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

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Exit Paradox Podcast Notes

Episode Title

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

Podcast Overview Host: Anastasia Koroleva Guest: Barak Kaufman, founder of Post-exit Founders (PEF) Description: In this episode, Barak Kaufman shares insights gained from building a community of over 5,000 post-exit founders. He discusses the challenges faced after an exit, the importance of community, and the pursuit of purpose and fulfillment.

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Key Concepts and Discussions

Introduction to Barak Kaufman

Barak Kaufman is a successful entrepreneur and community builder, known for founding the Post-exit Founders (PEF).
His community grew organically to 5,000 members in four years through referrals only, emphasizing the power of shared experiences among exiting founders.

The Importance of Community

PEF's Mission: To support post-exit founders in their search for meaning and purpose, moving beyond mere financial success.
Community Dynamics: PEF is characterized by kindness, lack of ego, and empathetic listening. New members are influenced by the community's culture, improving their personal development.
Barak’s goal is to create a space for connection and support, encouraging members to explore their identities beyond their business successes.

Challenges Faced by Post-Exit Founders

Founders often struggle with identity crises after selling their companies, feeling lost or confused despite financial success.
The "Messy Middle": A phase where founders grapple with their next steps and purpose. Many jump into new ventures without sufficient reflection, leading to unfulfilling outcomes.
Barak emphasizes the need for a sabbatical or break to gain clarity, as many founders rush into the next opportunity without understanding their motivations.

The Three Phases of Post-Exit Founders

The Messy Middle: A period of uncertainty and exploration post-exit where founders reevaluate their identities and future paths.
Next Mountain: Founders find direction, determining what they want to focus on next, whether it’s starting a new company, engaging in philanthropy, or prioritizing family.
Actively Not Seeking: Some founders choose to step back entirely, often leading to a lack of fulfillment in the long run.

Personal Insights from Barak

Barak discusses his unique journey from investor to founder and back to investing, highlighting:
The realization that he enjoys supporting founders rather than being in a CEO role.
His commitment to helping others find their purpose, fostering a sense of community and connection among exited founders.

The Role of Intentionality

Barak stresses the significance of being intentional about one’s next steps post-exit.
He encourages founders to explore their passions and consider what they truly want out of their next chapter, rather than defaulting to familiar patterns (like starting a new company).

Finding Purpose and Fulfillment

The importance of understanding oneself and one’s motivations before diving into new ventures.
Discussion of how different founders derive their passions from distinct aspects of their personality (e.g., intellectual curiosity vs. relationship-driven motivations).

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Key Takeaways

Identity Beyond Success: Exited founders should explore their identities beyond financial success, seeking fulfillment and purpose.
Community Support: The PEF community serves as a critical resource, offering support, mentorship, and connection.
Intentional Exploration: Founders are encouraged to take time for reflection and exploration before jumping into new opportunities to ensure alignment with their true interests.
Diverse Paths: There’s no singular path for post-exit founders; each journey is unique and must be navigated with intentional thought and self-discovery.

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Closing Remarks

Barak and Anastasia agree on the importance of sharing experiences and wisdom within the community to foster growth and fulfillment among exited founders.
The episode concludes with a call to action for listeners to subscribe and share the podcast to continue building a community around post-exit entrepreneurship.

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Additional Resources

Connect with Barak Kaufman:
[LinkedIn](https://www.linkedin.com/in/barakk/)
[X (formerly Twitter)](https://twitter.com/barak-kaufman)
[Post-exit Founders Website](https://pef.xyz/)
[Vine Ventures Website](https://vineventures.com)

Connect with Anastasia Koroleva:
[LinkedIn](https://www.linkedin.com/in/anastasiakoroleva)
[X (formerly Twitter)](https://twitter.com/AnasKoroleva)
[Exit Paradox Blog](https://www.exitparadox.com/blog)

Listen to Exit Paradox Podcast:
[Apple Podcasts](https://podcasts.apple.com/us/podcast/exit-paradox/id1719806072)
[Spotify](https://open.spotify.com/show/7cC1er82lJBviXe6qjM158)

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This episode underscores the critical need for community and introspection in the post-exit journey, providing valuable insights for those navigating this transitional phase.

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Transcript

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0:00If you think what people will care about when you join is like the dollar figure of your exit, then we're reinforcing the wrong identity. That's not what PF is there for. It's there for you as a post-exit founder who is searching for that meaning and purpose and fulfillment. It's definitely what we aspire to inspire. Today's episode is a really special one for me. I'm sitting down with my dear friend, Barack Kaufman, one of the most beautiful people I know. He's the kind of friend who's always there when you need him. Barack founded the world's largest community for post-exit founders. Officially, it's called post-exit founders.

