#78: Jake Schwartz, Co-Founder and former CEO of General Assembly—Navigating startup chaos, what ...

Welcome back. This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to welcome Jake Schwartz to the podcast. Jake is the co-founder and former CEO of General Assembly, also known as GA, one of the very first tech education companies. He's currently the executive chairman at Brave Health, a mental health provider offering online therapy and medication management. Jake is a multi-time founder and entrepreneur, and he's a lot of great perspectives on the ups and downs of the entrepreneurial journey. We talked about the moment when he really got that he was meant to be an entrepreneur, and then what he calls the abandonment of fear due to desperation. We talked about how he met his co-founders and the role of serendipity, and how he now sees the GA team as a band finding their way with organic magic to it. Jake also talked about the early volatility of the team and their dynamics and how they dealt with them in some ways productively and in some ways not so much. Jake shared his raw thoughts about how they learned as they went along, lots of mistakes they made, what happened when they almost ran outta money, and what Jake would've done differently looking back on it. This is a fun and raw and very practical conversation from the perspective of a seasoned entrepreneur looking back on his early days. You're gonna love it, and I know you're gonna profit from Jake's insights. So please enjoy this great conversation with Jake Schwartz, co-founder and former CEO of General Assembly. Jake, welcome to the show. I'm so happy you're here.

Thanks for having me. I'm happy to be here.

I'm super excited because you and I connected, the folks at, um, Union Square Ventures connected us and we got into this like riff on just our initial conversation and I was like, you must come to my podcast. You must. And, and so I wanna ask you a bunch of questions about your experiences at, at GA and then also now currently what you're up to, but But first, when we were doing the mic check, I said, you know, where are you from? And you started answering me. I'm like, oh, that's too interesting. That's too— so save it for the podcast. So where did you grow up, Jake?

Uh, so I grew up in Oregon, um, on a farm, uh, outside of Portland. Um, basically the story was my— both my parents were kind of East Coast, you know, Jewish refugees, went to the West Coast. Drove around in a VW van. So, but they weren't really hippies because my dad was a doctor. Oh. But he like, he was a cowboy doctor in that he didn't ever do a residency, right? Which you could actually get away with in the '70s when he was doing this. And so he went straight into working in the ER, like after his internship. And that's what he did. And so And he around the same time was also like, you know, I think the '70s had a lot in common with the time where we live in now where everybody is kind of vaguely convinced that the world's about to end. Um, and so Hsiang's version of that was he wanted to live on a farm and be self-sustaining. So we had a year's supply of grain in the barn. We had a gas tank on the property. We had chickens and sheep. And, you know, he didn't really do that much with it because he was going off and doing like 48-hour shifts at the ER. But we had sort of, I grew up in this very sort of weird, you know, more, I guess it sounds much more romantic than I remember it being because it's sort of just in the middle of nowhere, which for a kid, I don't know how good that is for a kid, but it was, you know, I rode a tractor when I was 3, you know, those kinds of things. Wow. Remember, you know, dogs getting in with the chickens and things like that and having to deal with that.

That's fascinating. Yeah, you're absolutely right. What's old is new again, right? Like everyone now living off the land. I'm just curious, I did not know that about your background. Did that form— like, do you have any insights from that time that formed you as a, as a human, as a professional, as an entrepreneur?

I don't know. I honestly don't know. I mean, other than you know, I would say that I, we moved from there to the suburbs when I was, we were, I was about 6 or 7. And I would say, you know, my wife is a psychiatrist and what she likes to say about that time is that I was not very well socialized as a young kid. And so I think I've spent my entire life feeling a little bit like, but on the outside and like treating the ideas and issues of how to interact with other people as a bit of a science experiment. Because I didn't ever learn how to do it in a more natural way. So, you know, I would say that, that was my first, that first feeling of being an outsider was truly living, you know, outside. And I think I carried that, you know, I was also a Jewish kid in Oregon, right? And, you know, interesting ideas and stuff like that when everyone just wanted to play soccer. Or football and sort of, you know, then ended up coming back east for college and sort of found my people. The first time I ever stepped foot in New York City, I was like, oh, this is where I was meant.

Right. Totally. This place, like Jewish New Yorker transplanted like against your will, right? To the West Coast. And then you came home and found your people. I can totally relate to all that. And also the notion of being an outsider, which I wonder if that will show up in our themes as we go. But you know, I wanna talk first about, you know, I, what I think is your first big entrepreneurial venture, but correct me if I'm wrong, when you founded General Assembly. Can you tell us about General Assembly and, and, and the founding story and what that was all about?

Yeah, I would say it was not my first venture. It was my first venture that went anywhere interesting. Right. And I would say that was sort of the first thing is even when I was, when, when that started for me, my, My journey with it was that, and I actually think it's really relevant to the story of GA, is I had gone to business school. I'd actually started a couple, I'd started a performing arts space with some friends that happened. It was on 42nd Street in Manhattan and it was supposed to be bulldozed, but then it never got bulldozed. And so we had that 2 years and that not, that became a nonprofit. And then that nonprofit is actually still around today. And then I started a roving art gallery to try to help young painters and photographers figure out how to take their work to market. You know, these were, they were sort of half like fun, gee whiz, let's do these projects and half sort of learning like what does it mean to create something? What does it mean to do it as part of a team? What does it mean to do it yourself? And then I went to business school. I mean, and oh, by the way, while I was doing that, I was also working a day job wearing a suit and tie and going to a very like upper upper crust white shoe, long only equity investment shop, right? So I was really living in this weird world of taking all these different pieces of information and cultures and trying to figure out where I fit in any of them. And then I went to business school and graduated from business school and it was 2008. So, and because I had done work in investment, I knew Like it was, I remember I graduated in the spring of 2008 and you know, things were bad if you read like macroeconomic news, but it wasn't like everybody was talking about it so overtly. I think Bear had gone under, but that seemed like, okay, maybe that was just it. And that was an anomaly. And then, but I could sort of get the sense that something was bad happening. And so I was going to start a business. I was really intrigued by this concept of crowdfunding at the time, like before Kickstarter and stuff that was like Wow, all these different things you could do with that. But I decided instead to sort of take the safe route, which was to take a job offer I had gotten from a, you know, multi-stage private equity firm that was just really like half family office, half private equity firm. And mostly it's like a place to hide, but I spent about a year and a half there. And the day I started was the day Lehman fell. I remember. Now being on the buy side, I thought, I was like, this is the best thing ever. We're just going to like, we're in the middle of a crisis, like once in a century, like we can just buy everything. And I mean, that was sort of the naivete you come out of a business school. In theory, that was correct. But in practicality, there's all sorts of questions of capital calls, existing investments, you know, all that stuff that you don't quite understand when you're a newbie at the whole thing. And so we ended up not doing very much at this firm in that year and a half that I spent there. And I sort of would sort of was slowly sinking more and more into the sense of like, I don't know, it was depression, anxiety, a sense that I had like taken the wrong job out of my one chance to get back in the rat race after business school. Yeah. And I just sort of had this moment of like, Fuck it. Like, I'm, I don't care if I'm going to be sleeping in a gutter. I'm not gonna depend on anyone else to make my life what I want it to be. I'm not gonna depend on anyone else to be, to have a career, you know, to, for my career to be what I want it to be.

