Why Founders Feel Lost After a Successful Exit - Barak Kaufman - Post-Exit Founders - EP#117

When you build a company and you sell that company, you reach the milestone that many would only dream of. It ends up feeling very weird and very lonely.

My guest today is Barack Kaufman, an investor, operator, exited founder, and community builder. Co-founded Intello, a SaaS management platform, then sold that to SailPoint in 2021. Today, Barack is a partner at Vine Ventures, where he's made investments in a number of high-flying AI companies, including Wonderful, where he's now serving as the Chief Strategy Officer. I interview people for jobs for a lot of the companies I advise, and I ask them, where do you want to be 5, In 10 years, you want to go down this path, this path, or founder path? The percent that say founder now versus 5 years ago, 10 years ago, it's crazy. It's like everyone wants to be a founder.

I think founders are in many ways almost like the ultimate capitalists. You're never going to convince the real founder entrepreneur to not do it. Either they really want to start something and they will, or they just won't. But it's hard as shit. And like, you got to know what you sign up for.

Today's episode is a special one for me. My guest today is Barack Kaufman, an investor, operator, exited founder, and community builder. He started his career as an investor at one of the most well-known venture firms, Insight Partners. Then he decided he wanted to try his hand at being on the other side of the table as a founder. He left and co-founded Intello, a SaaS management platform. Then sold that to SailPoint in 2021. My company, BetterCloud, was also a SaaS management company. So Barack and I competed with each other for a number of years, and I'm lucky that we did 'cause it led to the friendship that we have today. After he sold his company, he was looking for other exited founders that he could bounce ideas off of and get advice from about what to do next. That personal need is what drove him to start PEF, or Post-Exit Founders. In 4 to 5 years, it's grown to over 7,000 members across 12 countries and 4 continents. Every single one of the members came through referral. I'm in PF and it's hard to describe the power of the network and the willingness everyone has to help in any way that they can. Today, Barack is a partner at Vine Ventures where he's made investments in a number of high-flying AI companies, including Wonderful, where he's now serving as the Chief Strategy Officer. Barack Kaufman, welcome to Not Another CEO Podcast.

David, that was awesome. I gotta take your air with me. We're off it.

I think, I think, you know, this feels literally like 2 years in the, in the making. I, you've referred a lot of the guests that I've had on and we know each other really well. So I'm excited to do this. I'm, I think we should start with a different question than I would usually ask because you have such a wide array of things that you're doing today. Maybe we just start with like, tell me what you're, in your own words, tell me what you're doing today.

Yeah, well, firstly, I just want to thank you for the friendship and partnership and mentorship over the years. You say 2 years in the making. I really kind of view it almost like 10 years in the making. I feel like you're the kind of person that so many of us have turned to for advice throughout, and you always somehow find time, and now you're able to put it out there in the world. So awesome job with this podcast.

Thank you.

And thanks for inviting me. Now, how do I spend my time now? I spend nearly all my time at the moment as Chief Strategy Officer at Wonderful. So just to kind of back up for a minute, as you mentioned, I started as an investor, growth investor, then I founded a company, exited that company, had a lot of questions, which led to starting a group chat for a few exited founders that were helping me and turned into PEF community. I went back to investing, but early stage investing at Vine. I actually don't enjoy investing even though I'm a partner at a venture fund, which I'm honest and real about. I still identify very much as as more of a founder than as an investor. The part that I don't like about investing is more doing all the pitch meetings to then decide what you're gonna move forward with. And if you're a good investor, saying no 95 or 99% of the time. So I structure my time a bit differently. I try twice a year to find exited founders, usually Israeli exited founders, which is where I spend most of my time, and help them build generational companies, try to get involved as early as possible, often pre-idea, and try to partner with them. With Wonderful, I didn't get involved pre-idea, but I was the first institutional investor in the company through Vine and supported from more of a board capacity for the first 9 or 10 months of the company. And then saw how special it can be and decided the most important thing I can do for myself, for Vine, for Wonderful, for Israel as a country that I care a lot about, was to help turn Wonderful into an applied AI leader. And so far it's working, but we have a lot of work still ahead of us.

Can you quickly just say what Wonderful does?

Yeah, so Wonderful is an applied AI company. We have an AI operating system to build, manage, and optimize agents, and we pair that operating system with forward-deployed teams to help enterprises get agents into production. So we started with conversational agents primarily for companies helping turn their customer-facing experiences into agentic experiences and expanded from there into back-office agents, into app replacements, and increasingly a lot more surface area that we're doing in the enterprise AI world.

Oh, I actually did not know. I knew the first part of that story. I did not know the current part of that. So it went, 'cause it was really customer service, right? Essentially in the beginning, that was like the primary use case.

Yeah, the first slide I ever saw for Wonderful, which originally started on a wall, was CX is a foot in the door. So from the very beginning, Bar and Rui, the founders of Wonderful, knew that it was never going to be a CX company. But you go back to early 2025 when Wonderful started, there were really only 2 use cases in applied AI that were really taking off. It was either coding or customer support. And they saw this opportunity to do customer experience specifically in rest of world at the time. So that means outside of North America where there weren't a lot of, at least good options for enterprises. There were local competitors, there were some, you know, big legacy companies that weren't able to kind of move fast enough. and they hit that gap and used that as a wedge to expand the scope of what we do. And so now it's grown way past that. A lot of it is because the intelligence has just gotten better and better at the same time, right? So Wonderful, I think, is, for all the founders listening, I think one of the things that Wonderful did really well was to think first principle into how they view the AI world shaping up. over the next 5 years and making sure the company is well positioned for that. And for the most part, that's exactly what's happened, right? So as the intelligence gets better, it's been a tailwind for Wonderful, right? As open source model gets better, that's a tailwind for Wonderful. Like pretty much everything that's happened, because if you are owning the customer value as the applied AI partner focused on AI transformation for large enterprises, then as the surface area of what you can do expands, so does the potential for that partnership. And so, um, the computer use agents kind of, uh, becoming more mainstream enterprise ready towards the end of 2025 really accelerated the expansion from customer experience into longer horizon workflows and rethinking agentic tasks.