0:37Most of us just say the PEF. In just four years, the PEF has grown to over 5 ,000 members, all through word of mouth. The only way in is if a current member brings you in. Barack himself is an exited founder, and these days he's also a VC at Vine Ventures. We are about to dive into his most powerful insights on life after an exit. and hear his vision for where the PEF community is headed. I never regretted selling. That was the right decision for us for many reasons. It's a really uncomfortable time. You're trying to explore. You're trying to recalibrate who you are. You're trying to reset what society or friends or your own expectations told you beforehand.

1:23I think I just started to think about what I didn't want to do more than what I did want to do. what's actually most important is using the time post exit to figure out like what is your mission 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 it's uncomfortable and confusing how do you do the work to figure that out like you know I made all this money and I get to spend all this time with my kids but I'm lost and confused. Your high school friend would probably say, fuck off and go figure it out for yourself. Other exit founders can really resonate with it.

2:03And so that's why the vast, vast, vast majority make the mistake of just jumping into that next company. My friends, we're here to help each other make better decisions post-exit with our time, energy, wealth, and relationships. If what we share here resonates, Let us know by subscribing or following. It helps us bring on incredible guests and reach more exited founders who need these conversations. Do me a favor, hit that subscribe or follow button. We're in this together.

2:48Hi, Barak. Hey, how are you, Anastasia? I'm very well. I'm so happy to see you. And this is the most important interview I've done so far. I definitely do not believe that that is true. Having listened to a lot of your interviews, the subjects in your previous interviews are going to be a lot more interesting than this one. Well, there's a reason. There is a reason for that. Because you are the most important person in the post-exit world, in my opinion. Because you came a few years ago and created this incredible post-exit founder community, PEF. which disrupted the whole post-exit world, which was very fragmented and disorganized and didn't even exist as a world, to be honest.

3:33And I know because, as you know, by the time you created the community, I had been in that post-exit world for over 10 years. And during that time, I basically felt extremely lonely. I made every possible mistake because there was nobody else to learn from around me. I blamed myself for all these mistakes. So my confidence, my self-esteem went down. And then I finally realized maybe five, six years in that I really needed peers around me. And I started painstakingly looking for them around the world. And that took so much effort, so much time. And then when we first met a few years ago, I told you right away that I was so happy that you created the community because it changed everything.

4:18Okay. So since then, the PEF has grown even more, has created so much value for all of us. And I want us to start talking about that. Then later we'll talk about you and what you're doing now and the lessons you personally learned along the way. That sounds great. Firstly, thank you for the kind words about PEF. I definitely don't believe that I am the most important person in some ways. The whole goal of building this community and network is that it is not about me. I created this spiral that kept it going. Honestly, it does feed the ego and feel good to know that I created that to enable that impact to happen.

4:59But it's really PF, post-exit founders. It stands for exactly what it sounds like. Some people call it PEF. There's probably a 50-50 split of people that call it PEF or PF. It's this community and this network of exited founders to really learn from each other. I do very little in terms of sharing. I just try to create the space in which people can deeply connect. And so to give a little bit more context, maybe for PF, for those that are not familiar with it, PF started about four years ago now, shortly after I exited my company. And I wasn't as patient as you to wait 10 years to try to find other people to really connect to.

5:40Well, you were much wiser. I don't know if I was wiser. There's a longer story there where I think if I reflect back on a lot of my life, not just professional life, but personal life. Community has been a core part of what's grounded me and helped me through some of life's biggest challenges. I'd say the highs and the lows. Community has always kind of been there for me. And so every step that I've taken professionally or personally, I've always seeked and sought out that community of folks that I can actually learn from. And usually I try to find the people that are slightly ahead of where I am.

6:20Not too far ahead where it's hard for them to almost go back and empathize and connect, but enough ahead where they remember the challenges that they went through and can actually share their real experience, not even advice. I just like to learn from the data points of what have others done and how they have done it. And so PEF started, and I'll just share a minute on it, But PF started as originally I was just calling a handful of exited founder friends and mentors for advice, people that I respected who were a little bit ahead. And eventually, maybe after a few months, I selfishly was thinking, you know, how much easier would it be if instead of having to call John and calling David and calling Samantha, I just had all of them in the same group chat to just post a question and see what they would respond.

