Boris Berenberg. I Regret Selling My Business
Episode - 15
Boris Berenberg. I Regret Selling My Business
Boris Berenberg. He thought he hit the jackpot selling his bootstrapped cash-rich software business. Two years later, he's filled with bitter regret. In this candid episode, Boris gets real about his exit — what he wishes he knew then and what we can all learn now.
What We Discussed:
00:01:00: Beginning and Introduction
00:03:36: Discussing the Financial Side of Selling a Company
00:04:32: Talking About Financial Expectations and Reality After Selling a Company
00:07:19: Concept of "Dragon Mode" After Selling a Company
00:10:07: Discussing Reaction and Regrets After Selling the Company
00:13:25: Lessons Learnt and What Would Be Done Differently
00:16:03: Understanding personal values and their influence on decisions
00:19:14: Reflecting on the aftermath of company sales based on other founders' experiences
00:20:46: The motivation behind starting Boris' business
00:25:05: Exploring new opportunities
00:28:08: The balance between work and personal life
00:31:38: Contemplating starting or acquiring a new company
00:36:15: Considering the impact of financial situation on personal choices
00:37:47: The concept of becoming a digital nomad
00:40:30: The desire to find stability over a digital nomad lifestyle
00:41:02: Life in New York and its impact
00:42:33: Future Plans & Ideas around AI
00:43:48: Struggling with focus & personal projects
00:44:21: Relationships after the exit
00:46:06: Positive outcomes post-sale
00:48:30: Building networks and relationships
00:49:43: Channeling dissatisfaction
00:51:24: Searching for a sense of purpose
00:57:13: Creating a "work playground" & Future aspirations
00:58:06: End of conversation & Looking forward
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Boris Berenberg: [00:00:00 - 00:00:05]
This sale impacted me individually a lot more than it impacted kind of anyone in my life.
Anastasia Koroleva: [00:00:05 - 00:00:22]
Boris Berenberg, he thought he hit the jackpot selling his bootstrapped, cash rich software business. Two years later, he's filled with bitter regret. In this candid episode, Boris gets real about his exit, what he wishes he knew then, and what we can all learn now.
Boris Berenberg: [00:00:22 - 00:00:51]
If you can think of something that you could do wrong, did all of it wrong, you don't have to be great. You just have to avoid enough mistakes. There was the category of people that went on to found something else, and then there were the founders that became alcoholics. The whole reason I want $25 million in a bank account is so it spits off the interest, right? So it means that you don't actually care about 25 million. You care about the interest, which is cash flows. There's so much bullshit in the United States, but it is so much less than every other place that I go to.
Anastasia Koroleva: [00:00:57 - 00:00:58]
Hi Boris.
Boris Berenberg: [00:00:58 - 00:01:00]
Hi Anastasia. How are you doing?
Anastasia Koroleva: [00:01:00 - 00:01:13]
Thank you so much for joining me today. You know, in this podcast, we focus deeply on what happens after a founder sells his or her business. So my first question to you, how long ago have you sold yours?
Boris Berenberg: [00:01:13 - 00:01:24]
Almost two years. It was May 2, 2022. That was the final close date on the transaction.
Anastasia Koroleva: [00:01:24 - 00:01:34]
Fantastic. I would say congratulations, except that I know for a fact that you actually regret selling, and I would love to hear your reasons for that.
Boris Berenberg: [00:01:34 - 00:01:42]
Yeah, I mean, I wrote a longer article on it. So if someone wants to google my name and I regret selling my startup, they'll find it.
Anastasia Koroleva: [00:01:43 - 00:01:49]
I will post a link to it in the comments. It's a fantastic article. I really recommend everybody to read it.
Boris Berenberg: [00:01:49 - 00:03:26]
Yeah, I think that the main reason why I regret it is because I have lost my kind of self definition of who I am as a result. Right. I think everyone defines themselves differently. Some people define themselves as a husband. Right. Other people define themselves as a parent. Other people define themselves as a marathoner. And I defined myself as a CEO and founder. And so when I sold the company, there was a very large gap left in my life, and I've been struggling to fill that. Right. When I sold the company, I was very confident that I had a very specific thing that I was going to work on, and I did, and it went very, very well until the market tanked. And in the fall of 2022, my new idea, which was a very, let's say, high budget item that I was working on, all the buyers basically got laid off and fired. And so that went to nothing. And then since then, I've just kind of been stuck trying to figure out what it is that I want to work on and not having that strong pull. And it's a morass of emotions and opportunities and feelings and risk and all this other stuff.
Anastasia Koroleva: [00:03:26 - 00:03:36]
In your article, you also talk about the financial side of things and why, purely pragmatically, it was not necessarily a good decision.
Boris Berenberg: [00:03:36 - 00:04:32]
Everyone sells a company for a different reason. I sold it because I had parts of the business which I really. It's not that I even disliked doing it, I just hated it, right? It was like this dread of like, oh, man, I have to deal with x again. And it had been a thing that I'd been dealing with for even before I started the company because it was an external issue. And after a decade of it, it felt like I was kind of like almost in an abusive relationship. And at some point you have to leave, right? And I was like, okay, I'll get enough money and I'll go work on this other thing. And I know everyone wants this other thing, and the market's happy with it, and blah, blah, blah, right? And so in terms of the financial outcome, first world problems, right?