Um, so you built a company, you know, same time that I was building BetterCloud, you were building Intello, and now you're, you know, There again, early stage company, of course, crazy scale and everything else, but, you know, early stage building again in this generation, this AI-first generation. What do you think is the same between building previous generation and AI generation, like SaaS to AI? What is the same and what is different?

Yeah, so I'll try to keep it concise, but maybe be a little bit long-winded because I want to make sure if you're listening, if you're an audience member listening to this at some point in the future, you kind of understand the context, right? We're recording this in like late September 2026. Wonderful got started January 25th, January 2025. So it's less than 2 years old. The company is now 850 employees across over 30 countries around the world. What's public on kind of the revenue is that we went from 1 to 70 as of a month or so ago. And so the growth has been Pretty wild, right? So yes, it was early stage, but so so you you add that context to the question, and it's like you know almost night and day, right? Like when we were building Intel, you know back in the day, it was one when you're selling SaaS, you're very focused on are you talking to an ideal customer persona? How acutely do they feel the pain that you're solving for them? And can the can the product actually position to Create enough long-term value, right? To kind of be there with SaaS management. You experienced too; it was challenging, right? Like there was a problem around SaaS sprawl, but but it wasn't always felt as acutely, and depending on who you were talking to, you got a different vibe, right? Like the the the more modern IT folks or CIOs felt it more than let's say the legacy ones. There was a lot of nuance with Wonderful. It's not the case. Every single enterprise CIO I've met anywhere in the world. there's demand for Wonderful's product, right? AI is a top 3 priority of every single large enterprise in the world. Almost all of them, if not all of them, are struggling to get AI into production. The question is why Wonderful versus why someone else, right? AI has also become one of the most competitive worlds, one of the most competitive markets in the world over the last year or so. I think Wonderful's very well positioned in that. I know Wonderful's very well positioned in that. But at the same time, like the questions are completely different, right? When you're building, it's not about trying to identify product market fit as much as it's trying to deliver value for those customers to be able to unlock additional opportunities to grow with them. And then the second part of that, just very quickly, is just the scale of the deals, right? Like, you know, the average ACV for Intello, which was smaller than BetterCloud, was about $30K per year, right? And our largest customers were very low 6 figures a year, very low, you know, in the $100,000 to $200,000 range. You know, Wonderful has already a few customers in the 8 figures a year or growing very quickly to 8 figures a year, right? For a company that's a year and a half old, and the vast majority of deals are, you know, over $1 million a year, 'cause you're looking at kind of labor displacement, you're looking at replacing kind of core tasks, and you're looking at a consumption-based Model, not a license-based model. So you're able to scale with them as you align it to value in a, in a much clearer way. So those are some of the big differences.

And the same, what's the same?

Look, building a business is still building a business, right? I think one of the things that, that we feel strongly about at Wonderful is like the company will either survive, thrive, or die. Based on our ability to attract A+ talent. I think we're living in a world where somehow that's become a contrarian take, right? We're living in a world where like, you know, debate if I wanna name names here or not, like a Lovable or a Replit is like showing off their revenue per employee and it's very impressive. I'm not trying to, you know, in any way throw shit at that, but I think at the end of the day, Like long-term value, at least within the enterprise, will come from having A+ talent on the go-to-market side, on the delivery side, how you embed yourself there. I think you see it with Palantir and a bunch of other companies. And so that is the same, right? How you find, attract, evaluate, assess, you know, top talent. A lot of that top talent is the same top talent, right? It's not even necessarily a totally different person. There's adjustments you need to make, for how you actually move into the AI world. But in high agency, high IQ, high EQ, hardworking individual can most likely provide a lot of leverage for AI-first companies. So that's the first thing that comes to mind that is very much the same. The second part is enablement, right? That comes hand in hand with the team, right? If you do believe that you're going to need to scale a team, then you got to enable that team. Now you got to do that at like 10x the speed of what you had previously, right? Because you need to make sure that you can actually onboard people around the world while your product is evolving on a week-by-week basis rapidly, like rapidly. Nobody's really figured out these problems. Like this is a very, like people's figured out enablement problems. So that part is like standard, but now you're trying to figure out how do you do that? How do you basically shorten the cycle? of what that would actually take to enable folks and do a lot more with it. And then enterprise sales is still enterprise sales, even if the contracts are bigger, right? Like how you actually engage with customers, how you actually show them that you care, how you take them to events, how you get in front of them or earn their trust, right? Like these are all things that it's not even just the same between SaaS and AI world. This is just the same between business world.

Yeah, I, so I have come to the realization now after 3 years stepping down as CEO and doing this podcast and all the stuff I've been doing, all the companies I advise, I think 80% of running companies is the same. Meaning I think regardless of the company, regardless if you, you know, if you listen to my calls talking to companies doing hundreds of millions of ARR, I'm saying like, Personal private calls. I'm advising them hundreds of millions and $10 million companies that have been around for 15 years. And like, there are things that of course are different in the AI world, but to your point, at the core, at the core, the people, the operating rhythm, they all have to evolve and for the speed, but they're the same. I mean, really, they're the same things now. And that for me has been very interesting because I think that that's what is getting lost. Today, where there's a lot of AI companies where it's like, yep, the people don't matter and it's all going to be technology. There's going to be one employee and multiple billions of dollars of revenue and just one, you know, everything else is contractors and I'm going to build this big company. And I don't think, at least for me, I don't think that that's— I think if we fast forward even in 30 years, it's going to be the same thing. Like, I think that people are going to be at the core still. Human beings will be at the core of this stuff, how you organize them, motivate them, you know, recruit them, fire them. Like, all of that stuff is is the timeless stuff. So I like that answer.

Just gotta accelerate it all, right? It's all just happening just like a—

Just faster.

