: Into the FIRE.

Show Notes

Summary: Into the FIRE with Stephanie Gubiotti, Advisor - Foundation for Innovation in Real Estate (FIRE) and the 2026 Academia Calendar, the next Emerging Manager call, fall events, and FIRE Summit 2027.

Special mentions

Transcript

(Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.)

[00:00:00]

Matt Knight: So first, let me apologize that this podcast is a bit all over the place, but Steph and I get on tangents, and we just keep going because... In our defense, we have a lot happening this fall, and fall is our busiest season. So another episode of Into the Fire with me and Steph, but just understand we will have more to come in the fall with more names and more specifics.

But this will give you a bit of an idea of what’s happening, where we’re going, and if you wanna get involved, you wanna help, you wanna support, or you wanna just see us, hit us up ‘cause we’re always down to connect. Enjoy it

Matt Knight: We’re looking at fall, planning our trips. Fall tends to be crazy. I don’t know how much you remember from last year, but fall is just bonkers. So [00:01:00] probably good to talk about what’s coming up, what we have planned, and curious how you’re feeling about it here sitting here in year two

Stephanie Gubiotti: first, fall is my favorite season. It’s the best, and I’m really excited to get on campus this fall, connect with students. Yes, it’s a busy time, but it’s also really fun, and I enjoy being able to have those bursts of busy. So for me, it’s nice to have this really busy part that we’ll be having for a little bit, and then we’ll get into the lull of the holidays, and then we’ll pick back up again and early next year as well.

Matt Knight: I’m into that. And, I’ll just add in for campus, it looks like Cal and Stanford are gonna happen. It looks like MIT and Harvard are gonna happen. Looks like Emory and UGA are gonna happen. And other than that, it’s a bunch of maybes. Do you have an update on OSU, or is that still TBD?

Stephanie Gubiotti: OSU is still [00:02:00] TBD.

They’re redoing a lot of their programming, so we’re waiting to finalize schedules. So as soon as they get back to us, we can lock in on some of these things.

Matt Knight: Yep, and Notre Dame’s out there. Shout out to Bruce if you’re listening. Princeton’s out there. Shout out to Chase if you’re listening. So there’s a bunch.

We have, I don’t know, a dozen now schools that are in our radar. And if you’re listening to this, I think w- what you should know is we have free tickets to all these events in the fall for these students, up to a certain number. So if you’re interested in coming, if you’re a student or if you know a student, send them our way ‘cause we have cohorts coming and we can do things with them, and, hopefully they’re over 21.

But if not, we’ll figure out something anyway. But, that’s sort of academia for me this fall is a blitzkrieg of basically October events on campus

Stephanie Gubiotti: Yeah, it is convenient with CREtech being in New York though, so, I’m hoping that we’ll be able to get a good turnout from our student population there.

You know, they’ve been very, very generous [00:03:00] with giving us a large portion of ticket allocation for students. So, if you’re a student specifically and able to get to the New York area, let us know.

Matt Knight: Yeah, if there’s anyone who cares more about students than us, it’s Beckerman, so shout out to Michael and his team at CREtech, ‘cause they do a great job.

Stephanie Gubiotti: Yep.

Matt Knight: But speaking of events, we got, Real World coming up in a few weeks. We got Blueprint, CREtech, and Optech in that order, and have all kinds of programming around both, right?

Stephanie Gubiotti: Yeah, yeah. I’m excited for you to experience your first Real World or your first software conference for a PMS, so it’ll be fun.

Matt Knight: If you say so. I, I’m, I am intrigued enough to fly there and spend my money on it. How about that? I’ve- I’ll see how it goes. Yeah. And I’m excited about RealPage. I think RealPage is doing... I think RealPage is trying really hard to do some cool things, and I think the jury is out on what they will or won’t do, but I love where they’re going.

I love that they’re making an effort, you know? And there’s a lot of companies that can, [00:04:00] just be big, and I don’t think Dirk and his team, are satisfied with that. I think they really wanna push the envelope, and I respect that. That’s not an easy thing to do with a company RealPage’s size. So I’m...

I was being glib earlier. I am interested in going.

Stephanie Gubiotti: Yeah, I think it’s gonna be great. I also... They have some really interesting speakers lined up, and I, I also think their acquisition of Cherre is really fascinating. So anyway, I agree they’re doing cool things. And after that, we’ve got Blueprint, where we’re working with Martin and the Inman team to put together some programming there.

We’ll be doing some tours, working on some really fun stuff for our group. Let’s see. Next week coming up soon we’ve got our next emerging manager call, which is super exciting. We should have a pretty good turnout for that one. We continue to grow and scale that group, which is also great.

Matt Knight: Yep. Peter Rosecrans of Burns Management out of New York is gonna be our guest speaker, and I’ve personally spoken to a dozen of our EMs in the last week, [00:05:00] and many of them will be on, ‘cause we have lots of new things we’re doing with them.

So that’s, that is, seems to be

accelerating more than any of our programs. Our EM program is really picking up, I think.

Stephanie Gubiotti: Yeah, I think there’s just such a need for people, especially those small to mid-size operators who really need that level of guidance and support, and just somebody to say, “Hey, don’t spend your precious limited resources trying to solve a problem that we’ve already solved.”

So

Matt Knight: Amen to that. Maybe it’s worth updating that I’ve been spending time on comparative tech stacks, just putting people’s tech stacks into a document and saying, “Here’s my PMS, here’s my back office, here’s my tenant screening,” and just showing to where we can compare and contrast and have them compare notes and people that have the same back office or, you know, overlaps or...

What’s interesting to me as I’ve started doing this is seeing where AI is replacing vendors. Because a lot of the ones, you’ve seen this, a lot of the ones I’ve started stacking have 40-plus vendors. Yep. And I [00:06:00] wonder if they’re... But a- academically, you wonder if there’s some steady state where we get down to 15 vendors and they’re all AI native and they all do, you know, half a dozen things well.

I mean, that’s kind of in the PMS playbook for 20 years, right?

Stephanie Gubiotti: Yeah. Yeah, I think so.

Matt Knight: Yeah. So anyway, that’s EMs. And like Stephanie said, there’s a lot. We have private tours at these shows. We’re gonna have happy hours. Got some custom intros I know I need to make, but it’s gonna be... We roll out the red carpet at these events, ‘cause there’s only, three of them in the fall, and- Yep

Maybe RETCON and HIS in the spring. So it’s not a ton of events we do this at, but since everybody’s gonna be there, it just is a great way to, to concentrate everyone in one place for 48 hours, and then we all go back to doing our day jobs.

Stephanie Gubiotti: Yeah. Do you wanna talk about some of our Fire City tours that we’ve been chatting about doing?

Matt Knight: Sure. Go for it.

Stephanie Gubiotti: So we’re looking at sending either myself or Matt to various cities, sometimes both depending on our [00:07:00] schedules, to be able to meet up with our network and be able to bring people together. We’ll host some sort of a happy hour, and likely after we’ll do some sort of an executive dinner.

So we’re still shaping what those will look like, but we’re trying to kind of align timing. If we’re already in cities doing campus tours, you know, and we’ve already got a group of executives coming to meet with us to speak with students, it would make sense for us to kind of do a dinner at the same time.

So we’re thinking through those types of things to start kicking off in the next few weeks here. And we also did something super exciting. Do you wanna do the big reveal about what we decided on?

Matt Knight: No, you can do it.

Stephanie Gubiotti: Okay. I’ll be okay. We decided to do our Fire Summit next year at, in Laguna Beach, California.

So we did change locations, and we are planning to ideally, uh, reserve the entire resort for our group. So very, very, very excited about that. I [00:08:00] won’t list the name of it out loud, but I’ll just say that it’s in Laguna Beach May 5th through 7th, and it is our exclusive off the record conference that we do once a year, where we...

I like to call it we work on the industry instead of in the industry, where we bring together people from different areas to collaborate, brainstorm, learn from one another, and solve real problems. And we’re also tapping into working on a new housing affordability initiative. So I think it’d be great for you to talk about that and what you’re doing with Anne a little bit.

Matt Knight: Yeah, it’s still early. Anne knows it better than I ever will and is a, a brilliant tactician when it comes to affordable. And affordable is such a hairy industry. We, we talked about this, me and the board, when we first started, is, is affordable can really dominate the conversation because everybody cares about it, and it’s so important that what, what I didn’t wanna do personally was like, [00:09:00] let’s not worry about silly things like mental health.

Let’s not fiddle with students and young people. Let’s just do affordable. And that’s not to say that affordable isn’t a incredibly big part of what we do. It’s just there were other problems that I thought a foundation would be uniquely suited to solve. Uh, and I knew there’s a lot of-- there are a lot of people working on affordable housing.

