Someone asked me once, in the very early days of Parachute, pre-launch, “What do you even do all day?”

I remember thinking, what do you mean? I do everything, every day. I was sourcing. I was building the website. I was talking to investors. I was figuring out the systems and processes the business could live on. I was building a brand. There was no one else around the table. Every single detail and decision had to come from me.

Any founder will tell you there’s a certain kind of magic in those early days of a company. You throw yourself into business school times a million, compressed into one year, doing everything yourself, learning how the entire machine works, bolt by bolt. Then you finally start hiring, and you realize, with equal parts relief and identity crisis, that other people can do certain things ten times better than you can. It’s insane. It’s amazing. And if I’m being honest, a bit devastating too.

Unlike being an employee, when you’re a sole founder, the pressure doesn’t scale down the way the workload does, even as the team grows. Even in the most exciting, thrilling times, when you feel on top of the world, there’s a frequency you learn to live with, that for better or worse, the whole operation ultimately rests on you.

In 2018, we had just raised thirty million dollars, allowing Parachute to expand into retail. We had stores popping up all over the country. The brand was on the path to a hundred million dollars in revenue, proof that what we were doing was working. We had become a staple in people’s homes. The company was booming. The brand was growing. And I found out I was pregnant with my first child. Little did I know I was about to learn a completely different version of what it meant to carry everything alone.

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Over the years that followed, I found myself parenting solo. Nobody goes into a partnership expecting to leave it one day. The experience has been all of the things people tell you it will be, heartbreaking, devastating, but what shocked me the most

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Holly Thaggard spent over 20 years building Supergoop into the brand that made sunscreen into a staple of our everyday lives before eventually selling a majority stake to Blackstone in 2021. Now she’s building something new, WaterOuai!, a canned water company, with her son Will.

We talked about her journey building Supergoop from the ground up, what it felt like to hand it over to new ownership, and starting over in an entirely new industry with her son as a cofounder.

Right before we started recording, Holly and I were chatting about second acts, how normal they actually are, how nobody just does this once. Coming into this in the middle of my own next chapter, that was exactly the reminder I needed to hear.

I hope you enjoy this conversation as much as I did.

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Ariel: I want to start at the beginning. You launched Supergoop in 2005, way before clean beauty was even a category, before anyone thought about sunscreen outside of a beach bag. What was the aha moment for you, what did you see that the market didn’t?

Holly: SPF was a very seasonal thing. It was a sleepy category in 2005. Nobody wanted anything to do with it unless they were at the beach or in a bikini. My good friend, my college roommate, was going through a dermatology residency and another friend of mine was diagnosed with skin cancer. She told me it’s not about beaches and bikinis, it’s about every single day exposure, and it’s cumulative. For most people it doesn’t turn into skin cancer until much later in life, but for my friend, blonde hair, blue eyes, it was age 29. I immediately thought, gosh, that could be me.

I looked at the category and there was no innovation. It was owned by mass. There were no beautiful brands, just Coppertone, Hawaiian Tropic, Banana Boat. The only innovation was how high the SPF number went. My parents were both entrepreneurs and always taught us to look at the white space. Before this, I was a professional harpist, and there’s a reason I wasn’t a pianist, there were too many pianists and not enough harpists. I learned to look for white space early.

When I asked people why they weren’t wearing sunscreen, it was because everyone thought of it as an icky, sticky mess that burned their eyes and irritated their skin. I also learned UVA rays are present 365 days a year. They don’t know what the weather looks like. They’re cancer causing whether or not they change the color of your skin. One in five people will be diagnosed with skin cancer in their lifetime.

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My mother was a breast cancer survivor, and her oncologist gave us, her kids, a book on preventing breast cancer. Skin cancer is sixteen times more common than breast cancer, and it’s primarily preventable with a magic lotion. I started reading ingredient labels and found oxybenzone, parabens, chemical fragrances masking that terrible sunscreen smell, in every mass product on the market. That’s why nothing made people want to reach for it daily.

Ariel: How did you keep deciding what to build next at Supergoop? You never just sat back with one formula, you kept finding new ways to get people to wear SPF.

Holly: I’m going to say this and it’s going to sound ridiculous, but I literally began to dream about SPF. I’d wake up with ideas for how to slip it into people’s routines. But when our children were little, and our son is 18 now, going off to college, he’s our youngest, our daughter’s a senior in college, but when they were young, I used to put peas in their peanut butter and jelly sandwiches to get vegetables into them any way I could. I started thinking about SPF the same way. Twenty plus years ago it wasn’t popular, so we almost hid the SPF number on packaging, because seeing it made people go, oh, I don’t want it. We called our body lotion a body butter. We wanted people to appreciate a beautiful product first and know it had broad spectrum protection second.

I remember when we launched our Glow Oil SPF 50, Josie Maran was launching Argan oil at the same time, the hottest thing out there. I think we were on QVC the same night as her, or something like that. She was talking about how beautiful Argan oil and Meadow Foam seed oil are, not sticky or greasy, you could put it on right out of the shower and put your clothes on. I thought, this is fantastic, but why doesn’t it have SPF? So I started looking at every product in a daily regimen and asking how we recreate that with a foundation in broad spectrum protection.

Ariel: I mean, that’s the thing though, you actually changed a behavior, not just sold a product. Getting people to reach for it every single day instead of just at the beach, and making it not feel like a chore, nobody really talks about how hard that is.

Holly: We crushed it. And it’s interesting, just hours before this conversation, I was making this exact point to our social team at WaterOuai!, that we’re not going to change consumer behavior by scaring people. I lived this through Supergoop. We couldn’t talk about the truck driver with sun damage on one side of his face. We rarely even said the word cancer. We were going to do it by being aspirational, creating beautiful formulas people wanted to apply on repeat. I’ve put our Glow Body Oil on before bed because I know what’s in it and it feels great on the skin. That’s how you stop people from putting sunscreen in a drawer.

Ariel: Yeah, the fear-mongering thing, so many brands lean into it and I just don’t think it works. I’m with you, it’s about empowering people, not scaring them into it.

Ariel: In 2021 you sold a majority stake to Blackstone. I don’t think people talk enough about what that’s actually like, going from being the boss to having one. What did that feel like for you?

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Holly: It’s a transition. Sarah Blakely, one of my dear friends, told me, you’ve got to remember you don’t own the company anymore. I wish she’d said that before the acquisition, because I might have understood the process better. I was still so vested, still dreaming about SPF, still had a lot of work to do. The shift went from a founder-led brand that was always scrappy, always said yes, to a business with a lot more structure, process, and rules. I’m a complete rule breaker, so in those years I tried to keep leading the way I always had, which is that strong leadership isn’t about having all the answers, it’s about listening. I learned that from my former CEO, Amanda, who went on to run Olaplex.

Ariel: Having relationships with other founders is something I’ve leaned on through every high and low, the transitions, the milestones, knowing what to prepare for. It’s the kind of thing where you can just call someone and say “hiring” and they already get it, you don’t even need to say more. What does support look like for you, who have you leaned on through the different seasons of building, and what’s some of the best advice you’ve heard along the way?

Holly: In the early days I really refrained from asking anybody’s opinion. Supergoop was the first playful, spirited name for a brand doing serious skincare, and everyone thought the name was terrible. Every serious skincare product at Sephora had a doctor’s name on it. Even ten years in, during our Series A, about 40 percent of the private equity folks I sat down with said I had to change the name. I said, okay, this meeting’s over. You have to trust your gut, because if you start flexing for everyone, you end up with a big mess.

I think I’ve won the only grit award from Sephora in skincare that they’ve ever given out, because I was not going to stop until that six inches of shelf space became six rows.

As we scaled, I had the fortunate opportunity to meet other founders, Sarah Blakely, who founded Spanx and is now on her second act with Sneex, and Brown, who did about eight or nine things before launching Jones Road twenty five years later. We have a text chain going that’s been two, three years long. I keep a running list of founder friends on my reMarkable tablet. I started reading a lot about Warren Buffett, who said someone’s sitting in the shade today because someone planted a tree a long time ago. That’s how I think about entrepreneurship, it’s a marathon, not a sprint. He was also inducted into the Texas Business Hall of Fame, and I had that unique, crazy opportunity last year to be inducted in myself. I think only former inductees can vote on future ones, and I think they all probably shut their eyes when they were voting, because I don’t know how I got in there.

I think about Babe Ruth’s advice too, don’t let the fear of striking out prevent you from playing the game. Sometimes I think, I had such an amazing success, what if I can’t do it again? I let myself think about it for about two and a half seconds, and then I’m like, no, that’s not me.

Ariel: I have those thoughts also. Almost every day. And while most of the time they’re fleeting, I think it’s important to name them. To acknowledge them. And remember that no matter how good you are or confident you are, fear lives in the shadow. And then I look at those thoughts and think… get out of here, go away, I’m not buying into that.

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Holly: And as long as you’re making the world a better place. I often go back to my father’s advice, which was always don’t do things that have been done before, make the world a better place, bring innovation. As long as you’re following those things, the world needs you.

Ariel: That’s so true, and it’s the same for me, it can’t be superficial. I am a mission driven leader and builder. I need to know the impact is real, that it’s going to matter to the customer. When that aligns, you build real meaningful loyalty where people keep coming back.

Ariel: So onto your second story, your second chapter. You’ve launched WaterOuai!, and I’d love to hear about it, where did the inspiration come from, what’s it been like from inception to launch? And I know you’re working with your son, so I’d love to hear a bit about what that’s actually like too.

Holly: It’s been a part of Will’s entire life. When he was five, at an all boys pre-K, a guest speaker named Michael Gurian told the moms in the room, if you don’t take anything else from this hour, don’t let your boys drink from plastic water bottles, and talked about the effects on testosterone, focus, and ADHD risk. I went home and said we’re never having a plastic water bottle in this house again.

Going into his junior year, we took the kids to South Africa for a few weeks. We were having long dinners because there was no wifi anywhere, and Will said, mom, I’ve been thinking a lot about life. I want to do what you did in the sunscreen category, but for water. He said kids still aren’t getting the message, plastic water bottles are everywhere, and nobody understands how damaging they are to our health. I want to change the way the world drinks water.

He’d already been researching can technology, and told me most cans use a sprayed on plastic polymer liner that can crack and peel, especially in transit heat. And he said, well, you’ve always told me, if your idea doesn’t sound crazy, why bother. We found technology in Japan that builds the liner into the aluminum before the can is ever made, technology that hadn’t yet been introduced in the U.S. Our daughter Emery, who was heading to study abroad in France, said when he figured out the can, he should call the brand WaterOuai!, because in French the cool way to say yeah is ouai, and because mom always says where there’s a will there’s a way, and his name is Will. We were reserving the domain name from a tent in Africa.

The trademark was registered officially on his eighteenth birthday, and that’s when I decided it was time to step away from Supergoop and go all in, building this with him. This summer Will has been personally delivering water to one of our first accounts, the Hotel Jerome, 150 cases at a time.

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Holly: I keep telling him it reminds me of my early days at Supergoop, where I’d sometimes wear a baseball cap and go up the loading dock at Stanley Korshak or Fred Siegel, hoping nobody saw me, because I didn’t want anyone to know the founder was the one delivering her own product.

Ariel: I had a very similar experience. When we received our first batch of shipment I hand delivered early orders to LA thinking I was saving a buck, even though it was wasting my whole day driving around. I remember dropping off a box at an early mentor’s door on my way to an investor meeting, in heels, and her husband saw and was very confused! But she knew, and shared, that’s what founders do.

Holly: That’s part of what’s so important about the journey.

Ariel: I’ve been thinking a lot about the lessons, what I did right, what I’d do differently. It’s such a different era now, more tools, more access, AI. So I’d love to hear, are there things you’re bringing into WaterOuai! where you’re like, we could never do this any differently than at Supergoop, or things you’re turning totally on their head?

Holly: There’s a prevention first philosophy that carries straight through, and education at the core of the brand. The biggest difference is that I’m building this with the next generation, not just for the next generation. I’m learning from Will, because eighteen year olds today think very differently than I do. It’s also different having a co-founder at all, I didn’t have that at Supergoop, I just trusted my gut and went. Will loves the operational side and talking about microplastics, I love the sales side, and we’re complementary. There’s an advantage in not fully understanding food and beverage yet. We don’t know the rules, so we can write our own. I wasn’t from the beauty industry either, I was a harpist. I learned it by making thoughtful, grateful decisions, and we’re doing that again here.

Ariel: What does the second story make possible that the first one never could?

Holly: I have this calm feeling that I’m not in an urgent rush. I know a lot of the success is going to come from grit and perseverance that I don’t think I fully understood or appreciated with Supergoop. Having built that gives me this hindsight, and I feel really strongly about just not being in a hurry. Good things come to those that persevere.

When I decided to start Parachute, the first thing I did was visit fifteen factories.

I’d left my job in February, and by the end of March I had landed in Europe, rented a tiny Fiat, and was driving through Portugal and Italy with a suitcase full of sheets, scheduling meetings at 15 factories arriving at each one like Mary Poppins, spreading my bag samples across a table. ‘I like this.’ I do not like this.’ ‘ This is what I want to make, can you help me?’ There was no funding. No team. I hadn’t even incorporated a company. It was just an idea and a feeling I couldn’t talk myself out of.

I finally arrived at a family owned factory just outside of Florence. They let me walk the entire line, start to finish. Before my eyes, raw cotton turned into a single thread, then traveled through a machine the size of a football field and came out the other end a Queen sized sheet. The attention to detail was something you almost have to see to believe. Any impurity was caught immediately, in the weave, in the dye, at every step. The process was so beautiful it brought me to tears. I’d already spent hundreds of hours thinking, talking, and learning about bedding, thread count, raw fiber, quality control, you name it. But it wasn’t until that moment on the floor that my vision went from being an idea and became something real.

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Over the years I’ve been on many trips. Girls weekends, business travel, time with my family. Everyone has their own relationship to travel, their own reasons for leaving, and their own itinerary of what they’re looking for, but knowing when you need to get out of town is its own type of self-awareness. There’s only so much your routine can bring you before it’s time to shake things up.

I just got back from Copenhagen, a place that’s been on my bucket list for years. The city is known for impeccable design, delicious food, bike riding, and has a reputation of being one of the happiest places in the world.

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I went with a group of friends, some new and some old. I was in desperate need of a break from my day-to-day. Over the last few months I’ve been in the trenches, momming hard, working on my next chapter. I didn’t realize how badly I needed this reset until around day 2 of the trip, taking in an 11PM sunset. A different universe from my typical evening in Los Angeles! I was only there for a few days, but it was perfect.

It got me thinking about all the different boxes travel can check.

Some getaways are about turning everything off. No agenda.

That’s Cabo for me. When I’m there, I literally do nothing. I sit. I swim. I read. I get a massage. My only agenda, to spend as much time in the water, not get a sunburn and disconnect from life. It’s my eject button. I’m not looking for inspiration or trying to absorb anything. I think everyone needs a place like that, somewhere you keep coming back to that asks nothing of you.

Some trips are about waking everything up. A sensory explosion.