It's like when you listen, for those listening to this podcast at 2x, 4x speed, it's just the real world kind of happening that way. Like when you, you know, the engineers are wonderful, like don't write a single line of code anymore, right? And I think you'll find this in most AI-first companies in the Valley and everywhere else, right? very different way that you actually build products and how you think about some of the core problems, but you still need to think about stability and security and infrastructure and all those other things. Same idea with hiring and firing, right?

Right.

The core competency for really any startup or scale-up is their agility and speed. That's why you'll win over the legacy incumbents, right? Innovator's dilemma is still a thing. It does not change. And so Now you gotta be able to compete even faster. You gotta be able to move even faster. You gotta be able to hire even faster. You gotta be able to fire even faster and make the hard decisions without, you know, all the information that you would want to have. But culture still is important in all those other parts. So I completely agree.

Yeah. I wanna talk about the post-exit founders piece because I think you have a really unique view of post-exit founder life, the mindset that people are in. I mean, in terms of onboarding people to PEF, how many, what did you do? Talk to 1,000 people, like one-on-one, I think like the first 1,000 people you met or something?

I think a little bit more. So as you mentioned, we're a little over 7,000 exited founders now. The community started, let me think about it, it started 4 years ago, a little over 4 years ago now. And as you mentioned, it's all just grown via referral. I was pretty much full-time doing PF for the first couple years where it grew to maybe 1,000 or so, a little less than 1,000. But I continued to do onboarding calls with almost every member until we were about 2,000.

Oh, I didn't know that.

From 1,000 to 2,000, I started to do group onboarding calls with about 5 members at a time. So you don't get to go as deep. into maybe what, what your follow-up question would be on some of these challenges and things. But I've probably met, uh, 2,000 exited founders, either one-on-one or in a small kind of group setting.

And what do you think is the number one thing that is common across all of those founders? Is, is there a thing that you hear over and over and over again across those founders?

There are many things I hear over and over again, uh, across 100% of them, probably not much across, let's say 95%. The biggest thing is the, identity loss, right? So, you know, when you build a company and you sell that company and you reach the milestone that many would only dream of, it ends up feeling very weird and very lonely. And it's an uncomfortable thing to say. You don't want to go call your high school buddy and be like, hey, I just made all this money and I don't know what to do with my life and I feel even more lost than I did before. And it's not that you would take it back, it's not that you would, you regret selling your company. It's just that you had this identity that you didn't even know how much of you was tied to that identity. And it's just constantly reinforced. Again, all for logical, rational, well-meaning reasons. So what does that mean by being reinforced? Like when you're a founder and you're running your company, it's the first question your mom asks you, your sister, your high school friends, like how's the company doing? You know? And then all of a sudden that's gone. And then like they start the conversation like, So how's life? And you're like, good. I don't know. Like you're not, you're just not used to it and you don't, and, and you start to realize that how much of yourself was caught up in that identity. And it's very, very hard to untangle that. Now, the other part that most people don't think about, if you have not built and sold a company, is in the vast majority of those situations, you end up in a new job with a boss. You go from being the founder of your business to Someone to report to. So if it was a private equity firm, maybe like yourself, I won't put you on the spot. Like maybe it's the new board members at the PE that you technically work for now, right? They kind of, you know, own your destiny. If you're like me and you sell your company to a publicly traded company, you have a boss, right? For me, it was the chief product officer within SailPoint and he was great, but you don't really remember what it's like to have a boss. and to have responsibilities and working now like a corporate environment that again, for me, I had a fantastic experience at SailPoint. Most exited founders I would say don't have fantastic experiences. But it's, that's the biggest change that comes to mind. There's a lot of questions on the mundane, you know, tax involved stuff. Like you never, you know, came for money and now you gotta figure out what to do with it and how to do it. There's a lot of the same mistakes that all of us exited founders make. Mm-hmm. I don't care how many times you hear the advice, like you're gonna need to make the mistakes for yourself to learn the lesson. 'Cause I did do those conversations and the full cycle of it, even myself, right? Like I got that advice, I said yes, yes, yes, kind of ignored it and regretted it later. But you get into some of that. But so there's a lot of commonalities, but the biggest thing I would say is the loss of purpose and identity.

Yeah. When I first joined PEF and it was all being done on email, there were some threads that happened during that time around loss of identity and loss of purpose that I still to this day can't believe that people were writing all these things in public to another 2,000 people. And then I was even more surprised how many people were responding saying, I went through the exact same thing. I remember those threads literally like today because it was It was right around the time for me, right? You know, right as I was kind of exiting operating and to your point, losing a lot of that identity and and purpose. I mean, that that first period of time when I stepped down, I was sitting on the couch. I mean, literally doing nothing. I mean, my wife was like, "Are you depressed? Are you like?" You know, and and you really don't know what to do. I mean, you really, to your point, it's identity and and purpose maybe more than identity. You know, really, like you're just. What am I supposed to do now? And it's interesting because a lot of the people I have met through PEF, and you and I have had this conversation, I mean, even about myself, but a lot of the people I've met through PEF, it's not only that they have that now to go start another thing is really hard because you're also not naive enough to jump. You would never have probably started the company you started in the first place again because you would have seen all the mistakes and holes and challenges and And I'm sure— I know you've talked to a lot of people about that. I mean, you guys have run kind of brainstorming idea maze stuff. Like, can you talk about that a little bit? Because I think that's, that's a pretty interesting dynamic that I, I felt, but then I didn't realize how many people, you know, felt that. And then as I started reaching out to people on PEF, I was like, wow, everyone kind of has the same— other than the crazy, crazy people, like everyone else has that problem.