And so we are putting together sort of a brain trust around what are the problems a foundation should solve in affordable. And that can be big A affordable, little A affordable. You can call it attainable. You can call it workforce. It could be light tech. We can define that however we want. But the answer to-- that we, I think, are trying to extract from our brains in this industry is where can a nonprofit really move the needle?

Because what I know from affordable developers is like, “I need more deals. I need cheaper capital.” Well, great. So does everybody else. I don’t know that a nonprofit can help with that. “Well, I need you on, you know, Capitol Hill lobbying on my behalf.” There’s thousands of people already [00:10:00] doing that. You know, like, I would be bad at it.

So what else is there that moves the needle? And we have some theories, but I don’t want to skew anybody’s opinions on it. So does that summarize it? Do you see it differently than I see it?

Stephanie Gubiotti: I think that summarizes it, and what I’ll also add is what we’re trying to do is think together collaboratively and say, “How do we, how do we solve some of the key pain points which result when you’re specifically working, owning, and operating an affordable community?”

And that can be down to the truth of it from my perspective is that operating those assets is harder and typically costs more, and there’s more requirements and hoops to jump through, which ultimately are prohibitive. So that’s just my experience from working in the affordable space in the years that I did.

But I think that we’re onto something exciting. And I also think bringing together our tech lens to bring our experience and figure out how we [00:11:00] can work with different technologies to solve things in affordable housing is, innovative building materials, like you and I have chatted about before.

It’s hard for them to get underwriting for doing new and different things with the current setup. So that’s high level but that’s a, an area of opportunity for us, and we’ve been putting a lot of effort into trying to figure out the highest and best use for our time through the foundation, and then also for our services that we provide.

Matt Knight: Yeah, two things on that. One is I would say yes on the tech component, and the thing I have to be careful with is not being the proverbial hammer looking for a nail where I’m gonna techify every problem we have, right? Some problems are people problems. And to quote one of the home builders from the summit this year, it’s basically simplifying supply chain for home builders would radically reduce costs and make housing more affordable.

But there’s so many people involved in that supply chain that it’s just a broken system of OEMs [00:12:00] and distributors and product managers and procurement consultants and then subcontractors and general contractors, and everybody gets a fee, and all of a sudden it costs six times what it costs to make it, right?

And so not all of the solutions I think have to be tech, but I think coming with a tech and innovation lens helps, provide a long-term view with short-term tech applications to it, unless you disagree with that.

Stephanie Gubiotti: Yeah, tech certainly is not gonna solve many problems. But I do think that it allows us to solve some lower-hanging fruit problems, if you will, and be able to lean our focus into areas which we may not have otherwise been able to, which is what’s exciting for me.

It’s more about how can you lean your focus into higher value to be able to solve real problems, and housing affordability is something that everybody does care about. And whether you’re in the industry or not, we’re all affected by [00:13:00] housing costs and pricing.

Matt Knight: Yep, agree with that. And so part of what we’re gonna do with this program is bring in some large institutional backers that really care about this, and will put time and money and resources and brainpower behind it.

So a- again, if you’re listening and affordability is a big part of what you do, please reach out because we are building our brain trust and trying to accumulate capital around how to really do high-leverage solutions, not throwing money at lobbying or just having another institute for the sake of having an institute.

I think we wanna see high-leverage, high-impact solutions versus just, “We also do affordable.” That’s, I d- I don’t think that you or I have time for that.

Stephanie Gubiotti: No. And that’s why we really lean on the experts that are within our network. “Hey, Matt and Stephanie do not know it all,” so we’re leaning on others to help us be able to build this, and I think that’s something that is really impactful that we do throughout all of our programs.

Everything is built by our community and for our [00:14:00] community.

Matt Knight: Yep. And maybe, talking about solutions and hardware, that’s another thing that I think we forgot to mention or I forgot with our events this fall is we have the hardware and robotics zone that we do with all three of them... which we called our petting zoo, and I think people call it the innovation zone.

But it’s basically robots, drones, material science, anything you can physically touch, living walls. We’ve done it for three years now, and it’s really starting to get a life of its own, which I love, but it’s stuff to go touch and play with. So it’s another thing that we’ll be locking in the next 30 days is who’s gonna be in our booth and how they’re gonna present and how can we touch and interact with new technology.

So that’s another one that I think is a big part of this fall coming up.

Stephanie Gubiotti: Yeah, we’ve been working with some potential sponsors, which has been exciting. And the, the thing that I initially thought going into it was like, I, I’m not sure that this area is gonna be something I’ll be able to provide much value in for the foundation.

But as I’ve dug in more and more, I’m [00:15:00] realizing how broad this can really be, and it’s not just, it’s not just theory. And one of the things that I’ve come to really appreciate about it is there’s, physical things. And a lot of what we see at software conferences and at different events is talking about theory versus execution, and with this it’s a physical thing that you can actually interact with to see.

But I would love if you could talk for a second about what we’re trying to build also with the the interactive zone and having the headsets

Matt Knight: Yeah, we’re trying to have sort of an AR/VR program to this, because hauling around Magic Leap or Oculus or, Apple’s product is really not that big of a deal.

And we keep having more needs in our space for visualization, 3D models, 3D walkthroughs, remote work, remote control. You’ve seen those demos of a, a guy, a computer [00:16:00] controlling a bulldozer or a skid steer from across the planet, right? And all of that’s gonna depend on good, holography and visual cortices that are into your headsets that are already being built.

And so we’re thinking about a sponsor. We have one that we can’t name yet that’s thinking of sponsoring that for us. But it’d be a great way just to have people interacting with AR and VR and how it overlaps with our buildings and their construction and utilization and their maintenance and their occupancy and their safety and other w- other things that just need to be done in 3D world-building.

And that’s, at least that’s my take on it.

Stephanie Gubiotti: Yeah. I think it’s super exciting, and it’s always fun to get to interact with people and get them excited about technology just generally. It... The longer that I do this, the more that I realize how much there is for us to be able to support in this industry.

Every day I’m like, “Oh, there’s another thing we could do.”

Matt Knight: It is overwhelming, and I [00:17:00] am very grateful for our donors who let us do this and help us keep going.

Stephanie Gubiotti: Yeah.

Matt Knight: All right. Anything else before we wrap that needs to be known or discussed before fall kicks off?

Stephanie Gubiotti: Do we wanna talk about mental health briefly and, what we’re trying to put together for the mental health program?

Matt Knight: Go for it.

Stephanie Gubiotti: So we have a to-be-named donor who is planning to lead sponsorship, and she is working with other founders in the space to co-donate alongside to have this be something that’s a founder-led mental wellness where we are able to dedicate time for founders in the prop tech space potentially to do in-person or virtual meetups, again, leaning into that community space.

Where, something that we don’t really so much see in the real estate side that we really see the pressures of in the prop tech space is [00:18:00] the decision speed to- the decision is really important, but there’s also a lot of just different nuanced pressures that they experience. And so we’re trying to bring together a cohort of people that have that nuanced experience in the PropTech space, and putting them in a group to be able to collaborate, give resources, mentorship to others in the industry as well.

So again, another example of our for, built for the industry by the industry.

Matt Knight: Yeah. How many... I feel like this is the to-be-named sponsorship episode. We have a lot of people that are- ... doing cool stuff that we can’t quite name yet, but stay tuned for next episode. That’s my teaser for our next podcast.

Stephanie Gubiotti: Yeah, this is our secret, our secrets, and then next episode we’ll do all the name drops.

Matt Knight: Right. Paul McCartney told me not to name drop, so I’ll try and stop. But thank you for being here. I appreciate this. We’ll talk again shortly, but if you’re listening, appreciate your time. Co, show up, help us grow this.

[00:19:00] Reach out if we can help you, and we look forward to seeing you in person

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]]><![CDATA[What Matters This Week - 07.25.26]]>https://verticaltech.substack.com/p/what-matters-this-week-072526https://verticaltech.substack.com/p/what-matters-this-week-072526Sat, 25 Jul 2026 13:03:53 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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]]><![CDATA[PropTech Chatter Ep #11 - featuring Dom Beveridge of 20for20]]>https://verticaltech.substack.com/p/proptech-chatter-ep-11-featuringhttps://verticaltech.substack.com/p/proptech-chatter-ep-11-featuringTue, 21 Jul 2026 02:04:56 GMT

Series: PropTech Chatter.

Show Notes

Summary: A deep dive with Dom Beveridge of 20for20 on the three most valuable events this Spring for ConTech.