Tokyo, really all of Japan, was the first place that opened my eyes to this type of magic. I’ve never been somewhere where the attention to detail is so blatantly clear. The way of life is so different from how we do things in LA, it’s impossible not to feel like an outsider in the best possible way. There’s no such thing as autopilot in Tokyo. You’re so swept up in an unfamiliarity that something inside of you can’t help but get sparked. You notice things. You think differently. You come home with a head full of ideas your usual environment never could have brought you.

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Some places feel like visiting an old friend who knows exactly what to say, no matter the scenario.

When I’m craving that, I know it’s time to head to Paris. I’ve been more times than I can count, to the point that the second I set foot in the city, it feels less like exploring and more like sinking in. I have my favorite streets, neighborhoods, museums. Feeling like a local, in a city that’s not my own, fills my cup in a different way.

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Then there are the trips that alter your heart and soul.

Last year I visited Bhutan. I toured temples, learned about Buddhism, explored ancient places with a guide who knew every story. I’m a pretty spiritual person, but this was different from anything I could have expected. Everywhere you turn there’s so much history, so much meaning. Sometimes you need a few days not just to see somewhere new, but to learn something about the world, and your place in it, that you carry with you long after you’re home.

At the end of the day, it doesn’t matter which kind of trip you take. The reset, the eject button, the sensory explosion, the old friend, the heart-opener. All of them, in their own way, do the same thing. They remind you that there’s so much else out there than whatever’s going on in your bubble, and more often than not... that’s exactly where you need to be.

built Nasty Gal out of an eBay store, scaled it to over $100 million, wrote a book that turned “girlboss” into movement, watched Netflix turn her life into a show she didn’t write, and then watched most of it fall apart in public, all at once. She’s since started Trust Fund, her venture fund, and recently closed on the sale of the LA house that held all of it, the company, the marriage, the bankruptcy, the decade, and moved from Los Angeles to London.

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A few months ago I read her essay on Substack, “I don’t possess this house, this house possesses me,” and it hit me like a ton of bricks. I related so deeply to the words on the page, and her reflection of identity she spoke of that made so much sense. There’s a version of ownership, she writes, that looks like security but functions like captivity. That’s true of houses. It’s also true of companies, of identities, of the story other people decide to tell about you.

We talked about all of it, what’s left of Nasty Gal, what “girlboss” means a decade later now that it belongs to everyone but her, what it’s like to invest in founders after having been one, and what it actually felt like to walk out of that house for the last time.

I hope you enjoy this conversation as much as I did.

ARIEL: Hi Sophia, thank you so much for being here.

I remember the first time I met you in person. We were having coffee at Intelligentsia in Silver Lake. It was probably 2015. I got there early, and remember being so nervous to meet you. Not sure what to say, just simply honored that you would take a few minutes out of your day to say hi. I was blown away by your success, and at that point couldn’t really fathom how one got from launching a company, to building a household brand name. I know we could spend hours talking about Nasty Gal, and Parachute and all our lessons and learnings, and there is so much more for us to chat about - but when you look back at that chapter and era, what comes up.

SOPHIA: It was the most unexpected, fun, educational run I could’ve had. Hand-to-hand at first: I understood something well enough to scale it, and we grew and grew. And then it got messy: I hired a hundred people in a year, grew by a hundred million. What I do know is, I got the luckiest run.

There’s a difference between the naiveté of “this won’t be hard” and the naiveté of not knowing the thing itself. To be honest, I wasn’t even into fashion, I liked vintage. Nasty Gal was an expression of my taste, but the clothes were what people wanted, with my own spin on it. I wasn’t trying to get my personal fashion onto everyone’s back, if anything I’d think, oh shit, I need to wear Nasty Gal because someone’s taking my picture, I don’t know if I want to wear this crazy thing.

Now I carry it everywhere. It’s an advantage, a tailwind. But that story isn’t what I have to offer, what I learned is. I’m at odds with the version of me that’s expected to talk about what I’ve done. The person who just does things is more interesting to me.

ARIEL: People know me as the founder of Parachute, I see them light up when they say it. But having that public persona, you’re open to scrutiny too.

The tides changed as the company changed, and then there was the book, and the TV show, and you continued to be in the spotlight in a way that many founders never experience. You didn’t get to hide the way some people do when things get tough. And despite it all, like really despite it all, you just kept building in parallel to really hard, difficult things playing out publicly. How was that?

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SOPHIA: A few reasons I kept going. Mostly, I had to work: Nasty Gal made me money, but not retire-on-it money. And Girlboss got louder than Nasty Gal ever was, which was pretty big, a hundred million in revenue. Still the book was louder. Trump got elected the day we filed Chapter 11. The conversation about women was shifting. With Girlboss I started a media company, hired people from Refinery29, created the Girlboss Rallies: fifteen hundred women attended in LA and New York. Real energy. But I think now I realize I’d taken on a responsibility to speak for women I wasn’t qualified for.

Then the Netflix show landed: my story, the word “girlboss,” in 130 million homes, 195 countries. I thought, great IP. But I couldn’t tell if I was still inspiring or a pariah. There was Girlboss-the-symbol, Sophia-the-CEO who’d actually laid people off, and a Netflix caricature I never approved. By the time it dropped, all three had merged into one person, and I didn’t know which one I was. Headlines like “the worst thing about Girlboss is its source material,” that’s my life. The week of my wedding, Jezebel broke into my registry and published it as “ultra-rich founder wants ultra-expensive things.” Personal, mean.

I didn’t stop. Built Girlboss for three years. I’ve slowed down since: moving countries will do that, selling a house will do that. I’ve let my brain go offline more in the last couple years than in the eighteen before it.

ARIEL: Any one of those things, the media company, the show, the movement, would’ve filled someone’s whole plate.

SOPHIA: I had a business that gave me structure. Now I can be as busy as I want, and I don’t have to be, which means it’s on me to actually take care of myself, and I still don’t. People assume high performers have a system. Really, I just had the thing. Parenthood’s probably the same: not easier, just something to build everything else around.

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ARIEL: What does “girlboss” mean to you now, without the noise?

SOPHIA: It lives in culture now, it hasn’t been mine for a long time. It told people they had agency, that you didn’t need a pedigree. That was new then. I still get DMs: people who read the book and started businesses because of it. That long tail is what satisfies me, not the headlines or the academic takedowns. Today it’s a noun, not a verb, whatever anyone wants it to be, it’s theirs. I gave it away in 2014. Looking back, the book does sound a little cult-y. I was twenty-nine, writing to a generation that hadn’t been through what we’ve all been through since. We were more naive. It’s not possible for anything to be good forever.

ARIEL: What’s it like being the investor now, imparting experience, learning from founders doing it differently?

SOPHIA: It helps to have investors who’ve actually operated. Everything I honed at Nasty Gal, relationships, brand instinct, taste, turned out to transfer to a job that’s mostly an email and a good instinct. It’s so much easier than building a company, and it feels like philanthropy. Fundraising’s annoying: three years into Fund One, still haven’t raised the second, but I’ve written fifteen checks and angel-invested in twenty-five more. Founders come to me because I’ve been through the gauntlet, seen what it looks like when things go sideways, and how to right the ship. That’s the most valuable thing I have: not the wins, but knowing what it looks like when the boat’s actually sinking.

ARIEL: I want to ask about the house, leaving it, selling it. Your piece, “I don’t possess this house, this house possesses me” — it really touched me, I resonated with so much of what you wrote, it’s such a deep introspection about identity, who we are, our growth, and these containers and spaces that hold so much for us, both positive and negative. You walked away, you closed the door, you sold it, what does it feel like to walk away from a place that held everything? Nasty Gal, Girlboss, all the highs and lows, the friends, the memories?

SOPHIA: It took a long time to admit it was right. I loved it, but I didn’t want to live there but also didn’t want to be a landlord. I hadn’t slept there in a year and a half by the time I sold it. Moving out took a month, like a breakup where you’re still sleeping in the same house. I hadn’t missed it while I was gone. But walking through it at the end, seeing every corner where something had happened, it was like the Christmas Carol ghosts. I was crying in the shower, thinking, is this the last time. It was also beautiful, I got to say goodbye to it with friends there. Two weeks since closing, and I’m only just realizing I’m off all those insurance and property tax emails. If something feels existential now, at least it’s not about a house.

ARIEL: That door closing opens room for something else.

SOPHIA: I don’t know what fills it, and I’m okay with that not needing to happen right away. My tendency is to fill things, so I might start a company, get busy again, take on more admin I don’t want. But at least it’ll be in service of something generative, not maintenance.

ARIEL: I like to end these conversations with a question I ask everyone: what does your second story make possible that the first one never could?

SOPHIA: I’ll find out. What Nasty Gal took, a big software team, a CTO, a whole product org, you don’t need anymore. Now you can build lean. If you’re a solopreneur, someone who doesn’t want to manage headcount, you can still do great things without building that whole machine. That’s new, and it’s exciting.

I’ve always been fascinated by what motivates people. What drives them, what they actually want, what’s underneath what they say out loud.

I went to NYU, where I studied at the Gallatin School which gave me the opportunity to build my own major - I called it ‘Media, Power, and Persuasion’. In one of my communications classes, I was introduced to Marshall McLuhan’s Understanding Media: The Extensions of Man, the book where he coined the phrase “the medium is the message” - the idea that the form of a communication medium embeds itself in the message, shaping how it’s received and understood. The technology itself, not just the content it carries, shapes human behavior and society. Television didn’t just deliver news differently than radio; it changed the way people related to news, to each other, to the world. I was fascinated by that idea. That the tools and technologies we build don’t just carry information, they shift behavior, relationships, the way people actually engage with one another.

After grad school, I went to work at an ad agency as an account planner. My job, essentially, was to be the advocate for the consumer - not for the brand, not for the client, but for the actual person on the other end of whatever product or service we were selling or promoting. I was deep in both qualitative and quantitative research, which sometimes meant sitting with spreadsheets combing through data, and sometimes meant standing on a street corner doing man-on-the-street interviews, traveling to various cities, running focus groups, talking to people across different demographics and different cities.

I loved that work. Every day felt like a small sociology experiment, an ongoing attempt to piece together a puzzle. What was happening in the culture, the zeitgeist, at both the macro and micro level. How that connected to what people actually needed, wanted, hoped for, feared, cared about. My job wasn’t to gather data that backed up a decision someone had already made. It was to find what people actually cared about, underneath whatever they said in the room, and connect that to the brand or to a foundational insight that we could create a campaign around.

That instinct has stayed with me through everything I’ve built since.

At Parachute, I believed the relationship always came before the transaction. We wanted to be a source of education and inspiration as much as a place to buy sheets and towels - aspirational, helpful, a brand people trusted whether or not they were buying anything that day. The sale was never the point. At the end of the day, our mission was to help our customers create a more comfortable home. It wasn’t to sell as many sheets as possible, although certainly that was an obvious priority too.

Now I’m building in a new category, kids (and their parents). The category is different.

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Over the years, I’ve been given a lot of advice. Advice is a funny thing. It can feel like a breath of fresh air when you’ve hit a wall and don’t know your next move. It can be validating in a way that catches you off guard, when someone says exactly what you needed to hear. Sometimes it hits when you least expect it and sends a shock through your body. Sometimes it’s unsolicited - in the aisle of a grocery store, at school pickup, from someone who has no idea how much you needed to hear it that day.

I love the feeling of sitting with a friend, sharing what’s on my mind, asking for advice, and receiving something thoughtful back - wisdom shaped by their own lived experience. Sometimes you pay for advice: executive coaches, therapists, psychics. And sometimes it just finds you - a line in a book, a quote on Instagram, a casual comment you end up turning over in your head for weeks.

During this in-between, I’ve collected advice the way some people collect stones on a beach. I’ve shared my own experience and my deepest thoughts, and in return, friends, mentors, and strangers who’d been through something similar - or who simply felt compelled to share what they knew - reminded me, over and over, that with hard work and patience, there’s a light at the end of the tunnel.

I’ve said this before, but Substack has connected me to so many people who’ve shared insightful, deeply personal stories. We may be in different phases of our careers, navigating different leaps, fears, highs and lows - but we’re all in motion, all open to growth. This is one impressive community of builders, so I decided to ask a handful of them a single question: what’s the best advice you’ve ever received that’s stuck with you throughout your career?

Here’s what they said.

, Sparks From Culture

Early in my career in the investment management business at Angelo Gordon (circa 1995), I went to my mentor and co-founder Michael Gordon with an issue. A fund I was in charge of had negotiated, as part of its initial terms, a fee agreement with our investors that was going to give our firm an unexpected and significant windfall because we were making an investment that was structured in a way that we had not anticipated when we had sold the fund.

There was a conflict between following the documents and the spirit of the fund’s fees. I asked Michael what we should do. Without hesitation he said, “Well, we can’t charge the fee because it would be unfair to our investors.”

From that I learned that it was “both good ethics and good business to always be fair regardless of the legal documents.”

, Following Up

“Relationships are everything!” I’ve continued to cross paths with people throughout my entire career, from internships and previous clients to coworkers and industry peers. When I left my full-time job 1.5 years ago to start my own consulting business, those relationships became invaluable. I wouldn’t have been able to make the leap without the people who had supported me along the way. It’s a reminder to write the thank-you note, reach out for advice, send the compliment, and stay in touch. Some of the most meaningful opportunities in my career have come from relationships that were built years earlier. The world is small!

, Reframed

“The simple ways you talk about yourself/your business are more important than any business plan or strategy.” Early on, I’d walk into conversations and use hedging language “I’m hoping to work with clients on...” or “I’m just getting started as a coach”. I thought I was being humble and even truthful, but what I was actually doing was telling everyone (including myself) that I wasn’t serious about my business yet. When I led with what I wanted to be doing someday, people gave me advice and wished me luck. When I led with what I was actually doing (my services, client results, my philosophy), people asked how to hire me. A former coworker finally interrupted me when I was doing my humility thing and said: “You aren’t trying to do this, you are doing this.” Then she hired me.

Now I’m very cognizant of the words I use. When I jumped into entrepreneurship three years ago, I wasn’t a “new” business owner, I didn’t *only* have one client, and I didn’t *just* start coaching. I had clients, I had a business, and I had a responsibility to scale.

, Self Involved

‘Don't apologize for your standards’. Having a really high level of excellence and expertise is a positive. By holding yourself to that, you'll naturally attract clients/jobs/projects with people who do the same. There are sometimes moments in your career where it can be easy to fall into the trap of comparing yourself to others or ignoring your intuition. Maintaining a really strong sense of self and what your best work looks like should always be your North Star.

, Scrollodex

Anytime I’ve had a career goal or vision for a business that I see has longer legs to become something successful in the future, the best business advice I’ve ever received is “keep doing what you’re doing.” Sometimes (most times), things take time, perseverance, and hard work. It’s easy to compare yourself to others and think that people are overnight successes, but what you (usually) don’t see is that successful people have been at it for a long time - creating, trying things, making mistakes, and putting in the hours. When you have a vision or idea, keep at it. Don’t give up, even when it feels like it’s never ending.

