5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman

30:57And so now to actually kind of share that story, right? Like, so I, you know, University of Michigan for college, studied business, partly because that was the most obvious path to do that. I was very fortunate to work at UBS on the sales and training floor for two summers, just like as an intern. But like, usually those are the internships that, you know, the people I was working with were MBA interns, or they were towards their undergraduate degree. And it helped me realize that I don't want to do that. I was making really good money at a very young age. And I realized that I spent most of that time looking at the clock for how much money I was making per hour for the end of the day to go home and be done with it.

31:40The actual work was really, I mean, I use this word a lot around what drains my energy or gives me energy, but like really drained my energy. And I was fortunate to kind of just explore something totally different. Went to Israel for a bit, worked at a startup accelerator there, got a feel for startups and like fell in love. But I didn't, I wasn't ready to kind of jump into starting something. I did some small things on the side in college, but I wasn't really ready to start something because I didn't have the risk tolerance because of going back to that financial anxiety and wanting to provide.

32:15And so the default was like, what about venture capital? But venture capital, you know, this is 2012, 2013. Like it was not easy to get a job in venture capital, especially straight out of school. I actually accepted a job at a consulting firm at very last minute. Insight Partners, who's one of the largest VC firms in the world, actually came to recruit on campus for the first time. Long story for how that happened. Got the job. Was at Insight for three years doing software investing. Great path, great people, interesting job. And I mean, this will be recorded, but it's okay. I'm at a position where I could share this.

32:54I honestly looked up, I kind of poked my head up one day. And I looked at the people that were kind of 10, 20 years ahead of me at the firm or on the same path. And not only did I not envy them, I didn't really want to be them. Yeah. So all of a sudden I woke up and I was like, okay, I've got my dream job. I'm compensated very well. I can solve for that financial anxiety piece just like, you know, by staying there and you know, there's the job is interesting, but it's not really what I want to do. And I think that like that deep rooted desire to build something of my own was kind of always there.

33:35And if you think about my job, my job was like sitting across the table, selling money while the other person was like building and like, you wanted to be them. I wanted to be them. And at some point, I had this idea. I couldn't shake. And I started talking to entrepreneur, founder, mentors of mine. And they were all like, I had no fucking clue what I was going to do or what I was doing and how I was going to do it. Just go try. I was like, what do you mean? I've never had operating experience. I've never hired anyone before. How am I just going to go start a company? They're like, just do it.

34:05and yeah, I grew the courage to just like, you know, leave the investment firm, start, you know, my last company was Shlomo who runs PF with me as well. It was a software company, went through a lot of learnings and then exited in early 2021. So it was about four years from start to finish. Brilliant. Yeah, and it was a financially life-changing event. I was just turning 30 at the time So I was a pretty young age to do that. And it was the questions kind of coming out of that experience that led me to start PEF and to look for those mentors and advisors to help on the tax and wealth questions to the more existential identity purpose fulfillment.

34:52So from there to here, that's very interesting, right? Very relevant because now we're in the post-exit territory. And I think it's wonderful that you are talking about your childhood because what I've observed is that lots of post-exit founders who are going through this experience really, really well, they find that deeply fulfilling path for themselves. They find their mission. They find their tribe. At some point, they do go back to their childhood to find out who they really are because that's where we need to start, right? And that's the luxury of being post-exit, that suddenly we don't need to go find the job that our parents or somebody else thought would be the right thing for us to do, but we can finally find our own thing.

35:39And again, you and I will go back to talking about mission very deeply, but how did you find your mission? Because I love you. Can you share your mission? Because I love your mission. My mission around helping exited founders find their meaning and purpose of fulfillment? Their mission, right? Your mission is to help others find their mission. I think for me, Which is perfect. Yeah, and for me, it's really, really focused on the exited founders find their mission because I get energy from, as I mentioned, I'm biased, but I really think it's the most impactful persona in the world. Well, I am as biased as you are.

36:17I know, we both spend our time there. My mission, too. Exactly. Okay, so how did you find that mission? So first thing to note, as typical in a lot of exits, I had committed to stay at the Acquirer for a number of years. So I'd say most of the rest and vest phase for Exit Founders, I'd say the median is like four years because that's what most of them look like. But it would range from some people don't have to stay, pretty rare, some are six months. For us, it was two years, which was pretty fair. So shortly after exiting, you now have a job and you have a boss. And all of a sudden this identity that you've built up is God.