Yeah. So yeah, I could talk about this for a while. So let me try to You know, collect my thoughts and share it in a way that could be most valuable to folks. So this was not your question, but one of the things that, but it's related to it. One of the things that I learned, and again, that I was, it was advice that I got that I didn't necessarily listen to, is once you're free. So this doesn't include when you're still allowed to acquire, but when you're actually done with the rest and vest or you're done with you know, whatever the cycle is, take a year off. Ideally it's 12 months. It's not 6 months, it's not 24 months, it's 12 months. And in those 12 months, you commit to yourself, you will not commit to anything. So you're committing to yourself. You, you are not going to say yes to anything. You will explore, you'll have conversations, you'll catch up. You'll like, explore doesn't just mean business ideas and catch up with founder friends to hear what they're working on. Explore means like explore yourself. Explore hobbies, read books, travel, see the world, be a parent, right? You know, focus on dating or your physical health that you never got a chance to. But tell yourself that you have 12 months. Like you, you, you need to put a time on it that will help create some urgency to kind of what you do. And you also need to put a time on it so you don't jump into something before you're truly ready. Because the biggest mistake that I've seen exited founders make is to get so uncomfortable In that in-between phase, they just jump into the next one, right? So there, there is a, a big cohort of folks that can internalize what you were, what you were saying around knowing how much harder it is to kind of jump in and do it. There's also a relatively large percentage of exited founders that just immediately say, all right, I'm onto the next one.

Hmm.

They don't stop to think about like, what were my motivations from the beginning and what, what is my goal? And like, how much do I care about the problem that I'm solving every day? Like maybe you wanted to be in the same space, maybe you don't. And again, many exit founders say, okay, what will make me have founder market fit to a VC? And so, you know, it's this, like let me jump into it. And maybe that's the answer, but I don't think enough exited founders take the time to really think about it. So that was kind of my biggest learning. And then once you get there, and again, most don't take that year off, but you know, once you start to explore, there tends to be, if you're an exited tech founder specifically, there tends to only be a few paths that most people take. There's always the small percentage of other kind of rare situations. One path is deciding to start the next company. Usually what that looks like is like, I don't know how to do anything else, right? There's something about the challenge of starting something. I know how hard it is. And so maybe you say, okay, I'm gonna do it differently. I went, I was venture-backed last time, so I'm gonna, Bootstrap and control my own destiny. Or you go the opposite way. You were bootstrapped, and you say, you know, I'm going to go venture scale outcome this time. Almost always the grass is always greener, by the way. There's there's like almost always. So you tell yourself, you know, you have some new chip on your shoulder, or you change titles. Maybe you were the CTO or COO, and now you want to be CEO. And that's kind of the chip on the shoulder that you kind of like give yourself, or you solve a problem that you are you know missionary about solving. Right? Yeah. And that's what pulls you in. Like those are all kind of different motivators for how, you know, some exit founders end up deciding to start the next thing. But really it comes down to them feeling like it's an inevitability, right? Like, I don't know what else I'm gonna do with my time on this earth. I, I, I wanna spend it doing the hardest thing I could do. The hardest thing I could do is starting a company. I know that now for sure. And fuck it, let's, let's, let's run with it. The, the other path you could go down is, is kind of become an investor. which I think we've both done in kind of different ways. Some people do it as operating partners or venture partners. Some do it as GPs. Some start their own funds and say like, that's my company, it's my own fund. There's a lot of exited founders with their own funds, right? Like that's kind of one path they take and we're gonna do it differently. And all the power to them, they do do it differently. It's just, it's how you justify the end goal of where you're trying to get to that I kind of joke about. But being an investor is another path. So sometimes people do that. temporarily to try it out. Sometimes they go all into that. The third path is like, I'm done. Like I'm post-economic and I don't want a traditional job. I don't want to be an investor. I don't want to be a founder. I don't want to be an employee. I just want to focus on family or to focus on some nonprofit endeavors that I care about. Not necessarily as a full-time operator, but to get involved in different ways, be on a few different boards. You know, sometimes the coaches and advisors fall into that and sometimes they take it way more seriously as a business and fall into kind of being a founder doing it that way, which is another kind of common path. Yeah. Then the other, what I've seen a lot in the AI world that I didn't see until the last year was a lot of exited founders take jobs, usually at like Anthropic or OpenAI or one of the big names. But I think at least for tech founders, there's a bit of FOMO. Around kind of missing out. And so they just want to be, you know, on the front lines of what's happening with AI.

Yeah. You know, one, uh, when you're saying all this, one of the founders that I've spent some time with, he told me he was exited founder, small business, but made some good money. And then he told me he started the other company pretty quickly, didn't wait that year. And he said the goal was to, after doing some, maybe some therapy or whatever, he's like, I realized that I started this company to have the feeling that I had when I exited the last company. Like the moment that he's like, I'm literally building a whole company just for the, for like that moment of time.

Dopamine hit.

When I like had, you know, for the dopamine hit. And he's like, but I'm going through all this suffering and like, you know, to, to, to go back to that, just that, that single moment. He's like, I'm sick. You know, like it's, it's, uh, it's, and I think, um, I think there, there is a lot of that. And all those paths you said, I, I think are really, um, Really clear. I think there's also something I just maybe we could talk about this because I I think there's also something there's different spectrum of exited founders, right? And even within PEF, there's a real spectrum. I mean, there are people who are billionaires, like actually liquid billionaires, and then there are people who were acquihired, you know, and and there's a pretty wide spectrum. And I think there's also kind of a there's what you just described also depends. Kind of where in that they are, right? Like, I, I talked to a founder the other day, you know, sold for a couple billion dollars, and he's probably 40 years old, and he told me, yeah, I'm retired. And I said, retired? But you're 40, you know, like, and he's like, yeah, but why? I don't want to work ever again. I don't want to work for someone. I don't want to start, you know. And he's just like, but he doesn't need to. He doesn't want to. He doesn't, you know, he's like, I'm just gonna golf. I'm like, okay. I mean, you know, to every person— I remember there was someone in one of those threads who was like, I race cars, like expensive Cars like around the world on racetracks. Like, and so some people kind of can do that and go down that path. And but there is, I think people who maybe are like people who haven't been founders before or investors, I think they feel like, I don't know, the founder archetype, it's like very glorified. I would, I guess I would say it's like it's a very glorified. I interview people for jobs for a lot of the companies I advise and I ask them like, where do you want to be 5, 10 years? You want to go down this path, this path, or founder path? The percent that say founder now versus 5 years ago, 10 years ago, it's crazy. It's like everyone wants to be a founder. It's, I think it's like held up as this thing, but, but I don't know if people realize it. Anyway, you have exposure to that, right? Because across those 7,000, there's, there's kind of, you see that, you know, is that like, what, what is your view on that?