, Time Less

“Clarity comes before creativity.” As a designer, I’ve learned that the strongest ideas emerge from a deep understanding of the challenge, not from rushing to generate solutions. This advice has stayed with me because it reminds me that curiosity and insight are often more valuable than certainty.

, Watch Me Work

This advice comes from my dad: ‘don't procrastinate, stay organized, follow through.’ As a perfectionist, people-pleasing young professional, it was nearly impossible to actually do any of them. With experience, I understand the value now. My spin: do the icky thing first, before the fun stuff. Lean on others to help you stay organized — hire a good project manager when you can. Say no. Only commit to what you can do well. Tell someone if you're not going to make a deadline.

, False Start

“Do things that don’t scale.” The phrase comes from Paul Graham, co-founder of Y Combinator, and I’m sure I first heard it at one of the early-stage startups I’ve supported. As a marketer, I’ve taken it to mean: go out of your way to know your customers and give them an exceptional experience. I know it’s good advice because I’m also applying it to audience growth effort for my Substack, False Start. I respond to every LinkedIn message, email, and comment. I take calls and coffee meetings with readers. I accept every interview opportunity that comes my way. It works.

, Btwn Meals

“You don’t get what you don’t ask for.” One of my first bosses shared this advice with me when I was in my early 20s. Most of her employees were young women and she was always very vocal about us sticking up for ourselves. Asking for what I want hasn’t always been easy (honestly, I’m still pretty terrible at it), but every time I do I am pleasantly surprised with the outcome. If you think you deserve more (more money, more responsibility, more flexibility) you probably do!

Something is brewing. I’m building again. The momentum, the excitement, that part feels familiar. But the playing field is new. There are tools and questions that didn’t exist the last time I did this. When to use AI, when not to. The question of when to trust the data and when to trust yourself has always been part of the process, but it feels more alive than ever right now. I’m figuring it out in real time, which is honestly part of the fun. In a few weeks I am taking a concept and moving it into a version of reality. I’ll be back on set, alongside brilliant creatives, as an idea, a vision becomes a story. I have always loved being on set. The inspiration becomes tangible and the energy is palpable. I have a feeling that’s the moment it’s going to truly click. There is a next thing and it is entirely different than anything I’ve ever done before, right down to aesthetics. Primary colors, shapes, direction. I can’t wait to tell you all about it.

So in the meantime, I’m taking full advantage of this summer while I have it. Here’s what I’m loving and looking forward to over the next few months.

Outside Living

I have seen much discussion online about this being the summer of outside. This season, the beautiful weather, fresh hot air commands attention and true celebration. So far, I’m off on the right track. Long walks listening to podcasts. Going to the beach with friends every Sunday with a big bag of snacks and no agenda. Early morning hikes. Outdoor concerts. I find when I’m outside, the urge to grab my phone disappears. It’s the best and I’m craving that connection so much. I plan to hold onto that feeling as much as possible before the next chapter begins.

London & Copenhagen

In a few weeks I’m leaving town for a week, off to London and Copenhagen. I’ve been to London many times and always enjoy my time there. This trip is quick and will include Wimbledon. I love tennis and am ecstatic to experience one of the best tournaments in the world. Copenhagen has been on my list forever. I’ve actually been once, but it was more than 20 years ago and in February, so it was dark and painfully cold. I’ve decided that doesn’t count. Any and all recommendations are welcome! I’m planning on eating my way through the cafes, shopping at all my favorite CPH based brands and vintage stores, with some museums and park visits as well. Leave your recommendations below!

Montana, Upstate & New York

Raising kids in Los Angeles is amazing and a privilege, but our life is very go-go-go and sometimes we need to log off. While I look forward to Europe trips and other big adventures with them in the future, right now I am all about easy trips, showing my kids the beauty of national parks, and small town living. Nature, outdoors, getting dirty, jumping in lakes, touching grass. There’s only so many years we’ll get to experience this type of simple pleasure together. This summer we are going to Whitefish, Montana for the first time. I’ve never been and neither have they. Later in the summer we will visit my sister in upstate NY for our annual family trip. More fun playing in the dirt, blueberry picking, cookouts, cobbler, and cousins. We’ll end that trip with a train ride into the city and a few days running around. My daughter has been before but it will be my son Van’s first trip. I can’t wait to watch him take it all in.

Taking Great Care of Myself

I recently joked to someone that I feel like I’m preparing for battle. Trying to get as strong as possible before this next chapter begins, because I know my time will look different and I want to show up ready. Trying to prioritize me time when I can slot it in. Facials, pilates, drinking lots of water and electrolytes. All of it. The investment feels different when you know something is coming. Like getting a good night’s sleep before the first day of something new.

Bermuda Shorts

True story, I haven’t worn a pair of shorts since having kids. I thought that chapter was over. They just didn’t feel right. This summer I bought two pairs of Bermuda shorts, one from Frame, one from H&M, and it turns out I love them. A colorful tank, a great flat, a strappy heel when I feel like it. It’s easy to fall into the athleisure uniform of LA, but there’s also no denying how a great outfit can change your day, your mindset, everything really. Turns out the same goes for a pair of shorts.

Amina Belouizdad Porter is someone who has never been afraid to start over. Born in Algeria, raised in Abu Dhabi, educated in Montreal, she has lived in seven cities, speaks five languages, and built a career across three continents. In 2018 she was in Houston, working in private equity, building a life with someone she loved. Her husband Alex died suddenly in a sports accident. In the months that followed, she said yes to a phone call that would take her to Los Angeles, to start a company called PS, and to a life that would surprise her.

PS is the private airport terminal that has reimagined what it means to travel. Amina and her team built the business from the ground up, in a city she had never lived in, in an industry she had never worked in, while still learning how to carry what she had lost.

We talk about all of it. But what I kept coming back to was the becoming. How you go all the way through the worst thing that has ever happened to you and come out on the other side not just intact but more yourself than you have ever been. More open. More alive.

I hope you leave this conversation as inspired as I did.

ARIEL: You’ve lived this incredibly expansive life. Seven cities, five languages, careers on multiple continents. I love to travel but I have only really lived in a few places, and I fantasize so much about having that experience of truly immersing yourself in a new culture, a new season, a new language. What keeps drawing you to the new place?

AMINA: The first time you do something scary is usually the scariest. And when I left Abu Dhabi at 17 for Montreal, that was terrifying. My parents dropped me off and left, and I remember within a couple of weeks going from nervous to just ecstatic. All of a sudden I was in a four season climate — snow and winter and freedom, which is a word we don’t really use much in the place I grew up. The anonymity. The newness. Meeting new people. I remember thinking, I need to do this again. I want to bottle up this feeling.

And I did. Six or seven more times. Because I quickly realized that my world became so much bigger every single time. And I constantly wanted to recreate that.

I’m now eight years into living in LA, which is really the longest time I’ve lived anywhere since I was 17. I’m 42. And you know, if it were up to me and I didn’t have a husband and kids I’d probably have left sooner. But this is a different chapter.

The mental exercise I used to do — I called it “and then, and then what.” Okay, I’m going to move to China. What if I don’t like it? And then what? Okay, go on Expedia and buy a ticket and in three hours you can be gone. Like, yeah. So what, right. We get so tripped up on decisions that are reversible when we really shouldn’t be.

ARIEL: I love that. There’s a playfulness in there, of not taking life too seriously even when you’re making really big decisions that can feel very serious. And that curiosity that comes from being in new places. I think we get so tripped up on the fear of permanence, the impact, all of it. It is just so easy to talk yourself out of things.

AMINA: Exactly. Most decisions are reversible. Really reversible. With the exception of having a child, that is kind of it. Even getting married is reversible, you know what I mean? So there are very few decisions that are truly irreversible. And hopefully that lessens the pressure. Hopefully it gives people, and it certainly gave me, the freedom to try new things.

ARIEL: In 2018 you were in Houston. A career, a business you were building on the side, a life with someone you loved. And then you lost your husband. I’m almost afraid to ask this, because I know there is no good answer, but: how did you keep going?

AMINA: At first, I didn’t.

I did not keep going. I did not go anywhere or do anything. I kind of just sat in it. And I actually think that was really important. Not because I knew to do that, or because I’m some savant or I’m enlightened. It was frankly because my family and friends allowed me to. Maybe they knew to do that. I’m forever indebted to them for it.

For literally a month and a half — what I can only call sitting sessions. Just hanging around in like week-old clothes, talking to whoever was there. My mom, my dad, friends rotating in and out. Crying. Thinking about Alex. Thinking about a lot of things.

I think about how sitting Shiva is forty days. And I actually think it is well designed. Because I think that is what grief needs. Not to fight through it. Not to keep going. Just to sit there.

I remember in those early days I had created three things in my mind that I was absolutely certain were true. I will never laugh again. I will never be happy again. I will never love again. I held those as facts. And then about a week after Alex died, in one of those sitting sessions, someone said something and I just burst into belly laughter. True laughter. And I remember thinking, I have dispelled my own myth. The thing I was so sure about. Which meant maybe my other two truths weren’t true either.

It took longer to feel genuinely happy again. I remember walking back from Love Yoga in LA — rest in peace, they closed — the sun was setting, and LA was doing its beautiful pink sky thing, and I caught myself thinking, I am so happy right now. And I was almost shocked by it. Like, whoa. I never thought I would be so happy.

ARIEL: I used to live basically on that block. Right by Love Yoga. And I know exactly what you mean. Those moments, after hardship, after having your universe turned upside down, where all of a sudden you catch yourself in a true moment of joy and gratitude and just peace. They are so beautiful. And so incredible. And I think they reinforce just how layered we are in that resilience. It doesn’t take away from the experience. It just makes us deeper. More able to go to those depths.

AMINA: Yes. And to let the story continue evolving. Alex died. I was in tremendous grief. And then I had that pink sky moment where I was just so happy. We get stuck on grief as if happiness is the fleeting thing and grief is the permanent one. Maybe they are both permanent. I don’t know the answer. What I do know is that grief is not your permanent state.

And eventually I fell in love again. I have Josh, and we have two kids, and it is the best. But the point is: we tell ourselves things that are powerful and dangerous at the same time. It is okay to tell yourself things. But it is also okay to disagree with yourself.

ARIEL: I’m excited for you that you found something to throw yourself into. Because it is not easy to sit in the void.

AMINA: It isn’t. And the void can be quite loud and also quite quiet. I think both of those things are really true. But I had sat in the grief so deeply and so intensely that honestly I felt like I couldn’t sit in it anymore. I was antsy. Antsy to do something else. To stop being backwards looking. I wanted to create a new narrative.

I had already quit my private equity job because I knew, I just knew, that was not it. And when the PS opportunity came up, a few other things came up around the same time too. Maybe culinary school. Maybe Paris for a year. I was presenting myself with options. But when I saw PS, I cannot explain it. I felt like I was designed in a lab to run this business. I read the job description and I was like, yes. I’m here. I’ve arrived. I’m the person you’re looking for. The skies parted. The universe gave me what I needed in that moment. And I believe that happened because after Alex died I was the most open and receptive I had ever been in my life. Which made me realize how unopen and unreceptive I had been before. I had created all these constraints for myself. I can only be here, do this kind of thing, be what someone expects of me. And then all of that just fell away. And amazing things happened.

ARIEL: That ties into something I think about a lot. Grief has a way of stripping everything away. The noise, the distraction, the version of yourself you show the world. It breaks you down in a way that very few things in life do. And I think there is so much that grief teaches you that success never could. It’s similar with failure. Those rare moments in time where things implode in a way that is completely unexpected, personal, professional, and often both at once. All of a sudden you’re like, what just happened. And I think it takes time, but at least for me it got to a place where I could be like, thank you universe for creating this.

AMINA: Isn’t it. I used to tell myself, the worst thing that can happen happened. It’s gone. It happened. It’s behind me. So now, let’s make cool things happen. Because it cannot get worse than what I just came from. That is very liberating once you come out on the other side. I know it doesn’t happen for everyone. I know I was lucky. But once I came out, I felt like a superhuman. Not obviously. But kind of.

There is post-traumatic distress and there is post-traumatic growth. If you get to the growth place, it is really powerful.

ARIEL: That resonates so deeply. I’ve spent a lot of time in therapy talking about the path to abundance and the limiting factors that are so controllable but so hard. That get in the way of really opening yourself up for that growth, for that next chapter, when things feel hard. Because the hard stuff is so much easier to hold onto. You can loop it forever. But getting to the other side, having that perspective, that appreciation for the hard stuff you’ve gone through. It sets you up for something incredible.

AMINA: And you have to be open to the luck too. Right place, right time, luck is part of everything. But it only gets you so far. You also have to be in a position where you are searching for it. Where you are able to see the magic. Because I have been in situations where I would not have told you what luck looked like if it stared me in the face.

ARIEL: Yes. And I think the opportunity is only presented to you because someone really believed. And that belief comes from yourself. I have certainly had moments where I’m like, these people believe in me more than I believe in myself. And that is a really real and inspiring thing to experience.

AMINA: It is. But yes. You have to take it and run with it. That is where you come in.

ARIEL: PS required you to learn an entirely new world from scratch. TSA, airlines, airports, Congress, policy, litigation, land planning. All at once, all from scratch. What does it take to build something that has never been done before?

AMINA: During the grief I did a lot of reading. Soul searching. Reading on spiritual doctrines, things like that. And I ended up going really deep into Zen Buddhism, and there was a concept that really stuck with me. It’s called Shoshin. The beginner’s mindset. About approaching life with openness and curiosity and the complete absence of preconceived notions.

Before, I thought I knew everything. But my grief broke that open. And when I started at PS, I actively chose to practice shoshin. Because it was required, yes, I had no idea about TSA regulations or any of it. But also because I had been convinced through everything I had read that this was just a great way to move through life. It fosters creativity and team building and deep thinking and real questioning.

I still do it. Even now in a meeting I’ll tell myself, beginner’s mindset. Don’t jump to the conclusion. Ask questions. Learn. Even when the answer seems obvious. And just because I’m the CEO doesn’t mean I have all the answers. What I hopefully have is a lot of really good questions. We are an N of 1 business. We can’t look left or right and see how anyone else has done it. We have to do it from scratch ourselves. The only way we do that is by asking a lot of questions and constantly questioning our own answers.

ARIEL: The superpower is actually being proven wrong. Asking questions and learning together. And I think when you go through hard things and make the choice to really go through them, not to become a victim of them, you grow this deeper self-awareness. You are digging in, asking why, really in touch with your feelings and who you are. And as a leader, that is what you are supposed to do for yourself and the people around you. Move through hard things. Because a business is really just a set of problems that need to be solved.

AMINA: That is right. That is all a business is. A set of problems that need to be solved, done differently.

And the other thing grief teaches you is about ego. How easy it is to lose it. And how best it is lost, frankly. I am not saying I have lost mine entirely. But I have become more conscious of when it appears. And I think that has made me a better leader. A better student of this business.

ARIEL: It makes you deeper. More able to experience the full depth of challenges in a very specific way. And that self-awareness, I think it just happens when you make the choice to be on that journey of growth. When you are always asking, how do I get better, how do I get better. It becomes its own kind of drug.