Special mentions

Transcript

(Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.)

[00:00:00]

Matt Knight: Hey, guys. Matt here. Another podcast episode, this time with my friend Dom, whose accent is much better than mine. But we’re talking about events. I thought this was timely to reflect this summer on what happens in the spring as we look forward to the fall, and he’s got a really interesting take on it that, is a perspective I don’t have.

So listen to this 15 or so minutes of me and Dom waxing on spring and other events

Matt Knight: All right, Dom. Thanks for being here, man. I appreciate the time. I know we saw each other a bit this spring, but I thought it’d be good this summer to reflect back on spring events in real estate construction tech and kinda talk about why those matter. How does that sound to you?

Dom Beveridge: Sounds great. Thanks for [00:01:00] having me.

Matt Knight: Yeah, man, I think this is important. If you’re young or you’re starting up a startup or you’re new to the space or maybe a student, I think it’s good context because, all of us have limited budget most of us have limited budgets, and so knowing which events are for whom and what they’ve...

how you can benefit from them and who they’re targeted towards and who shows up I think is super useful, unless you disagree with that

Dom Beveridge: No, I I agree completely. I I have quite a lot of conversations about that very thing as well.

Matt Knight: And maybe a good place to start is maybe run us through your spring lineup of events, and then I’ll go through mine, and we can talk about overlap and maybe reflect on what each one maybe strengths and weaknesses for the ones and where we think they’re best fit.

Dom Beveridge: Yeah. I tend to ration myself to events that I speak at, right? So I’ll usually go to some number of client conferences or, y- just user conferences for companies that I work with. And for the most part, I try [00:02:00] to focus on the public events, the commercial events that where there’s an opportunity to speak, to develop some content and so on.

And my... the first sort of big public event I do each year is usually AIM. AIM is a really interesting show. It’s been growing for quite a while. Very, a very tried and tested formula. It, it built its reputation around marketing, but for the last few years, it’s been growing its executive presence quite impressively.

They had a really good attendance this year, very interesting audience. And yeah they try to... steve Lefkowitz is the, probably the best curator at event content in the industry. He really pushes to have kind of very current kind of stuff. He wants he wants whatever is new in the industry to be on the stage at his show.

And yeah, he’s built a community around that that event. So it it’s fun. It’s a great place to go connect, but it’s also got quite a commitment to [00:03:00] learning about it, and so I like it for those reasons

Matt Knight: Yeah, I I’ve spoken at AIM, and I think very highly of Lefkoe and Dennis.

And I wanna come back to AIM ‘cause it’s... you mentioned something that I’ve had a suspicion about for a while. But for me, I’m similar in that I tend to filter for things where I either have a direct speaking or content line or I have something unique that I can add to it, versus just I need to go to Vegas again.

I don’t have time for that. But on the other hand, I do have things I go to where I’m trying to discover. With what I do with the foundation, I go to CES every year because I wanna see what’s happening in consumer electronics, ‘cause a lot of B2B companies are there and selling their hardware.

A lot of countries come to that, and here’s what’s innovation in Germany and Denmark and Korea. And so I do CES in Vegas every January just to see what’s even possible in the world of technology, and then it’s my job to bring it back to the real estate and construction industries. And then the very next month, there’s one called IBS, the International [00:04:00] Builder Show, which is a very similar flavor, but it’s all home building tech.

And so same thing, is how can I take what the most innovative home builders and suppliers and OEMs are doing and bring it into multifamily or office or retail or hotel, right? So I do those two generally just to see what’s even possible and how I can bridge the gap between those industries and our industry.

And then I also usually go to RETCON, which is a very, I would call it analogous to Blueprint and CREtech to a degree, but it’s in the spring. It’s a different company. It, it would have a similar vibe to those two, but it happens every spring. I think it was March this year. I don’t remember. But it was in Vegas again this year, and I did those three before doing my event in La Jolla right after AIM.

So that’s my spring is the two where I go scout. RETCON is a down-the-fairway PropTech company, and then my event right after AIM, which is in May. Those are my four, give or take.

Dom Beveridge: Yeah, no, I’ve been to RETCON before. The the problem with that show is I live in Texas, and [00:05:00] they always hold it during Texas spring break which which means it’s it’s less popular with with people from the Lone Star State.

But no, I’ve been there before and and have generally good feelings about it.

Matt Knight: Yeah, and with, to your point on AIM, I think the world of Lefkoe. He’s been in my angel group. He’s one of the greater minds in our space, and a great... He’s got a great voice, got a deep one. He doesn’t have your buttery British accent, but he’s got a really good speaking voice and a good presence, which I always appreciate.

And I was on the board of his MICA Conference when it was in Atlanta, and when he did the FLEX Conference in SF, I went to that. So I agree with you on the top-tier, thoughtful curation of content and people.

What I have hesitated is I’m not a marketing person, and of the stuff I touch, 10% of it is marketing. Top of funnel leasing strategy, website content, all of that’s great, but it’s 10% of the stuff I do. And so I’ve held off on going recently, but I’ve heard what you said is that it’s become a lot more than that, and I hear the same thing about Real Comm.

But I’d love for you to expand on that a little bit where, [00:06:00] yes, the CMOs and the marketing folks come, but it’s evolved into blank. What is that blank to you?

Dom Beveridge: Yeah. I’ve been going to AIM for probably about like 12 years or something like that. And so it always used to be...

So when I used to sponsor it as a, when I was the CMO back in the day, like I, I used... When I used to sponsor it, I used to primarily see it as a very good sort of see and be seen kind of conference. Like it was a, there was just this big social network around the the conference.

They’re not the people that ink deals if you’re a software company, but they’re but they’re people who are usually in the room when the when w- when your product is being discussed. So I had that kind of I had that kind of perspective on it, and it was worth doing for those reasons.

But nowadays, like where I tend to show up at conferences basically just to network, just to keep connected with with people that I work with or who I, who at some point I will need to answer to have them answer the phone to me. That’s the big objective for me in most of [00:07:00] these conferences.

What’s really happened over the last probably two or three years is that they’ve been running this C- a COO forum where they do I think like a half day of of behind closed doors meetings with a group of of operational leaders. And that h- is being increasingly successful because, when you flick through the attendee list for AIM, it’s now really good.

So again, for someone like me it’s now an excellent place to to go listen to a few new ideas, go to a few events by the beach, bump into multiple of the people that I y- that I tend to build my network around in this very sort of convivial y- event.

And so yeah, it’s it’s this combination of they’ve been making the audience more senior. They keep trying to push the envelope on content, so it’s not all about marketing. And the, just the the general level of enthusiasm for the event means that, y- social events are really well attended.

[00:08:00] And no it’s it’s a really great use of a couple of days in at the beginning of May each year.

Matt Knight: Never a bad time to go to Huntington Beach. And I don’t know if you’ve heard of Real Comm, but I’ve heard the same about Real Comm. Do you know that conference?

Dom Beveridge: Yeah, I actually, I spoke at Real Comm last year.

I did I did a session when it was in Savannah which is a great place to hold a a conference. I wish we could have more of that. But yeah, that, that was good, but it’s very much commercial real estate. Residential is very much out at the fringes of that event.

Matt Knight: Yeah, I guess s- to me, Real Comm started, from what I understand, as an IT conference, right? It’s Excel spreadsheets and CRMs and stuff that’s more for directors of IT. But that was, like, I... 20 years ago. That’s an older conference. Older in terms of prop tech, but not old in terms of all conferences.

Where it was procurement and IT best practices, and it’s evolved recently where a lot of startups say, “I gotta go to Real Comm,” which I think is usually in the summer. It might be right around now, here in June. We’re recording in [00:09:00] June. But I’ve heard it’s evolved into much more startup friendly, more forward-thinking, better content.

Not better, but more in my wheelhouse better. Does it, does that make sense? There’s no good or bad here, it’s just more- Yeah ... relevant to me on when you’re talking about AI and innovation and buying a startup or versus investing in a startup. Should I invest in a venture fund, right? Those are things that didn’t happen- Yeah, it was, at IT conferences 15 years ago

Dom Beveridge: Yeah. Yeah no, it’s it was it was a very sort of grown-up conference. It’s very well attended very credible sort of sponsor base and yeah, no like you say it was heavily tech-orientated.

Matt Knight: Got it. I guess if you were to advise someone and say, “Hey, I have a limited budget.

Where do I spend my budget on spring and maybe early summer conferences if May is summer and real come is summer?” How would you tell people to think about that?

Dom Beveridge: All right it all depends on your objectives. You’ve got a range of what these events cost. If I think about events like, for [00:10:00] example if I think about Retcon and Blueprint Blueprint I’ll be speaking there again this year.