Yeah, well, you know, a lot there. So, In terms of the kind of last comment, I think it's great that the world ideally looks up to entrepreneurs and founders. I don't know that that's necessarily a blanket state. You're seeing definitely a rise in socialist politics in both the United States and elsewhere in the world. And 'cause there's a little bit of this fairness and not all, yeah, I think founders are in many ways almost like the ultimate capitalists, which is why I think exited founders are maybe the most important persona in this world to make an impact because they can choose what they want to spend time on. They know how to solve problems. And I think entrepreneurship is the lifeblood of capitalism and GDP growth. So overall, if you're a country, encouraging entrepreneurship, turning them into heroes, I think that that's always net positive. You're never going to convince the real founder entrepreneur to not do it, right? So You know, either they really want to start something and they will, or they just won't and we'll talk about it forever, right? So if you're listening to this and you feel like, you know, that's a wake-up call, then good. I'm glad I pushed through it. You know, actions speak louder than words. You could say whatever you want, right? But it's hard as shit. And like, you got to know what you sign up for. Like, but the rewards are there. I don't think, you know, if I look at, you were mentioning, you know, how hard it is to Build, you know, manage and, and, and scale a business. Do you have any regrets starting BetterCloud?

Zero.

Exactly. And that's kind of the flip side. It's like if you polled the 7,000 exited founders and you say, did you, do you regret starting your company? I think if you also polled 7,000 failed startup founders, do you regret starting your company? I think you'll have 90% plus that won't regret it. Now, at the same time, would they start it again knowing what they know? Probably not, right? Because of how hard it is, right? So there's this weird, Contradictory sort of situation there. So now you have these executive founders, right, that also have made a lot of money, usually the ones that go kind of retired. Vast majority that I talk to describe it as I'm running my own family office. You know, that's kind of like, at least the ones that make it to that wealth level. And yeah, there's a huge difference in what exits look like. It's probably one of the bigger challenges between, with running the the PF community. Like, we felt it was actually really important not to focus on the size of the exit of the founder. Why? Because everywhere else in society, the notion is, uh, reinforced that how much you make or how big your exit was somehow dictates how successful you are as an individual. Again, with that, uh, you know, identity is tied to it. And so we didn't want to focus there. But what ends up happening when you get to 70,000 exited founders is like the conversations are completely different. So we have a separate group within PF called Ultra just for ultra high net worth individuals to talk about, you know, challenges for that. And we have different groups and forums that kind of meet around with exited founders with different scale and size of exit. And we've had to add minimum thresholds for size of exit in order to join PF because If you kind of need to work right after your exit, it's just a very different situation in life. And so we at least want to get the exit of founders that like they have a very long runway. Maybe it's not infinite, but a very long runway post-exit. And those are the kind of questions that we think our community is best set up to help answer and provide support with. So I don't know if I answered your question, but I tried.

Yeah, yeah, you did. I mean, do you think that it Across those founders of the different scale exits, do you think there is an attribute that sets them apart or set of attributes or something, or is it luck?

Whew. It's somewhere in between, right? There was actually a whole conversation in the Ultra group of ultra-high net worth individuals about this exact question. And there were very opinionated perspectives on both sides. You know, one person even calls himself lucky to remind himself every day that he's only in the situation that he's in because he got lucky, right? That he was saying he knows founders who are, have much stronger work ethic than he does, that are smarter than he is and just failed like, you know, time and time again. And he, you know, has reached, you know, real generational kind of wealth and success. So that, that's kind of one perspective. And then people on the complete opposite side, uh, where it's like, I worked harder. I, nobody thinks about how much I, I, I slaved over the company and how much I sacrificed during those years. Some people sacrifice marriages and relationship with kids, like real sacrifices as founders. And then they reach the finish line. They feel like people just look at them like, hey, I got lucky. I don't think that there's anything unique in the personality traits. of the exited founders that made it really big that says, oh, those were the ones. I think you needed to pick the right idea at the right time, the right kind of inflection in the world, have the right founding team or hire team kind of around you. So I think it's a multitude of variables that would be impossible to pinpoint. I do think that there are kind of, you know, core character traits that any successful founder needs to have, which is really high agency, really high work ethic, high EQ, not just IQ, because most of what you do as a founder, especially if you're the external-facing founder, is sales in some way, selling money, selling hires to kind of join you versus all their other options, selling customers, of course, selling partners, selling lawyers. To give you discounts on their fees or whatever else it is. So I think there are some similarities in kind of character traits, but but there's you know it's not just luck and it's definitely not just skill.