Boris Berenberg: [00:04:32 - 00:07:18]
I'm doing very well. Let me start by saying that, right? I am in a very good financial position compared to pretty much anyone in the world, except a very tiny minority of individuals. However, I am also not in a good enough position where I can sit and never work again. Right? And there are plenty of people who have sold companies who do fit into that category without ever becoming billionaires or anything like that, right? And I can even tell you one of the things I've been figuring out is there's this term of a fuck you number, right? So what's the fuck you number? And fuck you number that I figured out is $25 million, roughly, right? And the reason why I say that number is very specific. I say $25 million with a 4% rate of return gives you a million dollars in passive income per year. Government's going to take half of it. Leaves you with five hundred k, two hundred and fifty k to live a good life in New York, and then two hundred and fifty k a year for experiments, fancy trips, whatever, to live an exceptionally good life. I think that this is like the amount, and if you account for inflation and all these other things, it really is kind of like the minimum safe number. If you want to just stop working now at I'm 35, so if I want to stop working now, that's kind of what I figured out I'm not there, right? I can tell you that. So, yeah, I think that having sold the company a and B since selling the company, having better understood how one should sell a company, it's made me kind of more aware of just how much money I had left on the table, right, and how much. Forget even waiting two more years to sell, right, or this or that. It was just like, I did a bad job of hiring legal representation. I did a bad job of hiring financial representation. I didn't run as aggressive of a process as I should have. If you can think of something that you could do wrong, I did all of it wrong. And so, yeah, financially, it's also not as good of an outcome as I'd hoped. And when there's any kind of an exit, you immediately become a target, basically, right? So from marketing stuff, right, where after the exit, I immediately got harassed by every single wealth manager in the world to people who think that now they can sue you to whatever else, right?
Boris Berenberg: [00:07:19 - 00:08:05]
And so especially if you don't have a great exit, right, like, you become a target. And now that money is even more at risk. And I think in the article, I mentioned this concept of what I call dragon mode, right, which is like, you read a book or you watch a movie, and there's, like, a dragon sitting on his pile of gold, and you're like, well, why does a dragon need a pile of gold that he just sits on, right? And it's like, once you've sold a company, or I would assume that even people who just inherit money, right, have the same problem where they're like, okay, I have this pile of money, and now I have to protect it. And it's not just a case of going out and adventuring for more gold, which I looked at your history, and I guess you've exited five companies now.
Anastasia Koroleva: [00:08:05 - 00:08:06]
Four.
Boris Berenberg: [00:08:06 - 00:08:08]
Okay, the fifth one coming soon.
Anastasia Koroleva: [00:08:08 - 00:08:18]
Probably not all exits were equally great, right? They were very different. I've learned my lessons and made my mistakes. For sure. I can relate to a lot of what you're saying.
Boris Berenberg: [00:08:18 - 00:08:42]
The funny thing about advice is that all advice that we hear is very trite. It's like, work hard, right? Be honest. Right? Like this kind of thing. And you're like, oh, it's all useless. And then after you go through all the mistakes, you're like, it's all correct. That's all the advice that's really out there, right? It's the straight stuff of, like, get good lawyers, get good accountants, right?
Anastasia Koroleva: [00:08:43 - 00:09:04]
I totally agree with you. It's quite a funny phenomena that we all know what to do. We all know what's right, what's wrong, but actually internalizing it enough to act on it or having enough conviction is hard. And that's why we keep learning lessons from our own mistakes instead of other people's mistakes. I'm absolutely with you on that one.
Boris Berenberg: [00:09:04 - 00:09:36]
Yeah, I listen to a lot of audiobooks and business histories and podcasts on these topics, and I'm trying to basically turn it into a situation where I hear it enough times that maybe I internalize just a little bit of it. Right. Just avoid a couple fewer mistakes. Right. It's like the old mongerism of like, you don't have to be great, you just have to avoid enough mistakes kind of thing, which hopefully I'll get better at.
Anastasia Koroleva: [00:09:36 - 00:10:07]
I was writing a blog for a long time, and one of the reasons I started doing a podcast is because I realized that when people actually see another person sharing their mistakes with them emotionally, that creates a very different level of conviction than if you read the text, which is much less personal. So I love that your face shows quite a lot of emotion about your lessons, because that is exactly what helps people get the message.
Boris Berenberg: [00:10:07 - 00:11:28]
Yeah. Even with the blog post that it got on the front page of hacker News, and I was reading the comments and I was trying to stay out of the comments as much as possible because people were attributing a lot of tone and emotion and things to what I had written that I hadn't. Right. Like, I avoided talking about how much the exit was for. Right. I avoided talking about aspects of my personal life that I've mentioned here. I did go in into one comment and kind of responded, and I was like, hey, I'm not saying my life is bad because I sold a company. My life is great. I'm not in a situation where the acquirer is some bad company that's treating me poorly. That's not the case. They treat me very well. I have a lot of autonomy in the new organization that I'm in. I have the freedom to try build things in my spare time, in nights and weekends. I have a good partner. I have a very healthy relationship with my family. I get to travel a lot. I have a great life. Right. It's just I have a gap in it also from this internal perception of things. And yeah, hopefully that comes across a bit clearer here than in my writing.
Anastasia Koroleva: [00:11:29 - 00:11:53]
For what is worth, my first exit was 13 years ago, and I talked to hundreds of people who exited businesses. And this regret is usually a very temporary thing. And then you move on. And then you look back at it with a lot of gratitude that your exit taught you so much. So sadness will go away, I'm sure.
Boris Berenberg: [00:11:53 - 00:13:22]
No, I'm confident it will. Right. It's this beauty of how our brains work, of, like, we rewrite the past to romanticize it, right? I always say it's like, I got engaged when I was 18. And long story short, let's say she cheated with my friend. And at the time, I was heartbroken. Literally. I'd been working in tech already by the time I was 18. And for like, two years, something like that, maybe even three. And at that point, I was like, oh, I'll just get another tech job. I'll move back home, whatever. And I couldn't do it. I was completely broken. I ended up washing dogs at Petsmart, which, if anyone is seriously depressed and can't afford therapy, go get a job at Petsmart. Washing dogs. It is highly effective. Is getting paid for therapy, basically. But I look back at it now, and I'm like, oh, man, that was such an important growth moment for me, right? And it pushed me to change my behavior in many ways. Right. Because I get why she cheated on me and left me. Right. I was pretty shitty at the time. I'm still not amazing, but I was much worse then. So I think, in the same vein that this experience will kind of get rewritten in my mind of like, okay, well, I learned all these lessons, right? I'll build something else.
