5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman
Episode - 57
5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman
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.
What We Discussed:
00:00 – Why your exit dollar figure doesn’t define you
00:16 – Introduction: Barak Kaufman & Post Exit Founders (PEF)
01:08 – Life after selling: discomfort, confusion, recalibration
02:11 – Supporting exited founders to make better decisions
03:07 – Barak reflects on being interviewed
08:18 – Origins of PEF: growth, community DNA, culture of kindness
10:02 – Challenges of scale: 5,000+ members and maintaining trust
12:50 – Dating, cofounders, and tribes within PEF
14:24 – Building “intentional serendipity” in the community
16:47 – The importance of in-person connection
22:32 – Lack of judgment and welcoming messy post-exit journeys
24:58 – Why PEF doesn’t ask about the size of your exit
27:10 – The “golden cage” of financial freedom
28:25 – Barak’s unusual path: investor → founder → investor
35:44 – Barak’s mission: helping exited founders find their purposeafter acquisition
37:32 – Early post-exit struggles
39:11 – Joining Vine Ventures and rediscovering purpose
42:35 – From negative one to zero: finding clarity
44:44 – Angel investing regrets & lessons learned
46:39 – Fulfillment, family, and life design
58:46 – Parenting identity as post-exit mission
59:40 – Hiding behind noble roles: parenting, philanthropy, boards
01:02:18 – Why many rush into a new venture too quickly
01:03:50 – The three typical post-exit paths: messy middle, next mountain, not seeking
01:06:52 – The “wasted decade” risk if clarity is delayed
01:17:15 – Different founder motivations: curiosity, relationships, efficiency
01:18:51 – Closing thoughts & gratitude
-
Anastasia:
[00:00:00 - 00:00:00]
Hi Barack.
Barak:
[00:00:00 - 00:00:02]
Hey, how are you, Anastasia?
Anastasia:
[00:00:02 - 00:00:10]
I'm very well. I'm so happy to see you. And this is the most important interview I've done so far.
Barak:
[00:00:10 - 00:00:18]
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.
Anastasia:
[00:00:18 - 00:01:47]
Well, there is 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. And 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. So since then the PF 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.
Barak:
[00:01:48 - 00:02:51]
That sounds great. Firstly, thank you for the kind words about pf. I definitely don't believe that I am the most important person in some ways. You know, the whole goal of like building this community and network is that it is not about me. You know, I created this spiral that kept it going. And so honestly, you know, it does feed the ego and feel good to know that like I created that to enable that impact to happen. But it's really, you know, pf, post exit founders. It's, it stands for exactly what it sounds like. Some people call it PEF, right? There's probably 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. Right? So it's not, you know, 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, you know, patient as you to wait 10 years to try to find, you know, other people to.
Anastasia:
[00:02:51 - 00:02:52]
Well, you were much wiser.
Barak:
[00:02:52 - 00:03:41]
I don't know if I was wiser. There's a longer story there where, like, I think if I reflect back on a lot of my life, not just, you know, professional life, but personal life, community has been like a core part of what's grounded me and helped me through some of the life's biggest challenges. I'd say the highs and the lows, like 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. Not 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.
Anastasia:
[00:03:41 - 00:03:42]
Yeah.
Barak:
[00:03:42 - 00:04:53]
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 PF 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 them in the same group chat to just post a question and see what they would respond. And 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 the 12 people. Their first degree of separation for me, and it did. It's completely been referral since then and career.
Anastasia:
[00:04:53 - 00:04:55]
It's more than 3,000 now, isn't it?
Barak:
[00:04:55 - 00:04:56]
It's almost 5,000.
Anastasia:
[00:04:56 - 00:04:57]
It's almost five. Oh my God.
Barak:
[00:04:57 - 00:05:30]
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. And they're like, oh, you should join pf. Like what's pf? And that's what's created this viral loop.
Anastasia:
[00:05:30 - 00:07:14]
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 device. 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 in how. And I think that when I met you I thought, oh, of course, that's just Barack'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 Delesman in this, which is important to mention, but we are talking about you right now. So your DNA is very much in the PDF. 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 pf. So if somebody joins and they are not necessarily at this level of kindness and goodness as you are and some other pfs are, they naturally get very inspired and drawn to it and they grow into better people. That'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 PDF.