AMINA: It really does. And you can push it to its limits. But done thoughtfully, it helps you step out of yourself in the best possible way.

ARIEL: I ask everyone in this series the same question to close. What does the second story make possible that the first one never could?

AMINA: Gratitude. And something I can only call fullness. I feel like if I died today, I am happy. I didn’t miss it. Because of my loss, my life since then has been so full. I have been seeing things in color. Before, I was seeing things in black and white. I have been so present. So aware of what I have.

I am not sitting here pretending I’m enlightened. But it has created such a shift in how I approach my life and the gratitude I have towards it. The good, the bad, the ugly. It is fulfilling in a way I didn’t even know I was missing.

And I’m sure I am still missing a lot. I look forward to what comes next.

And then I left.

Not because Parachute failed. It didn’t. Alongside my team, we turned an idea into a highly successful company. I made money. I bought a house. I hit major life milestones that the success of that business made possible.

For the first time in forever I found myself with a lot of free time on my hands and didn’t have a clear path on what to do with that. On top of that I actually love working. I love creating, thinking, learning, collaborating. I thrive in high intensity environments, in uncertainty, in solving complex problems. It brings me joy. So the idea of just stopping was never an option.

The most obvious thing was to consult, offer another business the kind of experience that can only be earned by living through the highs and lows of having been a founder. I talked to executive recruiters. I explored boards, VC funds, fractional work.

“Send me over a deck” was something I heard frequently, after coffee meetings and in texts from people who found out I was ready for something new.. I had survived getting a company through a global pandemic, of course I could make a deck. I had tons of valuable experience to share. But every single time I sat down to work on it, I found myself doing anything else. Organizing the fridge. Cleaning out my closet. Sorting through the kids’ toys. My body was telling me something my brain wasn’t ready to hear.

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I had a call with an executive coach I’d been working with. She asked me a simple question: “Why?”

“Why consulting?” “Why boards? “Why any of this?”

And then something harder:

“Who are you? What do you actually like to do?”

I didn’t have a good answer. Luckily, she did.

“You’re a visionary. You have ideas, and you know how to execute them. Forcing yourself into a role that isn’t a full body yes, it’s just not in alignment with who you are.”

When I had the idea for Parachute my life was completely different. In almost every scenario I can think of, knowledge is power. But entrepreneurship might be the one place where that equation flips. At the time, unknowing was a gift. It let me move fast, take risks, believe things were possible before I had enough information to be scared of them. If I had known then what I know now, what it actually costs, what the years in the middle look like when no one is watching, I’m not sure I would have gone for it. I’m also a single mom with two kids I support. My overhead isn’t insignificant.

But in the same way I knew I had to start Parachute, I knew deep down she was right. I was trying to do anything but start something again. And it wasn’t working.

So I asked myself honestly: what do I actually love to do?

Two things stood out: working out and being a mom.

I was at the gym constantly, sometimes twice a day. And I was spending all my time with my kids, moving through the world with them. So I started paying attention differently. Not just experiencing things but asking, in every ordinary moment: what’s missing here? What do I keep reaching for that doesn’t exist?

At the gym, before and after classes, I started noticing things. Why aren’t there better, cooler, chic weights? Why don’t performance wipes exist that actually clean your skin, protect the barrier, and hydrate? With my kids, I started paying attention to the things I was buying. My daughter loves makeup. I was buying her these gross kits from Amazon with terrible quality products an

d thinking: why hasn’t anyone built this properly? I looked at my pantry differently. What were the snacks I wished were made better? What did my kids actually need?

Being a founder is isolating. You are the person everyone looks to for answers, the one holding the vision, the one in the room making the call. Over the years I’d built an amazing community of friends and mentors to bounce ideas off, but for the most part the best and worst days of the company came down to me.

One night, probably when I was supposed to be working on the deck, I opened ChatGPT.

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Alli Webb needs no introduction. She built Drybar from a $40 mobile blowout business into 150 locations and $255 million in revenue, and in doing so invented an entirely new category. And then, in March of 2020, almost ten years to the day she started it, she sold the business. A major accomplishment that came with a whole new chapter.

We cover everything, the highs, the lows, the in-between. Alli talks about the identity free fall that follows selling something you built, the faith she held onto when nothing had taken shape yet, what her kids said to her that stopped her in her tracks and changed everything, and Messy, the brand she built once she found her footing again.

I left this conversation feeling hopeful in the way that only comes from hearing someone who has really gone through it and come out the other side grateful.

I think you will too.

ARIEL: Okay. I want to start at the beginning, because I think about origin stories a lot, and what it takes to actually begin. When I look back at who I was when I started Parachute, I was 28, I had no “experience,” and I had no idea what I was doing. What I did have was a crazy amount of conviction that there was something missing in the market and that what was available, I could do better. I think there’s something really specific about that state, that naive certainty, that makes the leap possible. You started Drybar as a stay-at-home mom with no business plan and no outside funding. What got you there?

ALLI: I definitely had the passion for hair. I got my license when I was around 20. But I didn’t start Drybar until I was 35. My kids at the time were two and four, they’re now almost 19 and 21, which is just bananas. I started this mobile blowout business in LA, just blow-drying my mom friends at their houses around town. I had that skill, and I was looking to get back into something. You know that feeling, you’re home with your kids and it’s the greatest thing, and I felt so lucky that I could be there. But I also felt this feeling of, I’m bored and I want something for myself. At that point, I had stayed home for almost five years and realized, I don’t think this is what I want to do for the next 18 years.

ARIEL: Yes. That tension is so real.

ALLI: So I started the mobile business. I was only charging $40, which in retrospect was insane, I was driving all over LA, but it was fulfilling. And I inadvertently stumbled onto the idea for Drybar because I was like, there’s really not a place for women to go. There was Fantastic Sams, or you could go to your cut-and-color stylist for a fortune with an experience that was often terrible. My parents were entrepreneurs, so I had that in my blood. But I had no real idea how I was going to do it. So many people I talked to were like, how do you make a salon work that’s only doing blowouts, when haircuts and color are where the real money is?

ARIEL: And you went there anyway.

ALLI: I was like, let’s just try it at one shop and see what happens. We started at $35 a blowout. I remember going to sleep at night thinking, if we can do 40 blowouts a day, this business will work. Looking back, that was terrible math. But pretty quickly after opening, we were doing 70 to 100 blowouts a day. Women were lining up. People couldn’t get in. We captured lightning in a bottle. And then of course a million other problems happened that we had to just figure out. I always describe it as whack-a-mole, there’s one problem, you solve it, and there’s another one.

ARIEL: They never stop.

ALLI: Never. They just get bigger. You hope you make the best decisions you can and you learn from the ones that don’t work out.

ARIEL: You made a lot of decisions at Drybar that I think people in boardrooms would have told you were risky, no mirrors, no cuts, no color, naming styles after cocktails. I’ve had my own version of that as a founder, moments where I just knew something was right and couldn’t fully explain why. Where did the confidence to trust those instincts come from?

ALLI: You just want something nobody’s doing well. And putting my consumer hat on, I always wanted a blowout, especially growing up in Boca with humidity off the charts and my hair so big and crazy. If I didn’t have a blowout it was up in a bun.

The no-mirror thing actually came directly from doing the mobile blowouts. I was usually in someone’s living room or kitchen, never in front of a mirror, because it felt weird to go into someone’s personal bathroom. So when I finished, they’d go find a mirror, and there’d be this big squeal of delight. And I was like, huh. When we were concepting Drybar with our architect, I said, I want to recreate that moment. And also, who wants to stare at themselves in wet hair for 45 minutes?

ARIEL: It’s so true, look at us now, we are all looking at ourselves on Zoom all day long.

ALLI: Right? And historically, that was the entire salon experience. The movie idea came from years earlier. I was briefly living in San Francisco, getting a manicure, and Sex and the City was on the TV. I was like, that is so smart. You’re just sitting there, you don’t want to watch a car chase, you don’t want the news. It became this core memory. So when I was concepting Drybar, everything kind of fell into place. It was going to look and feel like a bar where women are watching a chick flick instead of staring at themselves.

The cocktail names, my brother was not a fan. He was like, no, that’s so cheesy, women aren’t going to want that. And I said, I’m telling you, they are going to sit down and say, I’ll have a Cosmo or a Manhattan.

ARIEL: And of course you were right.

ALLI: Of course. And look, hair salons in LA and New York always had this feeling that if you weren’t wearing the right thing, had the right bag, were a celebrity, you almost felt out of place otherwise. I wanted it to look high-end but feel mom-and-pop. I wanted women to feel like a million bucks. You’re escaping your life for an hour. A one-hour blowout that felt like a whole ritual, a little sweet treat, something good to watch, your phone charged, your scalp rubbed. Where else do you get to check all of those boxes?

ARIEL: You built Drybar to $255 million in revenue and then sold it. I think a lot of founders, myself included, hold the exit up as this milestone you’re always building toward. And then when it comes, or when a version of it comes, it’s not always what you imagined. What did you understand about that decision at the time, and what do you understand now that you didn’t then?

ALLI: It was complicated. Drybar was really two businesses, the product and the salons. At the time we sold there were 150 locations, and we knew early on that there’d be a different buyer for each, because with the stores you’re inheriting an HR situation of 10,000 employees. Helen of Troy ended up buying the product division and the brand. Our plan was to separately sell the stores. If you wanted Los Angeles, you’d be buying 25 locations all doing around a million in revenue. It would have been a great payday. LA, Chicago, Boston, New York.

But this all went down in March of 2020. We sold the product division, and the next order of business was to sell the stores, and then COVID, and the stores went to zero overnight.

ARIEL: Oh wow I didn’t realize that.

ALLI: What was supposed to be temporarily closing turned into two years. So, talk about things not ending the way you think they will. We raised $75 million over the life of Drybar and were able to take a little money off the table each time we raised, so we did fine. Life is good. But it could have been crazy.

And then it was like, OMG, we just sold the company, but you’re trying to make content at home during COVID, and that whole period was a major identity loss. You’re like, who the hell am I now if I’m not at the helm of this thing?

ARIEL: That’s the question I keep coming back to. I built Parachute for 13 years and it became completely fused with who I was. And when that chapter ended, I didn’t even have language for what I was feeling. It wasn’t just grief. It was more like, I don’t know who I am in a room anymore without this thing attached to my name.

ALLI: That’s exactly it. And I don’t think anything prepares you for that.

ARIEL: You’ve been open about the fact that after Drybar you went through a lot at once, divorce, losing your mom, your son going through a really hard time. I’ve been through my own version of it. And what I’ve found is that the personal loss and the professional loss kind of collapse into each other. What did it actually take to rebuild yourself, not just as a founder, but as a person?

ALLI: It was a multi-pronged approach, and it’s interesting even now, six years later. It was March 2020, almost ten years to the day we started Drybar. I felt very, very lost and was dealing with so much at once. A lot of retreats, a lot of therapy. I really did a lot of work on myself to try to get out of that phase.

Part of it was also just changing my environment. I recently moved to Tennessee, Franklin, Tennessee, and I was just starting to feel like I needed to get out of LA. I felt like I was dealing with a lot of irrelevance. I look out my window now and all I see are trees. In LA it’s like, who are you friends with, were you invited, are you relevant, all of that stuff is just so much noise. I needed to distance myself from it for my own sanity.

ARIEL: I want to stay here for a minute, on the identity piece, because I think it’s the thing that people talk around but not through. I know for me, even now, there’s this difference in how a room responds to me when someone says “founder of Parachute” versus just “Ariel.” And I hate that I feel it. But I do.

ALLI: Almost embarrassing to admit, but yes. Being at an event, someone introduces me just as Alli, and you feel it. And then they say, oh, she’s the founder of Drybar, and everyone wants to talk to you. That was always hard to navigate. It’s all ego, right? Self-importance and wanting to be relevant. Especially, I’m about to be 51. There are so many new beauty brands, so many new things, so many young women doing incredible things, and you’re like...

It takes very active recognizing. FOMO is very real. That kind of stuff still gets to me, which I can now recognize as my ego wanting to feel that level of importance. And yet, I’m probably happier now than I’ve been in quite some time. Ridiculously in love, an amazing relationship, I live somewhere beautiful, my kids are doing well. Life always has a rub. But I’ve learned to sit with it for a day and then just go, who cares.

ARIEL: That’s my mantra this year. Who cares?! When I find myself having these existential moments, getting so worked up about things in my life, I get to a place where something in me just goes, who cares? Like, why am I carrying this?

ALLI: It’s so powerful. And I think there’s a reason these things keep coming up, everything’s a teacher. It’s all grist for the mill.

ARIEL: I think it never stops.

ALLI: It doesn’t. And once you surrender to that, once you accept that it’s just part of it, it somehow gets lighter. And honestly, no one else really cares. Everyone is just in their own version of it.

ARIEL: So let’s talk about Messy. Because I think this is such an interesting chapter of your story. You weren’t just building something new, you were in some ways challenging the category you created. I find that kind of evolution really compelling. What does it feel like to build something that complicates what you built before?

ALLI: I tried a lot of other things in those six years first. Joined some boards, I hate board meetings, what was I thinking! I do a lot of mentoring. But for me it was always hair. And just like anything, we go through so many iterations, with our hair, with fashion, with ourselves.

I very much incorporated my own journey into the brand. All of our products have mantras on them. The Rough Dry Cream says “I Am Enough.” Our silk spray is “I Am Transformed.” Our shampoo is “I Can Begin Again.” When you look at the bottle, you read it and you feel something. That all came from the work I’d done on myself, feeling like I’m enough, feeling like I don’t have to be this level of perfection to feel good about myself.

When I pitched Sephora, that was basically the pitch. I think there’s a hole, not a product hole, but a storytelling hole. Giving women real, tangible ways to feel good about their hair without the pressure of the perfect blowout.

ARIEL: Which is so beautifully ironic.

ALLI: Incredibly ironic, I know. I built the church of the perfect blowout and now I’m like, actually, you don’t need it. But that’s what’s happened to me personally. We all shift. I’m not anti-blowout, I love a good blowout. I just also want something else. I don’t want women to feel like if they don’t have one, their hair is a disaster. I want to give them the tools and the confidence to work with what they have.

ARIEL: I want to talk about motherhood, because you’ve been a mom through all of it, building Drybar, selling it, the in-between, starting over. I have a five and a seven year old, and I feel it so acutely right now, this experience of trying to show up for them while also being in the middle of my own reinvention. How has motherhood shaped the kind of founder and person you are?

ALLI: One of the biggest things, and I don’t think I’ve ever really talked about this publicly, is that when your kids get older, they start really telling you how they feel about you. Mine pulled me aside during a rough time and said, “We sometimes don’t know what version of you we’re going to get.”

ARIEL: Oh god.

ALLI: It’s not a fun thing to admit. There was a lot of emotional volatility with me. And looking back, I can see I was like that as a founder and a leader too, creating an environment where people felt like they had to walk on eggshells. My brother told me back in the Drybar era that people were scared of me. I didn’t fully understand it at the time. But when my kids said it, with no ulterior motive, just honesty, that stopped me in my tracks. I was like, I have to change this. That was a really big turning point.