Anastasia Koroleva: [00:13:22 - 00:13:25]
What would you do differently if you could turn back time?
Boris Berenberg: [00:13:25 - 00:15:48]
Oh, everything. Absolutely everything. Again, I outlined a lot of this in the blog post, but I think the first thing is, before even considering selling, is I would restructure how I thought about running the business. So I started by saying, okay, I want to do x, right? With x being like, not deal with the people who I didn't want to deal with. And I was like, so the solution is throw everything away so that I don't have to deal with them, right, and take the money and then try again. And that's a very extreme solution. Right? And instead, I think what I should have said is like, hey, here's the thing I want to do. What is the minimum I actually need to do to achieve it, right? So, for example, hire a CEO, right? That could have been the minimum to achieve it, right? Like, hire someone to be the CEO. Check in with them once a month to make sure everything's on board, use the free cash. And just for context, also, my business was 100% bootstrapped and very cash flow. Positive, right? So I had plenty of money to do whatever I want with. Had no investors that I had to go and appease anything, right? So could have just hired a CEO, let them kind of run it, whatever. Could have hired the business had different parts of it, and it was really just one. Well, let's say two out of the three parts that I didn't want to deal with, I could have hired general managers to manage those parts of the business, right? I could have gone to therapy and talked with a therapist about my emotional problems of dealing with the parts of the business, right. I could have hired a business coach. One of the downsides of not having investors was there was no board, right? So there was nobody to call me on my own bs, right? Like I was the end all, be all. So I could have hired a paid board whose job was to challenge me and hold me accountable. And all these things. I could have sold part of the company and not all of it, right? I could have run again. I could have hired better representation throughout the sales process. The spectrum of everything I could have done is literally everything other than what I did, because I took such an extreme and narrow kind of approach to solving things.
Anastasia Koroleva: [00:15:48 - 00:16:03]
So in that article of yours, you also mentioned how you didn't fully understand what your values were and how when you did understand your values after you sold your business, you realized that you shouldn't have sold it.
Boris Berenberg: [00:16:03 - 00:19:14]
Yeah. So the values thing actually came out of something different, where I had something going on in my personal life after I sold the company, went to a therapist, started working with a therapist to deal with this unrelated personal stuff. And the therapist was kind of like, hey, how do you benchmark your own decisions against yourself? And I was like, what do you mean? It's like, make a decision. Think about it, what feels right? He was like, okay, yeah, that doesn't really work super well. You may need some kind of guidelines and guidelines that you would review it and assess over time and understand, are they still actually your guidelines or not? Because it's very easy to trick yourself situationally. And so he gave me this exercise, and the exercise is, it's a sheet of paper with a list of, I want to say, 30 or 40 or 50 values that are commonly held by individuals and that you pick the top ten most important. You ignore the rest. And then you take those top ten and you stack rank them, right? In terms of importance to you, you'd think, like, oh, why not just stack rank all 50 stack ranking? Even ten takes a surprising amount of time. I think it took me a few hours in multiple 30 minutes increments. Kind of like to restack rank, restack rank, restack rank. I kept doing it on different flights I was on, actually. But it's amazing how clarifying the process is of what you give a shit about and how much relative to one another, right? Like, how much do you care about friends versus family, right? Different for everybody, right? How much do you care about wealth versus power, right. How much do you care about power versus recognition, right? There's all these things that are very personal and stopping and asking yourself to understand why. What do you actually value and why does that matter? And for me, what happened was I had these top ten, right? And I looked at them, and selling the company, I think, impacted negatively four or five of them. And I was even teasing my partner the other day. She was like, what would happen if we broke up? I'm like, yeah, that would impact one of my values, right? And selling the company impacted four or five. So think about the psychological harm that happens in a breakup, right? Versus imagine if it was four to five times worse than that, right? That's kind of the degree of impact that it had on me. And unfortunately, I'm very lucky that I have good management tools at my disposal, right? Again, like we were saying, it's the basic things that we all know, right? It's like, go talk to a therapist, work out, eat healthy, sleep consistently. Right? Like, spend time with friends and family. Don't drink, don't do drugs. Right?
Boris Berenberg: [00:19:14 - 00:20:12]
It's pretty well understood set of things. Yeah. So I've been able to manage it, I think, pretty effectively. But I think actually, in the group that you and I are both in is also Patrick Campbell, if I remember correctly, is his name. I remember his twitter, I think is Patticus. But he's the co founder of Profitwell. And I listened to a podcast with him where he went through the sale of his company, and clearly somebody much smarter than me, because he's like, oh, before selling my company, I did research on the process of selling companies and what happens to founders. And I was like, oh, that's interesting. And he says he's like, there's two categories of founder that he found. There was the category of people that went on to found something else or work on something else really important to them. And then there were the founders that became alcoholics or abusing some kind of substance. And he was like, that's it.
Anastasia Koroleva: [00:20:13 - 00:20:14]
Pessimistic view.
Boris Berenberg: [00:20:15 - 00:20:31]
Maybe he'll hear this and be like, no, you totally misunderstood what I said. But that's how I remember this segment. It's a reminder to, you have to keep it on the straight and narrow, or you burn down the rest of your life.
Anastasia Koroleva: [00:20:31 - 00:20:36]
Okay, I'll invite Patrick to my podcast, and we'll debate.
Boris Berenberg: [00:20:36 - 00:20:38]
Yeah, we can have, like, a talk, right?
Anastasia Koroleva: [00:20:39 - 00:20:46]
I like that. So, Boris, going back to the time when you started your business, what was your motivation?