37:06And for me it was four years. For others it's 10 years, 40 years. But regardless, those four years are a long time of like this self-reinforced identity building and building. because all the people that you love that you know mean something to you it's the first question that they ask you about like whether it's your parents or your siblings or your friends from childhood like they ask you oh how's the company go because they mean well because they know that you're devoting all your time and attention to it it's like it's perfectly the right question well meaning question becomes very uncomfortable first exit and it becomes very uncomfortable because it's not just that it's not even just the question that they ask it's also that like you've told yourself that this is who you are.

37:51And so, you know, I never for, I never regretted selling. Uh, that was the right decision for us. I, I believe for, for many reasons. Um, but it was a really uncomfortable, it's a really uncomfortable time that rest invest period where you're trying to explore, you're trying to recalibrate who you are. You're trying to reset, not from a position of, as you were describing, what society or friends or your own expectations told you beforehand that you wanted, but really for yourself, what you care about. But it's hard to do because your day-to-day is still running the team within the acquirer with a boss and different expectations.

38:30So I don't think it's spoken about enough, but the rest and best period can be a really strange one where it's hard to do the full exploration that you might want to do, but you start to kind of figure it out. And that's where it started for me. I think I just started to think about what I didn't want to do more than what I did want to do. and at least at that time the the two most obvious paths that most exit founders take that are you know late 20s early 30s and and and have a exit is either they go bigger start a new company jump right in and try to build something bigger than they did last time you know now that they feel like that they can kind of swing for the fences or become investors yeah now as you've alluded to, I have become an investor.

39:21I work at a fund called Vine Ventures as a partner. And the way that that kind of came about was gradually over time where what I've really found meaning and purpose in is helping exited founders find their meaning, purpose, and fulfillment. And I still love building. I love creating something from nothing and being part of that creation. I realized that I don't care to be the person from like being in the CEO. So I actually prefer to be behind the scenes trying to be impactful however I can. But I really, really enjoy that the act of like the creation, which when you then translate that to company building life, that is the negative one to zero phase around like just figuring out what do I want to spend my energy on?

40:19It's not just for profit. It could be nonprofit. But like what is the problem area that I want to wake up every day and spend the rest of my life trying to solve? And then that's for about the individuals we're getting in. And the second part is the zero to one of getting it to a point where, okay, this is a real company. What I really don't enjoy is the one to end scaling operationally part. What I also don't enjoy is just, putting money in a company, which I did. I've done a lot of angel investments and not really being impactful. And so within Vine, I started as an operating partner, then a venture partner.

40:58Now I'm a full-time partner, but it's always been focused on just working with exited founders. And increasingly, I moved to part of the personal life side is I I moved to Tel Aviv, as you know, almost three years ago now. Born and raised in New York. It was a pretty big life change to go to the Middle East and move there in October 2022. And it's been pretty eventful. But I've found this extra meaning of supporting the country. I am a proud Zionist. and I now spend all my time from the Vine perspective with Israeli exited founders at the inception stage. So before this podcast interview, I had three different calls with Israeli exited founders today who are at that, you know, what should I do next?

41:48How should I spend my time? I start with the question of like, you know, I try to push them on like, why are they building a company in the first place? Why go back on that path? How do they think about it? who really gives them energy to be around and how they think about you know uh what they care about solving and uh and then you know two to three times a year those exit founders find the path that you know they really want to go on uh that i'm energized to be part of that in some way and i end up you know uh investing capital is my way to be involved uh but it was a it was quite a journey of trying to do that in different ways i'm trying to do it on my own as like a co-founder but without the title for a while and i just felt like it was really hard to align the the incentives expectations and everything with the founders i was working with and just you know wearing the investor hat is actually the easiest way to do it and that's how i i've ended up becoming an investor okay so so you're saying you are the zero to one person naturally right that's how you i'd say even negative one to zero more than zero to one like when you're just lost and you're trying to figure out like how do i get back to the beginning uncertainty and chaos yeah okay great uh but why not start your own company then i um i really don't enjoy the job of being a ceo and that was uncomfortable for me to recognize and say for a while because i felt like a door would close a door would close in terms of like my ability to attract people to whatever if I did decide to, you know, be a CEO.