Barak:
[00:07:14 - 00:07:23]
It's amazing to hear. I hope that that's true. I mean it's definitely 100%. It's definitely what we aspire to, to aspire to inspire. Right. And to create better.
Anastasia:
[00:07:23 - 00:07:29]
Can we quickly talk about how you actually look at growing the community because it's such a unique approach?
Barak:
[00:07:30 - 00:10:06]
Yeah, I think it's, it's, you know, to go back to what I was saying. Right. Like there was never an intention of, 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, there's conferences, there's experiences, there's programs, there's resources. It's 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 is something that's just like deeper, like that there is this level of 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 control. And so we had to ask ourselves the question probably a year or two ago already, do we want to cap the size of pef, 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 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 that network and 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 or 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 communities within that network.
Anastasia:
[00:10:06 - 00:10:21]
Yeah, I'm very happy to hear that you're not capping the number of people. That would be unfair. That wouldn't feel right. 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.
Barak:
[00:10:22 - 00:10:24]
We've had quite a few members that have asked for a dating.
Anastasia:
[00:10:25 - 00:10:30]
Well, of course, because so many companies now have co founders who met at the PDF. I know lots of those.
Barak:
[00:10:31 - 00:11:13]
Yeah, that's how they met and that's co founders. What about life partners? Right. So like we've had quite a few 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 life partnerships, 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 something. We're trying to figure out how to support for members.
Anastasia:
[00:11:13 - 00:11:49]
Absolutely. You need a tribe. You know, what worked for me in this 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, as I find close friends within that community, that community becomes more important.
Barak:
[00:11:49 - 00:11:50]
I love it.
Anastasia:
[00:11:50 - 00:12:18]
And 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. 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.
Barak:
[00:12:18 - 00:12:19]
Yeah. The question is like, how can you.
Anastasia:
[00:12:19 - 00:12:20]
That's super valuable.
Barak:
[00:12:20 - 00:13:23]
Yeah. So basically all of our time now, you know, PF will continue to grow and people will hopefully continue to inspire each other. But 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 you're 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 tribe, or connecting on a shared major challenge and experience to push through together, or just having fun with folks. And so we're doing a lot of different ways to try to bring those people together, to be able to connect and find the people that give you energy. Because at the end of the day, just because the other 5,000 members are exited founders doesn't mean that you want to be spending time with all of them. You start to figure out for yourself who are the ones that you actually enjoy.
Anastasia:
[00:13:23 - 00:13:47]
I love the term intentional serendipity, because that's exactly what we need. We don't want to just be intentional. We don't want a tight kind of dating network. We actually want to have a general idea of what we want, but then have an opportunity, the space and time and energy for serendipity to happen, because that's where magic happens. Without that, we can't go very far.
Barak:
[00:13:47 - 00:14:13]
I completely agree. It's not easy to do in this world where people revert to online interactions versus offline in person interactions. So 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 when you're there with someone in person.
Anastasia:
[00:14:13 - 00:14:42]
Yeah. And intentional serendipity is exactly what we need to find our new mission post exit. 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. So as of today, what is your ideal PEF member?
Barak:
[00:14:42 - 00:17:35]
Yeah. So I think we're really spoiled. Right. 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 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 exited 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. So 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. And 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, you know, 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 the value of the community kind of coming together. The same thing is like this kindness, right? And this level of empathetic listening. There's also, I guess the opposite of that. Empathetic listening is someone who they're usually lost in that post exit identity. And so much of that identity is still being ripped away and like 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.
Anastasia:
[00:17:35 - 00:17:36]
Can I challenge your thinking?
Barak:
[00:17:36 - 00:17:36]
Please.
Anastasia:
[00:17:37 - 00:17:59]
And we talked about this before. I think your community is exactly for people like this because they need it more than anybody else. It's your chance to help them become better people through the community. It's probably the biggest impact you can have. Not one of just one of them.
Barak:
[00:17:59 - 00:19:57]
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, 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. Maybe you're at the acquirer but you're not running it standalone and exited via secondary. So that's what we really look for, who qualifies. And there's a bunch of know manual work to make sure people don't, you know, sneak in. But like that's what we look for. What I'm really describing is like 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 like this contagious aspect of it. When 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, even if you take that Persona of somebody just wants to share everything that they've accomplished, they very soon realize that nobody really cares 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, 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.