Boris Berenberg: [00:20:46 - 00:25:05]
So I was working for a company, and they were making decisions that I was not in agreement with, and I felt that they were violating both the company values and good business practices and all this other stuff, right. And I was completely ineffective at getting even teams to listen to me forget the company as a whole. And so my manager at the time kept being, saying something along the lines of, like, if you think you're right, why don't you quit and start a company and prove us wrong, right. This kind of thing. It was like I was a bad culture fit there, right? So I think he was trying to very politely be like, hey, we want you to quit. But I was doing good work, but I was a bad culture fit. So they were like, you can leave anytime you want, but until then, please focus and do the shit we care about. But it was literally a lot of that, right? So it was a lot of that. And then eventually, I did quit, and I didn't start a company. I went to go work in house for similar stuff that I was doing before my salary went up. I ended up at an Uber small company. No one's ever heard of it. And I was on the most amazing team of my life. And the team was, I think, four of us, and we did not even need to communicate. That's how well we understood the subject area and each other. Right. I remember there was one occurrence where some news thing came out very important that we had to deal with. And this was like an eight page document, right? And we did not have to discuss it. Everybody knew what everyone else thought. Everybody else. Everyone knew what they needed to do. And it was just this, like, it was a really amazing team I was on and probably the best of my life. And I was working probably like 6 hours a day. It was very easy hours was 100% remote. Living in New York, the team was all over the place. And I just realized that that was it. I, at 27, had reached the apex of my career. If I took a different job at any other company or even moved to get a promotion, I would have had to take my debt, my boss's job. There's only one role, right? There were three of us reporting to him. So the chances of us getting it are low. And if I moved into a role somewhere else within the company, my pay would decrease because I provided a lot of value, kind of as a niche contributor. And I was like, shit, there's literally nothing else. That's it. I have quite literally reached the apex of my career financially and in terms of everything else. And I was like, I just got to start my own thing. I was like, there is no way up unless I do my own thing. And I started by finding consulting customers to work with nights and weekends. And then once I had lined up about, I think, $70,000 of consulting income for the coming year, I gave notice. And so I knew that $70,000 was roughly, I think it was about 25% to 50% of my time was taken up for the coming year with that. And so I knew that 70k was enough for me to live on. And then I still had half my time free every week to find more customers and grow the business, et cetera. And so that was it, right? It was like I had enough security in terms of income to start, and I had free time to grow. And I also had the confidence that should the business. Just like, let's say I start working with the customers, I do a terrible job, I lose them in the first couple of months, right? I also knew that my skill set at the time made me extremely hirable back into this type of role that I had before. So I knew I could probably find an in house job within a few months at the time. And so I was very confident that it was a fairly low risk, high reward activity.
Anastasia Koroleva: [00:25:05 - 00:25:13]
So basically you wanted autonomy and you wanted to grow rather than, for example, prove yourself or have financial freedom.
Boris Berenberg: [00:25:13 - 00:28:06]
I think it would be a mixture of things, right? I think very much a chips on shoulders, put chips in pockets kind of situation, right, where I'd been arguing with people for a long time, saying, you know, there's like, the Google way of doing customer support, which is like, the fuck you, we're not doing support, right? And then there's the, like, I'm blanking on the name right now. It's one of the hotel chains is, like, famous for. The staff at the hotel are authorized to approve anything up to $500 in expenses to make a guest happy without any management oversight or anything. Like, any employee on the floor can do it. And there's a sliding scale of everything in between. And I was like, we need to be more like, we're working with enterprise customers like B two B SaaS enterprise customers. I'm like, we need to be much more in the bend over, make them happy, and treat them in a much more respectful way. And not only in the way we do support, but also in the way we develop the product itself. And culturally, they just didn't want to do that. So a lot of it was me saying, like, hey, I want to prove that my way is right, that enterprise customers highly value a high touch, high service model of support for this. There was this element of proving my own thinking, right. There was also the element of like, hey, I want to grow my status socially, right? Because saying, like, hey, I'm a support engineer or whatever is pretty low status to saying, like, hey, I'm a founder. CEO is pretty high status. So I think a lot of it was me chasing social status. A lot of it was chasing money, right? I always find it funny if we're building a company to change the world, and I'm like, yeah, there are some of those, right? But for a lot of B two b SaaS stuff, we're like, we're here to make money, right? I know that slack is like, we're connecting work or whatever. I don't know what their slogan is, right? But everyone has these nice slogans. But ultimately, let's be clear here. And for me, like I said, I had felt like I had reached my financial cap. There wasn't a clear path to how I was going to make more money. And autonomy, like you said, I've never had a particularly good experience working for somebody, right? They've usually not had a particularly good experience employing me. I've never in my life had a promote gotten promoted, not once I've changed titles by switching jobs. I've gotten demoted, especially now after selling the company. But I've never gotten a promotion, right? Which I think will tell you, kind of like, I'm not good at working at someone else's set of ideas and ways of working, et cetera. And I have kind of my own thing, and working towards that autonomy is important for me.
Anastasia Koroleva: [00:28:06 - 00:28:08]
Are you now working at the acquirer?
Boris Berenberg: [00:28:08 - 00:29:09]
Yeah. And one of the reasons why it's working for me to work there is that I have almost 100% autonomy, okay? The only autonomy I don't have is that I have to set financial targets and report those to the CFO and then provide updates on how we're trending towards them. But that's about it. And I get asked to go to some meetings. But outside of that, right, like, I hire, I fire whoever I want however I want. I guess I don't have control over comp scales for my people. That is one thing that I don't have. But largely it is a level of autonomy that is probably nearly unheard of in companies of this size. And they are very understanding of how I want to do things and are even interested in working together to see how I can expand influence on other parts of the company to kind of try and get them to learn from how I do things.