Yeah, yeah. I think that's a good way of putting it. I I as I've asked people this, some of the most successful I had Ronen Harari on the show. He's the guy who yeah started. Yeah, yeah. And he he did Paw Patrol and. Bakugan, all the stuff my kids play with. Anyway, when I asked him, you know, he wrote this book recently, great book. And when I, when I asked him about this question, it was like, he's like, I think a lot of it is luck. Like actually a vast majority of it is luck, but it's not dumb luck. It's luck that you kind of have created for yourself in some way, shape, or form, you know? And, and it was, that was a good way of putting it because I actually think that's a, that's the right thing. It is lucky. I mean, you have to get lucky with, you know, especially the exited founders. You have to get really lucky with the liquidity window at which you sell, at what the multiples are in the world, at what— if you're Miro as an example, or Airtable, you were lucky and then unlucky because you missed that window. You were lucky to start your companies when you did. You got the $600 million of ARR, whatever they got to. And then you missed the window of exiting at $17 billion and instead you exited at $1.2 billion. That's, that's luck. That's not really like a skill thing. I mean, at some point that, that's a luck thing. But again, they put themselves in the right place at the right time when they went up and, you know, they couldn't exit fast enough, you know, to, to, to catch that window. And that, that's, um, anyway, so I, I do feel like there's—

I think I somewhat— so, so on the last, so I agree with you with what you said about Vronet, right? Like you turned the Toy-Con idea into Paw Patrol. And I think like there, there's no question. luck plays a role. I wouldn't personally look at Airtable and Miro, like to chalk it up to kind of timing feels to me like a bit of a cop-out. What I mean by that is just like, of course that played a role and you can't control, you know, that there was a huge technology, you know, shift that kind of happened underneath you with kind of AI. But at the same time, you know, if you have the distribution and you have the leverage and you have the customers and you kind of got there, it's like, you know, WeWork, you can look at very similarly. Like I think the founders that I respected the most, even the ones that have kind of been through that up and down roller coaster, look at themselves in the mirror and only feel like they have themselves to blame if it didn't work out. And that's also what drives the intensity in sometimes a really unhealthy way. that you just feel accountable and you feel this level of, yeah, like control over your own destiny. And I think most founders do. And again, I think Airtable and Mirror are great successes for what they're able to build. Definitely. You know, it didn't end up working, but I hope that the founders look at themselves. If they don't feel happy with the outcome, they don't blame situations and say, you know, we could have done X, Y, and Z at this time when we saw this happening. Yeah, we didn't move fast enough. I think that would be a bigger factor.

Yeah. Yeah. I think that, I think when it's macro stuff, when it's macro stuff that you just do not, like literally don't control. I mean, I think, I think COVID is the example, right? Like when COVID hit, no one could control the outcome. Like even if you were the best founder, if you had a business like a WeWork, You have no control if your revenue goes to zero, do you? Right? I don't—

Yeah, but I actually know more businesses where the opposite happened, right? I know more of those businesses that like found ways to survive and then thrive post-COVID than knowing businesses that like took off because of COVID right? Digital health companies, virtual event management companies, et cetera. That couldn't move or pivot back into the world in the post-COVID environment kind of fast enough. And again, like I'll give you an example. In, in, there's a nonprofit I was very involved with that was playing a large role in my life prior to COVID. And it felt like in the 2 years of COVID they just were like, all right, finally get to take 2 years off. 'Cause it was a very in-person oriented kind of nonprofit. And I stopped giving to that nonprofit after. I was just like, look, you're a founder. Like, yes, it's of a nonprofit. The world shut down. It's unfair. But like, there's still people to impact and there's a way to adapt and change with the environment. That's not a time to kind of go on a spectacle of anything like the world needed you more. And so I think, you know, look, I don't mean to say it's easy. It's not easy at all to go through massive macro tectonic shifts. I mean, you see it playing out right now in the public markets, right? But there are companies moving fast in the public markets. I know you're close with the Box founder and he's doing everything he can. He's out there and he's repositioning the company. You see Palantir and how they've been able to move as a 20-year-old company, right? It's not obvious that they were gonna be able to move kind of in AI wage. You have companies like AMD, right? Sure, you could say HPE, you could say some of them got lucky because of the positioning or they positioned themselves really well. Hard to know. But I just do believe in the agency that we all have. And yes, there are always macro events you can't control. I live, I primarily, as you know, I moved from New York to Tel Aviv about 4 years ago, and now I get to experience a very, very different culture here in Israel. But the last 3 years, in Israel have been, I mean, insane. Like, you know, a normal person would call it kind of hellish sort of like environment. It has not affected the startup ecosystem here at all, right? Like, I know thousands of individuals that like juggle between being on reserves and taking their computer where they're serving in reserves to where they're going elsewhere. And so I think resilience and agency is not something that's easily taught. It's kind of like maybe something that's innate, maybe something you're kind of, that like grows on you when you're younger. And yeah, I just, I believe in the agency of founders and individuals to control the outcomes in most, the vast majority of scenarios, not all.

Yeah, I think that the resilience piece, I agree. I mean, I definitely agree I think the resilience, I mean, I had, I, as a good example of all this, I had Ryan from Convene, you know, on, as on the podcast and I've, I've become close with him since then. And he like, that's a good example actually to your point of a business that, you know, all in-person, all event space, all of that stuff went from hundreds of millions of revenue to zero, literally zero, and made it through the entire pandemic and then came out the other side and just dominating and buying companies and rolling everything up. And it's a good, it's a good, I think the resilience part though, I think that's an important call-out of the— and that resilience comes deep down. I don't think that's trained or taught or learned. That's just something, something from people's childhood, something from people's DNA. I don't know, something from people's background, something from where they live and what they've had to go through as a people. So that's a good call-out.

It's dangerous because sometimes you don't know when to call it quits. Right.

Right. That's a good— that's the other side of that. Yeah.

Yeah. It's, it's, uh, if, if you really kind of built with that, then you like, you just won't give up and you end up with a cap table that you own 3% of your company and you're building from scratch. You're like, wait, how'd this happen? Uh, you know? And so, you know, you gotta be real about the situation, make sure you're like, you know, structuring the company well to be successful in that situation. But yes, I,

yeah,

resilience can help.

I'm curious, you know, you mentioned New York and Israel and Tel Aviv. I'm curious what you see, you know, are they, how different are the startup ecosystems between the two countries? Because you spent a lot of time here, you built your company here, and then of course now you've been there and been doing a lot of investing there, working there. So what is your, what, how have you experienced that? Have you experienced any major differences between the two?