43:25But it was really the work of like being honest with myself. The best CEOs, and I'm not a CTO, but like the best like CEOs, founders that I know who devote themselves to a mission, what they love more than anything is creating that like culture around the campfire that just brings everybody in. Like they're just like the person that they love recruiting the best people, seeing how that comes together. It's really about the one-to-end scaling that I described, then the zero-to-one or the negative one-to-zero. I think actually the best CEOs hate that stage. They hate the stage of like, shoot, what do I want to devote my time to and try to figure that out?

44:10That's actually what I enjoy. I enjoy like, I like not having a boss, but I love not having anybody report to me. I don't intend for anyone to ever report to me, you know, for the rest of my career. And that's why I don't think I would be a very good CEO. Like, I think I can be a good one, but I just don't enjoy the role. And so once I realized that, I realized I'm not going to start something on my own. So instead, how do I be an impactful, small part of the best founders that I can work with, the people that I should be working for if my life played out differently, and try to help them when they really connect to a mission that they want to go solve in the world.

44:51Do you feel you are able to focus on each business enough? Because, for example, for me, when I did a bit of angel investing, as everybody else, that's after post-exit, one of the reasons I stopped is because I realized that I'm a creative person, So I like to channel all my energy into whatever creative project I have. I want to own it. And I want to sort of have full control of it and not be distracted by anything else. And when you have several companies, for me personally, that didn't work. I felt very dissatisfied. But you seem to not be having that problem. My answer is somewhere in between.

45:35So I've done a lot of angel investing, and that turned out to be a mistake. And I think for most exited founders, they fill that void by angel investing. And look, it's part of the path. I'm not going to tell anyone what they should or shouldn't do because like we each, you know, figure that out on our own by making whatever decisions we make. But it's the most common regret. Yeah, it's the most common regret. I would agree. And usually also, I mean, I think my path is typical. I'll just talk about myself. Like my check sizes were much larger at the beginning when they became, you know, over time because you also just like start to remember, you know, practically the illiquidity and, you know, what small influence you actually have.

46:13I really don't like angel investing. I've done about 70 angel investments, which is a lot. And, you know, those won't go away. At this point, it's on an exception-only case in only exited founders that I have first-degree relationships with. And it's not about me supporting them. It's not about how I get fulfillment from doing that. It's more about just wanting to learn and be a small part of what they're doing. So when I do it, that's why. But I don't enjoy angel investing. I'm trying to actually stop entirely, but just every once in a while, there's the exception. I found that wearing the Vine hat and being a more significant investor and only doing it at the inception stage with Israeli exited founders and only doing it two to three times a year has given me the space to be impactful in the ways that I feel like I can be without feeling like I should be doing more or I'm not doing enough.

47:20enough. Uh, and it's the right level of, uh, I feel like making a difference. And so I'm new. I mean, well, we should do another podcast interview in a few years. I'll, I'll see if I'm still an investor of what's going on in my life. But like, um, so far it's been really, really good. Like I honestly, I'm, uh, I think not, I think I am the happiest I have ever been in life. I'm the most fulfilled I've ever been in life. I've got three amazing, beautiful little children that I get to spend time with. I'm able to split my time between living in the best city in the world in Tel Aviv and being in New York for the summer, which is good too, but different.

47:57And I get to help be a small part of, you know, working with the most amazing founders, builders in the world and trying to increase the odds of success for them. And I also designed it in a way that like, I try not to be a board member. I try to just be a board observer. So I'm there, but I'm not in any sort of power position. I try to be a large investor, but smaller than a couple others so that I'm not the person that they need to turn for just the capital side. I can truly be the partner, the confidant, the supporter of the exit founder and leverage it in the way that I can. So it sounds like you found your fulfillment by having the lifestyle you want and being able to spend time with your kids and doing things you love, living where you want to live, but also having the mission that you care about a lot.