I’m a big fan of that event. If I think about those two events, they for me feel like tech ecosystem shows. So you’ve got first of all there are multiple different food groups in terms of real estate, but it’s also, you’ve got everything from small startups to mature companies.

You’ve got both buyers of and investors in technology from the from the property management company side. I think the I think there’s a different kind of conversation that happens at those events. For for years we’ve had Optech, which has been growing steadily for, a decade or more.

Last year was the first time it shrank a bit, and they’ve changed it. I think they made it members only, and the effect of that was they lost some audience by doing that. It’s always in Vegas. Optech you have to be there, but because of when it is, it’s right before [00:11:00] Thanksgiving normally, it means it’s the last event of the year when salespeople get to make their numbers, right?

Where it’s the last time you’re gonna get to try and meet people you’re trying to close business with, which means you have this enormous attendance of vendors. And it just means that there’s this kind of form to Optech, which is everyone’s trying to pitch stuff at this... you’ve got roughly 2X the number of vendors to property management companies.

That, that number has been the same for many years. So people complain about it a bit, but it’s always the same, which means that the industry is largely comfortable with having this, 2X vendors to potential buyers attendance at the at the event.

And what it means is that you’ve got this subset of the audience who are property management companies who are constantly being assailed by vendors. But it’s a productive way to, to go and see, people will go and meet every supplier of this, say [00:12:00] it’s fraud prevention or something like that which has been hot for the last few years.

You’ll get people who will use Optech to go and meet with every single vendor of that kind of technology. And it’s quite a productive way to do it even if it’s a bit annoying that you’re, you’re constantly being pestered for various parties and dinners and and so on. So Optech is also...

it’s a membership event, which means that the content is organized in this sort of particular way. It’s good. Content isn’t as good as something like AIM, but it’s much better than something like NAA, right? It’s the RETTC people do take the content really seriously and try and make the program be really good.

And yeah, it’s generally generally popular. But if I think, if I contrast that event, which is the very much the mainstream technology event, to things like Retcon and Blueprints, I think there’s a slightly more, there’s a slightly more relaxed, slightly more mature conversation that goes on at those other events because first of all it’s nearly all senior people that go from the property management [00:13:00] companies.

They’re not going there purely to listen to pitches, which is mostly what Optech tends to be about. They’re looking at potential investments as much as they’re looking at technology that they might want to use which means the nature of the conversation is different. What I hear from suppliers that I work with is it’s a very relaxed, quite grown-up kind of conversation that you have around the the show and you get really high quality sort of meetings there.

So I actually think, blueprint is the lens that I tend to look at this through ‘cause I’m, I’ve been heavily involved in this for a while, but I I think they bring something very positive to the to the industry. I would be an advocate for that.

Matt Knight: And you brought up, Apartmentalize, I think that’s what you’re saying, with NAA, and that one maybe you can help disabuse me of a stereotype, but when I think of Optech versus Apartmentalize, ‘cause they’re both tech conferences focused on the multifamily space, right?

And what I think about in Optech is it’s smaller, but it’s very senior, it’s members only, a lot of [00:14:00] decision makers. Apartmentalize to me seems much bigger. John Deere shows up and roofing tile guys show up. It’s not all tech people. It’s not all tech in general content. It’s 14,000 people or something this year.

How do you compare and contrast those two if you say, “I want to be in multifamily, I care about innovation. I’ve got to pick one of those two ‘cause I only have the budget.” How would you think about that decision?

Dom Beveridge: So first of all if you think about the audience it’s not a technology conference, right?

It’s an educational conference, which means most of the attendees are act- people who work in multifamily communities. So it’s, there’s a lot of maintenance people there, there’s a lot of community managers and regionals that that show up to it. And so it’s a real mixed bag of content, right?

It’s not, you’re not just there to learn about technology. In fact, most of the sessions tend to be about, more HR kind of motivation, how to avoid burnout, all of these kinds of more sort of personal development, HR-orientated kinds of kinds [00:15:00] of sessions. So the sort of mission of the show is very different.

If you think about it from the perspective of a tech company, again you’ve got to be there. Now, it’s the biggest trade show in the industry, and what happens at the trade show in at NAA is that loads of people just do their meetings wandering around the trade show.

So for me, I’ll spend a few hours at the trade show one, one day of the event, and I’ll just be texting with people, say, “Okay, where you at?” And, you’ll spend a couple of hours just meeting with people, and it just becomes this... it’s a zoo. It’s crazy busy chaotic atmosphere.

But it’s quite productive if you think about it that way. I always, again, if I go back to the days when I was I was responsible for the budget for a software company I viewed the booth at NAA as a cost of doing business. I just I thought, I I do think we’ll get some business done at this event, but it’s more like I simply can’t not be on that trade show floor, because I know that [00:16:00] everybody at some point is gonna be spending some time wandering around just connecting with everybody.

So in the context of the way I see shows nowadays, NAA is very different from the others because I essentially see it as a social event. You basically go there to connect with, 30, 40 people around the middle of the year who you haven’t seen for a few months.

You go to a few parties. For me i’ll watch a few of the sessions, but candidly it’s the least curated program of content in the industry, right? So they have this slightly odd way of building their program, which is they open the program for submissions.

You’ll get something like 250 different proposals. They have a committee structure where people score each each session, and that determines what gets into the show. Of course, what happens then is you’re all over the map in terms of quality. If you look at the program overall the balance between different topic areas is quite random.

Because you don’t have an ultimate sort of [00:17:00] curator of the event because it’s this sort of democratic way that you do it, you don’t have the equivalent of Lefkoe who’s saying, tell me something that’s gonna blow my skirt up,” to get on the stage.

Yeah, instead like this year, if you look through it, you have tons of t- tons of sessions about sort of policy, about like I said earlier, about how to avoid burnout, about how to motivate your teams, and fairly samey topics, but there’s not really a good way to avoid that because it’s like I said it’s largely a democratic process that that, that picks the sessions.

I’ll go and find a few things that look like they might be interesting so that I’ve, I find it a really good discipline at shows to, to try and find something that’s interesting about them, and then I write about them just because it helps me collect okay what did we learn last week at this at this show?

And yeah, and other than that, NAA, it’s most it’s mostly I would say a social event. And one, one that you tend to have to be at if you’re a if you’re a supplier. But yeah the technology part of it is not [00:18:00] the main point of the show in the way that it is at Optech.

Matt Knight: And to play devil’s advocate on the content side, to your point, you have to have some content, one, that Gives, gives credence to your sponsors, right? Sponsors pay to be on stage and want to hear their products talked about. Fair enough, right? You also have content that caters to the first-timers. Oh my gosh, you can use AI in property management?

No way, right? You and I are gonna roll our eyes at that because we’ve heard it 986 times. But the first-timers need to have cool stuff to listen to. So I guess the thing that maybe you and I are agreeing on in, in terms of Lefkoe is I think he does a good job of “Here’s the things we need to revisit.

Here’s some intro stuff, but here’s things you’ve never heard before.” And I think that’s, as someone who manages his own event, that’s a challenge to do as an event coordinator. And, I think as our last question- Yeah ... ‘cause we’re out of time is if I were to, restrain you and say, “Hey, you can’t speak at any of these events, but you gotta go to three.”

I’m curious. You can pick fall events, winter events, whatever you want. Pick the three that you can’t miss even if you’re not [00:19:00] getting on stage talking and doing thought leadership. What would your three be?

Dom Beveridge: I would I would probably say I’d probably

say Optech definitely, NAA, and gosh, depending on what kind of company you’re representing, I would say either NMHC annual, just ‘cause it’s a very senior and very well-attended event or I would say Aim for the reasons discussed earlier.

Matt Knight: Nice. I appreciate you doing this.

Thanks for walking us through some of the spring schedule and how you view these events. I think it’s gonna be very helpful to some young people in particular.

Dom Beveridge: Awesome.

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]]><![CDATA[What Matters This Week - 07.18.26]]>https://verticaltech.substack.com/p/what-matters-this-week-071826https://verticaltech.substack.com/p/what-matters-this-week-071826Sat, 18 Jul 2026 13:00:54 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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- Morgan Housel

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]]><![CDATA[What Matters This Week - 07.11.26]]>https://verticaltech.substack.com/p/what-matters-this-week-071126https://verticaltech.substack.com/p/what-matters-this-week-071126Sat, 11 Jul 2026 13:25:40 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“The only way to win is to learn faster than anyone else.”
— Eric Ries

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]]><![CDATA[VC Unfiltered: Ep #3 featuring Courtney Cooper of Alate Partners]]>https://verticaltech.substack.com/p/vc-unfiltered-ep-3-featuring-courtneyhttps://verticaltech.substack.com/p/vc-unfiltered-ep-3-featuring-courtneyFri, 10 Jul 2026 00:54:00 GMT

Series: VC Unfiltered

Show Notes

Summary: This episode of VC Unfiltered covers Founders, Investments, and ConTech Portfolios, with Courtney Cooper of Alate Partners.