Yeah, I mean, culturally, you know, Americans and Israelis are very different. There's a lot of shared values and commonalities, but very different, especially kind of the founders and the operators. I'll try to answer it simply, and then I'm happy to double-click if you find it interesting and helpful. But I think the startup environment in New York, or really generally in the US, they have the benefit of being closer to the customers, right? Almost all tech companies, not all, but almost all tech companies sell into the US market as the largest market for software. It's who the end buyers are. And there's a certain level of cultural familiarity that you don't even realize you have if you're born and raised in the US. If you also have that network and understanding, it also gives you the ability to kind of empathize. in different ways and play to different strengths around especially matching a product to value. Because let's say you're selling to law firms in the US, if you're an Israeli company selling to law firms in the US, the legal system in Israel is completely different, right? If you've never lived in the US, you don't really understand the legal system in the US, right? Forget even being an expert, just like some basic things. So I think that's a huge advantage that specifically also the New York Tech ecosystem has even over San Francisco. San Francisco kind of live in their own bubble in many ways. I could give a couple examples, but but but generally I think that's one huge advantage that New York founders and New York tech community have. The Israeli you know startup scene, like as as I mentioned, the resilience and the tenacity and what they call chutzpah right of of of the people in Israel, including the founders and including the people that work there, is second to none. Like, you know, they just won't take no for an answer. They will find a way into every account. They're the kind of, you know, like founder and teams that you would hate to compete against. They're just like, they just, they won't stop, right? No matter what is thrown at them. And I've learned a lot through that. I didn't realize that what true intensity and resiliency looks like until I was like living here. I thought I had it, but it's just a different relative, you know, scale. And I think that's kind of the biggest difference. But what they lack though, right, is necessarily the, again, cultural nuance of how to engage in business, which again could sometimes be good and sometimes be bad, right? Like, you know, no priors, can be a really good thing to do things differently, but it can also be very harmful when you don't even realize, you know, how you're being, how you're coming off to the person that you're engaging with. So that's the biggest difference between them.

What is the talent war like there? Because I feel, I feel from what I hear, it's even crazy. I mean, it's, it's crazy. Like, for engineers in Israel.

So it really just kind of depends at, you know, what you're looking for, right? So in Israel, because 8200, which many people are familiar with, which is an intelligence unit within the IDF, within the Israeli Defense Forces that mostly focuses on computers, they're the largest unit in the IDF, right? There is, and it's growing, right? So there's, a huge amount of young qualified engineers that are technically savvy, that have worked in similar to startup-ish environments in the way that kind of IDF works. So like there's a constant funnel of hardworking, smart, young engineering talent, which is increasingly, at least from what I was finding, harder to find in the US with a little bit more coddled youth, a little bit more, less rigorous environments to kind of, you know, learn coding, et cetera. And the same happens on the experienced side, right? Like, you know, Israel's been the startup nation for a couple decades. So there's a lot of pretty savvy, you know, engineering folks. If you compare the talent war in Tel Aviv to Silicon Valley, it's, it's much better in Tel Aviv, not as intense relative to Silicon Valley. Silicon Valley, I'm hearing some insane things. I just heard of a friend of a friend who is 25, no PhD, and one of the, uh, frontier labs offered him $450 million package to join.

Come on.

Like, I, I— he's special. I've heard this person's special, But like, like crazy, crazy thing. Obviously that's, that's an outlier, but like, you know, like FDE with opening high in, in some markets, they're, they're making like $1 million per year plus, right? Like, so it, it's, it's insane what, what a few companies are able to pay. So relative to that, Israel's not too bad relative to pretty much any market but San Francisco. Everybody knows who the most talented engineers are in Israel. They've all served in the same units. They know who their commanders were. Like within 30 seconds, you backchannel reference everyone if you don't know them, uh, and you know how good someone is. And so that makes like all the known commodities, known commodities. And so the same few companies that can afford to chase those people are chasing those people. Now there's still a ceiling relative to other markets of like where that will go. Plus a lot of the most talented engineers in Israel, like They wanna make money, but to a point, and then they just wanna work on really interesting, hard challenges with people that they admire and respect. And so you, you, you have a much better chance of recruiting those people, uh, uh, in Israel than you do in, in some other areas. So those are just some, some of the differences.

Yeah. Um, do you, I wanna talk about from an investor. I know the investor is not what you do. You know, as much anymore, but you, you are a partner at Vine and you have made a bunch of investments yourself. Um, and you were at Insight before. What, what do you think it is from a founder perspective, like the founders don't understand about the other side of the table?

So first thing is I, I love supporting founders through investments. I just don't love, you know, investing. As kind of going through it day to day. And I guess partly because I am generally an optimist and I fall in love with founders. And so I've made over 100 investments in that, not including the Insight ones, just like either personally or through Vine, et cetera. And so I've—

I didn't know it was that many.

And I was running an exit founder community that almost all exited founders, but at the same, like, It's one of those pieces of advice that you get from almost all exited founders that have, you know, that are 5 or 10+ years from their exit. It's like, don't angel invest for a while or like take some time. I think that was a big mistake. I went very hard very, very, very quickly. You don't even realize how it kind of compounds. But I think what I've learned is the ability to paint a clear vision for what you're building and what you're doing and why you'll be a very important player in it is extremely important. And I think the vast majority of founders can't do that so well. And what it takes is really being able to look at yourself in the mirror and truly believe Every word that you're pitching about that vision and about you know the future for the company. I think most founders, if they were true and honest to themselves, I know that I was this way with Intel, and I would step into the room with the VC and tell a story for how we're going to build a you know ten billion, fifty billion, whatever. I mean, back then it was probably one billion dollar company. Like I don't know that I believed what truly truly believed what I was saying. I wanted it. I To be the truth. I thought it was plausible, but I don't know that I really believed it. I think the biggest thing that sets aside founders that can bring a lot of capital behind them, that can bring the best talent behind them, that can build real outlier companies is the ability to have a vision of the future that they really believe in and view their company as truly essential. and being able to be part of that future and confident that they will go do it. And if you have those 3 things, you generally can tell a really strong story. Mm-hmm. And so yeah, that, that, that's probably the biggest thing. I think the other part is that like, you know, most VCs don't really have their shit together. I think a lot of founders kind of know this, but there is way more FOMO that happens than probably should. Now it's kind of this self-fulfilling notion, right? It's like in many companies in AI era, and we live this also in kind of 2021 days where capital can be an unfair advantage, right? In a world where there's less and less moats around the product you build as AI gets cheaper and easier to build things, distribution becomes the way you create an earned moat. And therefore capital becomes pretty important in your ability to kind of go deliver and do that. And so if you are this hot commodity amongst VCs, it actually matters 'cause more capital then chases you. And so I don't think any founder or the vast majority of founders like to chase or create that like FOMO type games. Unfortunately, it's important. And so You've gotta, you know, you shouldn't just be walking into a pitch meeting kind of unprepared. You shouldn't be taking just like the cold email inbound that you get from an investor. You gotta be very tactical for how you run a process, how you turn yourself into a hot commodity. Like these are, there are known ways to playbook this and do this, but you need the right people around you, people like yourself that, That have seen this in multiple companies that can actually advise those founders for how to run their processes.