Anastasia:
[00:19:58 - 00:20:44]
I'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 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 and 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.
Barak:
[00:20:44 - 00:22:17]
Should become I completely agree. And I think, I think we just. 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. We've had many members over time strongly encourage, suggest, recommend that we also include a minimum dollar threshold of what does it mean to financially exit. I'm sure there's someone listening to this podcast right now who maybe 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. We don't ask 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 supposed to exit is it self reinforces the wrong identity shift of what we have like tried to, you know, walk away from 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 people will care about 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.
Anastasia:
[00:22:18 - 00:22:18]
Yeah.
Barak:
[00:22:18 - 00:22:29]
It'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.
Anastasia:
[00:22:29 - 00:23:09]
Brilliant. I love it. Thank you for explaining because of course I also heard that a lot. When people say people have such 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? That's very subjective and I love that about.
Barak:
[00:23:09 - 00:23:55]
Yeah, that's right. And you've written about what does it really mean to what are those numbers really mean? And I will just add like there are practical implications of that. You know, the size of the exit that like opens up or closes off, like what can come next, you know, as an example to make that more real. Right. Like if you don't have financial, if you don't have, you know, 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, you know, the, the money does afford, but it's not what we want to reinforce.
Anastasia:
[00:23:55 - 00:24:35]
Right. Because. Because if you are thinking of yourself now as a social network, which you should, because at 5,000 people, you really are. It's not even, you know, traditional community, then you can break it up based on, you can slice and dice it and 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 they 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. But it doesn't mean that they cannot be part of this network.
Barak:
[00:24:35 - 00:24:36]
Completely agree.
Anastasia:
[00:24:36 - 00:25:14]
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, but the second group is also not liberated because they're often trapped in this golden cage that they created in their minds.
Barak:
[00:25:14 - 00:25:15]
So true.
Anastasia:
[00:25:15 - 00:25:24]
And they also may not be missionary in their mindset, but for a different reason. So I can totally say or have.
Barak:
[00:25:24 - 00:25:26]
Figured out how to be missionary in their mindset, right?
Anastasia:
[00:25:26 - 00:25:47]
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.
Barak:
[00:25:48 - 00:25:51]
Yeah, that's how we think about it.
Anastasia:
[00:25:51 - 00:26:21]
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.
Barak:
[00:26:21 - 00:30:59]
Yeah, I'm going to go back to childhood even actually, because as I've. I think it's important context. I'm four and a half years past my exit and I think I've continued to learn more every day. But 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. I grew up in New York. I grew up comfortable, amazing, supportive parents, family, community. The part that I'm really going to go back to and zero in on without going too much into my childhood is like I grew up in a community where people spoke about money a lot people spoke about money from the perspective of like, sometimes it was what they didn't have, or sometimes it was showing off what they did have. But money was, was brought up a lot at like, you know, tables with family and friends, either you know, directly or you know, as like a subtext. And I remember in like sixth or seventh grade actually calculating, you know, to live in New York and to have a family and to provide for them 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, already 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 until 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, 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, 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 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. The actual work was really, I mean, I use this word a lot around what drains my energy or gives me energy, but really drain, drain my energy. And I was fortunate to kind of just explore something totally different. Went to Israel for, 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, and wanting to provide. And 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 like 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 would be recorded, but it's okay. I'm at a, at a position where I could share this. Like, I honestly looked up, I, 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. 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 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. And if you think about my job, my job was like sitting across the table selling money while the other person was like building.
Anastasia:
[00:30:59 - 00:31:00]
And like you wanted to be them.
Barak:
[00:31:00 - 00:31:44]
I wanted to be them. And at some point, like, I had this idea I couldn't shake and I started talking to, you know, entrepreneur, founder, mentors of mine and they were all like, I had no fucking clue what I was gonna do, you know, or what I was doing and how I was gonna do it. Just like, 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 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 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.
Anastasia:
[00:31:44 - 00:31:44]
Brilliant.
Barak:
[00:31:44 - 00:32:11]
Yeah. And. And it was a financially life changing event. I 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.
Anastasia:
[00:32:11 - 00:33:10]
So from there to here. That's very interesting. Right? Very relevant because now we are 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 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.