Anastasia Koroleva: [00:29:09 - 00:29:13]
How many hours, realistically you spend a week working?
Boris Berenberg: [00:29:14 - 00:29:15]
I don't know if I should say that.
Anastasia Koroleva: [00:29:17 - 00:29:18]
You don't have to. It's okay.
Boris Berenberg: [00:29:20 - 00:31:26]
I would say this, right? The way that I work is very clear in my mind. Right. Which is, first, I do all of my obligations to my employer. Second, I do all of the obligations in my personal life. So, for example, I've been remodeling a house right now. So the amount of time I spend running back and forth to the house to see how the building is going and deciding on materials and all this stuff, I could not have imagined how much time that took. And then finally in the evenings and stuff, I will spend some time building new things to see. Kind of like, is this something I should be working on? How should I be working on it, right? And then after that, then I also do some self promotional stuff like recording this type of podcast on a weekend or something. I don't know how you classify work, but I would say I probably work somewhere between 40 and 80 hours a week across all the different things I do. And there's also times of intensity. Right. We have a conference that we're going to in end of April. So that's going to be probably like 1416 hours days for the entire week, including the weekends, because there's going to be events around it, right? Even while you're there, you still in the evening, need to get your primary emails and stuff done and et cetera, et cetera. Right? So it's all over the place. I think one of the things that I'm lucky with is that at some point I really learned to, I wouldn't say enjoy work, but I feel like I'm not using my time well, if I'm not working right, maybe it's workaholism. I don't know, maybe it's not trendy now, right? You need a good work life balance. But for me, if I am actually sitting down and doing a lot of stuff that makes me feel accomplished at the end of the day and even maybe to a certain point of detriment. Maybe I should be working smarter, not harder. But, yeah, that's kind of my approach today.
Anastasia Koroleva: [00:31:26 - 00:31:38]
So you mentioned that losing your identity was number one reason for regretting selling your business. So what are some of the ways you are thinking of solving that problem for yourself?
Boris Berenberg: [00:31:38 - 00:35:59]
I think that the main approaches that I'm looking at right now are two. Right. One is start a new company. The other one is acquire a company, right. But basically, it's like, get back into the CEO game somehow. I think. It's not like, the point is that when you have four different values compromised, you can't find a solution to one of them at a time. Right. Like, you need to kind of solve it in a cohesive manner. And so there are very few things in life that will impact this many values all at once. And I've looked at, for example, volunteer, right? So I run a lot. A couple of the members of my running group are joining this group called Achilles right now. Achilles are the people that run alongside disabled athletes and marathons and things. Like, if you like, I did a New York City marathon in November, and you're running, and there will be kind of along the right hand side, there will be like, for example, a blind runner, and they will have, like, a tether connecting their hand to the hand of an Achilles runner. And then they run together, and they're able to kind of complete a marathon as a result. And so I see volunteering opportunities like this and other stuff which I think could address, like one, one or two, maybe values, but nothing really hits all of them at the same time without. I have a hard time answering specifically because it's like, it's owner, founder, CEO. There's this weird trifecta, right? Like, if I was hired as a CEO of some PE roll up, it probably wouldn't hit that trifecta, right? Maybe owner, CEO, maybe CEO, founder. Right? There's some two out of three necessary there. And so I'm looking at all that. I think part of the big forcing function is that one of the values is kind of the money side of things, right? I think it's written down in the list as wealth. But one of the big learnings also was, I don't care so much about wealth, right? Like, yes, it would be nice to have $25 million sitting in an account spinning off interest, right? But I care actually, a lot more about cash flows, right? So I care a lot more about a business. The whole reason I want $25 million in a bank account is so it spits off the interest, right? So it means that you don't actually care about 25 million. You care about the interest, which is cash flows. Right? And so having the business that can kind of offer me those cash flows is, I think, important. I grew up, I wouldn't say poor or wanting or anything like that, right? But also there were very clear things of like, well, we can't afford this. We can't afford this, right? Et cetera. For a while prior to selling the company, I'd gotten to a point of, even you go to the grocery store and I would stop looking at prices of cherries, right? I want cherries. I'm going to buy cherries. I'm not talking about the people that go out and buy lamborghinis whenever they want, right? I'm like, I would go out and I would buy cherries without looking at the price because I want cherries. And now I'm like, I'm looking at the price of every freaking cherry again, right. Or like, I'm renovating the house and it's like, okay, you can have this, what's it called? The pantry. Right. You can have a pantry, and you can have a pantry that is like, you pull out and then there's, like, shelves, or you can have. Pull out, and then there's, like, the system built into it, right. It's like $2,000 difference. Right. Before, I wouldn't even consider going for the. I just get the nicer option and not care. Right? And now it's like, okay, you have to stop and analyze every single thing, because if you spend it right, you're spending the principal oftentimes, of course. And so I think for me, going back to this, finding this CEO, founder, owner, whatever combo, I think at this point, founder is the least important to me. Right. I think at this point, CEO gives me the autonomy and owner gives me the financial side, and both kind of give me the social status, and I forget what the fourth one was that is impacted. Yeah. I think that's when I'm kind of aiming towards longer term.
Anastasia Koroleva: [00:35:59 - 00:36:15]
So, talking about wisdoms that everyone knows, have you considered actually taking a break and exploring whether it makes sense to detach yourself from the need for your status or particular labels?