48:54Yeah. Right? It's a life design thing. And I would say that, sorry to interrupt you, but even hearing it, one thing that I've really wrestled with over time and continue to wrestle with, you're just catching me, I guess, on a good day, but continue to wrestle with is like the balance and equilibrium of those things. It's uncomfortable to say, but being a dad is not enough for me. And it's uncomfortable conversation with my wife even sometimes about that because like I love my kids. I love my kids more than anything I sometimes think about like this cycle that we're all on evolution which there's something so powerful about bringing life to this world and like I you know I wouldn't trade that for anything anything and I hope and wish on everyone that they can experience that themselves because I think once you do you realize like how special that actually is but I also want to make an impact outside of that you know uh family evolutionary dynamic of like you know procreating and contributing hopefully you know and raising amazing little ones like uh and to me i've been able to uh you know get that impact in the right life design way um by being a part of you know uh these founders building their next company and running the post-exit founder community and doing things like that and it's not perfect.

50:22There's actually trade-offs on both sides in order to have that life balance. And it's like a seesaw of like, if you start being on a plane too much because you're traveling around helping the founders and you're not seeing your kids, like it's out of balance and vice versa. If I'm like, just prioritizing being there for everything for my kids and pick up and drop off, like there's not enough hours in the day to be impactful on the other side. So it's this constant balance that I actually struggle with to be very clear. But I feel like it's a right, at this stage of my life, it's the right balance for me.

50:57So can you share some of the things that helped you create this balance? Like some people have clear boundaries. Some people have something else. What works for you? I know it's a challenge. Yeah. It's a challenge for everyone. Yeah. I'll say like the first thing that comes to mind is religion. So religion is an interesting one. I grew up, you know, Orthodox Jewish. I still identify in the world of modern Orthodox Judaism. I struggle with faith and call it the, you know, faith is the belief in God. But I really see the power of religion as a construct for meaning, purpose, and fulfillment. And that's a big part of who I am and what's helped me there, meaning I observe the Sabbath.

51:47And so, you know, for one week, sorry, one day every week, I'm completely offline and fully observe it. Like, it's like I'm not on my phone, not watching TV, I'm not getting in cars. I'm Amish for all intents and purposes, right? Like, and it's amazing. And I think even for those that are, you know, non-Jewish or non-practicing, like, just observing a digital Sabbath, It just breaks you from this, you know, like pressures of the world that constantly is thrown at you. And so I think that that's been a big part of a few aspects. One, giving me the space to truly introspect. Two, giving me a guidebook for how to introspect and how to think about, you know, the meaning and purpose of myself on this earth that's bigger, that's more about the collective rather than the individual.

52:40And then three, community. like a big part of religious Judaism is that community is the support is to be able to see you know uh mentors ahead and support people kind of uh behind which looks very similar to you know what we've tried to embody and create within the post exit founder community in some ways but um that's the first thing that comes to mind in terms of what's actually helped me the second thing that comes to mind is uh the growth of the post exit founder community I've met one-on-one a couple thousand exited founders since selling my company like there's nothing like that experience of just like learning from others and seeing others pass to think about how would that you know fit with you like I you know I the the exit was was meaningful enough that I don't need to be doing anything from like the for-profit perspective everything I've built is like independent of that but going back to we're talking about you know the some of the investing side we're talking about some of uh the family side also have this post-execal family community that's like you know a lot of work uh and i actually realized for myself that like running a community wasn't going to be enough for me either which is why it's like part of this yeah holistic whole uh of how to have those like different buckets uh and yeah so i guess you know trial by fire, right support around me, religion as like a grounding construct, and then, you know, the firsthand experience of like learning from other exited founders and their journeys.

54:14Great. I want to talk about parenting, because we both know that full-time parenting is a very typical path post-exit founders take. And it's very understandable. We lose our community that was mostly in the business, and then our family has to satisfy all our social needs, really, which sometimes is unfair on our spouses who suddenly have to deal with our neediness for, you know, all that love and belonging, right? But what I noticed is that most of us only loved, like really loved doing it 100 % of the time for about a year. After a year, we all feel this kind of need to do more. So I think there is no reason to feel guilty about it.

55:07It's natural, right? So the way I see it is that, A, we satisfy this need for love and belonging within that year by being with our family. we engage in this incredibly beautiful experience of being with our kids and our spouses full-time and not being distracted. But then we naturally want to do something else because we actually want to give more, right? We have more to give. Being a parent is not all of us. We have more to give. And specifically for post-exit founders, we have so much to give because we give already. We've grown in that contribution sense, right? We are at a stage where we have a hunger for contribution.