Barak:
[00:33:10 - 00:33:14]
My mission around helping exited founders find their meaning and purpose of fulfillment.
Anastasia:
[00:33:15 - 00:33:16]
Their mission. Right.
Barak:
[00:33:16 - 00:33:18]
Your mission is helping exited founders find their mission.
Anastasia:
[00:33:19 - 00:33:19]
Find their mission.
Barak:
[00:33:19 - 00:33:34]
I think for me, 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.
Anastasia:
[00:33:34 - 00:33:36]
I am as biased as you.
Barak:
[00:33:36 - 00:33:37]
I know we both spent our time there.
Anastasia:
[00:33:37 - 00:33:42]
My mission to. Okay, so how did you find that mission?
Barak:
[00:33:43 - 00:34:58]
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 from. 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 gone. And for me it was four years. For others it's 10 years, 40 years. But regardless, for those four years or a long time of 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 going? 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.
Anastasia:
[00:34:58 - 00:35:00]
A well meaning question becomes very uncomfortable.
Barak:
[00:35:00 - 00:35:09]
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.
Anastasia:
[00:35:09 - 00:35:11]
Yeah, of course.
Barak:
[00:35:11 - 00:35:29]
And so you know, I never for, I never regretted selling. That was the right decision for us, I believe, for many reasons. But it was a really uncomfortable. It's a really uncomfortable time that rest in this period where you're trying to explore, you're trying to recalibrate who you are.
Anastasia:
[00:35:29 - 00:35:30]
Mm.
Barak:
[00:35:30 - 00:36:36]
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 the boss and different expectations. So I don't think it's spoken about enough. But like 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 two most obvious paths that most exited founders take that are late 20s, early 30s and have an 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.
Anastasia:
[00:36:36 - 00:36:37]
Yeah.
Barak:
[00:36:37 - 00:40:00]
Now as you've alluded to, I have become an investor Yeah, I work at a fund called Vine Ventures as a partner. And the way that that kind of came about was, 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 being in the CEO. 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, the negative one to zero phase around like just figuring out what do I want to spend my energy on. It's not just for profit, it could be nonprofit, but like, what are the. 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 working on it. And the second part is the zero to one of getting it to a point where, okay, this is a real company. And what I really don't enjoy is the one to end scaling operationally part. What I also don't enjoy is just, you know, 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, now I'm a full time partner. But it's always been focused on just like 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 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. What should I do next? How should I spend my time? I start with the question of like, 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 do they think about what they care about solving? And then two to three times a year, those exit founders find the path that they really want to go on, that I am Energized to be part of that in some way. And I end up, you know, investing capital as my way to be involved. But it was a, it was quite a journey of trying to do that in different ways. I was 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 incentives, expectations and everything with the founder that 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 have ended up becoming an investor.
Anastasia:
[00:40:01 - 00:40:06]
Okay, so you're saying you are the zero to one person naturally, right? That's how you.
Barak:
[00:40:06 - 00:40:14]
I'd say the negative 1 to 0 to 1. Like when you're just lost and you're trying to figure out, like, how do I get back to the beginning?
Anastasia:
[00:40:14 - 00:40:21]
Uncertainty and chaos. Yeah, okay, great. But why not start your own company then?
Barak:
[00:40:22 - 00:42:09]
I, 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 be a CEO. But 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, they. 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 that, 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, like, what do I want to devote my time to? And trying 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. Like, 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.
Anastasia:
[00:42:10 - 00:42:52]
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 does 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 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.
Barak:
[00:42:52 - 00:43:09]
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 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 we each figure that out on our own by making whatever decisions we make.
Anastasia:
[00:43:09 - 00:43:10]
But it's the most common regret.
Barak:
[00:43:10 - 00:45:57]
Yeah, but 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 than they became over time because you also just start to remember practically the illiquidity and 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 you know, those won't go away at this point. It's, it's on an exception only case in, you know, only exited founders that I have, you know, 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 like wanting to kind of learn and be a small part of what they're doing. And you know, 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 an 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, okay 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. And it's the right level of I feel like making a difference. And so I'm new. I mean, we should do another podcast interview in a few years. I'll see if I'm still an investor of what's going on in my life. But like, so far it's been really, really good. Like, I honestly, 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. And 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 like I'm there, but I'm not in any sort of power position. I try to be a 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 partner, the confidant, the supporter of the Exit founder and leverage it in the way that I can.