Boris Berenberg: [00:36:15 - 00:37:47]
No, because I don't believe that that's possible with the financial situation. Right. Like I said, if I had sold it for enough money where I never had to work again, sure. But we can even. I try and look at it very practically. Right. So let's say I get married in the near future. Let's say I have kids. Right. Let's say my partner wants to work, right? Okay, cool. So if she works and living in New York, that's not enough money for us to live on, right? It is, but not at a standard of living that we want. Great. So now I also have to work. Great. So now how much do we have to pay for the kid to be in daycare or whatever? Right. If you want a good daycare, like in New York, that'll be like $50 to $70,000 a year. It's a full time employee at that point. You can just hire a nanny almost. So the question then becomes, right, how do you pay for it? Right? And so for me, this idea of like, oh, take a break. Do you even want to be doing this stuff? Maybe, but I'm not rich enough to do that yet. Right. And I think that's where a little bit of the lack of satisfaction, or whatever you want to call it, with the transaction comes from the financial perspective. Right. It's like, I could have had that, right? And I kind of blew it.
Anastasia Koroleva: [00:37:47 - 00:38:23]
It's absolutely very understandable. I'm just throwing ideas at you because obviously I've seen enough people in your situation, and I've seen various ways people deal with it. And another way that's quite popular, and I'm just curious if you thought about it, is digital nomading for a bit? Because that suits people without kids really well. You get so much out of it and your expenses drop so dramatically that suddenly you feel rich. It's very hard to feel rich in New York. I lived there for eleven years. I know.
Boris Berenberg: [00:38:23 - 00:40:28]
Actually, I sold a company, wild digital nomadic. So I was doing it for about four and a half months, five months. It was nice. But I'm a very kind of, like, add person, and I find that kind of the best way to manage add is to have routines. And when you're digital nomadic, not having routines is the name of the game. So there was a lot of discomfort around that for me. And then the other thing is, every place you go to, there's a new set of bullshit you have to deal with. Like, Medellin was gorgeous, right? I highly recommend everyone go there. Absolutely beautiful. Weather's great, food's delicious, cheap, right. People are mostly know there's a lot of tourists and expats or immigrants, whatever you want to call them, but they just don't have good mattresses. No matter what I did, I couldn't find a place with a good mattress, right, which you sleep on it every fucking day. And so how are you going to really enjoy a place for an extended period if every day the first thing you think of is like, fuck, my back hurts. And that was bad sleep. Everywhere I went, there was always something like that. And I remember when I was younger, I would travel to, let's say, italy or Spain, right? I love Barcelona, right? So I'd go to Barcelona, man. The food is amazing, everything is cheap, the weather is gorgeous, the beach is right here, right? The people are nice, spanish. I could probably learn it. Airport. What else do you need in life, right? And you spend a couple of weeks there and you have a great time, and you're flying home, like, everything's wonderful, and then you get back to the US, and every single time, the thought that would go through my head is like, fuck, I'm happy to be of, there's so much bullshit in the United States, but it is so much less than every other place that I go.
Boris Berenberg: [00:40:30 - 00:41:02]
Me, I guess my personality of just not liking to deal with that bullshit precludes, I think, a long term digital nomad lifestyle. I would say in the last twelve months, I have been away from home, probably at least half of it. So I'm borderline digital, nomadic. But it's because I'm back and forth between Germany and New York. But even there, right, where I'm going to the same spot in Germany every time, to the same town where I know some people et like, I even know where to go running now, right?
Boris Berenberg: [00:41:02 - 00:41:44]
Because I've run so much around the town that I know where I am. I don't need a map or anything. It's still. It's not the same. It doesn't fit as well. And I think in particular, for me in New York, it is that I am very lucky to have figured out a place that really suits me. And it's not even New York, right? It's specifically Manhattan, right? Like, I left Manhattan in 2020. I've been living in Brooklyn, and I'm moving back now once the renovation is completed, because it's like there's just something there that does it for me, and I don't get it anywhere else, right.
Anastasia Koroleva: [00:41:46 - 00:41:48]
I totally understand your happy place.
Boris Berenberg: [00:41:49 - 00:42:31]
Yeah. It's small things, right? You cross Second Avenue, right? And you forget that you're crossing Second Avenue because you're listening to a podcast or whatever, and you're walking and you look to the right and you just see the Chrysler building there, right? And it's just these weird little moments of, I am here. New York has all of its problems, right? Like, anyone who's lived here knows. But yeah, it is an amazing place to be, and I'm very grateful to have just stumbled across it at a fairly young age, and I hope that I continue to enjoy it into the future.
Anastasia Koroleva: [00:42:31 - 00:42:33]
So what's your plan now?
Boris Berenberg: [00:42:33 - 00:43:48]
My plan is either keep trying to build new things, right? Like, I have been building things, and they've mostly not been working, or keep trying to look at acquisitions, which I'm doing regularly, and trying to find kind of a path forward there. And it's a mixture of trying to build networks, right? Like everyone else, I have my own idea around AI, who doesn't? So I have some ideas around AI, right? But I'm technical enough to write some code, but not technical enough to build my own AI products. Trying to find a co founder for that, maybe, right? Or I also have some ideas around what I would call, like, a cockroach operating company of like, how do you take small SaaS businesses that are being run efficiently and run them much better under an operating umbrella, which would need financial partners, right? So I don't know. I'm looking at a lot of things, and I think that the big thing I'm trying to get right now is figure out how to focus better, right.
Boris Berenberg: [00:43:48 - 00:44:21]
Because I'm trying to do too many things at once. But, yeah, that's the professional side. And then personally, I guess I'm just trying to get this damn house construction fixed and get moved into it. I'm so excited. It's the first time in my life I'll be living in a near new apartment, co op, whatever, and that's built largely to my standards in a great neighborhood. Just looking forward to that right.
Anastasia Koroleva: [00:44:21 - 00:44:29]
Now, tell me, how did your exit affect your relationships with your partner, first of all, but also the rest of your family?