Special mentions

Transcript

(Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.)

[00:00:00]

Matt Knight: Hey guys, if you don’t already know Courtney Cooper, then shame on you. She’s awesome. I’m gonna talk to her here for a few minutes about Alate and Canadian PropTech. We’ve known each other for a minute, and she’s just working on cool things and is just a wonderful person to know. So enjoy this time with Courtney Cooper

Matt Knight: All right, friend. Thanks for being here. I appreciate it. I guess you and I met more than five years ago. It’s been a while, but I’d love, if you don’t mind, can we start with who’s Courtney? What’s your background? Talk to us about Alate. What’s going on now? Let’s set the scene before we get too far down rabbit holes.

Courtney Cooper: Yeah, I joined Alate in [00:01:00] 2018. So that, Alate is a vendor fund that invests in early stage prop tech in Canada and the US. Before that, I spent my whole career at the intersection of real estate and tech. I started at Dream, which is a large owner/operator developer based in Toronto, but has assets across North America and Europe.

And I worked with them on a big technology overhaul. We were building some of our own software. We were implementing third-party software. And that was really when I got introduced to software development and the opportunity of technology in the industry. And then, led me I took a little bit of detour, but led me back into prop tech when I joined Alate.

Matt Knight: And tell me about Dream. What’s the portfolio and scope of Dream, and how did that affect kind of what Alate did?

Courtney Cooper: Yeah, so Dream is they do a little bit of everything, and what they do depends on the year that you that you’re looking at them. So they’re about 30 billion in assets right [00:02:00] now.

They have, they own offices, industrial. They do, d- they do development of master plan communities. They have land, housing. They do condos. So it really kinda has spanned a bit of everything, and for me was an opportunity to learn about all aspects of real estate early on. And we were... some things we were doing, we built a y- we built a platform, an internal platform for property management and leasing, doing some of the lease workflows that VTS would do now.

We were trying to bring together everything that anyone needed to know about the property. We, I helped implement some software on the home side. I think they they’ve transacted large portfolios. They’ve continued to expand the business. And so I think I was there 2011, 2012 until 2016.

That was when I was initially involved with them. And then Dream is one of the co-founders and LPs of Alate, so I’ve been working with them since 2018 and seeing the business grow and change and seeing their strategy [00:03:00] on technology change. They, some of the things they built lasted.

Others were cycled out and replaced with the new technology providers that had spun up since we started that initiative. And it’s been cool at Alate to actually get to invest in some of the ideas that we had in, in 2012 to 2015 when we were trying to build things ourselves.

Matt Knight: Were you involved in that building of things, or were you more tangential to it, just out of curiosity?

Courtney Cooper: No. I was core to it. I wasn’t a software developer or on the tech team from the start, but we did it in sort of two ways. We hired a consultant to help us do a big analysis of our processes to understand what we were doing that we didn’t need to do and how we could improve.

And so we did an eight-week mapping exercise where we brought all the stakeholders together in all the different workflowsand identified what were the biggest opportunities on the process side and technology side. And so I was in all of those meetings and part of hiring the consultants and project management for that [00:04:00] process.

And then we were working with one of the board members who’s the CEO of Klick Health, which is a large marketing company for healthcare and pharma, and they had built a lot of internal software. So we were working with the VP Of corporate services who ran all the operations side of it.

the board member helped hire that whole team and help with the strategy, change management, project management, pitching in where there was gaps. ‘Cause as we’re building a team like a startup, there’s a lot of things to do and not people to do it. So I was a product owner on one of the products and helping really bridge the gap there.

So that was really my sort of introduction to being around software development and on that team and yeah, learned a lot

Matt Knight: Got it. And then, I know we have talked about this a lot off the recording, but how do you think about Alate in the pantheon of real estate construction tech, proptech funds where, is Canada, is Dream, is there a unique angle on here’s how we do it different?

Because the thesis, as is we have the users of the technology as our LPs, so [00:05:00] it makes us vet and deploy better. How do you think about what Alate does or did relative to kind of other funds? I’m curious.

Courtney Cooper: So Dream is one of our... they co-founded Alate and was part of the initial capital, but then we raised a fund and brought in other LPs.

So all of our LPs, for the most part, have a strategic real estate business or focus. And so we do have that sort of lens that we work closely with our LPs, and they can help us on testing out ideas and software, although we don’t have a tied relationship. I think that we try to when we’re doing diligence, we’ll involve people in our network and our LPs to help vet what they’re doing and the ideas and help us understand what the objections might be in the industry.

But we’ve generally seen that real estate companies adopt at their own pace, and they have different priorities at different times. And so many of our companies we’ve invested in- involved partners during diligence, but then, some of them adopted immediately, others it took a year or two or three and they [00:06:00] just ended up using them when that project came around.

So we definitely work really hard to help our portfolio companies on getting in front of the right people at the right time. That starts with our LPs, but also all of the relationships we have in the industrythrough our experiences and our extended team and LPs.

And so we work really hard to try to tap into that and make introductions. But also people like you and being part of PTAG, I think there’s a lot of connections that startups make with other founders, and so we work as hard as we can to deliver on the promise of actually making those introductions and helping with BD where we can and being a good partner.

And, I think that other funds have similar approaches. And I think we try to deliver on it

Matt Knight: And how do you think about portfolio construction? Being Toronto-based and, there’s been some cross-border let’s say media recently with coming in out of the US, but obviously you’ve built a good portfolio.

Atticus is a stud, like I know a lot of your investments, but talk to me about portfolio construction, how you [00:07:00] thought about that, how you’re thinking about that. Lead, co-invest, deal size. Just give us a flavor for what’s in Alate’s portfolio.

Courtney Cooper: Yeah. We primarily do early stage, so for us, we’ve entered at pre-seed to Series A.

We’ve got some other later stage investments through acquisitions and other sort of unique opportunities. But bread and butter would be a million, 500K to a million and a half first check into, normally pre-seed, and seed is where we get started. We obviously have a soft spot for Canadian founders, and we’ve made investments in a nu- about half our investments are Canadian.

Maybe slightly more, but around half i- in Canada, and we love Canadian founders and have seen great companies coming out of Canada. But we also invest in, in the US as well and have built and invested in great founders there. We so we don’t g- geographically, it’s kinda ended up 50/50, but that’s yeah, but it’s much more about the company and the stage and if [00:08:00] everything lines up for us to be part of the round.

And we’ve done a mix of residential, commercial and construction, so we haven’t been bound by by a specific asset class.

Matt Knight: Yeah, I was gonna ask about that because certain funds have certain strengths. Do you feel like you guys are pretty utility players across ConTech, resi, and commercial, or is there one where you feel like you have more depth than others?

Courtney Cooper: touch residential and commercial, and we’ve done a few on, on the construction side, but we’re not as... we’re construction isn’t... There, there’s funds where construction is their core focus, but a lot of our LPs obviously build a lot, and so we’ve been successful in making connections there.

But I would say that we have less inve- if you look at our portfolio, we have less on the construction side than the others.

Matt Knight: Sure. Yeah, me too. What about wins? Any big wins, gains, portfolio brag you wanna get on the record before we talk about lessons learned?

Courtney Cooper: Oh, man. I feel like this year we’re, there’s a lot of momentum in the portfolio.

I think that it’s been it’s been an interesting few years. But no, a lot of our companies are [00:09:00] doing well. PadSplit you mentioned. They’re doing awesome. They’re the largest co-living platform in the US, and, it’s incredible the impact they’ve had on people. they have 30,000 rooms on the platform, and that’s mostly working class people who, need a place to live where they, near where they work.

So that’s been really exciting just to see them grow and see the impact that they have. In Canada we, I would say maybe the, we’ve invested in Mave and OwnRight who are on the residential real estate side. One’s for tech enabled real estate closings, the other one is marketing tech for realtors, and both are doing great.

we invested in Unity AI last year. That’s on the sales and support for real- like bringing AI, so they’re doing great in self-storage, manufactured housing, co-working going into multifamily. So the it’s exciting. I feel like I don’t wanna keep naming just all of our portfolio, but we have yeah, I just think really exciting things are happening and we’ve just seen a lot of the [00:10:00] portfolio really embrace AI and seeing those gains and wins and being able to move quicker.