7:10And so I asked 10 or 12 of these founders and mentors and advisors of mine if they would be interested in meeting each other. And they all said yes. So I put them in a group chat and I hoped it would turn into something larger. I had no intention of it becoming what it's become or expectations that it would. But I hoped that it would gradually turn into this slightly larger community than 12 people. There were first degree of separation for me. And it did. it's completely been referral since then and it's more than 3 000 now isn't it it's almost 5 000 it's almost like yeah yeah so we're we're at 4 800 members now we have about 200 to 250 new members joining every month the only way to get into the community is to get referred into the community there's no we've never marketed it it's probably the most i've ever spoken about the community right now you hear about it from another friend because you're probably talking or calling at post-exit founder for advice or friendship or mentorship or co-investments or whatever it is.

8:13And they're like, oh, you should join PF. Like, what's PF? And that's what's created this viral loop. Exactly. And because it grew like this, you know for a fact that there's a need for post-exit founders to be together in a community. And I think this is exactly what changed everything because now we all know where to go for any kind of advice. And I am a member of so many different organizations, and all of them are very valuable for me, very meaningful for me in different ways. But I think that PEF stands out with its very unique DNA. And I think that when I met you, I thought, oh, of course.

8:57You know, that's just Barak's DNA. And it's so beautiful to see because when we found a company, oftentimes the company reflects who we are. And you have a co-founder, Shlomo Delizman, in this, which is important to mention, but we're talking about you right now. So your DNA is very much in the PEF. Sometimes I don't think you even realize how much because for other people it's very, very visible. and there are things that are very unique. Like, for example, there's so much kindness and lack of judgment and lack of ego in the PEF. So if somebody joins and they are not necessarily at this level of kindness and goodness as you are and some other PEFs are, they naturally get very inspired and drawn to it and they grow into better people.

9:53That's what I've seen in the last few years. And that's why people don't leave, right? That's the stickiness. You actually become a better person by being at the PEF. It's amazing to hear. I hope that that's true. I mean, it's definitely what we aspire to inspire, right? And to create better humanity. Can we quickly talk about how you actually look at growing the community? Because it's such a unique approach. Yeah. I think it's, you know, to go back to what I was saying, right? There was never an intention of it becoming what it's become. So as this has grown from this 12-person group chat on Signal at first to this community of we've got chapters in 20 cities with two chapter leads per city, organizing once a month events.

10:38There's conferences. There's experiences. There's programs. There's resources. It's like taking on a life of its own. And I think historically we've been a little bit more reactive than proactive. And we've gradually tried to make that change over the last six months to be really thoughtful and intentional as to where we want to go. What kind of members do we want to attract? What kind of programming resources value do we want to bring to those members for how it all comes together? One interesting new challenge we have is I don't think that you can have a 5 ,000 person community. community inherently means to me something that's just like deeper like that there is this level of like trust and vulnerability of the people that you can be with and i would love for that to be true with 5 000 people and we do everything we can to create that environment of trust and vulnerability but it becomes a little bit harder to you know control and so we had to ask ourselves the question um probably a year or two ago already uh do we want to cap the size of pf which i think would be a perfectly logical decision to say we want to keep this core trusted vulnerable special community the way that it is where people really get a chance to just go deeper with each other rather than more people joining or do we want to maximize our impact of the people that we can touch and also we believe help members themselves by learning from an increasing new and growing amount of other exited founders that have their own paths and journeys and we chose the latter and when we chose the latter to allow the growth to just continue you know again only referral based never through marketing but to allow that to grow we began to think about pef as less of a community and more of a network and that our goal is to build the communities within in that network.

12:33And that's where we really spend our time now. How do you get the right group of people that could connect around the right shared experience, right? They're in the same geography together, whatever it might be, to meet each other, to support each other, to be vulnerable with each other, to push through together. That's how we think about it. So network and then kind of communities within that network. It sounds like a great approach to me. lots of challenges along the way it's a social network it's almost almost a dating network we've had quite a few members that have asked for a dating uh well of course because so many companies now have co-founders who met at the pf i know lots of those yeah that's how they met and that's co-founders what about life partners right so like we've had quite a few um uh post-exit founders that you know honestly like if you think about the typical journey you're so busy building devoting yourself to whatever that company was that sometimes you know your love life or your you know life partnerships uh your sex life all of it actually gets kind of put to the side and all of a sudden you wake up and you're you know whatever stage of life whether age or wherever you are in life and you start to think about the things that you want and maybe it's companionship maybe it's kids maybe it's just fun but you're looking for other people that you can actually have that with.