Boris Berenberg: [00:44:30 - 00:46:06]
Family. It was kind of like, they're proud of me and they're happy for me, right? But in general, I have a very supporting and loving family. I think I'm very fortunate in that sense. I think that that was all fine. I think I'm also pretty lucky in the sense that while we started off not having much when we immigrated to the US, everyone has kind of earned their own money at this point, and in fairly sizable amounts. So I don't have the problem of being so rich that people are coming to me and being like, oh, can you buy me a house? Type of thing, right? Because everyone has bought their own houses, right? Everyone's doing well, so I don't have any problem of that type of stuff, which I know happens to some founders, friends, everyone has been mostly cool about it. There have been limited exceptions, which I cannot talk about. And then my partner, well, the person I was dating at the time that I sold the company, I'm no longer dating, but it was not related to the sale of the company. She supported me kind of when I went through with it, and I kind of wish she'd pushed back more, but it's fine. And, yeah, now I'm dating someone else, and everything's going great. So I would say that, for me, the sale impacted me individually a lot more than it impacted kind of anyone in my life.
Anastasia Koroleva: [00:46:06 - 00:46:08]
What are the good things that came out of the sale?
Boris Berenberg: [00:46:09 - 00:47:31]
It's tough for me to answer to some degree. Right. Is wealth. Right. It's hard to argue with the fact that you have a certain amount of money. I would say probably the biggest one right now is that it has given me access to certain communities. Right. Like the one you and I are in, others that I'm in. And that has given me an access to a network almost. It's not really a network, right. I'm not building close friendships with anyone yet. Right. But I hope to build kind of more acquaintances and relationships with people in these communities. They are, on average, much more intelligent than I am and much more experienced than I am. And I think that having kind of those relationships is just a force multiplier for what I can do in the future. I didn't go to Harvard, right? I didn't grow up rich. I wasn't an early employee of Paypal or whatever, one of these mafia type situations that we talk about in tech. And so finding a community through which to build meaningful relationships with people who are smarter than me and more experienced than me is probably the biggest benefit of the sale.
Anastasia Koroleva: [00:47:31 - 00:47:33]
Do you feel lonely?
Boris Berenberg: [00:47:35 - 00:47:37]
Now? I felt lonely before I sold the company.
Anastasia Koroleva: [00:47:37 - 00:47:40]
Okay. I felt a lot lonely now.
Boris Berenberg: [00:47:40 - 00:48:18]
Yeah. Well, it's like. Because part of the problem before I sold the company was I was trying to find communities like this, and they wouldn't have me. Right. There were either communities that were like, you're not far enough along on your journey, or there were communities that would take me, but they were like, their members were like, I looked at them in the same way where I was like, all of you guys are way too early on your journey relative to me. And I felt like I was in this dead zone. I wish I could be in the communities I'm in now prior to having sold my company, because I definitely wouldn't have. That would have made things a lot easier and better.
Anastasia Koroleva: [00:48:18 - 00:48:20]
Earnes you ticket.
Boris Berenberg: [00:48:20 - 00:48:21]
Yeah.
Anastasia Koroleva: [00:48:25 - 00:48:30]
You mentioned you are not looking to build friendships in these communities. Why?
Boris Berenberg: [00:48:30 - 00:49:43]
No, I would love to build friendships. I'm just saying it's not an expectation. Yeah, it's not an expectation. It's like, the people in these communities, their number one thing that they have at this point that they care about is time. Right. Most of the people are very sensitive about their time. Right. So, for example, again, in the community that you and I are in, there is a person who's in the New York group where I've invited them to come running with the running club that I run in, right. And this is a way that he can kind of get his exercise in. And at the same time, I can work to build a network, but it's tough to just be like, oh, hey, person XYZ, come to my barbecue. Right? Or something like that. I think that it's good if you can build friendships, right. But you should start by trying to build acquaintances first, okay. And then just try and be helpful to them with whatever problems they have in their lives. Right. And let the friendships naturally evolve, rather than trying to just be very calculated around that.
Anastasia Koroleva: [00:49:43 - 00:49:49]
Okay. So this dissatisfaction you feel, how do you channel it? Where do you channel it if you do?
Boris Berenberg: [00:49:49 - 00:50:46]
I'm very much, like in the camp of people that use negative emotions as fuel for what I do. So I'm not sitting here saying, like, well, my life is bad. I mean, there are days, right, where I'm down, but generally right now, right, we're having this conversation. I can feel the emotions as I'm talking through these things, and I'm like, I'm dissatisfied with what I've done, with what I've achieved. And I'm like, I want more. And it's not a hindrance. It's like the fuel in the engine that's like, okay, you want more, go get it, right. And so I think that's a lot of what's driving my hunger and the constant action that I'm taking around, whether it's the things I'm building or the topics I'm researching or the people I'm connecting with or whatever I'm working on in my spare time. Right. That's a key part of that.
Anastasia Koroleva: [00:50:46 - 00:50:52]
So on a scale from zero to ten, how would you rate your level of fulfillment at the moment?
Boris Berenberg: [00:50:54 - 00:51:20]
I don't know. Maybe a six and a half. Not terrible, right? Again, good family, good life, good health. Right. What is it that the new year's eve thing, like wishing you health, wealth, and something else I forget. But I have all the good things, right? I'm just greedy and I want more.
Anastasia Koroleva: [00:51:21 - 00:51:24]
I can see that. That's okay. Do you have a sense of purpose?