Yeah.

I'm gonna be my own boss from now on.

Yeah. Right. Well, hang on. So that moment though, that moment of clarity and truth for you, did that come from nowhere? Was it like a, a blinding, you know, 3:00 AM moment? Was it sort of a, a weeks-long process?

Well, I don't look for a long time. I had this sneaking suspicion that was a terrible employee and that working for other people was just not what I was meant to do. I mean, I'm terribly ADHD. I'm very opinionated. I mean, I don't even like my, my, my wife laughs at me because I can't even like take an exercise class because I hate people telling me what to do in that hot case. Right. So it's like, it's that level of that. Yeah. So I was wrestling with this the whole time. I think that final bit was the bit of the fear that there was this other easier, more, what's the word I'm looking for? More like, you know, remunerative existence that like, you know, was sort of represented by going to Wharton and like what my peers wanted and that I was sort of like thinking I could have it all. And the moment that really changed everything for me was this moment. And I'm, I think it was probably preceded by a crisis or like a nervous breakdown where I didn't sleep for 2 days or something where it was like, I just don't care anymore. Like I just don't care about that other thing. This thing is more important to me and I'm going to let that be my spiritual guide, which is to say I will not work for someone else and everything else is is up for grabs, but that is not. On that anchoring that, I would say in weird ways, stuff started to happen, right? I mean, I literally that next month met my now wife, right? And so there was almost like sort of like an abandoning of fear out of desperation, right? This sort of like, I thought of, I think of it almost as like hitting my bottom. But The other thing I started doing was just hustling to try to get people to pay me little bits of money to do work, right? Because my first business that I started, because I now am my own boss, was to try to go get clients to be a consultant, right? And I sort of done little bits of that before, but it was just literally going around anyone and anyone I could talk to, big company, small company, startup. Hey, let me pitch you on what I could, how I could help. And, um, got into some weird, interesting projects, right? Uh, some of my early clients are now some of my best friends, right? Just 'cause it was just a weird moment. Um, and, uh, but I always left one day of a week, even when I was, I, I got myself pretty booked up, right? And I was paying my rent by doing this, uh, which was an early success, I would say. And then, um, I always left a day of the week for the projects where I owned equity, right? That wasn't about paying my rent. One of those projects was working with some commercial real estate brokers I had met on a lead gen site, you know, using like a PPC kind of lead gen strategy for that.

Wait, wait, wait. PPC lead gen. What's that?

Pay-per-click. Like just like classic, like Google, somebody Google something, like turn them into leads for this commercial real estate broker.

Oh, lead gen.

Under the theory because Commercial real estate brokers, I don't know if people know this, like make a lot of money, right? Because each of these tenants, if they sign a lease, it's worth tens of thousands, sometimes hundreds of thousands of dollars.

Yeah.

So the theory was there and I thought this was going to be the thing that was going to make me rich. And I had this other little project that was sort of related to my real estate thing, which was I'd met really at this kid who had just graduated from my undergrad alma mater, Yale. And he was like, uh, had already started a company and raised venture money. His name was Matt Breimer and he was talking about this idea and his vision of getting a space for his friends to start companies. And he was calling it Superconductor. And I was like, well, let's chat. Like, you seem neat, right? You're neat and interesting. And I know a few things 'cause I went to Wharton and, uh, why don't you come over and have some beer? I'll, I'll, you know, and And I'll, maybe I'll help you like model out what this might look like. And I'll introduce you to some people in commercial real estate, things like that. That sort of started this cascade, the snowball of what was just at the time another project in the portfolio called Super Adapter. And he brought in one of his co-founders from his previous startup, Brad. And then we met another kid who was, you know, recently graduated from Columbia who was talking about doing this. More with the design, till it was sort of his passion at the time. And that was Adam Pritzker. And we all, because this was sort of a formless project, it was sort of all like, hey, well, let's do this together. And then, you know, we ended up forming this partnership, renting a space that was too big for us. On sort of going for it, right? Everybody brought things to that equation in interesting ways. And, um, you know, for a very long time it wasn't clear what it was. And then once it started to take form, it started to get this momentum, momentum, momentum. And as that momentum happened, everything else that I was doing sort of fell away because I was like, this is way more interesting and seems like it's just got this energy behind it. And I want to put all my time into that. But yeah, you know, that was sort of this weird journey and it happened slowly and then quickly and then all at once, all of a sudden I was the CEO of this thing. Most just 'cause I was like slightly older than everybody and had a little bit more, you know, a little bit more like I would say like emotional maturity and emotional intelligence about it by the nature of my, you know, Agedness, your seniority, right?

Your seniority. And maybe you—

I think I was— we're talking about like maybe I was like, you know, 5 years old. It just seems so much at the time.

Yeah.

And, um, and so it was like I could kind of hold the pieces together.

Mm-hmm.

And I mean, the sort of— I mean, we'll probably get into this, but I mean, you should never start a business like this really. Like if Like no textbook would say just form a partnership. We, yes, the way, I mean, let's, I'll talk about how we did this. We all split the equity evenly with two parts for Adam 'cause he was bringing some money of his money to the table. And so that was sort of like the way we did it. The voting was very, you know, it was all very amorphous. We didn't really have clear roles and responsibilities and we didn't even have a vision for what this business was going to be other than what was right in front of our face. Right. So, I'm sure we all had different pictures in our heads. And the sort of analogy that I've sort of taken with it is that really what we did was form a band and we started doing gigs, but before we knew it, we had like a record contract, right? And that was when we like took our first VC money. All of those dynamics that you see play out again and again, even in like the best bands in the world. Basically played out with us.

Yeah.

And, um, you know, that to me is like that when I think about like the Beatles story, you know, you go like that. I don't know if you saw that documentary Get Back on Disney.

Yeah.

It's like 9 hours. I was wrapped.

Yeah.

The reason I was wrapped is because I was seeing these dynamics play out with like literally some of the most famous people in the world that reminded me of my most like intense formative experience. Like it was not Right. Because I think it just, it had this magic to it. And to this day, I couldn't quite tell you why it worked.

Mm-hmm.

Timing was right, right? We all had different things to it. We invested in certain ways, we focused on it. But like, I think at the end of the day, it's like everybody got there, was passionate about it, brought 110% for that, not fully knowing what we were going to get out of it. But I think we also, we all in our delusions all thought we were gonna get 110% out of it. Right. And that's sort of what then engenders weird issues later on.

Yeah. Well, and of course I wanna get into those weird issues. Sorry, were you gonna say something else?