13:51It's something we're trying to figure out how to support for members. Absolutely. You need a tribe. You know what worked for me in various organizations is that I look at them as the top of my social funnel. And then I just commit to spending actually years to find my people within that community. And I invest time and I invest effort to create a smaller tribe. But what's interesting is that that doesn't mean that I lose interest in the community itself. Quite the opposite. I start appreciating it even more. As I find close friends within that community, that community becomes more important. I love it.

14:31And that's just kind of how it worked for me. If I look back at the last 15 years after my exit, when I started desperately looking for people, exactly as you mentioned. And what you seem to be thinking about now is that you will facilitate that process, right? Instead of me spending years filtering through an organization, you'll find ways to help me find these people faster and have that close group. Yeah, the question is, like, how can you... It's super valuable. Yeah. So basically all of our time now, you know, PF will continue to grow and people will hopefully continue to inspire each other.

15:09But like we think about it as creating the almost intentional serendipity of it all around. Like right now the way that it works is you go to our conference chapter X and you meet people or you go to your local meetup or your messaging on the Discord and you're connecting over a shared topic. But we increasingly think about how can we personalize and curate these relationships. and it should be both like you finding the people that you're seeking for your own you know tribe or connecting on a shared major challenge and experience to push through together or just you know having fun with folks and so like we're doing a lot of different ways to try to bring those people together to be able to connect and and find the people that give you energy because you know at the end of the day just because the other 5 ,000 members are exited It doesn't mean that you want to be spending time with all of them.

16:01You start to figure out for yourself who are the ones that you actually enjoy. I love the term intentional serendipity because that's exactly what we need. Like we don't want to just be intentional. We don't want a tight kind of dating network. We actually want to have sort of a general idea of what we want, but then have an opportunity, the space and time and energy for serendipity to happen. I agree. Because that's where magic happens. Without that, you know, we can't go very far. I completely agree. It's not easy to do in this world where people revert to online interactions versus offline in-person interactions.

16:36So we really try to also invest in the in-person opportunities to me because I think that's really where serendipity could thrive. Because no matter how you're connecting online, you're distracted. You're not fully present versus like when you're there with someone in person. Yeah, and intentional serendipity is exactly what we need to find our new mission post-exit. Yeah. And we'll talk about it later because I want to spend a lot of time talking about finding a new mission with you of all people. But before we do that, can we talk a bit deeper about what kind of people you want to attract? Because you said you're thinking a lot about it and your thinking has evolved over time.

17:19So as of today, what is your ideal PEF member? Yeah. So I think we're really spoiled, right? Like I think the exited founder persona is both the most interesting persona in the world. And I know we're both pretty heavily biased there, but like the opportunity to make an impact on whatever they choose to spend their time on. I really think I don't think that there's a better persona in the world than Exit founders who have had experience, have had some level of success, have a blank canvas to explore how they want to devote their energy and time into what problems. And so it is really impactful for me, for us to be able to try to do our little part on shaping and paving the right road for these members.

18:08So that's kind of the first thing. So I think, you know, from a baseline, exited founders tend to just have a persona that I think is amazing and energizing. And what it usually embodies and what we really try to look for is like, first and foremost, a give first mentality. There's something just really special about the give first persona. And I'd say most founders kind of, it's either innate or they build that because in order to be successful in building something from nothing, at some point you start to realize that like you have this, you know, karma based energy that you want to give in the world and you've realized how you end up getting more as a result.

18:53And I think when you're post-exit and you have even more to give, you hopefully take that mindset of give first. But every once in a while, there's a member who will kind of jump in and share how they're trying to raise money for their new venture or they're looking for X, Y, and Z. And that is the wrong mindset. If you just come into the community, into the space, you explore, you meet people, you find ways to give to others. you'll get way more in return both in terms of whatever your goals are and also in general so that's like one of the biggest things we look for because it also drastically affects the community and and the value of the community kind of coming together the same thing is like this kindness right and this um this level of um empathetic listening you know there there's also um uh you You know, I guess the opposite of that empathetic listening is someone who they're usually lost in that post-exit identity.