ARIEL: I carry so much of that. I think as women, especially with the duality of being both a founder and a mother, there’s this mental load that is genuinely all consuming, managing decisions that have enormous impact while also navigating whatever is happening personally, while also trying to be present for your kids. And there’s just no space built in to actually feel anything. So there are days where it’s all incredibly invigorating and I feel like I’m in a flow state. And then one thing shifts and it can completely crumble.

ALLI: Yes. And you don’t know what version you’re going to get. I’ve been very reactive my whole life and I almost wore it like a crown, because in business the buck stops with you and you have to make split-second decisions. And with that comes this power and ego. But it’s the worst thing you can do in a team. And with your kids. When my kids told me, I was like, I have to be more even. I can actually catch myself now when I feel it coming. I want to be the kind of leader, and the kind of mother, where people aren’t guessing.

ARIEL: Second Story View is built around this specific moment, the chapter after something ends, before the next thing fully takes shape. It’s uncomfortable and disorienting and also, I think, full of something. When you were in your own in-between, before Messy had a clear shape, what did you hold onto to keep going?

ALLI: Faith. I had something on my phone that said, “What if it all works out?” Especially while navigating all the personal stuff at once. That’s served me really well, coming back to what’s important now. My peace, my mental sanity. Which is part of why I moved to Tennessee, why I live at a slower pace.

I’m not ultra woo-woo about it. I’ve read Gabrielle Bernstein. It can appear very woo-woo, manifesting, think about it and it’ll happen. I don’t completely subscribe to that, and honestly, neither does she. Her real point is: you have to work hard, and you also have to have faith. For me, that’s what’s gotten me through. I constantly remind myself, it’s all going to work out.

ARIEL: I love that. I think faith is underrated as a practical tool. Not faith in some outcome, but faith that you’re going to be okay regardless.

ALLI: Yes. Exactly that.

ARIEL: And lastly, what does the second story make possible that the first one never could?

ALLI: Intentionality. I’m so much more intentional with my time now, how I spend it, where I give my energy. Back in the day I used to say yes to everything. Whatever I had to do to get to the next level. Whereas now it’s like, does this bring me peace? Does this bring me happiness? And if the answer is no, I won’t do it.

I think we all struggle with the difference between what we think we should do versus what actually feels right in our body. There are those decisions where you know it’s a no, but you try to convince yourself otherwise, you talk to 17 people, you flip a coin, you ask strangers on the internet, and you find yourself going, what am I doing? Whereas now I try to listen earlier. To trust that.

ARIEL: The full body yes.

ALLI: Always. The full body yes.

Before you have kids, there are a lot of things people warn you about: that you’ll never sleep in again, that certain moments will pass so fast and others so slow, and that you’ll feel a love so big you’ve never felt anything like it before. There are also the details that are impossible to predict — my daughter’s love of musical theater, my son’s sense of humor, things that bring me a type of joy I never knew before becoming a mom. And then there are the women you meet along the way who are also on this crazy, beautiful ride with you. Sometimes they’re right there next to you in the trenches, and other times they’ve made it to the other side, living proof that you will get through whatever phase you’re in. I don’t have another word for them besides lifelines

There’s a specific kind of friendship that forms between moms, forged in the chaos, in the shared understanding of what this actually takes. It doesn’t require explanation. You just get it, because you’re living it too. These are the people I can say anything to: ask the questions I’m embarrassed to ask anyone else, admit when I’m struggling, be completely honest without worrying about how it lands. They’re the late-night text when your kid is sick, the first call when you need a resource or a second opinion or just someone to tell you you’re doing fine. They show up in a bind. They make me feel confident on the days I’m not sure I know what I’m doing.

They love my kids. They celebrate the good moments and show up for the hard stuff. And they make it fun, somehow, even in the thick of it.

Motherhood can be a thankless job. The work is invisible until it isn’t, and the validation doesn’t always come. Which is why I think it matters so much to stop and honor it, not just on one day, but genuinely. To look at the moms in your life and say: I see everything you’re carrying. I see how hard you’re working. I see you.

This past year, I’ve felt that more than ever. There’s been a lot of change: leaving Parachute, navigating what comes next, all while trying to make the best decisions for the two kids I’m raising. The moms in my life showed up for me in ways I won’t forget. This Mother’s Day, I wanted to do the same for them.

One of the rituals I’ve kept for years is always having fresh flowers in the house. It’s a small thing, a weekly act of bringing something beautiful into our space. My kids have grown up with it, and it’s become something we share. A reminder, even in the busiest weeks, that there’s room for joy in the everyday. Fresh flowers are the kind of simple and special gesture to send to mom friends. On Mother’s Day, on birthday’s or just because. Something that says thank you without having to find the words. Something that just shows up at the door and makes the house feel a little warmer.

I love using The Bouqs Co. for making moments like this happen. They’re the best flower delivery service I’ve found, and I keep coming back for a reason. Every stem is sourced directly from the farm, which means they last longer in the vase. A mix of blooms and buds, so they stay fresh for days and you get to watch them get even better at home, which feels like its own little gift. No matter the season, the arrangements are gorgeous and responsibly sourced, and you can feel the difference the moment they arrive.

The Bouqs also does subscriptions, which makes the whole thing so easy. Fresh flowers on your schedule, starting at $48 with free shipping, and you can skip or cancel anytime. A bright spot in your week, every time they arrive on your doorstep.

This Mother’s Day, I can’t think of a better gift idea than sending the moms in your life something beautiful. Something that tells them you see them. That you’re grateful. That you couldn’t do this without them.

Simple and beautiful and exactly the kind of thing that says I was thinking of you. Because she is thought of. Even on the days it doesn’t feel that way.

Send her something beautiful.

We were deep into a COO search. Months of conversations. He’d flown out multiple times. We’d had meals together, he’d spent time in the office, he’d gotten to know the team. We’d talked through the offer. We were essentially done.

As a final step, we invited him and his girlfriend to come back to Los Angeles, not for another interview, but to start getting comfortable. Look at neighborhoods. Picture the move from New York. It was a gesture of welcome more than anything else.

That’s when he booked $12,000 flights for the two of them. No ask. No heads up. Just an invoice.

When I brought it up, he mentioned almost offhandedly that his current company had a policy limiting travel spend — so he knew this wasn’t standard. He knew. He’d been inside our world long enough to know who we were. And he did it anyway.

That was my answer.

I didn’t hire him.

Over more than a decade building Parachute, I probably interviewed hundreds of people. I made great hires and costly ones. I learned to trust my gut, and when my gut was wrong. And I developed a clear framework for what I was actually looking for, and what I was trying to avoid.

Before I get into the framework, I want to be honest about something. Most founders talk about revenue, growth, press. When I look back at Parachute, none of that is what I’m most proud of. It’s the people. Countless employees who stayed five, seven, ten-plus years. Retention isn’t a metric most founders talk about, but it should be. Every person you bring in either adds to the culture or chips away at it.

Here’s what I know now that I wish I’d known at the beginning.

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Two Things. That’s It.

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One of the first people who came to mind was Gregg Renfrew.

Gregg built Beautycounter into one of the most mission-driven, community-powered brands in clean beauty. The company was acquired. She watched it fall apart. Then she bought back the assets out of foreclosure and launched Counter. She’s been through the highs and lows in a way very few people have, and she’s come out with a clarity that’s inspiring to witness.

We talked about identity, letting go, releasing the need for closure, and what it actually feels like to start over with all your scars and all your wisdom.

I hope this conversation gives you as much as it gave me.

We could have talked for hours, so parts of this Q&A have been condensed. You can also find Gregg on Substack at Counter Programming.

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ARIEL: Hi Gregg. It’s great to see you! We have so much to discuss, so let’s dig in. I’d love to start at the very beginning. You started your first company at 19, which is so impressive, building The Wedding List, selling it to Martha Stewart, and then you built Beautycounter. When did you realize that you’re a real visionary and builder?

GREGG: I believe that you either have an entrepreneurial spirit and have the ability to anticipate where things are going, see solutions to problems that have not yet been solved, or to ideate on things that are not yet clear to someone else or you don’t. I don’t think it’s a skill that you can take classes on and learn how to become one.

I realized two things very early on as a young woman. First and foremost, I grew up with some financial insecurity and I always had bold dreams and ideas and things that I wanted to do. Traveling among them, which is how I started my very first company, which was a cleaning company. I had to figure out ways to creatively make money beyond the basic babysitting jobs or waitressing jobs.

From the very earliest days of business, I had a conversation with a person who was kind of like a second father to me during my college years and early twenties. I was working for an advertising firm. I said, “I just don’t think they really get it.” And he responded, “well, most people in business aren’t actually smarter than you are. You actually do have a really high level of emotional intelligence. You’re able to see things clearly. So use that skill set to your advantage.”

I know that people would say I’m a visionary. I don’t look at it quite like that. I look for problems or opportunities in the world that can be best addressed through business. Because business is the medium through which I believe I can make a difference in the world.

ARIEL: I totally relate to that. I think some people have an innate desire to build things and a risk tolerance that sets them up for entrepreneurship that perhaps other people don’t. I could draw a parallel to a great sports team, you have individual contributors, but someone has to lead it. And you win and lose together. Business is not all that different.

GREGG: Yeah, different flavors of the same challenges and opportunities and skill sets that piece together to create something that’s really powerful. Different problems to solve, different parts to play.

ARIEL: You built Beautycounter into this massive household name. A mission-driven brand with one of the most devoted communities. You raised a lot of capital and ultimately got acquired. That process often changes the founder’s relationship with the business. What did you wish you had known before taking institutional money?

GREGG: I think what people often overlook and get really caught up in is the name of the firm and valuation. I always remind people, you’re not worth a single dollar until capital is in the bank account. And whatever valuation you think looks really sexy in Women’s Wear Daily or The Wall Street Journal, your investors are expecting a three or five-x return. If you just took an $800 million pre-money valuation and you don’t think you can deliver a $3 billion exit, you better not take that money or you’re going to be doing a down round.

And I think the other thing that entrepreneurs and leadership teams don’t recognize is that with every dollar you take in, you lose a little bit of power. That’s not always a bad thing. But it can be a bad thing when the intentions or desires of your financial sponsors are misaligned with those of the founders or the leadership team. Unfortunately, they tend to work on spreadsheets. And we tend to work in the real world. For example, when our holiday packaging got dropped into the port in Long Beach during an unprecedented closure. Who on earth could have anticipated that was going to happen? So now we have to air freight new packaging and redo things with lost money, even with insurance. Those are things that become challenging when you have institutional investors, because they see things all about increasing points of margin. And that’s just not how the world works.

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ARIEL: There are so many layers, and they seem to continue to unravel and show themselves as you go along.

ARIEL: There was a period of time after Beautycounter was acquired and deciding to buy back the assets and launch Counter. How did that look and feel for you? That in-between time and uncertainty?

GREGG: The hardest part for me was actually the period of time when I was not at Beautycounter. I had been removed from the company and was watching it slowly fall apart as a result of a series of poor choices made by the leadership team. That was excruciatingly painful. I was watching my baby fall apart. And I felt like my entire identity was wrapped up in it. I didn’t know how to extricate myself from it emotionally or physically. It was really challenging financially, for a million reasons.

GREGG: When I bought the assets of the company once it had gone into foreclosure, my immediate reaction was, ‘Oh my God, what have I done?’ I literally had a full-blown panic attack the next day or so. Even though I didn’t acquire the debt, when you acquire the assets of a company, the reality is that the debt doesn’t just go away. If somebody made lip gloss for us and there was a million dollars outstanding on that bill, they’re not going to just say, oh, don’t worry about it. So we had to go back and renegotiate all these things.

But once I calmed down, I thought, I have a clean sheet of paper. I can reimagine the business. I can start a completely new company that is based on some of the core tenets of the old company— my commitment to safety, to the highest standards, creating a new definitive standard for clean. What I had to do was emotionally distance myself a little bit from it so I could be a better CEO and just take the time to think about: What does the world need from me and from my new company today?

ARIEL: I relate to so much of that. It is excruciating to watch things change. To hear anecdotes from team members and customers. Knowing that decisions and so many changes— especially those that I worked so hard to build and protect—are happening so quickly.

GREGG: If I can give you one piece of advice, just because I’m farther out. I spent too much time allowing myself to feel like a victim as opposed to just looking at the facts. Which is: you started a company, you built a great company. It had a significant impact. A decision was made and you are no longer part of the company. Those are the facts.

ARIEL: You are so right. And I played a huge role in many of the decisions along the way. And as a result, the consequences of that too.

GREGG: You can come up with a million reasons why something isn’t working for you. And I let myself linger in that moment. I wish I had given less time and energy and my emotions to something over which I had no control. Sometimes you’re just not going to get that answer you’re seeking from a relationship that ended or a transaction that went awry. Sometimes you’re just not going to get the closure you seek. You’ve got to find that within yourself.

ARIEL: I think we spend so much time searching for an ending that can be wrapped in a perfect bow because we think that would feel so good. And if you could make that happen, that would provide some sort of release or clarity that just doesn’t actually exist.

GREGG: It doesn’t work that way. Someone told me during that journey of letting go of the old company that I was seeking validation that I was not going to get. So I needed to learn how to move on. And once I did, I harbor no grudge. I have no anger. I have no resentment. It’s completely behind me. I wouldn’t have had this opportunity had everything gone perfectly. And if you look at really successful people in general, they’ve had more failure than success.

ARIEL: You are so right. Those failures are where you grow. It has been energizing to think about all the lessons, all the wisdom, all the ways that I will do things differently.

ARIEL: You can do something completely different with Counter that you couldn’t do before. Not because of resources, but because of who you are, because of your experience. What can you see in a different way?

GREGG: When I started Counter, I was able to do so with a little bit of emotional distance, which makes you a better leader. It makes you more decisive. It helps me be more focused on what is fiscally responsible and good for the brand and good for the people.

I’m much calmer. It’s harder to ruffle my feathers than it was before because I’ve been to hell and back. I think really good leaders have desensitized themselves to criticism and realize that if criticism is given to you in a constructive way, it actually only makes you better. I try really hard to take responsibility for my actions, to catch myself when I’m falling back into old patterns of behavior. I think I’m a much better leader today than I was prior to all of this going down.

Time, experience, and challenges give you wisdom. You read the fine print on the details of a contract with an investor. You hire slowly and you fire quickly. You’re just different than you once were.

ARIEL: It also creates an ability to model a different type of focus and energy within the organization, which is so powerful.

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GREGG: It’s very focused now. I understand why Counter exists. Clean means nothing today. But it still means everything to me. I can be very direct and clear and concise in my communication and my expectations because I know what I’m fighting for and why I’m fighting for it.

ARIEL: You defined clean beauty with Beautycounter and now “clean” has been diluted and saturated. What are you doing now with Counter to hold the line?

GREGG: Clean means absolutely nothing today, unfortunately. And therein lies my opportunity. All the retailers have created their own standards, whether that’s Target or Walmart or Sephora or Ulta or Credo or Detox Market or Amazon. Everybody has a different standard. Brands are left to their own devices. They just slap the word clean on because they know it’s a good marketing term, the same way greenwashing became cleanwashing. And yet once again, the consumer is completely confused.