I was gonna say, and I, I, the other thing is that, so at some point we, um, we, because Adam was very passionate about design, we invested a lot in brand and that involved, he brought along, so one of his sort of people that he brought to the table was Mimi Chun. Who was this incredibly talented designer. Um, she had done this really cool project that I remember seeing before I met her, which was that she had like cataloged the colors of her food and then made like infographics out of them.

Wait, wait, say that again. She did what?

She had cataloged the colors of her food.

Ah.

And then made like infographics out of them. I mean, she's just an artist, you know, like really really deep thinking, really, really experienced that she'd worked for a long time in an IDEO. And so this was like a big get for us. And so she invested her time in building like the brand, some of the brand assets that we, they still use today. But one of the key conditions to helping us was that we had to change the name because she thought Superconductor was too not cool enough, I guess, basically. And it was really funny. I think it was like, and, and so we went through this whole design process with her on, you know, had a bazillion names and directions and ideas and sort of formulated down and through, through a lot of collaborative, you know, wrestling that landed on General Assembly. But we were still just a coworking space. Yeah. Yeah. But we had happened to have this idea that the The metaphor of it was a college campus, right? It was sort of a college campus in the city. That idea of the common room. Mm-hmm. And everybody that we were also young and out of college, like we missed that, right? That was what we sort of fantasized about and found that the world of work didn't really provide that at all. And so what couldn't we provide that for all these entrepreneurs? And so we had this room that we called the classroom.

Mm-hmm.

And that decision turned into a— and by the way, I think we called it that because we didn't know what else to call it because it didn't have any windows. And so otherwise it was just gonna be this like weird dungeon. And so by calling it classroom, we sort of got out of like this problem of what do we call this room?

Right.

Um, and that decision led to then a whole sequence of other stuff that happened that led to a complete pivot, right? From what, when the original idea was to this idea of of, um, maybe the revenue engine that's gonna make this organization grow is, is education.

Yep.

Yep.

Well, I have so many questions, so many things to follow up on, on this.

I don't, I don't know if that was like a coherent founding story, but it, it, it, and I think I'm trying to be, I think part of the reason I like telling it like that is because it does have a sort of organic magic to it that I think is really special. I think the farther I've been away from it, that's how I think about it more and more is like, is like I'm not 100% sure why it became what it became in all those different steps. And it was out of this stew of stuff and this desire to create, desire to be part of something, desire to create a community that all these things happened. Now, of course, along the way there were lots of steps of, okay, how are we going to pay the lease that we just signed. Now we're going to pay that monthly rent on that. What are we going to do? That went to, okay, well, we could keep selling more real estate, but that would involve taking more leases. And that seems like a recipe for what, what happened in 2008. Yeah. So that is the answer to why we didn't become WeWork, right? And by the way, WeWork visited our space, took the inspiration and took it into inform— to help inform their model, and they went on to do that. Right. So, yeah, which I felt very stupid about for the longest of times.

Um, right. And now, and who's laughing now? In the fullness of time, yeah. Yeah.

Although he took home about $3 billion.

Yeah, he did not do— but don't cry for me, Argentina. Adam Newman, I agree. But hang on, I want to back up. So I love sort of the, the story here and also how organic it was. I also love how you were the CEO because you were more emotionally intelligent. Obviously all that work with the chickens and the dogs from your early, from your early childhood. But as, as you said, textbooks would not tell you to do this. And in fact, my own book, From Startup to Grownup, would tell you don't do that. And so I'm curious, what are, you know, sort of, it sounds like you didn't have hardly any conversations about roles and responsibilities and kind of vision for the future. You just went with it. And there's, there is a magic to just kind of going with it. But did you have any conversations early on to kind of get rooted in your partnership?

Definitely not in the partnership, right? I mean, I mean, look, yes, I'm sure we talked about it, but it was all in like, okay, where are we going to sit and what are our roles around running this real estate rental business, right? I mean, that was the level of it. And, and in terms of vision for the future, we had all these grand ideas or possibilities, but it was all very abstract, right? Because, because none of us had really ever done that journey. But well, that's, that's not true 'cause I had started these things and Matt and Brad had started their things. And so we had like a sense of it, but it, you know, that zero to one phase is so sort of raw and it's so primordial in what can, what can happen. And every decision can have these impacts. Yeah. And I think the way I did it was I brought my Wharton sort of spreadsheet to it and I was like, what's they grounded in now? Because the one thing I do know is that if this idea that we're working on right now doesn't work, we're, we're gonna have a really hard time doing anything else.

Yeah.

One idea was that we were all just gonna take space in that, in this coworking space we were building and then start our own re— the real ventures.

Yeah.

Right. So that was the level of which, of the amorphousness of it now. Yeah. I bet you, if you asked the 3 people and, and, and the other early people that were there, they might have all said, oh, I thought this was going to happen, or we definitely talked about that. But I think this idea of pictures in your head that everybody's coming with a different picture is something that I think is, you know, I learned a lot from. And as I talk to entrepreneurs now, I think understanding the pictures they have in their heads and the ones, especially the ones they're not saying, are sometimes the most important. I was going to say the other piece of it is, this is something I struggle with a lot, is that yes, you would not have told anyone to do it like this. Right. And yet in many ways, I mean, I would say we had a much more successful outcome, you know, 11 years in the future than a lot of people who did it the right traditional way, right? Or the textbook way, or even the way that, you know, people on blogs would say that you should do it. And I wrestle with that because it sort of says that like, okay, there is a best way to have it happen. But I think there's this, this thing that nobody says is you also have to have a little magic, right? You gotta find that magic from somewhere. And now I will say that, that magic almost got crushed by our lack of structure and, and, you know, that work on that partnership early on. Yeah. And it made the first 2.5 years incredibly volatile.

Yeah.

But, and, and, you know, I can look back now and say, yeah, obviously there would be ways to avoid that. But I'm not sure if we had done that, we would have gone down the path that led to what it was.

Yeah.

And I don't need to live in that paradox of like, I don't, I don't know how to, how to talk about that.

Yeah. I totally get that. And, and I, I think that's really just honest. Like on the one hand, we made every mistake in the book and on, on the other hand, we were like enormously successful. However, there was those, there were those volatile times and I, I'd love you to paint the picture of some of those early days and the volatility in those early days.

Oh man. I mean, well, I mean the volatility was everything of like, who's gonna clean the toilet on day one? Like literally it was like that kind of stuff.

Who ended up cleaning the toilet?

Matt Bremer cleaned the toilet, but I can't remember how we made him do it, but I, I still feel bad about it. It's a lie, but I feel bad about it. He was the youngest. That was probably like netted out to be that he was the youngest, but I think he ostensibly was sort of in charge of the community. He had really did all the early work to build the community of people on rented space for us. And I mean, he must have given like 100 tours of the space before it was built telling stories about what it could be. And that really is his genius, right? Is that, and, and so that was sort of, I think that was sort of his job because he had made it his job, right? And so, and then, you know, I mean, I mean, I, I mean, it's so funny now to look back on it because I would say like, I mean, all of these little things that happened, you know, from, from that to our first employee to firing our first employee. Right. We, we, we hired someone to work the first, first, the front desk, and then we had to fire that person like, what, 2 months later realizing they weren't the right person. Cuz we had to remember, okay, fire fast.