19:56And so much of that identity is still like being ripped away and like kind of crumbling where they try to solve for it by not listening, but speaking, talking about themselves and what they've accomplished and who they are. It's like, this is not the community for you. If that's what you're looking for. Can I challenge your thinking? Please. And we talked about this before. I think your community is exactly for people like this because they need it more than anybody else. And it's your chance to help them become better people through the community. It's probably the biggest impact you can have.

20:37Not just one of them, but still. I think we're saying the same thing, but in different ways. So let me maybe rephrase what I was saying. So the first thing to note, what makes someone qualified to join post-exit the PF community? You exited a company, financially exited a company that you founded and are no longer involved with, right? So that can be you sold it to a, you founded a company. So you can't be like an early employee or even like a founding employee. Otherwise, we filter you out. You financially exited. So there was some sort of financial result of it. And you're no longer part of that company.

21:13Maybe you're at the acquirer, but you're not running it standalone and exit to be a secondary. So that's what we really look for for who qualifies. And there's a bunch of manual work to make sure people don't sneak in, but that's what we look for. What I'm really describing is what is the persona of a valuable member that we want in the exit-founder community? So does everyone that meet our criteria that join embody these traits? No. Do we aspire to have a community of people that embody those traits? Yes. And it goes back to what you were saying earlier, where there's this contagious aspect of it.

21:50When you're in this wider group community of folks as successful, if not more successful than you are, at some point, even if you take that persona of someone who just wants to share everything that they've accomplished, they very soon realize that nobody really cares. Yeah. And that's actually part of that growth. to get to empathetic listening. So what I'm really describing the traits is like, what do we look for in the kind of members that you want to be around? And I think stating it out loud, the give first, the empathetic listening, the kindness, like these are traits that therefore, to your point of like the DNA, hopefully being part of it, like that's how you start bringing this ecosystem closer together and creating an environment that people feel energized to be part of.

22:38I'm so happy that you explained the difference because for me, this lack of judgment is extremely important. Like if you were saying, oh, we interview everyone and then we decide if that person is give first or not. I wouldn't like that because that's too subjective. Right. Plus, it's perfectly normal for post-exit founders to go through a pretty nasty period when they may not be very pleasant people. I know I wasn't very pleasant for a while after my exit. Because we are dealing with so much. And sometimes we are so self-focused just because we need to address something that is very difficult for us.

23:15And we can come across as very selfish because we're so self-absorbed. And these are people whom your community is helping a lot. And they should come in, right? And should become... I completely agree. And I think it's about creating the environment that enables those people to grow as quickly as possible, to your point. I'll add one thing to it that you didn't share. So I mentioned one of our objective criteria is you financially exited a company that you founded. it we've had many members over time uh strongly encourage suggest recommend that we also include a minimum dollar threshold yeah of what does it mean to financially exit i'm sure there's someone listening to this podcast right now who um maybe they they viewed their exit as not life-changing like would i qualify for pf and the answer is yes and it's actually purposeful that we don't ask that question.

24:12We don't ask, you know, how much did you make from your exit or how big your exit was? And look, it gets clicks on podcasts and gets people interested. And also it changes your ability to think about what you want to do next. All of that is true. But the main problem it has when you ask that question to someone who's post-exit is it self-reinforces the wrong identity shift of what we have like tried to you know walk away from you you exit and everybody was talking about your company before and then they're talking about your exit after and if you're if you think what what people will care about when when you join is like you know the dollar figure of your exit then we're reinforcing the wrong identity that's not what pf is there for pf is there for the individual.

24:59It's not there for you as a founder. It's there for you as a post-exit founder who is searching for that meaning and purpose and fulfillment and everything else that comes from it. Brilliant. I love it. Thank you for explaining. Because of course, I also heard that a lot when people say, oh, you know, people have such a wide range of financial circumstances in the PEF. Do they actually speak the same language? I personally agree with you because I think our common denominator is different in PEF. It's not our finances. It's the unique experience that we have, which is emotional. Because what is a life-changing exit?

25:45That's very subjective. And I love that about PEF. And you've written about, you know, what does it really mean to, what is that, what do those numbers really mean? And I will just add, there are practical implications of that, the size of the exit that opens up or closes off what can come next. As an example, to make that more real, like if you don't have financial means to support yourself and your family for a while, you might feel this urgency and concern around that provider identity you have to go solve for that. And it limits the ability to explore and figure it out. And so there's definitely something that the money does afford, but it's not what we want to reinforce.