55:54Because I've yet to meet a successful exited founder who hasn't moved from being very selfish to being this person who has to contribute a lot, right? Because we do it with our employees. We do it with our customers. If, as a business founder, you did not at some point evolve into someone who truly genuinely serves customers, the business will not be very successful. Okay, you may have a small exit, but if a business was really impactful and relatively big, it means the founder made this leap into somebody who is give first. But many of us don't realize it. What I find is that a lot of exited founders don't realize that they're much more given than they think.

56:48Yeah, I think so too. Going back to the Judaism part, the word for love to love in Hebrew is lehov. So in Hebrew, there's something called a shoresh, which is the root of every word. And the root of that word is actually to give. Have is actually to give. The more you give, the more you love. And I think that that's true in parenting for what we do with our kids and how much we give to them, the more we end up loving them. I think it's the same with the companies that we give to, the employees that we give to. I think you can actually extrapolate it to everything. It goes back to how we started this podcast where like that give first mentality is like it's so special because you will get 10 times more than you give when you have that mindset of giving.

57:40And I completely agree that like there's a lot to be taken from parenting that you can kind of apply in that in that world. And nobody should kind of box you into whatever identity and nobody should tell you like, you know, how you spend your time. So maybe full time parenting is the thing that you really find meaning for. Like I don't believe that there's one path for everyone. And so when I'm like describing it, at least this is my personal belief, like when I'm describing it for myself, it's just more about how I, you know, get fulfillment and energy. And I have met people that, you know, are exited founders that really end up getting all in on their, you know, children.

58:15And the one thing I would, I always try to push and encourage them to think about is the stages of life, right? and so that's great and wonderful but it's always important also not to get caught up in like what's in the future but to think about it you know so if you're full-time parenting and your kids are younger or you know in their teen years or they're out of their house just to think about like how much of a presence they want you to be to you and how much of a presence you will be and sometimes at least for myself I find I am the best dad I'm the best spouse that I can be when I have the meaning and purpose and fulfillment to throw myself into outside of it.

58:54100%. I know quite a lot of exited founders who focused on full-time parenting, and then for whatever reason, they continued on that path without finding another mission. And when I talk to them in year 8, 9 post-exit, and they're still only doing parenting, What I notice is that to me it often looks like it was an excuse not to deal with very difficult decisions. Like for example, should I go back to building a business? It's very scary, right? We know it's hard. When you do it the first time, you just don't know it's very hard. But to make the decision to do it again is a hard decision. And I find that some people are just kind of hiding behind the parent identity.

59:45And that's not very healthy. Yeah, and I think the parent identity is just one of the many ways that people hide. But it's so noble that it feels very comfortable to say, oh, I'm a happy full-time dad and I haven't done anything else for the past 10 years. But I find that oftentimes it doesn't come from a good place. It's important to be aware of it, that maybe we are lying to ourselves if we are just focusing on that identity. Not always. I'm not saying that as always. I'll go back to, I think what I'm hearing and I agree with is what's actually most important is using the time post exit to figure out what is your mission, what is you care about.

1:00:29Honestly, I think one of the reasons people find identities to hide behind, whether it's the parenting one or one of the many other ones, I'm a philanthropist. I'm sitting on nonprofit boards. Angel investor. Exactly. There's a lot of these that people have. Yeah. But at the same time, it's more about just like it's uncomfortable and confusing and amorphous to figure out, like, how do you do the work to figure that out? And I think it's how you're spending your time with some of the smaller sessions you're doing with people to do it. But, like, there isn't a place to turn and there isn't a playbook.

1:01:06And it's also not a comfortable question to go, you know, talk to your high school friend about. Like, you know, I made all this money and I get to spend all this time with my kids and I get to, you know, invest in what, you know, all these interesting companies. And I'm on the boards of these nonprofits, but I'm lost and confused. I don't know how, like, it's not doing it for me. I don't know how to get my energy. Your high school friend would probably say, fuck off and go figure it out for yourself. Other exit founders can really resonate with it. And there are some programs out there that people do for aspects of this, like the Hoffman process, for example, or doing deep work with a coach on your ikigai and things like that as frameworks.