Right. Fire fast.

Okay.

Right. We didn't know.

I, I don't think I'd ever fired anybody before. Right. I don't think anybody. Of us had. So like, right. I remember calling somebody, getting advice from somebody. I think Adam, one of Adam's people, advisors sort of said, I'll give him advice on how to fire. And I heard all these things of not what not to do, you know? And I'm like a nervous wreck going in there and doing it.

And, um, how did you do it?

I mean, you're asking me about what I did 12 years ago, and I'm sure I just sat down and said, okay, this isn't working out. I hope, you know, and I'm sure I got some like overly raw advice, like make sure she doesn't have email access already. You know, these like, corporate things that were not relevant and then tried to pretend like I was really a grownup doing that. But, you know, I think there's a lot— I think back on this time now, you know, I'm now in my 40s. We were all just kids, right? I mean, I was the oldest at 30. I mean, I think in some contexts I would've been considered an adult, right? But in terms of this, this was all, it was all pretending. Playing dress up of, of like business people, right? Yeah.

Yeah.

And it was super fun and funny and tons of amazing experiences came out of that and stories. But it's hard to take any of that seriously now other than to say, wow, we really didn't know what we were doing. And every problem that we had, we created. Right?

Yeah.

And, um, I, I, I almost have like, I have a sort of empathy and soft spot for that, that crew, right? Mm-hmm. That was just doing everything so passionately on and were so focused in using everything that we could find to try to make this successful that it actually worked.

Yeah.

But I, I, I do sometimes think that it was like in spite of our efforts that it worked, right?

Because, right.

God knows how many ways we've gotten in our own way.

Well, I'd, I'd love to hear that. I mean, I, I, you, you refer to that, like, what are some examples? Like, what was a point where you could now look back on and say, oh, that crew was getting in their own way?

A great example is when, when we started offering classes and they were working.

Mm-hmm. Right.

But everything was so raw. Like, everything was in, okay, is this aligned with what we, our spirit is? And I, you know, how are we gonna do it? And, and I mean, I remember our first long-form course. This was like the big— when it was— we went from selling tickets for a one-night class, which I sort of always described as like being like a shitty off-off-Broadway theater.

Yeah.

Because they're changing the play every night was sort of a business model. It was horrible.

Yeah.

When I was like, okay, if we need to be able to like at least get people in here for multiple weeks at a time, and then all of a sudden it could be an interesting business. And so we did that, but we were so scared of like that we would damage our reputations and they, look, maybe this was the right decision, I don't know. But that, you know, we kind of like thought about everything and, but, and then to our credit, we didn't do it. But then of course it was a disaster and like, you know, I think half the people, we were so lucky they didn't just demand their, our money back, right? Their money back. Because I think at some level they all knew we were a startup too. Yeah. And we, our hearts were in the right place. But I remember one day, I mean, this is the way that we would make, but this is the way we built it, right? So one day we had these teachers, it was everybody we could find. We didn't like to ask, like, is this person gonna be a good teacher in front of the class? Are they gonna? So one day we heard, I was like, so how did class go last night? Well, it ended after the first 30 minutes because they couldn't get the projector to work. What?. So I was like, okay, maybe we should have someone from our team who sits in the class to make sure that things like the projector work. And that created this role called the producer role. And then that was like, that became part of the operating model, right? I literally, we just did that over and over and over again. There was no intention. There was no like, okay, let's think about this ahead of time and model this out. It was like, let's figure out everything in real time and see what we can get away with. Right. I mean, that's kind of how we did it. I mean, you know, the real breaking point was, I look at the end of the day was I would say like one of my biggest mistakes that I think about all the time is among the four of us was that I was trying to keep a bunch of young men, males' egos to somehow go in the same direction. And I think what I tried to do was sort of yes everybody and sort of placate everybody and try to keep it sort of all hunky-dory. But meanwhile, like these ideas in people's heads were getting bigger and bigger, bigger. Adam, you know, Adam comes from an incredibly successful business sort of dynasty in a way. Mm-hmm. And, and, but he was carrying his own baggage with him around that of what he was going to be and how he was going to do it. And so he had tons of this weight and expectations, but he would sort of take that out on this and what he thought his role should be. Um, and I don't think I was willing to necessarily confront that, right? Well, we're gonna have to figure this out. Meanwhile, Adam and Matt and Brad were both like younger but more experienced, but in some ways more naive, right? And, and they sort of had, and, um, they had this other image of we were this happy band of pirates going and doing this. And it would get, you know, their feathers would get ruffled when all of a sudden there was this vibe of, wait, why is this guy telling me what to do? Or what, like, why are there, why is there pressure? You know, it was a very, we were just feeling it all out. And I think instead of saying, wow, this is a real problem. I think I kind of just tried to keep it at peace, right? And the reality with those kinds of problems and that is they don't get better with time if you don't talk about them. And we were fortunate. I mean, it really came to a head when we, when we got an offer for venture capital investment. You know, that was where the pictures in the heads got wildly divergent, right? I don't know, should we, shouldn't we? Everybody was sort of on the fence. We all sort of came on a spectrum of whether we should or we shouldn't take, take the money, take the funding, take the money.

Right.

And because we were, I mean, we were ostensibly cash flow positive, right? And because we were just, we were renting space, it was not, you know, hard to do that. And that was sort of the moment where it seemed like the whole thing could just already split apart at the moment where we were being offered millions of dollars, right?

Yeah.

But that was, and I would say that was where probably some of the most lasting scars came from of the whole thing was that moment and how it sort of got pushed through.

So paint, paint that picture for us. What happened and how did the scars get created?

You know, I think if I remember there were, I mean, this is so long ago. It's almost like not fair. Like, 'cause I'm like representing how other people were thinking and stuff on like, literally we were children. We were all children. But I think it came down to if we take his money, we're like basically signing up for the rat race and we won't be in control anymore. And I think the other side of it was, yeah, but then we could be potentially really built. But we, you know, and that divide, we made one decision and I couldn't tell you if it was the right or wrong decision today, even today. I can tell you, you know, with how the outcome happened literally a decade later, it was the right decision. Yeah. But I can tell you there was plenty of points along that way where I was like, man, I wish we just hadn't taken that money.

Yeah. What were some moments where you would've said to yourself, I wish we hadn't taken that money? And by the way, what you're saying is you're looking back on yourself 12 years ago. I hear you, but guess what? The listeners of this show are in your shoes 12 years ago. Yeah. And so you're speaking to them.