And some of our companies are AI at the core, and others, have been leveraging the platform in their operations. And so I just feel like the last six months and year, we’ve just seen so much progress.

Matt Knight: Yeah. You, we made it, maybe we should congratulate ourselves. We made it 10 or 15 minutes in this call without saying AI.

So since you broke the seal, I’m curious, has that changed or evolved your underwriting around startups? And I can give you context and put words in your mouth if you want for why I asked that, but I can leave it vague as well.

Courtney Cooper: Sure, let’s hear what you have to say

Matt Knight: I just hear a lot of people worried that my point solution that eventually wants to be a platform looks less and less appealing the more capable Claude and Gemini and ChatGPT get.

And so I think I’ve heard people changing their underwriting saying the wedge you have has to be so specific, compelling, or obvious for real estate or [00:11:00] construction that there’s no way AI guys are even gonna think about it, right? Some- something like that. And that’s a, that’s one narrative, but I’m curious if that’s gotten into your underwriting or ethos around portfolio construction and analysis

Courtney Cooper: Man, I feel like it’s a bit wacky with AI right now.

I was having breakfast with another investor this morning and, what some companies are raising with no revenue and big ideas for what they can do with AI feels ba- like we’re back in, in 2020, 2021 and there’s just so much belief in what companies can do and so much capital going into it.

And, I think that, yeah, we’re, it’s gonna, it’s gonna play out and there’s gonna be winners and losers. I still think that real estate companies aren’t gonna do everything themselves. I think what we don’t know and I have some ideas a- about it, but, what we don’t know is how quickly things are gonna evolve and, how that’s gonna change the software stack of real estate companies or construction companies and every company.

Some r- tech companies are changing much faster than industry, but it’s [00:12:00] happening everywhere and so I think what we’re seeing is that even in our portfolio, when companies, some of the companies when they’re pitching, they’ll have customers say “I can build... look at what I can build.

This is what I’ve built. What is different about yours?” And when they’re going internally to make the business case, there is the real question, especially if you’re talking about software that is $100,000 or in the hundreds of thousands of dollars, can we build this ourselves? So I think that, there, there is much more of a real question there.

But I think there’s still just so many opportunities for companies in real estate and, I do think that real estate companies are going to have to work with tech companies to get the full value from AI. So I’m, I think our underwriting and our views on it have changed.

But and I... And there are areas where on point solutions there are so many people building the same things and so many real estate folks that are building the same the same things for themselves. Just a point so I guess on back to your point, on underwriting, it’s so much easier to build a product and get something to market now, or get something that’s [00:13:00] usable very quickly that just, that’s not enough.

it has to be really valuable. And I do worry that a lot, that there’s gonna be a lot more companies that can get to a million or 3 million in revenue and then stall. So I think we have to have a lot of conviction around, what the impact is gonna be and how you, how they’re gonna get over just early adoption.

So I don’t know if that answers the question, but it’s definitely something we think about a lot. But I still look at opportunities There’s,

Matt Knight: there’s two big rabbit holes there about corporate’s ability to build tech themselves and crossing the chasm. But I, before we ... I doubt we’re gonna have time for that.

That, that’s version number two with you. But I’m curious, like how has, how- other than AI, how have things changed? What are you looking at in the future? I know we only have a few minutes left, but what does ‘27, ‘28, ‘29 look like? Investment thesis, scope, opportunities, cross border. Tell me what the future looks like with what you’re seeing across your desk right now.

Courtney Cooper: Oh man, I don’t, I have, I don’t know. We don’t have time for going deep into this. I [00:14:00] would just say that we’re as excited as ever. I, I think that if we look at the portfolio companies of ours that are truly AI first and building platforms that allow them to leverage AI, it’s so exciting to see what they’re able to do and how much more efficient they’re gonna be able to work themselves.

And actually n- it’s not just about can we do exactly what we do today, but how do we leverage the platforms that we have and work with the models the way that they work to do things in new ways that are incre- that are faster, more efficient, and help people do the work that they love doing and get out of a lot of the administrative, just all of the things that are non-value add.

I’m really hopeful and optimistic that we’re gonna see a lot of changes in the industry in the next couple of years. And so we’re looking for the companies that are gonna be driving that and really change, like creating real value and really helping people dig out of the sort of weeds so that they can do the strategic work that helps them actually drive business value.

So I [00:15:00] think that’s like a very ... I don’t know if that’s too high level, I think that we’re looking for sort of the transform- the companies that are gonna help people transform the way they work.

Matt Knight: This is why you and I get along. We share optimism about this industry. Last two questions and I think one is maybe most germane, is when I see blank, I should send it to Courtney.

What’s in the blank that like clearly that’s a Courtney Cooper deal?

Courtney Cooper: I don’t know. Ultimately if you’re, if you take the call and at the end of the call you’re like, “Wow, I, I’m, like, I’m impressed with this founder. This is the team that’s the right one for this problem.” M- you, Matt Knight, if you’re impressed, then I want you to send me the deal. So I think it’s mu- much more about the

We’re early-stage investors, so it’s really about the founding team and why this team is the right team to solve this problem.

Matt Knight: I ... Hopefully you think I already do that, but I’m curious- I know,

Courtney Cooper: but it’s not, there’s not just a one-

Matt Knight: Yeah. I’m just thinking if someone’s listening to this and they’re like I’m a [00:16:00] startup that’s doing X, I should talk to Alate,” I kinda wanna have a filter so you don’t get inundated. But if something fits that criteria, do you have a online portal?

Should people reach out to you? What’s the best way to get in touch?

Courtney Cooper: Yeah, reach out to me courtney@alatepartners.com, LinkedIn.

Matt Knight: Perfect. We need to do a round two ‘cause there’s some rabbit holes we should go down, but I really appreciate you doing this first round with me.

Courtney Cooper: Thanks so much, Matt.

Anytime.

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]]><![CDATA[What Matters This Week - 07.04.26]]>https://verticaltech.substack.com/p/what-matters-this-week-070426https://verticaltech.substack.com/p/what-matters-this-week-070426Sat, 04 Jul 2026 13:59:17 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“Difficulties strengthen the mind, as labor does the body.”
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]]><![CDATA[The Director of Innovation 2.0]]>https://verticaltech.substack.com/p/the-director-of-innovation-20https://verticaltech.substack.com/p/the-director-of-innovation-20Tue, 30 Jun 2026 13:11:42 GMT
This is what Gemini thinks we are talking about

The herd is running for the hills, which means it’s time to start buying up the valley.

Right now, institutional real estate is undergoing a quiet, panicky purge. Across the industry, the Director of Innovation is being quietly scrubbed from team pages or left vacant after a timely resignation. To the average executive, this looks like fiscal discipline—cutting the corporate fat now that interest rates have sucked the easy oxygen out of the room.

But to the rest of us, it’s the ultimate buy signal. While the rest of the market is zigging into a defensive crouch, the smart money will zag.

Our industry's instinct in a downturn is to cut perceived fluff. Innovation today is not fluff! This is exactly why the firms willing to do the opposite, and put a real operator in that seat, will outrun everyone else when the cycle turns. - Dave Marcinkowski, Madera Residential

The mass exodus from innovation roles hasn’t happened because the need for innovation disappeared; it happened because the industry’s first hypothesis about tech failed. We tried treating innovation like a cosmetic upgrade—the corporate equivalent of slapping a smart lock on a rotting door and calling it a smart building.

Now that the tourists are clearing out, the real work begins.

The market just created a massive supply of high-caliber, battle-tested tech talent that can be scooped up at a discount. If you play this right, your next Innovation Director won’t just be an IT line-item.

They will be your next Chief Operating Officer.

“The next innovation role should actually be the COO. The hardest part of innovation isn’t generating ideas, it’s prioritization, implementation, adoption, and measuring value. Those are fundamentally operating disciplines. The COO is uniquely positioned to balance strategic vision with operational reality, understanding where friction exists, how resources should be prioritized, and where technology creates leverage versus unnecessary complexity.” - Khushbu Sikaria, Collective Residential

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]]><![CDATA[What Matters This Week - 06.27.26]]>https://verticaltech.substack.com/p/what-matters-this-week-062726https://verticaltech.substack.com/p/what-matters-this-week-062726Sat, 27 Jun 2026 12:44:39 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“Tolerance for uncertainty is the most valuable human trait.”
— Sahil Bloom

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]]><![CDATA[What Matters This Week - 06.20.26]]>https://verticaltech.substack.com/p/what-matters-this-week-062026https://verticaltech.substack.com/p/what-matters-this-week-062026Sat, 20 Jun 2026 13:41:31 GMTWhat Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing.