1:01:53But it's less prescriptive. And I think exited founders that got to that point, they had some sort of path that they knew how to do it, and all of a sudden they restarted. started and so that's why the vast vast vast majority make the mistake of just jumping into that next company because it's actually the easiest thing to do it's actually easier than hiding behind the angel investor identity and the founder identity because at least those force you to pause in some way um jumping into the next thing without thinking about it is the the you know the most logical it's back to your comfort zone yeah which is which is so paradoxical because we as entrepreneurs, we think, oh, we are always willing to come out of our comfort zone.

1:02:36But I'm sure you see that a lot in post-exit founders as well, that the whole challenge that we face post-exit, when life suddenly becomes much bigger, not just our business, but we face everything else that we hadn't faced for a very, very long time and don't know how to deal with it, it can be so overwhelming, so scary, that it's very easy to just go back to what we think is a comfort zone. The problem is, of course, it's not a comfort zone because a startup never is, right? And that's why there are so many failures. I completely agree. I think that's why we try to create the space in the community for it.

1:03:14Go back to what is the Post-Exupounder network community today? It goes back to what is our goal. Our goal is to be the most valuable community and resource for exited founders. And so I think exited founders can be at those different stages that we've spoken about. The rest and vest, messy middle, the on the next mountain, the actively, you know. Can we slow down here? Because that actually brings me to the next section. because I'd love you to tell all of us how you see the most typical pattern and most typical paths for post-exit founders. Yeah, for sure. So the first thing to note is like, I think the journey, you know, it forks in different ways for people, but like most exited founders fall into one of three buckets.

1:04:12so one is that they're in what what often referred to as the messy middle now within the messy middle when you double click what does that mean the messy middle it's more of a feeling of like you know uh not really sure what kind of comes next so during that messy middle if you think about you know reflecting on my own journey that was like during the rest invest phase when you might still be at the acquirer maybe you left and you're taking a sabbatical which i think uh the exit founders that end up having the most clarity usually do take a somatical almost exactly one year. Yeah. Um, agreed. Yeah.

1:04:46And so it's hard to do really, really hard to do like to not get pulled into something and do something and just really give it a full year. But I think once you do, you get a lot of clarity, um, as someone that didn't do it, I wish, I wish I actually did it more. Uh, but the, so the messy middle, uh, is that kind of figuring it out phase. Then there's the, you know, rest invest. I mean, sorry, the, the, uh, next mountain phase, right? The rest part of it the next mountain of like i know what i'm devoting this next chapter to and again that can be anything like that can be parenting as we spoke about that can be starting a company that can be starting a non-profit um that could be starting your family office like but it's like okay i know what that challenge is that i'm going to be devoting my time to for the foreseeable future and that's that next mountain phase and then i think that there's actually a third phase I think most fall within either the messy middle or next mountain.

1:05:38But the third phase is like, you know, called the actively not seeking and not exploring phase. And that persona could be at different stages of life. They can be, you know, retired, but actively not like they want to spend their time on the golf course and, you know, whatever other kind of hobbies that they have. They're not seeking in terms of the messy middle. they're not spending their time devoted to something that they know that they want to they're just kind of like doing their thing um and i think pf can't really be such a valuable community to those folks maybe for friendship but like it's not really where we focus on but within the next mountain and within the the messy middle that's where we double click and then the kind of paths totally differ as i'm alluded to right like you know there's some people that go back to school because they really have always wanted to get their PhD in history and go back to get their PhD in history or we were talking about an exited founder who always wanted to be a school teacher and wanted to become a school teacher and so I think what that next mountain looks like is very different what that exploration looks like for people is very different but those are usually the two main buckets Thank you I think that's great.

1:07:03You know, at some point, I started zooming out and looking at like 10 years or even more, 15 years post-exit. What actually happens to people who make each of these decisions, right? To actually take a year or more to do a sabbatical, to pursue some kind of mission, whether it's too early or too late, it's a different question. But at least to move in that direction or to retire. But what's interesting for me is that if you zoom out and look, say, 10 years, because 10 years is what lots of people who exited a long time ago, lots of people call it a wasted decade. Because they look back and they're like, oh, what have I been doing?