I'm happy to give advice from that, but I think, I think giving it the holistic perspective is actually better, right? So, um, so there were plenty of moments where the survival of GA as a— forget about going concern— as a vehicle for any kind of idea of personal success was completely like at risk and looked like it was already over. And I mean, that was basically every time we raised money from then on, right? Because every time is a— it's an existential moment and it involves legal structure and voting and And then can we get people to invest and who are we bringing onto the board? And every one of those rounds I would say was momentous and hard.

Yeah. And stressful.

And incredibly stressful.

And brought up dynamics among your co-founders.

Especially the B, the B was, I actually think that now that I'm remembering it, I think the B was the moment where it seemed like we might not make it. And I, I think, I think it was a lot my fault 'cause I think we had, We had hired some—

this is—

here's a piece of like practical advice. No matter if you're a venture-backed or not, you cannot— you will hire someone to do your finances because you don't want to do them. I'm not— I can almost guarantee unless you're like the luck— like one out of 50 companies, that person will fuck you so completely and not tell you that you are running out of money when you are. Because that first person you hire is not, is taking this job that they shouldn't take because they don't know the questions to ask.

Yeah.

And, and this will all end with you running out of money at a very inconvenient moment and having to solve it from there.

Oh my God.

I see this all. I mean, look, I'm exaggerating a little, but not by that much.

Yeah. So what happened to you guys in your beat? What do you mean?

So we almost ran outta money.

I remember you actually ran outta money.

We almost, we were like so close to running outta money. Yeah, me and Adam at that time were like, just, it was a complete war between the two of us. And it was, it was literally like, who's going to be, you know, he, he really, because he had put that initial investment in, which was like, I think it was like $200,000 or something. He, he wanted to be chairman and be at the top left of every, it was a fight about who was going to be on the top left of a fundraising slide. Meanwhile, we're running out of money. And this is sort of the, the insanity of the moment, I can reflect. And by the way, Adam and I are now like very close again. I mean, but we, and we can laugh about this now, but at the time it was life or death. It was, you know, we could have come to blows, we could have come to lawsuits. And I think it's to the nature of everyone around us that we somehow didn't do that. But it was, it was, you know, it was an intense time. And, but I would say after the bee,, and we got a new finance person in after the B, and I had sort of clung to the CEO title and the job by like the skin of my, you know, what, what do they say about the hair of the chin chin chin? Hair of the chin chin chin. I was like, literally, like by my claws had hung on barely, like almost it was the end. And that year, I think this must have been like, it was probably 2013.

Mm-hmm.

We beat our plan by like 50%. Mm-hmm. Grew by, I think, 3 or 4x.

Yeah.

And things started to get better. Yeah. Right.

Yeah.

So I, I sort of think of it, you can sort of think of it, that was the sort of founding years, right? When every good idea happened in many ways, like all the early, that, that early magic stuff happened. But every bad idea also happened, right? Every, every problem later. And some of them were, were these like structural things that had started to work out and would continue to work out over time. Um, but, but also on the business side, right? So every product idea we got really attached because our first, you know, classes were in person and worked and gave us, people paid us for them. We got so attached to that idea that even as we raised more money and we're intending to scale around the world, we didn't bother asking ourselves, is this really a scalable model for the future that's going to take us to a profitable, you know, promise role?

Yeah.

And part of it was, you know, that early stage VC game is all about your revenue top line growing, especially then. I mean, we sort of saw that almost redux and exaggerated in 2020 and 2021.

Yeah.

But in this was sort of the, that, that early first phase of it, it was that if your revenue was growing, I mean, this was in Fabri is like $100 million, right?

Yes.

And it was all on the basis of just the revenue going like this. It didn't matter that they, you know, I mean, Uber, same thing. Their revenue was growing like in a very, very steep line up into the right. And, and, you know, I mean, it is striking that even today Uber can't really turn a profit, right? Yeah. That, that sort of, that was what was created then. And we were, I think, children of that moment too. And so I, I think about it a lot now because, you know, that the, the problem of, okay, is this model profitable? The problem of, How is this going to truly scale? Was my problem later, right? And specifically mine is sort of the last remaining founding member who was the CEO who is stuck with this thing and has to figure out how to make something or get it to a finishing point or of some sort. And all of those decisions that we basically put off and put off and put off because we, as long as it makes revenue go up. Let's do it. Revenue go up. Let's do it. Revenue. Let's do it. Okay. And that works really well in those early times. And it's frankly what the VCs want, I think. But if I could go back, if I could, I think I told you this the first time we talked in, which is what I think probably what you got you to want me to, you know, do the longer form version of it. So I'll, I'll put this in light. I wish at that moment, I certainly did not have, I just told you this whole story of like what a train wreck I was as an early CEO and didn't know what I was doing. I did not have either the gravitas or even the thoughtfulness to say, we need to pause and figure out what's going to make this work well.

You're sure.

But I think if I had in the boardroom, you're sure, I think my VC would've fired me once.

Hmm.

Because that was not the idea was, oh, we have product market fit, let's go. Right, right. I understand that point of view and I think there is a time and a place for that. And I would say, and maybe it will get, again, it all worked out, right? But if I can sort of, if you can, like, it is nice to at least think for the long term. And, and, you know, as I construct these other ventures and work with startups, I, I often say this all the time is, you know, it's not necessarily bad if your model isn't scalable to them. You'd still, it doesn't mean you don't have product-market fit. It means you have to make adjustments to that. And it is way easier to make adjustments to that when your revenue is $1 million a year versus when it's $100 million a year. Yeah. Right.

Yeah.

$1 million a year is a, frankly, like a little bit of like turning up and down knobs on the, on the equalizer.

And you can experiment.

And you can expect $100 million a year. That is a full board pivot in midair and will probably lead to major, major issues.

Yeah.

At, at precisely the time when you can least afford it.

Yeah. Yeah.

And so I think, you know, and, and I, I think a cap on that, 'cause I was talking about the real challenge of this business was that it was built in real world. It was one of the magic of the biz.

Yeah.

And I think we could have kept version of that forever. But, you know, even, you know, 5, 6 years on, you know, I'm telling these stories to VCs, oh, we're gonna go be more online. And you're trying these online products. Well, you know, in March of 2020, right? We have, we're, we're now subsidiary of Adecco.

Mm-hmm. When did you, when did you get acquired?

Uh, 2018.

Okay. Yeah.

Um, we were subsidiary and you're still the CEO. I'm still the CEO. I mean, that funnel kind of like structure.

Yeah.

And the lockdowns happened.

Mm-hmm.

And it took us less than a week to turn the entire business completely virtual.

Yeah.

Yeah. Right. And frankly, the NPS of our core products went up during that period of time. Mm-hmm. We spent years and years and years being afraid of that, being cute about it, trying to innovate at the margins. Not wanting to mess with the thing, right?

Yeah.