26:36Right, because if you are thinking of yourself now as a social network, which you should, because it's 5 ,000 people, you really are. It's not even a traditional community. then you can break it up based on, you slice and dice it in every possible way. And you can have communities for people who are dealing with exits that did not bring them financial security. They have very legitimate interests of their own. But then there can be a separate group where people are dealing with the fact that they're no longer motivated to do anything in life because they think they have too much money and they're dealing with something else.

27:13but it doesn't mean that they cannot be part of this network. Completely agree. And then what I've seen a lot is that the last category, when people finally find motivation, oftentimes they actually start speaking to those who are building companies out of necessity in the same language because then they're building a startup again, right? Then issues are very similar, right? Once they stop thinking about how wealthy they are that they don't need to do anything else in life, right? It liberates them also. Like you mentioned that the first group is not liberated because they don't have financial freedom.

27:49But the second group is also not liberated because they're often trapped in this golden cage that they created in their minds. So true. And they also may not be, you know, missionary in their mindset, but for a different reason. Right. So I can totally see how you would. Or have figured out how to be missionary in their mindset. Yeah. Or they're not ready for a number of reasons. And that's where your sort of community within your social network can be created for these people specifically to address their very unique issue, which they cannot discuss with anybody else except for people who can relate to it.

28:29Yeah, I completely agree. That's how we think about it. So now let's talk about you. And your story is fascinating for many reasons. And one reason is that it's very unusual for me for an exited founder because you started as an investor, right? Then you moved to be a founder and now you're an investor again. That's not typical at all. And I want to understand why that happened. And I'm mostly interested in your decision post-exit to go back to the investing world. Yeah. I'm going to go back to childhood even actually. Please. Because as I've, I think it's important context, I'm four and a half years past my exit.

29:14And I think I've continued to learn more every day. But, you know, if you asked me some of these questions a couple years ago, I probably wouldn't have gone back. Or even a year ago, I might not have gone back to my childhood. But I think some of the work I've done has helped me realize that that's where a lot of this starts. And I grew up in New York. I grew up comfortable, amazing, supportive parents. family community um the uh the the part that i'm really going to go back to and zero in on without going too much into my childhood is like um i grew up in a in a community where people spoke about money a lot uh people spoke about money from the perspective of like sometimes it was it was what they didn't have or sometimes it was showing off what they did have but like money was uh was was brought up a lot at like you know tables with with family and friends either you know directly or you know as like a subtext and i remember in like sixth or seventh grade um actually calculating you know to live in new york and to have a family and to provide for them and and hit the core pieces of what i want to do how much i would actually you know a family would need to be making not me but a family would need to be making or to support them it's a really young age to be to be doing that and it kind of just was like self-reinforced honestly I would say throughout my life until that exit where like I think if I trace back a lot of decisions that I had made up to that point it went back to how do I remove that anxiety that was like sitting there on like that provider identity that I had in order to do it and so now to actually kind of share that story, right?

31:00So I, 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 as an intern. But usually those are the internships that the people I was working with were MBA interns, or they were towards their end of 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 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, I 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. And so the default was like, what about venture capital?

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32:19But venture capital, you know, this is 2012, 2013. like it was not easy to get a job in venture capital especially like straight out of school um 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 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 like i honestly looked up i 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 yeah 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. 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 gonna go start a company they're like just do it and uh and yeah i grew up i grew the courage to just like you know um leave the investment firm start you know my last company was sholmo who runs pf as well it was a software company went through a lot of learnings um and then uh exited in in early uh 2021 so it was about four years from start to finish brilliant yeah and uh and it It was a financially life-changing event.

34:32I was just turning 30 at the time. So it 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. So 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're 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.

35:16They 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. And 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 exit and founders find their meaning and purpose of fulfillment.

35:56Their mission, right? Your mission is to help others find their mission. I think for me, 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. I am as biased as you are. I 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.

36:44But 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. And 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 post exit and it becomes very uncomfortable post exit 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, you know, when you then translate that to company building life, that is, you know, 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 going 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 N 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 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 Middle East and move there in October 2022. And it's been pretty, pretty, 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 exit founders today who are at that you know what should i do next how 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 who really gives them energy to be around and how do 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.

42:35And just wearing the investor hat is actually the easiest way to do it. And that's how I have ended up becoming an investor. Okay, so you're saying you are the zero to one person, naturally, right? That's how you identify. 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? You thrive on uncertainty and chaos. Yeah. Okay, great. But why not start your own company then? 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.