Boris Berenberg: [00:51:24 - 00:54:12]
No, not really. Not beyond this kind of very personal sense of purpose. In the sense that I want to have a healthy family, right? I want to have physical health, right? These things actually matter to me. And after we record this interview, I'm going to go run 9 miles. And I have these kind of things that are important to me that I've spent a lot of time on. I think that that's as close to purpose as I am today. But even as I look at the things that I'm considering building next, I definitely weigh some ideas above others because they come with a purpose, opportunity, right? Like I said earlier, my last company was like, we did it for the money, right? We weren't like saving anyone's life or making families stronger or whatever. But one of my ideas is this thing I call family time, which is FaceTime, but built specifically for families, right? So with special features that are just for families. So I call my grandmother every day. She will answer on FaceTime, and some percentage of the time she'll answer in audio only mode. And then I have to be like, okay, grandma, you need to press the camera icon, which is the middle button, third from the left or third from the right. You need to press that right. It takes five minutes for her to get both because she has to find it on the screen, process that information like her hand is shaking, right? It's tough to press the button, et cetera. And I'm like, why can't I just enable the camera for her? And I get that there's answers around privacy, et cetera. And that's why this shouldn't be a thing in a general purpose tool like FaceTime. But then what I'm getting at is that if I were to build this communication platform focused specifically on connecting family members more, I have some ideas of how to make it more valuable, blah, blah. But that has an actual meaning to it, right? That has a purpose. I can say that, like, hey, we've facilitated over a million hours of family conversations that wouldn't have happened otherwise, right? And I think that some ideas would grant me more purpose than others, right? Like, I have an idea around forms for the web, right? Are forms for the web really going to change the world? Probably not, right? The money will be better, but it's not going to change anything. But I do consider kind of the purpose element of a given idea in terms of how it can impact my life when I'm picking amongst things I consider working on.
Anastasia Koroleva: [00:54:12 - 00:54:49]
We talked about it offline, how I find that exited founders who are not parents, surprisingly handle the whole post exit crisis differently. And it's often much harder for them because children actually give us so much meaning and they stabilize us so much. So I can feel it in our conversation now as well, that you don't really have that stabilizing factor of your own family yet. I know you're working on it, so hopefully you'll experience that soon and it will help you as well.
Boris Berenberg: [00:54:50 - 00:54:53]
Yeah, I can hear my mom and grandma right now.
Anastasia Koroleva: [00:54:53 - 00:55:38]
I know, I'm sorry I sound like them, but it is so true. Like, every time I talk to someone who just very young like you and either single or has only romantic relationships, there's always this feeling that there is no stabilizing factor there. Because children restrict your freedom on the one hand. On the other hand, they give you so much meaning that it's actually easier to have a purpose at this stage in your life because they give it to you. You may then grow out of that purpose and care more about bigger community and bigger society. But family does have that. Especially your children do have that power of giving us purpose for a period in our life.
Boris Berenberg: [00:55:38 - 00:55:45]
Yeah, I'm amongst my friends. I'm one of the last ones to be not married and without kids.
Anastasia Koroleva: [00:55:45 - 00:55:47]
You'll get there when you get there.
Boris Berenberg: [00:55:47 - 00:55:52]
Yeah. As usual, I'm a little slower than everyone else, but working on it.
Anastasia Koroleva: [00:55:52 - 00:56:01]
It’s just harder to exit the company and deal with it. Without that stabilization factor, how do you want to be remembered?
Boris Berenberg: [00:56:03 - 00:57:13]
I don't think I'm anything special. Right? Like loving husband, good father, right? Good son. I don't have a particular desire to be like, world renowned philanthropist, blah, blah blah. If it happens, it happens, right? But I think realistically, if I were just to be a good enough husband, father, son, whatever, friend to the people in my life, that would be number one. And number two is that with whatever I build next, part of what I care about is what I call the playground, right? I want to create a work playground where I don't want it to be this super professional thing. And that's kind of like why I, in part regret selling this cash flowing business is because there was enough cash flow where I could have just hired a CEO and then taken that cash flow and gone and hired two developers, a designer, a marketing person, and it would have been like us in an office having our own fun time building random shit.
Boris Berenberg: [00:57:13 - 00:57:31]
And just. It would have been fun, right? It would have been less of a business and more of, like, an entertainment. And if I can create that for myself, that'd be great. And if I can create that for others, I think it would also be great.
This is kind of like, where my interest in venture studios and this type of models are kind of also interesting to me.
Anastasia Koroleva: [00:57:31 - 00:57:46]
So it does sound like you're channeling your sadness in the right direction. You obviously have this amazing experience. You have all the talents in the world, and I'm absolutely sure your next business will be as huge as you want it to be. We'll see, and we'll talk about your next.
Boris Berenberg: [00:57:46 - 00:57:51]
Most likely, my next one will fail, right? But the next successful one, hopefully, will.
Anastasia Koroleva: [00:57:51 - 00:57:58]
Be, it's okay, they can fail first, but I'm sure you have a very bright future in front of you.
Boris Berenberg: [00:57:58 - 00:57:59]
Hopefully. Knock on wood.
Anastasia Koroleva: [00:57:59 - 00:58:04]
Absolutely. And let's talk in a couple of years. By that time, you will have sold your super successful business.
Boris Berenberg: [00:58:04 - 00:58:06]
There you go. Sounds good.
Anastasia Koroleva: [00:58:06 - 00:58:14]
Boris, thank you so much. This was very interesting. I really hope you feel better and you find that cash flow in business and your new identity again.
Boris Berenberg: [00:58:14 - 00:58:30]
Yeah. If someone's listening, right, and they're like, oh, I have a cash flow in business that I don't think I'll regret selling, then maybe they should reach out to me. Or if someone's looking for a co-founder or something like that, feel free to reach out to me. I'm very easy to find on the Internet.
Anastasia Koroleva: [00:58:30 - 00:58:32]
So you have a wonderful trip to Germany.
Boris Berenberg: [00:58:32 - 00:58:33]
Thank you.
Anastasia Koroleva: [00:58:33 - 00:58:35]
And I hope to see you soon.
Boris Berenberg: [00:58:35 - 00:58:37]
Yeah, absolutely. Let me know next time you're in New York.
Anastasia Koroleva: [00:58:38 - 00:58:40]
Absolutely. Thank you so much again, Boris.
Boris Berenberg: [00:58:40 - 00:58:41]
See you.