And, and it turned out that just doing it and being brave about it would've worked just fine. Now, there's a lot of revisionist history, sure. I mean, the, it was 5 or 6 years on, the product was more evolved, the team was more evolved. We maybe had those muscles, but imagine if we had just built from day one and been patient about the revenue growth. Mm-hmm. Right. We could've been to that place with half the capital raised. Right. And, and, and I think this is what being an old bong teaches you. He's like, oh, there are these early things that when you're planting those seeds, like if you're thoughtful about it, it will work. But I can say that not being so nervous that any one single move is going to lead to me being a failure. Yeah. So first thing, progression on, yeah.

Talk about that because that's important. You know, that's in everybody's way and that was obviously in your way then. So you have this inner experience of Uh-oh, I better not, I better not screw this up. And I, we, you know, everyone's saying we can't do this. Like, what was it like to have the inner experience of afraid of being a failure and just being afraid?

Um, I mean, I think so. We were one part of the sort of founding story and that messiness that, um, I didn't talk about is we were lucky enough to, to find Jerry Colonna, um, and get to work with him, and which helped make things better. They didn't get them all the way better, but it's what I— it got us at least going in the right direction.

Yeah, Jerry Colonna, another very well-known coach and also featured in my book From Startup to Grownup. Yeah, and a very good human.

Book, which is great, and his podcasts are great, and his journey Yeah. And, um, I would say one of the things that he does so well is really he allowed, he gave permission to have your feelings about this and to have emotions and to have good days and bad days and fears and voice those fears. And so that didn't make you a worse business person. You definitely did not.

Mm-hmm.

Uh, for me, that was a godsend because I, um, you know, that being allowed to release that and to not feel like I needed to be somebody else was sort of the beginning of my journey to be being sort of the leader that I had the potential to be.

Yeah.

That I was only just scratching the surface on. And, and so we, where were we going with this? Oh, so fear. So yeah, that was sort of began that feeling of Oh, I can talk about this. I can feel that now. I think that being able to voice that, that fear, that helped a little bit. And we could all share our fears together.

So that's what you did.

You've shared, you had group discussions and you could talk about like, what are we afraid of versus, right? But what, what you, what now I think I could see is, is like, and, and Jerry had this line is where I was going with this, was that, was that it, that early startup experience brings out everybody's narcissism. Right? Everybody. And you know, it's funny because with Donald Trump, now everybody like thinks they understand what narcissism is, right? And he has a very specific, like, malignant, you know, extreme form of that is what they would diagnose— malignant narcissist— which sort of means there's no coming back from it. But the secret is, is that we all have these wounds on the inside of these injuries and these places that we feel really weak or bruised or vulnerable.. And when those things get poked, these old defenses can come out, right? And they're typically, you know, it can be a lot of different things. It could, but it can be anger, it can be aggression, it can be histrionics.

Yeah.

It can be, you know, dissociation. It can be, and there is nothing like a startup where every day is a roller coaster of I'm a success, I'm a failure, I'm a success, I'm a failure. To really bring out your most primal defenses. And the problem with those defenses is they're not, you know, they're not based in reality and you aren't reacting to what's really around you. You're reacting to what's inside your head. And the challenge of a startup is trying to separate what's real from not in a place where nothing's real. And so that, you know, that's when things get ugly because that's when things get that's when those big fights happen. That's when really strange erratic behavior starts to come out and, and your team starts to wonder what's going on.

Yeah.

All of those things are all coming from that place of like, if you could just sit down and say, wow, I am triggered right now. I'm afraid.

Yeah.

Right.

Yeah.

Yeah. Um, I'm taking that out on the people around me.

Yeah. And, and acting out, right? I think what you're saying is so important. Like, you, one gets triggered and to your point, the stress and the ups and They trigger everybody. They trigger everybody in a startup. It's such an extreme work environment. And the second thing is you don't even know why you're being triggered necessarily. Like you said earlier, you know, that you don't wanna, you don't wanna tell you what to do. And if you're not aware of that and conscious of that, then it just triggers you. Right. And then you don't even know you're being triggered. So the normal thing to do is react, yell at someone, sulk, whatever it is, is your normal behavior. And then all 4 of you are doing that. It sounds pretty chaotic.

Well, by that point, by the way, there's more than just the 4 of us, right?

Yeah.

There's some, And, and I, I do wanna say this, this is actually something really important to me. There's so much focus on founding stories.

Yeah.

Um, there's a lot of mythmaking and what I tried to do in our little founding section was like sort of, you know, almost sort of a Mumblecore kind of way, like this deconstruct thought because I think it's a lot of mythmaking and yeah, you build it up and you build it up in your own head and everyone's got this story because it becomes this important fa— you know, it's a founding part of my life story. Well, yeah.

Yeah.

But it is, it's a multitudinal thing. But those early people, those early employees are so crucial and have, I can think of the people who are part of our, you know, let's call it the first year and not everybody in that first year that we hired, but some of those people, you know, did things for the business that were formative and long-lasting and, you know, were almost played savior roles time and time again throughout the course of it. And, you know, and they did it without the same level of ego promise to themselves to do it. And I think I often think about that a lot. I mean, especially because my co-founder now is Anna, who was really one of those people in early GA. Yeah. But, you know, I think, I think frankly, one of the best things I did as that early CEO was allow that early group of people who were all incredibly smart and talented to kind of just get the same level of autonomy and authority that I wanted for myself and say, go for it.

Yeah.

And let the ones that really saw that as their calling, like embrace it and run with them. Yeah. And so I think I want to recognize those people because I think in some ways those are the people, those first hires are who makes the culture, I think in the really, really long term, because those are the people The ones that are the, the, the success cases out of that are the ones that end up hiring everyone and keeping that flame, that idea of what the business really is and the culture of that alive. Yeah.

Yeah. I think that that is so powerful that you're just saying that and giving voice to that. Um, those early people being part of the founding story.

Mm-hmm.

Yeah.

And, and it's hard, right? Because the world wants these founder stories. They, they eat it up. Right? It, it, the media wants it. It, it helps kind of keep it in a nice little box and a nice little bow. And my experience is that it is very rarely as simple as, like, there's, I, so many founding stories are so much more complicated, right? Than, than the, the public version that gets told.

Totally.

And oftentimes there will be some sort of war or battle around what founding story gets told. Um, I mean, as an example that is sort of well known, it's, it's public, but I don't know how like commonly known is, is that like Elon Musk didn't found Tesla, right? Did you? Oh, you, I didn't know that. You didn't even know that.

Yeah, I didn't know that.

Tell, tell me about that. And ended up just sort of taking over the whole thing.

Really?

I did not know that. Jack Dorsey founded Square.

Yeah, that, yeah. Oh, that's interesting. Or Twitter. Yeah, that's a whole other story.

Everybody knows that story cuz it was so top of the— that was, that's like the poster child, right?

Totally. Totally.

And you have, it's funny when I think about that story now, and you can do it with the fullness of time, you have empathy for every player in that story, right?

Yeah.