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“Innovation is taking two things that exist and putting them together in a new way.”
— Tom Freston

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]]><![CDATA[Into the FIRE: Ep #5 with Skyler Chan]]>https://verticaltech.substack.com/p/into-the-fire-ep-5-with-skyler-chanhttps://verticaltech.substack.com/p/into-the-fire-ep-5-with-skyler-chanThu, 18 Jun 2026 14:29:05 GMT

Series: Into the FIRE.

Show Notes

Summary: A special episode of Into the FIRE hosted by Stephanie Gubiotti, Advisor - Foundation for Innovation in Real Estate (FIRE) and the Emerging Manager Program, featuring Skyler Chan of GRU Space.

Special mentions:

Transcript

(Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.)

[00:00:00]

Stephanie Gubiotti: All right. All right. Today we have something a little bit different. Welcome to Into the Fire. We have Skyler Chan, and I’m your host today. Instead of Matt, you’ve got me, Stephanie Gubiotti.

Stephanie Gubiotti: So welcome, Skyler

Skyler Chan: Thanks, Stephanie. Yeah, excited to join today.

Stephanie Gubiotti: Yeah. So for those who don’t know you, I’ll give a little quick rundown.

We had the opportunity to meet in person in La Jolla, which was fantastic. Thank you so much for coming and speaking with our group and spending time with us.

Skyler Chan: Thank you for hosting. Yeah, it was a great time.

Stephanie Gubiotti: Yeah. Super excited to hear about the things that you [00:01:00] have going on. But Skylar is the founder of GRU Space, and his mission is to build hotels on the Moon.

So Skylar, do you wanna talk to us a little bit about what the latest things are that you have going on, and any latest and greatest updates about the Moon Hotel?

Skyler Chan: Yeah. Thanks, Stephanie. And so as Stephanie mentioned, we’re the company building the first hotel on the Moon. Our mission is to make humanity intergalactic.

And so what that means is we start with building cities on the Moon and Mars. Working backwards from this vision, we’ve identified that building a hotel on the Moon is the fastest way to activate this feature. And so right now our main focus is building the technologies and systems necessary to enable us to live off of Earth.

One of the key theses is that in order to do this, we need to decouple our dependency from Earth, and we need to be using resources on the Moon and Mars and beyond [00:02:00] locally. The reason why is because it’s very expensive to have to bring all the material from Earth to the Moon. So what we’ve developed is a series of technologies that enable us to use resources on the Moon.

We’re starting with a machine that we’re sending to the Moon as early as next year. It’s a payload that our team is developing, which will make the world’s first bricks on the Moon. And really what it’s to do, it’s to prove that we can use resources on the Moon to create products. Humanity has never made a product on the Moon before, ever.

And once we figure out how to make a product on the Moon it’s like the discovery of fire. You can argue it’s the Promethean moment. No pun intended here. And that is going to enable a whole Cambrian explosion of technologies afterwards the, after that discovery, and so it’s very exciting. And so one of the other factors in this, which is relevant probably for this audience, is how do you think about lunar real estate?

How do you think about what happens once we start building structures on the [00:03:00] Moon? What happens to the titles? Who owns these things? How do you do conveyance? How do you do all these other things? These are all exciting unknowns. It’s very blue ocean. There’s a huge market and potential for this, and the activator that allows this future to occur- is using resources on the moon to construct things, right?

Because if you can’t build anything on the moon right now, there’s no value to the surface. There’s no value to the volume of land that sits underneath a certain area. But if we are able to develop the land up, then there’s a certain value that’s attached to it for all kinds of different purposes like landing pads, like data centers, like homes, hotels, hospitals, all sorts of other products.

So it’s a very exciting place to be building and, yeah, that’s a bit about us.

Stephanie Gubiotti: Very cool. Yeah. Yeah. So I know we chatted a little bit about this. Within our network we have something called our hardware and robotics or our petting zoo program, where we really work with a lot of hardware [00:04:00] and robotics companies.

And so there’s potentially some opportunities for some mining and robotics companies to get involved as you’re shaping the future of this. Does that sound right?

Skyler Chan: Yeah. It’s a exciting opportunity right now because our payload is going to the moon as early as next year, and it’s going to be making the first bricks on the moon.

And part of that payload that our team has developed is we’ve engine- we’ve done some really cool engineering with how do you fit a robotic arm inside this payload? How do you use mechanical systems to allow us to create a brick on the moon? And so part of this thought process is one of the things that we’re, that, that’s different about construction on the moon that isn’t the case for construction on Earth is mass, right?

And so the funny thing is, when you’re sending stuff to the moon, or space in general, it’s quite expensive. And you pay for your mass per kilogram. And so one of the ways that we’ve been able to bring down costs is find ways to decrease the mass that we send to the moon. And the second [00:05:00] aspect is power, right?

So also similar similarly with mass, power is constrained on the lunar surface too, right? And right now, power would be supplied by the lunar lander. And so what we’ve also been able to do is prove that our system is able to operate in low power environments. And so this is a great opportunity, of course, for folks who want to be involved in the construction aspect or the mining aspect or even the robotics aspect to really enable their brand to be one first on the moon.

Stephanie Gubiotti: Very cool. That sounds super exciting. So one of the things that’s probably one of my favorite moments of our time together in La Jolla, we spent some time together on the boat chatting a little bit, and we talked about how mental health is important to slow down, take breaks. It was nice to be able to spend some time kind of outside of offices and on the water and I’m just curious for you, a lot of founders are focused on [00:06:00] solving today’s problems, but how do you also balance taking care of yourself?

Yeah. And how do you balance long-term vision with the reality of execution today?

Skyler Chan: Yeah. Honestly, I don’t really do self-care or any of that mental health stuff. I think for me there’s, be- there’s a time before GRU and there’s a time after GRU, and the time before GRU I was just really unhappy because all I could think about was how we needed to build this set of technology so that humans could one day live on the Moon and Mars.

And so what I found interesting enough is obsession has allowed me to be happy because I’m engrossed and obsessed with this concept and this, the entirety of this company. It’s just been something that I’ve wanted to do my whole life. I’m just naturally happy by default. I think there are days, of course, where say, you’re traveling, internationally for different reasons it’s taxing or it’s a crazy day at work.

But I think the way to get through it is just to remind yourself that [00:07:00] the mission is the most important thing, right? Everything is working backwards from the mission. And so in other words, if something isn’t going well today, it’s an opportunity to ask yourself is this still moving the needle towards this end state mission that is, ideally in this, in, in everyone’s case, is the most exciting and inspirational mission that you can think of,” right?

Life is too short to work on anything else. I mean- Yeah ... you live once, right? And like, why work on something subpar? And so in other words, what I’m getting towards is being unhappy with day-to-day work on a daily basis is likely going to be a sign of- Of not being happy with your mission, like not being on the right mission Yeah and a tangent to this is burnout.

Another thing that I also believe is that burnout isn’t a real thing in the sense of classically people qualify burn- cl-like classify burnout as not being, obviously like just being burnt out, right? You overwork, right? You don’t sleep enough, blah, blah, blah. I [00:08:00] think burnout occurs when you don’t have clear intermediate milestones that are inspirational, that are attainable, that are challenging enough to push you far, right?

Burnout occurs when you don’t have ... when the goals seem like way too far in the future and, aren’t attainable. And so what I’m getting at is that I think this is actually good that this concept occurs in real life because it forces you to actually think about what are realistic, not realistic, but like attainable goals to work on every single week and every single month, and therefore every single quarter and year, et cetera, so that you don’t work on things that are just totally unrealistic.

I think that’s important when it comes to building very ambitious projects like our company.

So obviously when we think about schedule, it’s important to plot out working backwards from the end state. What are the series of milestones that unlock the next phase of the business? And when you think about that, it’s important [00:09:00] to also consider okay, how does this play into execution, right?

What ... how does this dial down to week by week? And if you can’t communicate it that this is be- able to be accomplished every week and breaking down week by week, then it’s probably not a good goal. And because of that, because we have that like pretty like this forcing function pretty baked in through our process, that group, it forces us and our team at large to be very mindful of what what we work on every day, and therefore I don’t think we really get burnt out as much as, say someone working on something that they’re not that passionate about,

Stephanie Gubiotti: yeah. And the benefit of working in the innovation space is you’re living in this world of ideas, right? Instead of the reality of some current problems, you get to at least for me, I’ve found that, doing innovation work, like I like both, right? Doing innovation and then solving problems as well, and a good balance of both.