Clean takes real work. It’s hard work and it’s complex. It’s not just about removing the chemicals of concern. It’s also which ones are you choosing to formulate with and why? Are you looking at the compatibility to the packaging? Is the packaging leaching those very toxins right back in? Are you ethically and responsibly sourcing ingredients? Are people being paid a fair wage? Are women safe in the fields?

My goal would be to really create one clean standard so everyone can live by the same set of rules. I think that’s a huge opportunity within our industry right now.

ARIEL: So many people just don’t know what it all means.

GREGG: That’s intentional, right? People don’t know because people don’t want them to know. You might not like the choices I made in terms of what I put into my product, but you’ll have made an informed choice. There’s nothing that’s going to sneak up on you that I’m not disclosing.

It’s really that trifecta: you educate through conversation, you formulate products and provide solutions, and you spend a lot of time advocating both in the industry as well as in Washington or at the state level. All of those things will help us build the next stage of this clean beauty revolution.

ARIEL: Second Story View is about the chapter after something ends and before the next thing fully takes shape, which is the place that I’m in. When you were in your in-between, what did you hold on to, to keep going?

GREGG: My wine.

ARIEL: [Laughs] Same.

GREGG: The one thing that did not take over my thoughts is that I’m not good enough or that I can’t do this again. I knew that I had done something extraordinary. I didn’t do it alone. I did it with a huge group of people. So I knew that I had it in me to do something powerful again.

I held on to my courage. Because courage and lack of fear are often associated as being one and the same. I think you can be scared and still walk through the door. I’m scared all the time. I think it takes courage to walk through the door. A lot of us walked back into the fire and did so with our eyes open, scared, but confident that we could do something important again.

On my last day, when I’m drawing my last breath, I want to feel that I’ve done all I can to make the world a better place. As tired as I am, I still get up every morning and I still face every single day, and I do it because I think the work I do matters.

ARIEL: That sense of purpose is such an important North Star.

GREGG: I think one thing that especially as women, from the youngest age, we were so focused on external validation. But the validation is actually from within. You can put on a dress and you feel like you look really good. And then you walk into the room and you wait until someone says, you look really pretty in that dress, to allow yourself to feel that. I wish we had more confidence in ourselves, that we actually have everything we need to be successful.

ARIEL: I think about that with my daughter every single day. How can we harness that sense of self-confidence and love that you have as a child as you move through the complexities of life.

ARIEL: We’ve reached my last question: What does the second story make possible that the first one never could?

GREGG: I hope that this second evolution, this new company, this new chapter of my life, affords me the opportunity to utilize the technology and the tools in a digital medium in a way that allows me to reach way more people. Not in terms of can I sell way more products. It’s, how can I have an impact on more people through conversation, through education?

Instead of talking to 1,000 women, I can be talking to 100,000 women at a time. Instead of 100,000, a million. Instead of a million, 100 million. I believe that women are the unlock to a path to a better future. We’re in a challenging moment in time, to say the least. And especially for women.

ARIEL: What a beautiful answer. Cheers to that! Thank you.

Today I’m launching paid content on Second Story View. Paid content will be focused on more tactical business advice. The playbook I wish I’d had. Shortcuts, insights I learned the hard way, the conversations that could change the way you build. Answers that exist, but don’t get shared until something goes wrong. I’m grateful to have them now.

Whether you’re in it, have been through it, or are just starting to imagine it — this is for you.

Making this content paid allows me to bring in the experts who have guided me through the hard parts. The landscape is constantly changing, and there’s always more to learn. If something is on your mind, send me a message — if you’re wondering about it, someone else probably is too, and it might just be the next post.

This month, I’m starting with something I wish I’d known before I ever said my idea out loud — that being a founder and being protected as one are two very different things. I’ve brought in a top lawyer at Cooley to provide invaluable insight. Someone I’ve known and trusted for over a decade. He’s worked with thousands of companies and has seen it all.

Thank you for being here.

Five Ways to Protect Yourself as a Founder

Part of leaving a company you built is taking inventory. Not just of what happened, but of what could have happened differently. The decisions you’d make again. The ones you wouldn’t. The things you wish someone had told you before it was too late.

And the biggest thing? I didn’t always know how to protect myself as a founder. I didn’t even know I could. I found that out too late.

When you’re founding a company, you don’t hire your own lawyer. You hire a lawyer for the company. And you are the company, so what’s the difference?

It turns out, a lot.

Read more

Since pressing send on my first piece, I’ve heard from so many of you who are also in this in-between, or who have been here before. You’ve shared painful moments, inspiring anecdotes, and personal stories. And I quickly realized that along with sharing my own journey, it would be so incredible to share the stories of others. People who have walked away from something, who had things taken from them, who are in the middle of figuring it out, and people who are on the other side and can reflect back and share. Life has many beginnings, middles, and ends. Starting over in your second story does not mean starting at the very beginning.

This series will be an ongoing conversation with people navigating reinvention, identity, courage, grief, hope, heartbreak and healing. The journey to find joy and peace while overcoming real challenges and realizing how much more there is on the other side.

I started working on Parachute when I was 28. I turned 30 just after launching the company. I was living a completely different life. Motherhood was a distant dream. And now, I’m 41, in this second chapter, my kids are the center of everything I do and every decision I make. I’m also navigating another in-between as a single mother.

You’ve probably already read Strangers. Or maybe you’re reading it right now, discussing it in group chats, passing it to a friend, seeing it everywhere you are online. There’s a reason this book has become a cultural phenomenon. What struck me wasn’t just Belle’s story, it was where she is now. Nearly six years after the night her marriage fell apart, she has built something remarkable. A number one bestselling memoir. A legal career relaunched. A life that is unapologetically hers, all while raising three kids largely on her own. As someone in the middle of my own rebuilding, I found Belle’s story to be one of the most honest and courageous things a woman has ever put on the page.

There is no better person to kick off this series with than Belle Burden.

We don’t just talk about the book. We talk about the beauty of shedding an old version of yourself, the fear and freedom of starting over, and the very specific experience of rebuilding while your children are watching. This conversation was so meaningful. It will stick with me forever. I am beyond grateful and thrilled to share it with you. Thank you for reading. I look forward to hearing your thoughts.

ARIEL: Belle! Hi! I’m so excited to meet you. I am such a huge fan of you and your book, Strangers. It has become a complete cultural phenomenon. I devoured it. Everyone I know has read it or is reading it and wants to talk about it. I don’t feel like I can remember the last time a book resonated like this.

As I mentioned in my DM to you — I’m coming to this conversation as someone who is in the middle of reinvention. What I’ve been calling my “second story.” The space between what was and figuring out what comes next. I found so much of the book relatable. The circumstances are different, I built my company for 13 years — it became my whole identity. I was married to someone and in a relationship I thought I could fix. I chose to ignore red flags and then made the choice to walk away. So the feeling of standing at the edge of a chapter of life you didn’t plan for is something I recognize deeply. And that feeling of rebuilding your identity while still showing up for your kids every single day — is something that I recognized on every page and was so moved by.

I started this essay series, Second Story View, because I think the chapter after everything falls apart can actually be the most important and significant one. Your story is honest and courageous. So I thank you for being here and thank you for being willing to discuss.

So my first question just to start, what do you wish you had known at the very beginning of all of this?

BELLE: Well, first thanks for having me — I get a lot of messages these days, and yours struck me because our marriages ended in different ways, but I think we had the same emotions, or similar emotions and feelings, about going from one life that you thought was going to be the rest of your life to having to really start from ground zero. And that there can be really beautiful things that come from that.

I was in such a state of total despair and fear. And I talk about being on the bathroom floor, because I literally was on the bathroom floor — not just a trope, I was there — and felt like all the pillars of my life were crumbling at the same time. My spouse was gone, my financial security was at risk, my place in my social world was crumbling. And at 50 years old, I just felt an overwhelming sense that things are just over for me. Like there’s just not going to be a part two, because the things that really mattered in my world were no longer there. And I was just heartbroken. There was just a lot of heartbreak.

So for me, I actually think it required the burning down of everything to actually find my true nature, my talents that I think had been buried for so long. And to really — it sounds trite, but — really become myself and be in charge of my life. To have autonomy financially, have autonomy just in the day to day. And I think none of that would have happened had my marriage not ended. And I never would have chosen to end my marriage, because of my childhood — I felt like an intact family was the most important thing to me. But now, someone said, “You almost should thank him.” And I almost want to thank him for it, because I like my life much better now.

ARIEL: I can totally relate to that. We thankfully, I hope, don’t have many moments in life where all of a sudden it feels everything has imploded and the world you know has burned down. But that experience can become the most powerful forcing function for change.

I want to talk about motherhood. Because mothers carry the mental load. And so even in the depths of grief, we’re expected to hold it all together — because our kids need us, and they need dinner, they need to get to school, they need to be held, and they need to feel steady and safe. And then of course there are all the logistics and all the things that you just need to be constantly on top of. We don’t get the same opportunity or space to process or fall apart. And I think that’s a uniquely female experience in a majority of relationships.

What helped you survive that, looking back? Was there a ritual or practice or a piece of advice that someone gave you that helped you move through the grief? And is there something you would share with someone who’s in that impossible position right now?

BELLE: Well, I’ll take it in two parts. The motherhood thing is really hard. When I talked about being on the bathroom floor, it’s because that’s the one place my kids couldn’t — wouldn’t — open the door. And it’s very hard, when you’re going through such an emotional upheaval, to continue to do all those things that your kids need you to do. And I didn’t do it well, honestly, for a very long time. I was pretending for them for a month that it hadn’t happened. My older daughter knew because she read a text on my iPad, and she could see I wasn’t eating and that I was barely functioning. And so she started to cook, to take care of me. She was 15. And it still just breaks my heart to think of that.

And I think I was protected from some of it because of COVID. We were on this island — I did not have to go to school pickup, I did not have to go to any meetings, I did not have to take them to sports practices. They were in the house all the time. So it was difficult because no one could get to me, but I had this sort of protected time where not a lot was expected of me.

But in terms of parenting them through something like this — I decided, after that period of trying to hide it, that I was going to be very open and honest with them and acknowledge their reality. Which for us was that their dad did not want joint custody, did not want to have a room for them in his apartment, did not want to do vacations with them or anything like that. And I found that it worked better for me to say, “Your dad’s going through something. I don’t really know why or what it is, but he can’t make a home for you right now or be that kind of parent. And that’s about him and not about you.” Rather than saying, “This is all fine, this is normal, everyone’s great.” But at the same time, not bad-mouthing their dad.

I found that it’s still a hard line to walk, it really is. But I think as women, we’re often taught to just be so cheerful about it and cover it all up. And I don’t think that serves kids. I’ve heard from a lot of adults who themselves were children in the situation that I was in, and they said, “It was so confusing — we couldn’t figure out what was going on or what had happened.” And they believe that eventually, my kids will be grateful for my openness. You know, time will tell, but it felt like the only path to me.

And as far as things that helped me get back on my feet — one of them was walking. I walked obsessively, starting at a quarter mile, and then would do these eight-mile loops. The meditation of that, and being in nature, really helped. And getting back to work — I had to work on a legal case pretty soon afterwards, and having to shift my focus to something that was needed and productive helped. And then writing, which took a little while to access again. But for me, to really write down what happened, kind of unlocked that part of me that I hadn’t been connected to since I was 18.

ARIEL: My kids are young, and for the most part, are unaware of the circumstances that led to the end of my relationship with their father. But I do think about the future — when it is time to tell my truth, honor my own experience with them, and still protect their relationship with him. And for him too, to tell his own truth as well. I do think our personal stories are important for our kids to know. As a mom, I want to be able to navigate that. And you sort of touched on that a bit, which was my next question, what did you get wrong before you got it right? And I do think writing your book will be so profound for them. But how do you lead with honesty so you can model making different choices and hopefully break cycles?

BELLE: I think it’s really important because it builds trust when you’re honest — even about pain and fear and those things. And I think you can encourage a relationship with the other parent at the same time as being honest.

ARIEL: Last night at dinner, your book came up — and for the record, it wasn’t me who brought it up. But the conversation focused on red flags. And the ones that become so clear in retrospect. And how we all relate to that experience, whether in relationships or in business — it’s so easy to ignore or talk ourselves out of what you actually experience and is in plain sight. And I think there’s this temptation to ruminate or spiral into the land of what ifs. What if I had just trusted my gut — which can be debilitating. And you touched on how at this point you could almost thank him, but how do you make sense of what you missed?

BELLE: I do think it’s easy to find red flags in any relationship. Whenever it ends, you can sort of handpick things. And I’ve spent a lot of time ruminating, going back, second-guessing. And I don’t see red flags of an affair or an abrupt departure — I don’t see things where I’m like, how that was so clear.

I do see many red flags around my financial story. I think he was completely self-protective from before we even got married. I think he had strong feelings about people with inherited wealth since childhood. And I think he was never going to share equally with me. There were signs of that throughout the marriage. And I write about this in the book, the flip side of someone being very protective and taking things on is also controlling — even if it’s gentle and seems kind, it does rob you of agency in a lot of ways.

In terms of personality — and kind of thinking about if I have another relationship, what are the red flags and green flags would be —I do think he was always a little bit removed, a little bit distant. And I kind of liked that. I think maybe close intimacy was uncomfortable for me for reasons from my own childhood. And it also kept me interested. He did have this past as a very rebellious teenager, kind of a wild child. And I was attracted to that.

But in terms of a switch flipping — it’s not so much that I should have looked at his past and said, “Oh, this is going to happen.” But I can sort of see the through line from the end going back to that person he was as a teenager. And that is interesting to me, at this point, it doesn’t seem like “Oh, here’s my answer.” but it helps me place it somehow.

[brief pause for technical difficulties]

BELLE: So, what we were talking about — red flags.

I think it comforts people to be able to look at the book and say, “Okay, this is a sign and this would lead to this.” I think it’s interesting to look at it that way, but I think we’re always taking some kind of leap when we marry someone. And there often isn’t a clear explanation.

ARIEL: A lot of my journey has been about self-compassion. I think it’s almost easier to forgive others, but there’s this forgiveness of self that is also really hard work. When you’re in that ruminating process — and I find it in my business too, all the what-ifs — you know, if I hadn’t hired this person, or hadn’t made this choice, or brought on this investor. And in my own relationship, if I had just said, “This is actually not working,” or “This is not okay.” All of the ways we could rewrite history. And then I bring myself back to the fact that the journey is the medicine, and this is the growth.

BELLE: Absolutely. And we really have to be compassionate with ourselves, because all of those choices and decisions felt like the right thing at the time. And we’re often led by respect and love and trust,

ARIEL: And hope I think too —

BELLE: And hope, seriously, hope. And we just have to value that in ourselves as strengths. It’s very hard not to spiral into kicking yourself. Taking responsibility and looking at your decisions is useful to a point, but beating yourself up is not useful.