Understand where they were coming from. And, um, and I think in some ways you could think of Twitter as like the big boy version of what happened to us is that sometimes it's like the success It, it's like when, when startups, when there's nothing at stake, you know, startups can kind of meander and do all this weird nut stuff and be cool, non-traditional things.

Yeah.

All of a sudden there's something of value there, right? And not value, it, it becomes like the ring, right? The, in the Lord of the Rings, right? All of a sudden, 'cause there's value there, everything changes. The genre has changed so quickly. And oftentimes it exposes the, the sort of places of instability.

Yeah. Oh my gosh, there's so much there. I, I guess, uh, uh, you know, I appreciate that you're looking back and, and I really appreciate how much you have this sort of perspective from the fullness of time. So if you were going back to yourself and just to talk about your co-founder relationship, what would you, what advice would you give yourself and your co-founders just on that relationship part?

It's so tricky. I probably, but the, the, let's, let's assume that the bandwidth is very, very slow, right? So you can't set, you can't write paragraphs. You can say, if that, I could probably, I'd probably write a novel, right? Yeah. Here's what's going to happen. Don't do this, don't do that. And here's what you should do though. Frankly, don't do any of this. Just buy Bitcoin, right?

Don't, I'm joking, but don't, this is not investment advice.

Yeah. Non-investment advice. But I probably would say, let's say I'll go with a one sentence. I would say nothing that is bad now is going to get better by accident or get better on its own.

That's very wise.

It's most likely going to get significantly worse when there is more at stake. So therefore, therefore you need to address it.

Ah, and how do you address it?

I probably have a farm conversations where you're vulnerable.

Yeah.

And where you are prepared to hear things that you don't want to hear. Very powerful truths that you don't want to acknowledge are true. Right here.

Right here. Yeah. And I, you know, I see that, that really, that really lands for you. I guess I'm curious, you know, if it, this might be another novel for you to write, but can you picture in that journey for yourself some of the ways that you grew as a CEO?

I'm gonna divide it into a couple categories.

Yeah.

Because there's one that I, you know, we haven't spent any time on it and I think I was sort of intentional and I like it, which is the skills part of them, right? Which is that running a business is not an art or not solely an art. It is a science and there is a lot of practitioners of that and there are a lot of useful tools and frameworks and things that you can learn that make you better at it.

Yeah. Right? Yeah.

Um, this is the way that it's not like a band.

Mm-hmm.

Right? Now, it's interesting that, like, say, a weathered 60-year-old session guitar player is never gonna go and write Let It Be. Right? And there's something to that. But I would say that, that is also not to say that, you know, George Harrison couldn't have learned a ton. From those elders.

Hmm.

And, um, and so there's a ton of skills, I guess, is what I'm gonna say. And it goes on a financial— it's like things like unit economics. And, and maybe you could summarize it all under the, the first truth is that you are running a business.

Mm-hmm.

And you can't escape that. You can't run away from that. That is the truth of it. Um, the second part of that is people have done what you are doing before and you can learn from them.

Yeah.

Um, on, but that involves being willing to admit that you don't know everything and that you don't know, actually know how to do that.

Yeah.

Involves being vulnerable, which then goes back to our initial thing, which is that you have to find a way to be okay not being the smartest person in the room, not being vulnerable, being able to sit with those feelings and, and still move forward. Yeah. It's a lot easier said than done.

Totally. Okay.

So the skill side of it, you develop a ton. Yeah. Right. And, and frankly, some of it is stage appropriate, right? So, so I'm not sure, you know, one of the things, you know, I'm now the co-founder and the exec chairman of Brave Health and it's a healthcare business and we're, you know, on our Series C and, and sort of, you know, we've gone through bits of that journey, but it's a different journey. And I would say in those early stages, I really had to unlearn a lot of stuff that I had learned because when you're doing over $100 million of revenue a year and you have a global team and you can afford to hire any executive you need to do any function you need and pay any lawyers you, right? It's like all of these things take on a very different shape and you have, it's a very different set of challenges when it's early. And I find this challenge more interesting personally, but they're both, but they do go on a spectrum and they do go on a journey and the things you don't do today become the things you wish you had done tomorrow. So that's, you know, that's another way to say it. So the skills, I think I learned a ton and it made me a better, but a lot of that then I would say circles back and it comes to a certain type of confidence tempered by experience, right? Which is the, the inner work is understanding that it's okay to be myself.

Mm-hmm.

Right.

Mm-hmm.

Um, that I can be a leader, but I have to lead from my own place and lead and be comfortable with that. Mm-hmm. Right. On, on, and not lose that sort of essence of that. While at the same time there's the external side of it, and that's what the temper room comes in. Um, there is a whole, um, skill of engaging with other human beings. In different contexts, in different roles, in different power dynamics, in different moments. And being able to both be— understand myself and bring myself fully to that situation and react honestly to it and with my own instincts, but then also know how to speak to that person and converse with that person, both so I can be heard.

Mm-hmm.

And I think maybe even the more important thing is so that I can hear what that other person's So, mm-hmm.

Mm-hmm.

And I think what I would say is all of that goes under the heading of being comfortable enough in your own skin to, to be present in the, in the conversations you're having and in the business that you're actually running and the problems that you're actually trying to deal with. That's sort of the, the overarching point of it. But a lot, there's a lot of little bits along the way. Yeah.

Yeah. Is there, is there one bit that you could just say sort of tangibly? One little bit?

Yes. Probably the best thing I, I got better at as a CEO was to learn to trust my instinct that when something was wrong, it was actually wrong. But that little spidey sense that no one else could have. And the other thing is, is to understand that as the founder and as the CEO, I have a vantage point and I have permission to be a little neurotic with my early warning sensors about what's gonna be wrong and how it might be best fixed. And that's okay. I have perm— you have a certain latitude and learning where those latitudes are and aren't, it was part, I think, of the journey. Yeah. But, but you have to be able to trust your instincts. Yeah. That's not to say that you're allowed to be a jerk to everybody because you're right, or that because every win that you have has to be followed by your entire team. And I probably erred a little bit on like, wow, I have all these people around there. They're all experienced. Like, what can I even offer at this point?

Mm-hmm.

And a lot of it was me finding my own confidence in my own seat and being like, it is okay, but I am the CEO. I'm allowed to be here. I'm allowed to have opinions. And in fact, in this seat, my opinion matters more than everyone else's.

Mm-hmm.

Yeah. That's okay.

Yeah. Yeah.

And I find with most young CEOs, at least the ones that I choose to work with, which tend to be a little bit, maybe a little more thoughtful and conscientious because of who I am, but I tend to have to give that message over and over and over again. Right.

Yeah.

You're allowed to do that.

Right. Yeah. Yeah, that's super powerful. I was just, I moderated a panel at Collision, the tech conference, and there was a, was so-called the Unicorn Panel. And both of these so-called unicorns said that there is a sense that you have as the founder CEO and that it just require, it, it causes you to zoom in all of a sudden. And people around you may not like it and may not understand where it's coming from, but you know. And when, you know, when you zoom in, it just turns out to be a thing. And you really, you're saying that as well, as well as the confidence to recognize that even though people, and I just talked to a, a founder yesterday literally who said, I'm now managing people who are 20 years older than I am. And yet you, the CEO and the founder, have so much to add to that table.