43:18A door would close in terms of my ability to attract people to whatever if I did decide to be a CEO. But it was really the work of being honest with myself. The best CEOs, and I'm not a CTO, but the best CEOs, founders that I know who devote themselves to a mission, what they love more than anything is creating that culture around the campfire that just brings everybody in. 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 n 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 yeah shoot what like what do i want to devote my time to and try to figure that out that'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.

44:25Like I think I'm, 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 a 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. Do 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.

45:09So 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. So I've done a lot of angel investing and that turned out to be a mistake. And I think for most exit 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.

45:51Yeah, but it's the most common regret. I would agree and Usually also I mean I think my path is typical just like by myself like my Check sizes were much larger at the beginning when they became you know over time because you're also just like start to remember You know practically the illiquidity and you know what a little what what small influence you actually have I really don't like angel investing. I've done about 70 angel investments, which is a lot. And 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.

46:34And 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 and and uh you know um so when i do it that's why but i don't enjoy angel investing i'm trying to actually stop entirely but just like every once in a while there's the exception i found that wearing the vine hat and uh 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.

47:22And it's the right level of, I feel like making a difference. And so I'm new. I mean, well, we should do another podcast in a few years. 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 oh wow 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 uh and i get to help be a small part of uh you know working with the most amazing founders, builders in the world and, uh, trying to increase the odds of success for them.

48:09And I also designed it in a way that like, uh, I try not to be a board member. I try to just be a board observer. So like I'm there, but I'm not, you know, in any, any sort of power position, I try to be a, uh, large investor, but, you know, smaller than a couple others so that, you know, I'm not the person that they need to turn for, for like just the capital side. I can truly be like the the partner the confidant the the supporter of the exit founder and 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 yeah right it's a life design thing and i would say that that um sorry to interrupt you but even even hearing it one thing that i've really wrestled with over time i continue to wrestle with you're just catching me i guess on a good day but continue to wrestle with is like uh the balance and equilibrium of those things it's uncomfortable to say but being a dad is not enough for me and uh and it's uncomfortable conversation with my wife even sometimes you know about that because like i love my kids uh um i love my kids more than anything i sometimes think about like this cycle that we're all on as evolution which there's something so powerful about bringing life to this world and like i i you know uh i want to trade that for anything anything and i i i hope and wish on 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 yeah 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 by being a part of these founders building their next company and running the post-exit founder community and doing things like that.

50:20And it's not perfect. There's actually trade-offs on both sides in order to have that life balance. And it's like a seesaw of if you start being on a plane too much because you're traveling around helping the founders and you're not seeing your kids, it's out of balance and vice versa. If I'm like, you know just prioritizing being there for everything for my kids and pick up and drop off like there's not enough you know hours in the day to be impactful on the other side so it's this constant balance that i actually struggle with to to be very clear yeah um but i feel like it's a right at this stage of my life it's the it's the right balance for me so 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 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 i grew up you know orthodox jewish um i still identify in the world of modern orthodox judaism um i struggle with faith in call it the you know faith is the belief in god but i um i I really see the power of religion as a, as a construct for meaning purpose and fulfillment.

51:41And that's a big part of who I am and what's helped me there. Meaning I observed the Sabbath. And so, you know, for one week, we're sorry, one day every week, I'm completely offline and fully observe it. Like I'm, it's like, I'm not on my phone. I'm not watching TV. I'm not getting in cars. I'm Amish for all intents and purposes. Right. Like, and, 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, like 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.

52:23One, 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. And then three, community. Like a big part of religious Judaism is that community, is the support, is to be able to see mentors ahead and support people kind of behind, which looks very similar to what we've tried to embody and create within the post-exit founder community in some ways. But that's the first thing that comes to mind in terms of what's actually helped me.

53:02The second thing that comes to mind is the growth of the post-exit founder community. I've met one-on-one a couple thousand exited founders since selling my company. That's crazy. There's nothing like that experience of just learning from others and seeing others' paths to think about how would that fit with you.

53:26The exit was meaningful enough that I don't need to be doing anything from the for-profit perspective. Everything I've built is independent of that. But going back to we're talking about, you know, some of the investing side, we're talking about some of the family side. Also have this post-exit family community. That's like, you know, a lot of work. 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 holistic whole of how to have those like different buckets. And yeah, so I guess, you know, trial by fire, right support around me.

54:04religion as a grounding construct, and then the firsthand experience of learning from other exited founders and their journeys. Great. 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 all that love and belonging. But what I noticed is that most of us only really love doing it 100 % of the time for about a year.