That's really good advice. I actually, that I, I talk a lot about the storytelling and I try to work with a lot of founders on the storytelling. You just said though, something that I think is really important that is probably not said enough, which is it's not the storytelling. The storytelling is the first part, believing that story and the believing the story. is I think the thing that if you've never been through it before, it's actually very hard to believe. I mean, you show up, you're like, I'm gonna create something outta nothing and it's gonna become, it's gonna change the world, gonna be worth, you know, tens of billions of dollars like that. That's a hard thing to actually believe.

Yeah.

But if you don't believe it, then the investors can feel that and the story kind of feels performative. Versus authentic. And that's such a good— I love that. I don't— of all the conversations I had, I don't think anyone's actually called that specific piece out. And I think the believing it, um, and some people really feel like they don't have the right to tell the story. And what I tell them is like, you have the right just like anyone else who told the story who has a public company today. I mean, what the— what— it's the same thing. I mean, these things got created out of nothing. And, and if you believe that And if you, you know, will you ever get there? Like the pure, like the statistical likelihood is very, very, very, very low, but you have to believe that you can, or that that's what you're gonna kind of go on the road. So that's, that's really good. And the FOMO thing is, the FOMO thing is, is so important. And it is so annoying as a founder to have to do that. Like you said, it is so annoying. You're like, I just wanna run the company. Yeah. I just want to operate. I just want to close this customer. I'm just— but you actually, for the kind of businesses we're talking about, fundraising is pretty much necessary. You know, I mean, you're not gonna be able to grow and do all the stuff that, you know, you want to do. And so I, I tell founders, like, as painful as it is, you, you're gonna have to get good at it if you're gonna go and try to deliver on that vision. So I think those 2 pieces of advice are The FOMO thing is amazing. I mean, to some level, investors can become like lemmings a little bit once you get that FOMO going. To your point, if they're following that hot thing, they'll follow it into wherever, you know, because they just want a piece of that.

I'm sure you're seeing it now. Like, now it's taken to the extreme where there are all these tranch rounds. I don't know if you've seen any of these recently, but There's one founder I just spoke with, he's gonna, it's not even closed yet, so it might even add more tranches, but it's gonna be like, it's an idea and it's like at $100 million, at $500 million, and at $1.2 billion all closing at once. It's crazy, right? Like there's basically the, what's also happened in venture that I don't know that all founders kind of recognize is like there's always been a focus on quality. There's always been this power law dynamic in kind of venture outcomes where like the top companies kind of return it. But the general belief is that it's going to be accelerated even more in an AI world where like the 0.1% will actually grab the vast majority of kind of winners. And so, you know, all these VCs are now chasing that next Anthropic and OpenAI. sort of like, or SpaceX sort of outcome. And so when they feel like they have it, they can kind of justify those valuations because like they're playing for a few trillion in exit outcome.

Right.

And so yeah, there's a real flight to quality. And so you, you know, if you have a chance to become one of those like really optimized, you don't need to say yes to the Tron trial. There's pros and cons to that, but You want to be able to have offers for the Toronto Raptors to turn down if you choose not to. Like that, that, that should be that goal. And if you truly believe, to your point, like you need to believe that in 5 years you'll be there. Like you might say you don't have the right to be there. That's great. You should be humble and real about, you know, what you need to do to kind of get there. But you need to believe that you will get there, that you will get there, not that you can get there, but that you will get there. Just you need to believe it. Nobody else.

Last question for you: Knowing everything you know today, all the experiences that you've had and and everything else, what is the one piece of advice you'd go back and give yourself before you started your first job ever?

None of this really matters, Peter. Don't, don't, don't, don't take yourself or your job or anything too seriously. Be a good person, be a kind person. Recognize that karma is important. Good things will end up happening, you know, for you. It doesn't mean that you can't go after challenging things. Doesn't mean that you can't work hard on, on hard activities, but like nothing or no one can take away who you are. And so I think most folks, including myself in my early 20s in that first job, like you put a lot of pressure on that job. You want to overachieve. You start tying yourself to your identity with all these different works as we spoke about it. And at the end of the day, your work doesn't define who you are. You define who you are and how you carry yourself is way more important. How you make people feel is way more important. Than what you do.

Good way to end this. And I think I would say that 100% of people— you may not know this, I'm sure you do, but 100% of people who come across you feel that like you've made a big impact in their lives and that you're an amazing person. I was just with someone, a common friend earlier, and They said, man, Barack is like something special. And anyway, you hear that over and over. So I'm proud to call you a friend, happy to call you a friend, and thank you for doing this with me. And I know you've been super busy traveling all over, so sorry we couldn't do it in person, but it was just as good. So thank you.

That means the world to me. I feel the same way about you. Thank you, David, for having me on.

Awesome. Thank you everyone for listening. If you enjoyed, which I hope you did, please share this out with your networks and we'll see you for the next episode of Not Another CEO Podcast.