And I think if you’re too focused on one [00:10:00] end of the pendulum, you end up feeling out of balance. Does that resonate with you at all?

Skyler Chan: I guess so. You could say that, yeah. Yeah. I think balance, one thing I’ll say is sleep is non-negotiable.

Stephanie Gubiotti: Yeah.

Skyler Chan: Yeah. That’s something that is just stupid.

People who just are performatively- Yeah ... not sleeping enough. Just go to sleep. All right, so-

Stephanie Gubiotti: And especially if you’re changing time zones. That’s something that I- I typically struggle with when I’m traveling.

Skyler Chan: Yeah. Yeah, exactly.

Stephanie Gubiotti: Yeah. Yeah. At FIRE Summit, you spent time with us with housing providers, operators, founders, investors, policymakers.

What surprised you most of, what you learned in that space or kind of the connections or conversations that you had with people?

Skyler Chan: Yeah, I think the exciting stuff definitely surrounded the possibility of what lunar real estate looks like. Especially with the crowd at FIRE. There’s a lot of folks who obviously have a deep [00:11:00] background and expertise in real estate, and working backwards from that, all of the different facets and industries that arise from that, right?

Real estate is one of the world’s largest asset classes. And so when you think about the moon as an asset class, I think that’s when things get very interesting. And the reason why is because no one has actually figured that out yet. No one has written the rules for what that future looks like.

And the opportunity to be a part of the very early missions that will write and demarcate those boundaries on the moon, for example, is a very exciting opportunity. And I think the feedback that we got when I gave a talk in La Jolla was people were interested to discuss what those look like.

Actually, I think I spoke with almost everybody who attended. It was a very small event. It was quite intimate. It was great event. Great job again for hosting. And, Yeah, I think there’s a huge amount of opportunity for that. And this is interesting to us because, [00:12:00] we’re engineers, right?

And so at its core, we care about solving interesting engineering problems. And obviously this is one of the most exciting engineering problems out there. But there is this also very exciting angle of real estate development on the Moon that is very blue ocean and hasn’t been solved yet. I would use an analogy and call back to history.

Look at the Louisiana Purchase, for example. Amazing deal in retrospect, right? Amazing deal. Great deal. And I would charter that there are going to be opportunities like that on the Moon, where vast swaths of land will be like, “Okay this goes to this entity and this goes to that entity.” And it’ll only be a matter of time when people realize “Whoa,” “that was severely undervalued.”

And hindsight is 2020, and so the meta to all of this is understanding that likely we are going to be underpricing no matter what on the Moon. So that’s why it’s very exciting [00:13:00] to have the ability to develop on the Moon with a construction company is so that you can increase the value of that plots of land

Stephanie Gubiotti: Nice.

Yeah, that’s super interesting. It’s it’s definitely uncharted territory, and it’s fascinating to think about and all of the implications and, who owns what and who has access to what and how things are done, and working with different groups. So when you’re sending, for example, rockets up, are you partnering with other companies?

Are you working with NASA, SpaceX, Blue Origin? Who are your dancing partners throughout your work?

Skyler Chan: Yeah. We’ve got, very grateful that there are some great dancing partners on the dance floor, as you said. The exact company that we’re working with to deliver our payload to the moon as early as next year will be announcing shortly.

But it’s... there’s only so many options and, relatively obvious. And so that’ll be exciting. But yeah, like we’re... [00:14:00] Yeah, that’s probably the most that we can say without,

Stephanie Gubiotti: Okay. ...

Skyler Chan: hurting any of the terms that we’ve signed.

Stephanie Gubiotti: All right. All right. All right. Noted. Noted. You’ve spent time with investors, operators, engineers, a lot of different people throughout your career, and I do wanna mention that you you’re 23, 24?

Skyler Chan: 23.

Stephanie Gubiotti: 23. That’s quite impressive. Thank you ... so what do you find that the most effective innovators consistently get right from your experience?

Skyler Chan: I think they just have a bias for action. You’re never gonna get it right the first time, and you just have to keep going, right? If it’s reversible, you just gotta execute.

I think that’s one thing, and the other part is the ability to predict the future and execute on that future ahead of the curve. So one of the things that I was really happy about with GRU in the early days and obviously early days are always early days. It’s still early days, but in the early days, was our [00:15:00] execution with the launch.

So when we did our launch in January- I remember everyone was like, “Moon Hotel is crazy.” Like, why would you launch that, right? When we’re queuing up our YC launch and preparing the big blast. Lo and behold, it was probably one of the most fruitful launches that we’ve had. And we’re still enjoying the fruits that that we, of our labor.

And the reason why is because we hit over 60-plus countries, we’ve got over a billion views across all the news articles, and allowed us to get a massive reach so that we can then work backwards, top-down, and work with important folks and different agencies, and the groups necessary to make this a reality.

And so when we did that as well, NASA wasn’t-- did not have the ignition event. This was pre-ignition. Ignition was an event where they talked about their plans for the moon base publicly. This was also before companies like SpaceX publicly declared that they’re gonna focus on the Moon. This is also before various other space companies started shifting focus to [00:16:00] the Moon.

We did this at a time that was at an pre-inflection point, so we’re riding right before the curve started going up. And I think the response we got was quite overwhelming and, ob-obviously, like early on, we hit a point where SEO was great. SEO is still great. If you Google Moon Hotel right now, just our category itself, GRU is the only company to show up first for multiple pages straight, which is great because obviously it demonstrates that we’re a category winner or just leader at the current stage.

And yeah, like whatever we’re doing next we’ll be rolling out soon is to just further execute on that aspect of being ahead of the curve. So I think those are the two aspects that I would say that innovators do. And honestly I’ve been pretty obsessed with this aspect of entrepreneurship for, I’d say about a decade before I started the company.

I remember reading Ashlee Vance’s bio of Elon when I was like 12 or 13. So yeah, roughly about a decade before I started. And I’ve just been [00:17:00] following the greats since then and studying like what has worked, what hasn’t worked, while also knowing that the path that we’ll take is going to be our own path as well, which leads me to the last thing, which is actually, I guess a third thing, is th- no one will give the best advice except for yourself, right?

Like you just... Scientifically speaking, every single one of us, including the people who are listening here, like- You have... You’re the only person in the world who has all the context, like context window in your life, ‘cause you are you. And so it doesn’t matter if like your role model shows up for five minutes and gives you, listens to you, all your problems, and then spits back advice.

They don’t have all the context window. You cannot compress all that context window into them. And so in my opinion, y- like you should never just listen to people’s advice. You have to process it and understand it, and then take it. And so one of the things again was like a lot of people were like, “This is crazy.

Why would you do this? Why would you launch with a moon hotel?” [00:18:00] But it allowed us to unlock the doors that are necessary so that we can further execute our mission. And that was the thesis that we had, and we tested it and in this case we’re right. And I think that’s another aspect that is important to note in thinking about what’s next.

Stephanie Gubiotti: Great. Great. I love that concept of a context window. I think that’s really great.

Skyler Chan: Yeah.

Stephanie Gubiotti: Thanks.

Skyler Chan: Yeah.

Stephanie Gubiotti: So I know we are almost out of time. I’ve got one last question for you. So let’s say we’re sitting here 20 years from now and we’re looking back. What do you hope people say about the impact of your work?

Skyler Chan: I think the future that we’re That is that is too existential not to work on that. Our team and our supporters are charging head forward towards is a future where the moon is no longer [00:19:00] just a place to look at night before you go to bed. The moon is a place where we have a constant human presence on the surface, where one day you will see the dark and night, the dark and light, and you’ll see like lights on the dark side.

Lights represent the structures and cities that GRU has laid the foundation for quite literally, like brick by brick. And I think knowing that the work that we’ve done will have accelerated the timeline towards having a step function increase in the human lives born in the future of human history.

Think about the billions of unborn lives on the Moon and Mars in the next 100, 200, 300 plus years, and accelerating that timeline up by a couple hundred years would be the most fulfilling impact. And that’s the future that we’re aiming for at GRU, and that’s what we want to be remembered by. Because at the end of the day like we mentioned earlier like the truth is life is short.

You do only live once. So life is too short to [00:20:00] be working on something that’s just been on Earth. It’s been an industry that’s been on Earth forever. Boring industries that you don’t, you’re not excited about. For us, like the moon beckons. And yeah that’s why we’re going after it and paving the road to make it happen.

Stephanie Gubiotti: Very cool. Very cool. Thank you so much for spending some time with me today, Skyler. I appreciate it.

Skyler Chan: Yeah. No, this is great catching up. Thanks a lot, Stephanie.

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