54:58After a year, we all feel this kind of need to do more. So I think there is no reason to feel guilty about it. It'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.

55:44We've grown in that contribution sense, right? We are at the stage where we have a hunger for contribution. because 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.

56:37But many of us don't realize it. What I find is that a lot of exited founders don't realize that they are much more given than they think. Yeah, I think so too. Going back to the Judaism part, the word for love to love in Hebrew is le 'ehav. 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. Hav 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.

57:25I think you can actually extrapolate it to everything. It goes back to how we started this podcast where 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. And I completely agree that there's a lot to be taken from parenting that you can kind of apply 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 um and so when i'm like describing it at least this is my personal belief like when i'm just when i'm describing it for myself it's just more about how i uh you know get fulfillment and and energy uh and i have met people that you know are exited founders that really end up getting all all in on their you know children and the one thing I would I always try to um push and encourage them to think about is the stages of life right uh and so uh that's great and wonderful um 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 and how much friends you will be and sometimes at least for myself i find i am the best dad i'm the best uh spouse that i can be yeah when i have the meaning and purpose and fulfillment to throw myself into outside 100 100 100 um i know quite a lot of uh 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 like eight, nine 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.

59:24Like, 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. And 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 when you dig it important to be aware of it that maybe we are lying to ourselves if if we are just focusing on that identity yeah not always I'm not saying that yeah well I'll go back to I think I think what I'm hearing and I and I agree with is what's actually most important is using the time post exit to figure out like what is your mission what is you care about and you know uh and honestly there aren't 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 non-profit boards you angel investor there's a lot of these that people have and yeah um but at the same time uh 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 to do it but like there isn't a place to turn and there isn't a playbook and 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 uh and i'm on the boards of these non-profits but i'm lost and confused and 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 figure it out for yourself other exited founders can really resonate with it and there are some you know programs out there that that people do for aspects of this like the 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. 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. Jumping into the next thing without thinking about it is the most logical. It's back to your comfort zone, 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 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. And that's why there are so many failures. I completely agree. I think that's why we try to create the space and the community for it.

1:03:14Go back to what is the post-exit founder 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 exit of 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.

1:04:06But like most exited founders fall into one of three buckets. So one is that they're in 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, 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 and best 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 sabbatical almost exactly one year yeah agreed yeah and 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 of us is 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 the 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 but the the third phase is like you know called the actively not seeking and not exploring phase and that persona can be at different stages of uh of life um uh they can be uh you know retired but actively not like they want to spend their time on the golf course and uh uh you know whatever other kind of hobbies that that they have um 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 uh you know go back to school because they really have always wanted to get their you know phd in history and go back to get their PhD in history.

1:06:40Or we were talking about an exited founder who always wanted to be a school teacher. Yeah. I want to go become a school teacher. Yeah. And so I think like, you know, 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, I think, I think that's, that's great. You 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.

1:07:27But at least to move in that direction or to retire, right? 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? Okay, 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.

1:08:15They're much worse socially. They're much worse emotionally. And we see, you know, 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. And most people, I found post-tags actually go down financially before they go up. but the struggling group doesn't go up, right? They keep making wrong decisions, and we can talk about why, but that is not uncommon. Like, 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, right?

1:09:10It's not necessarily that they decided to retire right after their first exit, but they got burnt. And 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 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 yeah because they made a conscious decision to explore something that they think gives them energy to figure out where 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 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 But we have to go inward first.

1:12:50Then 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 sort of 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, they go into apprenticeship.

1:13:41They 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 store 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 um the uh i think the the other part that 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 i think too many people actually uh 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 yeah 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 is 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.

1:20:10On this podcast, we are building a real post-exit playbook. together. If today helped, hit follow or subscribe so you don't miss the next one. And please share it with one exited founder you care about. Thank you.

From the publisher

Barak Kaufman, founder of Post‑Exit Founders (PEF), grew a 5,000+ member community in four years by word of mouth.

He shares what he’s learned from their stories: what works after an exit and what does not.

Barak is now partner at VC firm Vine Ventures in New York City and Tel Aviv.

Connect with Barak:
Linkedin: https://www.linkedin.com/in/barakk/
X: @barak-kaufman
PEF: https://pef.xyz/
Vine Ventures: https://vineventures.com

Connect with Anastasia:
Linkedin: https://www.linkedin.com/in/anastasiakoroleva
X: @AnasKoroleva
Newsletter: https://www.exitparadox.com/blog
About Anastasia: https://www.exitparadox.com/about

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