ARIEL: On the Modern Love Podcast, you spoke about how both your grandmother and your mother experienced infidelity. You’ve talked about feeling as though you had picked differently — and then it happened to you too. You have daughters watching you now. What are you modeling for them that’s different? How do you break a generational cycle like that?

BELLE: I think I grew up with it in my bones. There are these patterns. And my ex-husband had patterns in his family too, that were never talked about — because as women on both sides of the family, you were meant to just be very graceful and not speak of it, which served to protect the man in the story. And I think these things get passed down from generation to generation. And I think if we’re open about it — I think you’re right. It’s both being open about it, maybe trying to teach it at appropriate times. But also modeling it. What you will and won’t put up with.

ARIEL: Yeah, exactly. It’s hard, but I feel like it’s my life’s mission in some way — without becoming too obsessive and compulsive around it. But you just want what’s best and what’s better, as a mom for your kids.

I have a daughter and a son. One of the things I’ve taken from my own experience — I never want my daughter to sacrifice herself for anyone or ever question her own worth. Is that something you can actually teach, or does it have to be lived?

BELLE: I think it has to be both. You can try to name it and speak about it at appropriate times. But ultimately what children absorb most is what they see — what you model in terms of what you will and won’t put up with. The most powerful thing I can do for my daughters is to live differently. To show them, not just tell them.

ARIEL: You write about the loneliness of suddenly being on the other side — the shock waves that reverberated throughout your community. How friendships shifted, and some people treated you differently once you were no longer part of a couple. I relate to that too. I’d love to know how you made sense of that? And how did that change after Strangers was published? I imagine there might be a different energy.

BELLE: Yeah, it’s really interesting. Because I think people still don’t know what to do with me now.

And I think in any divorce — maybe more so with the “abandoned wife” identity — it’s so strange to go from being a part of something. Being something that people understand and know where to place you, know what to invite you to — to suddenly being something different. And I think we carry a lot of shame around that, regardless of how the marriage ended. Where you feel like you’ve done something wrong, that you’re not a part of something where everyone has done everything right — they’ve kept their marriage intact, they have their intact family. And I really carried that for a long time. And I think people just — I happened to be in a very married place at the time — and I think people just had no idea what to do with me.

And I tried to look at it as a learning process for me, because some people were so wonderful and really moved towards me and were very clear in how they felt. And some I didn’t know very well at all, and I could just see this window into their character that was so beautiful. It’s something I don’t think I would have move towards in this situation — I would have wanted to respect their privacy. But now I do try to reach out and just say, “I’m so sorry you’re going through this,” which is so simple but it really means a lot when someone says that to you.

And then the people who were harder on me, or who moved away — I really try to look at it through the lens of: they’re bringing their own fears, they’re bringing their own family of origin, their own marriages. And try to look at it through that lens, rather than just the hurt lens. And that helps me.

A lot of people from the club that I was a part of, that I am still a part of, have reached out and written to me. Men who I think can identify themselves in the book have written to me and said, “You’ve given me a lot to think about.” Not quite apologies sometimes, but — you know, they read it. I didn’t think any men would read it, honestly. And that’s been really meaningful.

I don’t know what it’s going to be like to go back next summer. My psychiatrist said, “If your book doesn’t do very well, you may get one reaction — but if it does really, really well, some people may want to jump on that train.” I think it’s definitely going to be interesting. I may have to — I’m not going to write another memoir, but I could write another book about the reaction to it, for sure.

ARIEL: Totally. Yeah, I would love to hear how that plays out. It’s really interesting.

BELLE: And for me, I had to change this image of myself in that process — where I was really holding on to this image of this kind of dowdy middle-aged woman who was never going to be loved again, who had been rejected. And really shifted to this strong, independent single woman who’s the head of her family, who has meaningful work and gets to decide how she’s going to live her life. Whose going to welcome grandchildren and be the matriarch of her family. My sister-in-law, who came in and cleaned my closet and really helped me see myself differently in a physical way — that really helped too. So I think you have to be really disciplined in trying to view yourself in a way that gives you confidence and doesn’t tear you down.

And now my secret is — I actually sometimes feel sorry for married people, because they don’t have the same freedom.

ARIEL: Yeah. There are certainly pros and cons, but I also appreciate the freedom and the opportunity to at some point do it differently.

ARIEL: You became a debut author, in the middle of rebuilding your life. I do think there is a narrative around aging right now, and what it means to be reinventing at a time where people think they’ve missed their moment. I feel it. And despite the beauty of getting older and wiser, there is still fear around aging and the unknown. I’m 41. I’m single and I’m a mom of two. I’m figuring out my next career and what I want in a relationship. And what it means to start over, but not start over, because I’m not at the beginning. I have everything I’ve built. What would you say to women who feel like they’ve missed their moment, or who are scared to take their own leap into the unknown?

BELLE: Yes. And I was 50 when my husband left, and I’m 56 now. And it really feels like it’s now that I’m kind of launching this new part of my life. And it’s pretty amazing to see it expand. And I think that would have happened even if the book wasn’t successful — you just are meeting new people and seeing yourself in new situations.

And now — maybe it’s easier at 50-something because you’re just like, why not? I think in your 40s you’re still crafting your life in some way, you still feel like you have control. But I’m at the stage where my youngest is a senior in high school and she’s going to go off to college next year. And I’m really seeing it as this open slate of opportunity. I’m very sad about her leaving too, but I’m seeing just this openness and possibility and the excitement of not knowing how it’s going to turn out. What it’s going to be and who you’re going to meet — and that feels really exciting.

And it’s almost better than your 20s, because in your 20s it’s almost too open. Now you have some structure — you have your two kids, you’ve built your company, you’ve made contacts. So now it’s really just the good part.

And I see people — I don’t know if you’ll find this when your friends enter their 50s — I see people, some who had big careers and some who didn’t, who almost feel like they’re winding down. They’re literally moving to Florida and I’m like, wait, I’m doing the opposite. I’m just getting going now. And as I watch both my mom and my stepmother — they’re so passionate about their work — I really think it’s the best way to go forward. I was a stay-at-home mom for a long time and I have such respect for it, but I think as we get older, just having work and trying something new, trying something creative — I see people just blossoming. And that I think is really great. So I’m excited about my second act.

ARIEL: Yeah, me too — for you and for me.

BELL: Yes. Me too.

ARIEL: After writing this incredibly personal book — the most personal book you could have ever written, your own life, your own pain, your own name on the cover — I read that you’re working on fiction next. I’d love to hear why and what’s that like?

BELLE: So fiction is what I wrote when I was a teenager and really loved and thought I was going to do — and got dissuaded from it. So I feel like I want to try it. I have no idea if I’ll be able to do it. I’m finding it very difficult so far. I don’t know what happens next for this book in the same way — with the memoir, I had a structure because I knew the story.

I just did an event at Books and Books in Key West which is owned by Judy Blume — a childhood idol —

ARIEL: An idol and icon! She changed all of our lives.

BELLE: And I said that in my talk there, that I was finding fiction very difficult so far — and Judy Blume came up to me afterwards and said, “The characters will tell you what happens next. You just have to listen to the characters.” And I just thought that was amazing.

I’m finding it hard to switch between promoting the book and writing fiction. I was writing up until the time it came out. It just feels very hard to switch my brain between the two. So I’m pretty much doing this book promotion and my legal cases for now, and then I’m hoping as this quiets down I’ll be able to go back to it — hopefully by the summer.

ARIEL: I have two more questions for you. Questions I’m asking everyone in conversation. When you were in your own in-between — before your new life had a clear shape — what did you hold onto to keep going?

BELLE: A few things. Therapy has been very important and a stabilizing influence on me. My therapist is someone who just really tells it like it is, and that’s been really important to me.

I have felt very connected to people in my life that have died. I wrote about some of them — I’m not sure why that happens.That has been helpful.

And the thing that has probably helped me the most is just to trust the universe and stop trying to grip and control. Let it unfold. And that has been the key thing — to do the next right thing and not worry so much about where it’s all going to lead. And I really did that with the book, starting with Modern Love, and then just following where the world was leading me. And it’s been pretty amazing to do it that way.

ARIEL: It seems that it is working.

BELLE: And believe in abundance, just picture abundance.

ARIEL: I think the abundance thing is really fascinating. Because I think it’s really easy — for me and I think a lot of people — to fall into a victim mentality. This loop of anger, or a vindictive loop, and all the things that could have been. And it’s such a limiting factor. Living a life that welcomes abundance has been a big ongoing topic with my therapist and coaches for the past few years. There are so many ways we hold ourselves back. But that’s truly and so simply what we want — a life of abundance. In love, in health, in wealth, in experiences, in friendships.

BELLE: In every way.

BELLE: And when you talk about anger — I think anger is more depleting, it’s sort of the opposite of abundance. And when I signed my divorce agreement, I made a commitment to myself that I was not going to live in anger anymore, or in that focus of what I got and didn’t get. Because I had seen many friends who had lived in that space for years after they were divorced, and I could see how corrosive it was for them.

And as I’m talking about this, some people will be like, “Well, you wrote a book.” But I tried to write a book that did not have a clear casting of victim and villain — that was more compassionate about him and really looked at myself. But I really think that is so key in divorce — to get yourself out of that place. Because it’s all true — the feelings that make us feel like a victim. But it’s so limiting.

ARIEL: Last question. What does the second story make possible that the first one never could?

BELLE: Oh, for me specifically — writing. I have a whole new career now as a writer. That was not possible in my first chapter as a married woman. And I think it allows for a more open and relaxed and loving posture in the world than was possible in my marriage.

ARIEL: That’s beautiful. Thank you. Thank you for sharing — for agreeing to have this conversation. It means more to me than I could ever express. I really do appreciate you taking the time, and I’m so grateful for your book. I really am.

BELLE: Thank you so much. And I love how you framed all of this, and I can’t wait to watch more and to see what you do. I can tell on your face that you’re going to have an amazing next chapter.

I was late.

It was January 2014 and I was at my storage unit. Every day I made multiple trips, organizing boxes and picking up inventory to bring back to the office. I didn’t realize what time it was until my phone started ringing. Multiple calls. I was missing a meeting.

At the time I was in an accelerator program, structured around pitch practice. Every week, we’d have five or six meetings with different investors, executives, and experts in various fields. The whole point was to pitch, get notes, refine, repeat.

I kept getting the same feedback: “This is a good idea. She clearly knows her stuff. But she is so chill. So laid back. Does she have what it takes to actually build this?”

I was frustrated. I was working constantly. I was obsessed. The only concrete thing I knew about building this business was that I had what it takes! But I also wanted to be seen as the professional, composed founder people would want to back.

On this particular day, I had no time to compose myself. I arrived back at the office flustered, apologizing for being late. Having missed half the meeting, I wanted to make the most of the time I had left. My energy was high, my passion was visible, and I was holding nothing back. I was operating from a place of pure controlled chaos.

After that meeting, the feedback changed.

“She’s got so much going on. She’s clearly juggling a lot. She’s going to figure it out.”

Everything shifted after that.

Being composed and articulate read as “not passionate enough.” Being flustered and visibly overwhelmed read as “committed.”

I couldn’t assume people would see the intensity beneath the surface. I had to let them see what was actually happening: the obsession, the hundred things I was managing simultaneously, the fact that I was all in.

For a long time, I thought the path to being taken seriously meant embodying traditionally masculine leadership traits. Decisive. Direct. Unemotional. Strong in the way strength had always been defined in business.

That’s what seemed to work in the rooms I was in, so I leaned in.

As a first-time founder, I received a lot of advice. And a reoccurring theme was that being that vulnerable was a weakness. Show your weakness and you’re not ‘good’ — not a good investment, not a good leader, not good enough for the job. It took me a long time to work through that belief, to land in a place where I could recognize that asking for help and being clear on what I know versus what I don’t know is the opposite of weakness. It’s a superpower.

I started taking investor meetings for Parachute at 29. Young, determined and ready to build something that would define my future.

From the very beginning, I was asked about my plans to have kids. About what would happen if I got married. About how I’d balance it all. These weren’t casual questions. They were posed by people evaluating whether to fund me.

I started wearing a fake wedding band to meetings.

For women, there’s often an underlying concern that family will derail everything. Men don’t get asked those questions. The assumption is that their personal life and their professional ambition can coexist.

The ring wasn’t a statement. It was a workaround. A way to redirect the conversation back to the business I was actually there to talk about. That I had to do it at all told me something important about the rooms I was in, and how much work there was left to do.

I decided the questions needed to go both directions.

‘How do you support your founders?’ ‘What kind of relationship do you like to have with them?’ I was trying to suss out how they’d react to big questions, to collaborative brainstorming, to solving real problems together. I’d ask other founders too: what happens when shit hits the fan, when you’re in code red and uncertainty is through the roof?

Most of these conversations happened long before COVID. And when the pandemic hit, those investors I’d vetted for how they showed up in uncertainty? They were supportive. They helped us navigate moments when we truly had no idea what was going to happen next.

As Parachute grew, something interesting happened. The culture I had built, one rooted in empathy, trust, and psychological safety, was incredibly effective. People did their best work because they felt seen and supported. They stayed because they felt valued. They pushed themselves because they believed in what we were building together.

When we were struggling to hit numbers, I didn’t hide it from anyone. I brought the executive team together and was honest: here’s where we are, here’s what we need to figure out, here’s how we’re going to approach it. That transparency built trust. People knew I wasn’t going to sugarcoat reality, which meant when I said we were in a good place, they believed me.

I used to say all the time: I love being proved wrong. The goal of the team is to prove me wrong. I have strong opinions, but viewed those as a starting point. Pushback wasn’t just tolerated — it was expected.

I remember early on, a team member challenged a decision I’d made in front of the whole group. My initial instinct was somewhat defensive. I’m human. But I paused, listened, and realized they were right. I changed course. That moment signaled to the rest of the team that your voice matters here. We’re building this together. Modeling that kind of self-awareness is contagious.

I also announced to the team that I was working with an executive coach, and I was proud of it. I saw it as a leadership skill, a commitment to growth. When I tried to encourage some of my male counterparts to do the same, it was met with resistance. They didn’t view it as a skill. They saw it as a weakness.

That gap said everything.

I’ve experienced cultures where leadership just wants “yes” people around them — people who won’t ask questions and will just get shit done. I’ll never forget my first job out of college, the owner of the PR firm saying repeatedly: “There’s always someone else who can do your job.” You don’t know where you stand. You don’t know what’s expected. Fear becomes the operating system and it’s no way to live. It definitely doesn’t create an environment where people can show up with their best foot forward.

I think the decisiveness that many women bring to leadership creates an environment where you’re less susceptible to those moving targets. We tend to be clear about what’s changing and why. We bring people along rather than leaving them guessing.

Women often lead with emotional maturity that allows for nuance. We can hold multiple perspectives at once. We notice subtle shifts in energy or morale. We pick up on tension before it becomes conflict and know how to address it without making it bigger than it needs to be.

I remember a leadership meeting where the energy shifted. Two people on the team were clearly at odds, but no one was saying it directly. I could feel the tension. The way one person’s body language changed when the other spoke, the lack of eye contact, the careful phrasing, the things not being said. After the meeting, I pulled them both aside separately, acknowledged what I noticed, and created space for them to address it directly. It didn’t escalate. It got resolved. That kind of attunement and ability to pick up on what is happening beneath the surface isn’t softness. It’s emotional intelligence.