1:07:46Okay, I learned something, but 10 years. So if you just think at that point, most people are not actually very fulfilled, whichever path they take. And those people who jump into a new business too early or who get crazy about investing aggressively often end up in what I call a struggling group, which is when they're much worse off financially compared to right after an exit. They're much worse socially. They're much worse emotionally. And we see drugs there and other ways how people try to... Fill the void. Fill the void or just not think about what's happening because they're in such not a good place.

1:08:36And most people, I found post-tags actually go down financially before they go up, but the struggling group doesn't go up. They keep making wrong decisions, and we can talk about why, but that is not uncommon. At this point, I think it's about 10 % and 15 % of post-exit founders that end up in that group. And the biggest one is the retired group, because lots of those who start a business early on then end up failing in that business. And that's when they join this retired group that you're also talking about. It's not necessarily that they decided to retire right after their first exit, but they got burnt.

1:09:17And then they're like, oh, I'm not doing it again. I learned my lesson. Thank you very much. I'm going to play golf. But this group, which is the biggest, I think it's about 70 % at that stage after 10 years, they are not very fulfilled either because they're missing the mission, right? Because playing golf doesn't give it to you. And then the smallest group, I call them human unicorns because actually they're not that many. It's about 10%. Other people who after 10 years, after all these challenges they face for 10 years, end up in a group where they do live the life that's fulfilling and impactful and beautiful, the kind of life everybody wants to have.

1:09:57And I find it extremely fascinating to reverse engineer what these people actually did that others didn't do. That's where the gems, the golden nuggets are. Yeah, I think it goes, I mean, to me, it goes back to the meaningful intentionality behind finding that meaning, right? Because it's like, you can tell yourself that you're finding meaning in pretty much anything that you're doing, but if you're really intentional about the introspection to identify it, like the meaning can come from a whole, like I have also met, you know, I haven't really studied it probably as close as you have, but like I've met many, many exit founders that are, you know, decades past our first exit.

1:10:38And it's not like there's one common path. I think a lot of people want like, what should I do? Right. And like, there is no answer to that. It's completely subjective based on who you are. And it requires to try to get to know yourself and figure out who you are and what you really want out of life. Because I know people that have started, you know, a hundred times more successful companies that second, third, fourth go around. And they realize at the end of the day, and fortunate, similar to you, to have some of these more vulnerable conversations, they realize at the end of the day that they are miserable because they were not there as a presence in their kid's life, as an example.

1:11:14Or vice versa. People that didn't start something and they feel like that they wasted away a decade plus because they were angel investing and being a parent. But that's why I'm most inspired by the exited founders that do things completely differently like you know uh they go into woodworking for a while or they you know um uh there was one guy that that uh ended up working on an amazon warehouse as like a uh figure because because because he wanted to you know work with his hands you know uh or farms and and farms there's a lot a lot a lot of folks also actually a lot that go into kind of you know farming and agriculture especially tech founders that kind of uh want involvement in the real world the point though is when it's like so weird so different from the path that they were on i always find myself like really admiring that the most because they made a conscious decision to explore something that they think gives them energy to figure out where it takes them and even if they go back 360 to where they started yeah yeah they they took the path yeah um yeah you know i have this uh framework for um kind of finding our uh next mission which uh goes like this that we first need to go inward right and to find those natural inclinations we have for whatever in life, right?

1:12:48But we have to go inward first. Then we need to go outward because we actually need to start experimenting with the reality. We need our findings about who we are to meet the reality. And this is when a spark often happens. And that spark, I find, sometimes is quite dangerous. Because if people at this stage two jump into a business, they're usually not ready for it. It's just this emotional thing. They see something, but they don't know why they're really doing it. But if we look at those legendary founders who created much bigger business, but also created an amazing life for themselves, every single time we see that after step two.

1:13:37They go into apprenticeship. They actually go and learn everything about that area where they had the spark. So instead of jumping into it, they take their time. And then they do very, very structured idea maze, which is not just experimenting, but actually creating a map for that maze for themselves. There's a lot of stuff that is just in their heads and they're thinking and they're learning. Like if you think about Elon Musk, right? He got obsessed about space exploration, but he wasn't thinking about doing a rocket company. He spent a lot of time pursuing that curiosity and doing lots and lots and lots of ideation, right?