Anastasia:
[00:45:57 - 00:46:14]
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. Right?
Barak:
[00:46:14 - 00:46:35]
It's a life design thing. And I would say that, 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.
Anastasia:
[00:46:37 - 00:46:37]
And.
Barak:
[00:46:37 - 00:48:15]
It'S uncomfortable conversation with my wife even sometimes about that because I love my kids. 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, 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 family evolutionary dynamic of procreating and contributing, hopefully and raising amazing little ones. And to me, I've been able to 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. And 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 like, you know, if you start being on a plane too much because you're traveling around helping, you know, the founders and you're not seeing your kids, like 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 be very clear. But I feel like it's a right at this stage of my life, it's the, it's the right balance for me.
Anastasia:
[00:48:15 - 00:48:29]
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. It's a challenge for everyone.
Barak:
[00:48:30 - 00:51:32]
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 in call it the faith is the belief in God. But I really see the power of religion as a construction 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. And 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, 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. 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. And then three, community like a big part of religious Judaism is that community is the support is to be able to see, you know, mentors ahead and support people kind of behind. Which looks very similar to, you know, what we've tried to embody and create within the post ex founder community in some ways. But 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 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? 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 the family side also have this post like the founder 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 hole of how to have those different buckets and yeah, so I guess trial by fire, right? Support around me, religion as a grounding construct and then the firsthand experience of learning from other exited founders and their journeys.
Anastasia:
[00:51:33 - 00:54:06]
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, you know, all that love and belonging. Yeah, right. But what I noticed is that most of us only love like really love 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. 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 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 gave already. We'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. 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. 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 are much more given than they think.
Barak:
[00:54:07 - 00:56:13]
Yeah, I think so too. Going back to the Judaism part, the word for love, to love in Hebrew is so in Hebrew there's like something called ashoresh, which is like 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. 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. And I completely agree that like, 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. 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 just, 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. And 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 and how much of friends you will be and sometimes you. 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.
Anastasia:
[00:56:13 - 00:57:06]
100%. 100%. 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 two, 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. 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 first time. You just don't know. It's very hard. But to make the decision to do it again is a hard decision decision. And I find that some people are just kind of hiding behind the parent identity and that's not very healthy.
Barak:
[00:57:06 - 00:57:10]
Yeah. And I think the parent identity is just one of the many ways that people hide. Right.
Anastasia:
[00:57:10 - 00:57:33]
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 it's always.
Barak:
[00:57:33 - 00:59:44]
Yeah, well, 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 like what is your mission, what is you care about. And, 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 nonprofit boards. You angel investor. There's a lot of these that people have and. 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. 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 and I'm on the boards of the 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 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. But 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 forces you to pause in some way. Jumping into the next thing without thinking about it is the most logical.
Anastasia:
[00:59:44 - 01:00:25]
It's back to your comfort zone, which is so paradoxical because we as entrepreneurs, we think we are always willing to come out of our comfort zone. But 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, it's 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.
Barak:
[01:00:26 - 01:00:57]
I completely agree. I think it's. That's why we try to create the space of the community for it go Back to what is the post examiner 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.
Anastasia:
[01:00:57 - 01:01:16]
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 most typical pattern and most typical paths for post exit founders.
Barak:
[01:01:16 - 01:02:03]
Yeah, for sure. So the first thing to note is like, I think the. The journey, it forks in different ways for people. But 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 not really sure what kind of comes next during that messy middle. If you think about 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 the exit founders that end up having the most clarity usually do take sabbatical almost exactly one year.
Anastasia:
[01:02:03 - 01:02:04]
Yeah, agreed.
Barak:
[01:02:04 - 01:04:16]
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 as someone that didn't do it. I wish. I wish I actually did it more. But the. So the messy middle is that kind of figuring it out phase. Then there's the, you know, rest and vest. I mean, sorry, the. The next mountain phase. Right. The rest invested 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 nonprofit, that could be starting your family office. Like, but it's like, okay, I know what that challenge is that I'm gonna 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 third phase is like, call it the actively not seeking and not exploring phase. And that Persona could be at different stages of life. They can be retired, but actively not like they want to spend their time on the golf course. And 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 do. They're just kind of like doing their thing. And I think PF can't really be such a valuable community to those folks. Maybe for friendship, but it's not really where we're focused on. But within the next mountain and within the messy middle, that's where we double click. And then the kind of paths totally differ, as I'm alluding to. Right. Like, 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 schoolteacher. I went 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.