And this is something, I mean, I see this all the time, you know, cuz I mean, Anna, who was really, I mean, so crucial to GA for years and years and years and became, you know, we became partners and she's the CEO of this. And, um, you know, this is a new role for both of us, right? She's used to me being the CEO. Yeah. And he told me what to do. And, and it was a whole exercise for us. And I mean, I wouldn't say we were being perfect at it of figuring out how to do this new role where I'm not gonna tell you what to do.

Right.

But a lot of my role has been to say, you're allowed to do this. You're allowed to have an opinion on this. You're allowed to piss this person off. Yeah. You're allowed to have this weird idiosyncratic quirk that no one else is going to understand because you're the CEO.

Right. Well, let, let's switch. Let's actually switch gears and talk about Brave Health. So you co-founded this with Anna, one of your former employees from GA. She's the CEO.

Yes.

You are the executive chairman. And I guess I am so curious, in addition to sort of obviously mentor— well, that's so fascinating. Like she looks to you and you're like, don't look to me, you're the CEO. So you're obviously mentoring her and helping her find her voice. But what else is different for you as now a, you know, another, it's, you know, a second time founder, but you're, let's say, a second time successful founder now with all this experience, especially with that 12-year run at GA.

I mean, I can say it's interesting because I'm sensitive even as I'm saying this, like I'm, I had my own, what I was bringing to it and Anna brought her own things to it, her own lessons on it is negotiating that, that makes our day-to-day lives today, you know, even today, 5 years into this new journey. Yeah. Is that I brought, I think, an understanding of how the game is played at every inning of it. Mm-hmm. And being able to see, okay, that matters, that doesn't matter. This matters way more than it seems like it does right now. You know, This isn't great now, but it doesn't matter. So we're not even going to worry about it, right? Like, what problems to fix, what problems to focus on. But it also created an incredible weight of a different type of expectation, right? And a desire. I wanted this to be bigger, better, the whole thing. And I mean, and I think part of this testament to you, I think Anna is like 10 times better than I ever was and is way more capable of running a much bigger organization than I was. And so I was like, let's go, let's go. You're going to be great. Like, I could do it.

Right.

And she's still getting, she was in the very beginning, like, okay, getting her orientation to it. I mean, now it's different. You know, now she has an incredible team and she's doing all the things that a CEO at that stage does. But early on, I was like, this is great. Let's go. Like, I could, might, I smell it. We're on it. Let's just do it. Let's not even, in some ways I was being the VC that I was complaining about. In that first thing, which is sort of, I think one of the lessons of all this is it all comes around. It is so much a function of role as much as personality.

Yeah.

And having a little humility around that, I think it's gone a long way.

Yeah.

So I thought, I think like the biggest thing is knowing, okay, when is this real? When is it not? Not being so insecure about, are we gonna be able to raise money? What are people gonna think? Because I think the one thing that being a second-time founder, especially a successful second-time founder, is that you can— people will write you checks pretty much just because of who you are.

Yeah.

Now I will say, I think with the fullness— now I can look back on our first couple rounds and our later couple rounds. I'm not sure that having that ability in our toolkit did us any favors because I think more and more there is a, there is a sort of formative, like pressure cooker of those early rounds that battle-hardened you for me. Mm-hmm. And I think we were a little relaxed and what, we were also in the middle of one of the craziest, longest bubbles in the history of the world. And it's, we'll never know how much was due to that. But I, I would say that, I would say the business today is in a much more you know, we have been out raising right now and I, you know, that's the successful outcome. And in our last round too, we're both sort of, as things were not quite as bubblicious, I would say we are much more battle-hardened, right? As a business, as a team, as a business model, right? Than we were previously. And so maybe that's the other really piece of advice is It, the challenges you face are where you build your muscles. Mm-hmm.

Very powerful.

And, um, I see people all the time who get hung up on the problems in their business and they feel bad about the problems in their business, right?

Mm-hmm.

And it could be anything and any challenges, but the secret is, is those challenges, like that is what it is to have a business. There's no such thing at any scale, at any stage of a business that just runs.

Yeah, that's so true. And it's so true. And that's where the, that's where you build your muscles to your point. I think that's great.

The practice of running a startup or being a CEO is the practice of solving problems.

Right.

Accepting that, right? That is your job.

That's so true. Okay. That's so true. I tell all my clients, problems, problems everywhere. Like, yep. Yep. Another day. We call it Tuesday.

If you, you and I, I could caught myself doing that during the years of GA of like catching myself fantasizing about some moment, right? Where everything's just running, humming perfectly and everything's just, you know, going as, as it should be. And you know, what would I even do about that? Right?

That's right.

And of course that doesn't happen. That's not ever going to happen. It's, it's not in the construct of what you're doing.

Right. Totally. I love it. Jake, just a couple more questions here. What do you wish you had known earlier on your journey?

I'm gonna give two answers. One's super emotional, which is to say that everyone has a leader inside them, and your job is to figure out what that— where that leader is and how to access it on, on demand. The second thing is much more practical, which is that operational finance is not anything like theoretical finance. And, um, you should take that very seriously from day one of your business. Cause I've, I've just learned that lesson over and over again. And I know, yeah, I don't think it can be stressed enough.

Enough. I love it. I love it. So you wish you'd known that on your journey. And then what advice, summing it all up, what advice do you have for founders as they embark on their journey to grow into leaders?

Give yourself permission. Um, let the world tell you what too little or too much is. Don't be afraid of— maybe it comes down to, there's an old sales saying that I like, which is that if you're not being told no, you're not asking for enough. And I kind of think that applies to being a leader as well. If you're not hitting boundaries and bumping up against things, you are not fully exercising yourself in what you cook.

I love it. Jake, what a joy it has been to talk to you. I appreciate your insights so much and also your style. It's just such a great discussion and everyone's really gonna take away a lot. So thank you.

I think, you know, I gotta tell you, like, I, I, this is probably the, the weirdest interview I've ever done. And not like, I mean, I hope it, I hope it's, listen, I, you know, I, I think like, you know, when you're media trained as a CEO, you literally are, are, Or, you know, you would have these packaged stories, right? And you would sort of say, and, and, and I, like a standup comic, I would be like sort of working on a bit, right? Okay. This is my thought on the future of education. And I would practice different ways of saying it with the goal of it being like a really tight, you know, 30-second soundbite that gets printed or, you know, gets highlighted. And so this is, um, this was like the exact opposite. This felt like almost like a shrink session. And so I appreciate it. It was fun. It was therapeutic for me. So I hope, I hope it's interesting to somebody else, but if not, I had a great time. So I'm okay.

Thank you so much. Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my my website, alisacohn.com.