1:14:25Anybody like Brian Chesky, another great example, Like he stumbled upon this idea for Airbnb by pure chance, but what did he do then? He didn't just jump into it. He actually spent a year of intense learning, like what hotels do wrong, why people don't trust to stay in other people's places, what goes wrong. So that learning is extremely important. When we skip it, then things don't work. So I think that if people take these three stages in the right sequence, then you get this founder problem fit combined with product market fit. And then it works. And every single successful story I looked at, people did these three things.

1:15:10Yeah, I think that I completely agree. I think how long that takes to do really depends on the kind of market you're going to go after and your background and the problem that you're choosing to kind of solve. and also how different that problem is from kind of where you were previously. I think the other part that, like that spark that you described, that takes the most work. How to discover that, you know, what the world needs and what gives you meaning and how that kind of comes together. Like it takes time for that spark to happen. And I think too many people actually jump to the second part of what you're saying, actually, where they'll say, oh, I did that, right?

1:15:51Like I looked at the market, I saw why it was so interesting. But they didn't spend time thinking about the spark of like, do they want this to be the last job they'll ever have? And I really encourage every exited founder that they are in this privileged position that like they should treat it as the last job they'll ever have. Like many just say, oh, I'll do it for five years or 10 years and I'll figure out, you know, after that what I want to do. It's like, why? What do you think is going to happen in five or 10 years? What, you want an extra$100 million? dollars like how is that gonna you know change your life and maybe it will but like talk to me about why that's an important goal i agree with you completely i i always get very nervous when someone tells me oh my next company i'll start i'll plan for an exit for day one and actually people come to me and say oh tell us how to plan for an exit i'm like oh my god don't do that because if you're planning for an exit you are locking yourself into this mercenary mindset and that will not make you happy.

1:16:44Actually, what I've seen again and again and again that these people never get to that exit because what happens is that they lose motivation because then it becomes very hard and if they have enough financial cushion, even if it's not huge but it's enough, they inevitably start thinking, why am I working so hard? Can I do something else? Can I do passive investing instead? If they need money or if they don't need money, they will just say, why don't I travel around the world or play golf, right? It's very hard to keep that motivation going if it's not missionary after your financial fears are addressed.

1:17:20It's super challenging. I agree. But talking about, just to illustrate your thought, you said everyone is very different and you don't know where you find it. I completely agree with you because if you look at some of those famous founders who did things right, their spark and their mission often came from very different traits of personality. So, for example, Elon Musk is all about intellectual curiosity. He has this insatiable need for learning more and figuring out something that has to do with engineering and that consistently drives him. But someone like Brian Chesky that I mentioned, he's all about relationships.

1:18:06He's all about community. He obsessed about behavioral psychology to figure out how to make it successful. And that's how he made it successful. He figured out how to help people trust each other. That was actually what he was after. And it's very different from figuring out your engineering thing. So I think for exited founders, it's very important to understand that what worked for Elon O 'Brien may be completely different. Like, Hastings is another great example, right? If you just look at his, I don't know, LinkedIn profile, you will think that he started Netflix the same year that he exited.

1:18:43But if you go and study what he actually did in that year, he also went to teach math in public schools. And then he spent all his time ideating with his future co-founder of Netflix about all these ideas. They just did it so intensely that he started, actually, Netflix in the same calendar year when he exited. And he exited for like$750 million, so it's not like he needed the money. Yeah. But in his case, it was actually the frustration about poor systems. He was obsessed about efficiency and that drove him. So you never know what will drive you unless you think about it, unless you understand yourself very well.

1:19:29What is it that consistently drives me? I completely agree. It's super important. So, Barak, thank you so much. This was absolutely amazing. We didn't have enough time, so we're doing it again for sure. We will. We need to continue, but you gave us... In person. Either you're coming to Tel Aviv, I'm coming to Miami, one of the two. Somewhere, somewhere. We'll do it again. And you give us so much food for thought and incredible gems today. Thank you. Everything you do for the world, for exited founders out there, for the resources you put out there. I'm a religious listener of the podcast and reader of all the content that you put out.

1:20:03So please keep doing it. Keep inspiring all of us. Thank you. I really appreciate you.

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