There’s a balance that I think many women understand instinctively. When to be direct and when to create space for dialogue. When to make a decision quickly and when to slow down and bring people along. When to hold firm and when to adapt. It’s not indecision — it’s discernment.

As my leadership team expanded and dynamics shifted, I started hearing observations about the culture I’d built.

“The culture here is very collaborative.”

“People seem really comfortable speaking up.”

“It’s interesting how much autonomy everyone has.”

These weren’t criticisms, exactly. But there was an underlying question: could a culture built on empathy and trust not only scale, but hold up under pressure?

And for a moment, I started to question it myself. Should we evolve to be more demanding? Less accessible? Create more distance?

The reality was, our culture wasn’t a liability. It was an advantage. Being willing to say “I don’t know” created space for collaboration. Being honest about challenges built trust. Creating room for people to disagree, to push back, to bring their full perspective — that made us better.

Showing real vulnerability makes you a real, complex human. And we are all real, complex humans with lives, opinions and experiences. That’s strategic.

When you have leadership teams that all think the same way, you move faster, maybe. But you miss things. You act with certainty, but you don’t account for complexity. Diversity of thought and approach isn’t just about fairness — it’s about effectiveness. Different instincts about what matters. Different ways of reading a room. That’s what makes organizations resilient.

The best leadership probably integrates both — decisiveness and empathy, confidence and self-awareness, strength and the ability to be vulnerable. Not because it’s the right thing to do, but because it’s the most effective thing to do.

I don’t need to question whether my approach is valid. I’ve seen what it creates. I’ve seen how people respond when they’re led with empathy and honesty and trust. And instead of asking women to lead more like the model we’ve always recognized, maybe it’s time to expand what we recognize as successful leadership in the first place.

For the past few weeks, everyone has been talking about transition. Leaving behind the Year of the Snake and what it symbolized, what we were meant to shed. And it resonated deeply. I spent the last year letting go of my founder identity, old narratives about what success should look like, versions of myself that no longer fit. The shedding wasn’t easy. It was uncomfortable, challenging, at times painful and necessary. And now we’re here. The highly anticipated Year of the Fire Horse.

And if I understand correctly, as an Aries, this is apparently a significant year for me. Fire Horse energy is about forward momentum, courage, independence. It’s about trusting your instincts, building with intensity, and moving decisively toward what’s next. After a season of letting go, I’m so ready to build again.

I’m not usually one for New Year’s resolutions. January can feel like this pressure cooker of self-improvement, everyone declaring bold commitments that mostly set them up for failure by February. I’ve never loved that energy.

But this felt different. I wanted to be intentional about what I’m bringing forward into this next chapter. Not grand resolutions or impossible standards. Just a few focused shifts. Small, sustainable changes that actually matter.

Everything I’m focusing on comes back to one thing. Being more present. Here’s what I’ve been leaning into.

Cutting Screen Time

I’ve set time limits on apps, which has helped more than I expected. Just the awareness of how much time I’m losing to scrolling is enough to make me put it down. I also bought a Brick, one of those lockboxes for your phone that forces you into actual downtime. I still need to set it up, but the plan is to use it all the time. During the day, weekends with my kids, or anytime I need to be fully present without the pull of notifications.

Cooking Consistently

My kids love to tell me how good I am at ordering delivery. They think it is hilarious, but also they aren’t wrong. Home cooked meals were a big part of my life growing up and I actually do like to cook. So this season, I’m committing to cooking dinner three times a week. Not elaborate meals, just real food, made at home, with my kids around.

I’ve been leaning on easy recipes from some of my favorite cookbooks, including my friend ’s Foodwise, which has become a go-to. I’ve also been dropping a few ingredients from my fridge into ChatGPT and asking for recipe ideas. It’s surprisingly good at this. And I just preordered cookbook Riviera which comes out in a few months. I can’t wait.

Regular Reading

I’ve always loved reading, but last year I let it slip. I’m committing to at least one book a month. I’ve already finished two: Keith McNally’s I Regret Almost Everything and Belle Burden’s Strangers. Not an intentional pairing, but the through line was impossible to ignore. Both are about what comes next. McNally’s follows the constant push and pull of the restaurant industry, his relationships, learning to rebuild after a stroke. Burden’s hit differently. As a woman who’s been separated for many years, with kids, there was something about her story that felt specific — heartbreaking, beautiful and true in a way I didn’t expect. That’s what I love about memoirs. How people navigate complicated lives, relationships, careers. Something that feels deeply personal and universally relatable all at once. Next up are Heart the Lover by Lily King and The Correspondent by Virginia Evans.

Improving My Sleep

After a stretch of letting go, rest feels more important than ever. I’m no stranger to insomnia. Sleep has always felt elusive to me. But I’m really trying to change that.

I’ve been reworking my wind down routine, and it starts with the Higher Dose Sauna Blanket. I use it for about 20 minutes before bed, and something about the heat just signals to my body that the day is done. I also started using Ozlo Sleepbuds a few months ago and they’ve been a quiet revelation. Less about blocking noise and more about what they do to the swirling end-of-day thoughts. Paired with my Manta Sleep Mask, I’m falling asleep faster, staying asleep longer, and slowly, it’s starting to stick.

Getting Dressed

I’m a creature of habit and I love a uniform. I live in Los Angeles, aka the land where workout sets, elevated sweatpants, and (very) comfortable basics are what we’re wearing to school drop-off and pretty much everywhere else.

What I’m working on now is moving beyond that uniform into one that makes me feel more productive and put together. Still casual, just a bit more intentional.

A great-fitting pair of denim (my very favorite at the moment), a white tank (my go-to that is only $8) or t-shirt (love both the short and long sleeve) and a belt. I’m belt gal, and really believe it’s the accessory that ties it all together. While I rotate between a few, my friend Erin who designs Déhanche, makes some of the best. Lastly a classic pair of loafers. I got these years ago in Paris in a perfect green color and they continue to be the pair I reach for the most. They pop-up on The Real Real and I’d like to have them in every color. That’s all I need to feel like a pulled together version of myself and embrace the day with a little pep in my step. It’s a small shift, but it changes everything about how I move through the world.

Fire Horse energy is about forward momentum. And sometimes, that starts with just getting dressed.

Substacks I Love

Now that I’m all in on Substack, I’ve swapped my scroll for actual reading. Some current favorites by friends I adore: Basic by for real talk on motherhood and the beautiful complexities of life, Night Shade by for the best shopping, travel, and food recs, Objects of Desire by for a whimsical escape into the world of fabulous women living their best lives, and most recently Rich People Shit by , which is exactly what it sounds like. Can’t get enough.

From the beginning, I called Parachute my first baby. Many founders do. I had poured myself into the company the way you pour yourself into raising a child. And now I had to figure out how we would both exist in the world without each other.

I know so many founders who have multiple ideas brewing, multiple businesses running, side projects, personal brands they’re growing in parallel. That was never me. All I ever wanted to do was build Parachute. Walking away felt like a breakup and a death at the same time.

Grief starts like a loose thread.

I loved walking through our factories. Watching as countless individual threads moved through the warping machines, then the looms, transforming into fabric. The rhythmic precision of it. Warp and weft interlacing, becoming these beautiful billowing sheets. And along the process the fabric would be inspected, people combing through every inch, at multiple touch points, searching for imperfections. Slubs. Pulls. Any flaw in the weave that needed to be caught before it could become a bigger problem.

So when I felt it starting in my own life—that small tug, that tiny pull—I tried to brush it off. To ignore the growing imperfections until that disorienting moment when I realized the company I built wasn’t the same company anymore. Decisions were being made differently. The culture had shifted. The priorities had changed. Parachute was no longer mine.

I told myself not to pull at it. That if I just left it alone, tucked it back in, didn’t touch it, it would somehow weave itself back in. But that’s not how it works. I knew that. Eventually, you pull the thread. And when you do, everything unravels.

Grief is not a word we use much in business. We talk about pivots and transitions and new chapters. We celebrate what’s next before we’ve properly acknowledged what’s gone. There’s this underlying pressure to move forward quickly, to have the next thing lined up, to prove that leaving wasn’t a mistake.

When I left Parachute, I followed this exact playbook. I told myself I was fine. That I was ready. It was the best thing for me. That this was exciting, not devastating. I kept myself busy with coffee meetings, reading, and thinking about what might come next. Working out twice a day. Anything to avoid sitting still with the actual feeling of loss.

Then there is the ending itself. The moment you walk out of the office and realize it’s the last time. The last board call. The phantom limb of checking Slack. The muscle memory of solving problems that aren’t yours anymore. Someone asking “how’s the business?” and you smile, tilting your head while you decide how much to share—it’s not your business anymore.

As a founder, you become so enmeshed with what you’re building that it’s hard to separate yourself from it. The company’s wins are your wins. Its failures are yours too. Its reputation, its problems, its potential—all of it becomes part of how you see yourself.

And when you step away, you don’t just lose the company. You lose the scaffolding it provided for your entire life.

For a while, I didn’t even recognize it as grief. I told myself it was just an adjustment. Transition. I minimized it—told myself I was being dramatic, that other people had lost much more. That this was a choice, not a tragedy, so what right did I have to feel this way?

It wasn’t until I started talking about it, processing and sitting with the range of emotions, that I began to understand. And truthfully, working on my first Substack post was cathartic and clarifying. This wasn’t just a transition. This was a loss. Real loss. And when I talked to other founders who’d been through similar exits, they all said the same thing: “Oh yeah, that’s grief.”

Minimizing the loss doesn’t make it smaller. It just makes you feel crazy for feeling it at all.

I’ve learned that grief, in the context of building, isn’t weakness. It’s information.

Grief tells you what mattered. It shows you what you loved, what you poured yourself into, what became part of your identity. And when I finally let myself feel it—really feel it—I started to notice something underneath. The grief wasn’t just about losing Parachute. It was about losing the certainty that came with it. The structure. The clear sense of purpose. The identity that didn’t require explanation.

But grief is also generative.

It’s taken time and work, but I do believe that hard things don’t happen to you, they happen for you. Understanding that framework requires you to integrate that belief into your body. Listening to what a feeling is telling you, instead of feeling something uncomfortable and trying to ignore it.

Once I stopped resisting and let myself sit with the loss, something shifted. I was able to accept that I was sad and maybe even a bit angry, and that that was actually okay. The grief didn’t disappear, but it started to clarify. I could separate what I missed from what I actually wanted to carry forward.

What I missed was the craft. Creative problem-solving. Starting with nothing but an idea and watching it become real. Working with people I trusted and respected. Making products that mattered to our customers. That made their house a home.

That’s what I’m carrying forward.

It also made space for something I hadn’t expected: relief.

Relief that I didn’t have to have all the answers anymore. That despite it all, Parachute is still my baby and will always be my legacy. Relief in knowing that I built this brand from just an idea, brought together a team of brilliant people who I loved working with and vice versa, and together, created a real community. Relief that I could be bored, unproductive, uncertain, and it would be okay. Relief that I could rebuild my life around what I actually wanted, not just what the company needed.

Grief and relief existed side by side. It can be hard to know which you’re feeling. You can cry because something is hard and sad and also cry because you know it’s finally over. Grief for me often feels like a heaviness in my throat, a desire to get small. Relief feels like your shoulders dropping, a lightness in your chest, your jaw unclenching.

Both were true. Both were necessary. Because grief isn’t the opposite of building. It’s part of it.

You can’t build something true if you haven’t reckoned with what came before. If you haven’t let yourself feel the full weight of what you’re leaving behind. If you haven’t separated who you were from who you’re becoming.

I’m still in it. Still figuring out what comes next. Still grieving some days and excited others. Still learning to hold both at the same time.

I can feel something underneath now. Not certainty, not clarity exactly—but possibility. Waking up energized and thinking about the potential of a new project. Researching and learning new skills that feel inspiring. I’ve even had moments where I felt, is this it? The all-consuming idea I’ve been waiting for? The kind that only emerges when you’ve stopped clinging to what was and started trusting what’s coming.

More on that as it unfolds.

I’ve been doing this for many years now. It’s a luxury, yes. But it’s also one of the most significant things I do for my mental health.

The flowers themselves aren’t the whole story. It’s what happens after they arrive. I carve out 30 to 45 minutes to trim stems, arrange them, choose vases and make bouquets of all sizes that end up throughout the house. Kitchen counter. Dining table. Coffee table. Bathrooms. Entryway.

I turn on music. I take my time. I make mistakes. I arrange and rearrange. I move slowly and intentionally through the process.

The whole experience is restorative. I’m working with a different medium each week. Different types of flowers that present different challenges. Some are much easier to arrange than others.

And here’s the thing: I get what I get. I don’t usually know what to expect when that bundle arrives. Sometimes it yields one big generous arrangement. Usually two or three. Sometimes I can make many bouquets throughout the house.

Most of the time I love what arrives and am in awe of the beauty. Other times, not my favorite. But that’s not really the point. The ritual is the point.

There’s something about bringing nature inside that makes my house feel alive. It adds a living dimension that shifts with the season and the week.

My house is always full of flowers. They are a conversation starter when I host. They make my home feel warm and inviting. I feel such a stark shift when flowers aren’t there. Those rare weeks when they don’t last or I need to replenish, I’ll run to the farmer’s market or Trader Joe’s to pick some up because my house almost feels empty without them.

Last November, in Paris, I went to the new exhibit at La Galerie Dior. As you enter the first room of the gallery, there’s text on the wall that tells the story of Christian Dior’s childhood. One of the first passages reads, “A passion for flowers inherited from my mother meant that I was at my happiest among plants and flowerbeds. My chief delight was to learn by heart the names and descriptions of flowers in the coloured catalogues of the firm of Vilmorin and Andrieux.” With versions of these catalogues from 1890 and 1908.

I had no idea Dior came from a family of passionate gardeners. His mother, Madeleine, cultivated renowned gardens at their childhood home in Normandy. This upbringing fostered a lifelong passion and as you walk through the rooms you start to see it everywhere. His designs and his use of florals remain a through line throughout his career. Flowers were a foundational imprint to how he saw beauty.

That stopped me. Because I realized I get so much of my creative inspiration and happiness from flowers too. The way I think about color, texture, dimension. What makes something feel alive and beautiful. It all comes back to this weekly practice.

I think about my kids, and hope that one day when they make their own homes, they’ll take this with them. That they’ll understand you can choose beauty. That the small things matter. I hope they may even say to friends, “growing up we always had a house full of fresh flowers.”

How simple is that?

Here’s what I’ve learned. Happiness isn’t almost never about the big moves or grand gestures. Sometimes it’s about the small things you do every single week. The thing that requires you to slow down. To pay attention. To work with your hands. To create something beautiful.

Fresh flowers are my version of that. They might not be yours. But I’d bet there is something you could commit to, or probably already do. Something that pulls you into presence. Something that makes your space — and your life — feel more alive.

For me, it’s flowers. Every Friday. Without fail. One of my favorite investments I’ve ever made.