Anastasia:
[01:04:18 - 01:07:28]
Thank you. I think 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. 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 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 gets crazy about investing aggressively, often end up in what I call a struggling group, which is when they're much worse off financially comparing 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 voice. Yeah. Fill the void. Or just not think about what's happening because they're in such a. Not a good place. And most people I found post exit 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, 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. 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% are the people who after 10 years, after all these challenges they face for 10 years, end up in a group that, where they do live the life that's fulfilling and impactful and beautiful, the kind of life everybody wants to have. And 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.
Barak:
[01:07:28 - 01:08:01]
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, the meaning can come from a whole. I have also met, I haven't really studied it probably as close as you have, but I've met many exit founders that are decades past their first exit. And it's not like there's one common path. I think a lot of people want what should I do?
Anastasia:
[01:08:01 - 01:08:01]
Right.
Barak:
[01:08:01 - 01:09:45]
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 somewhere 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 or 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. They go into woodworking for a while or they. There was one guy that ended up working on an Amazon warehouse as like a picker because he wanted to work with his hands or farms and farms. There's a lot of folks also, actually a lot that go into kind of farming and agriculture, especially tech founders that kind of want involvement in the real world. The point though is when it's 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 back360 to where they started, they took the path.
Anastasia:
[01:09:48 - 01:12:29]
I have this framework for kind of finding our next mission, which 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. 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 sort of this emotional thing. They see something, but they don't know why they're really doing it. But if we took. 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. 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 radiation. Brian Chesky, another great example. 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 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 found problem fit combined with product market fit, and then it works. And every single successful story I looked at, people did these three things.
Barak:
[01:12:29 - 01:13:42]
Yeah, I think that. I completely agree. I think how long that takes to take do really depends on the kind of market you're going 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 spark that you described that takes the most work, how to discover that 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 jump to the second part of what you're saying, actually, where they'll say, oh, I did that right? Like, 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 after that what I want to do. It's like, why? What do you think's going to happen in five or 10 years? What, you want extra $100 million? Like, how is that going to change your life? And maybe it will, but talk to me about why that's an important goal.
Anastasia:
[01:13:42 - 01:14:40]
I agree with you completely. I always get very nervous when someone tells me, oh, my next company, 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. You are locking yourself into this mercenary mindset and that will not make you happy. Actually, 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. It's super challenging.
Barak:
[01:14:40 - 01:14:41]
I completely agree.
Anastasia:
[01:14:42 - 01:16:50]
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 the 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 person consistently drives him. But someone like Brian Chesky that I mentioned, he's all about relationships, he's all about community. He obsessed about behavioral psychology to figure out how to make a business 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. So I think for exited founders, it's very important to understand that what worked for Elon o' Brien may be completely different. Hastings is another great example. 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. But 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 this, 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. But in his case, it was actually the frustration about poor systems. Right. 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. Right. What is it that consistently drives me?
Barak:
[01:16:50 - 01:16:50]
Completely agree.
Anastasia:
[01:16:51 - 01:16:57]
It's super important. So, Barack, thank you so much. This was absolutely amazing. We didn't have enough time. So we're doing it again. For sure.
Barak:
[01:16:57 - 01:16:58]
We will.
Anastasia:
[01:16:58 - 01:17:00]
We need to continue. But you gave us in person.
Barak:
[01:17:00 - 01:17:03]
Either you're coming to Tel Aviv, I'm coming to Miami. One of the two.
Anastasia:
[01:17:03 - 01:17:09]
Somewhere, Somewhere. We'll do it again. You gave us so much food for thought and incredible gems today.
Barak:
[01:17:09 - 01:17:19]
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 on the podcast.
Anastasia:
[01:17:19 - 01:17:21]
It means a lot of all the.
Barak:
[01:17:21 - 01:17:24]
Content that you put out. So please, keep doing it. Keep inspiring all of us.
Anastasia:
[01:17:25 - 01:17:25]
Thank you.
