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+$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too.

Moneywise

Tue May 20 2025

Summary

Moneywise, May 20, 2025: +$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too.

Host: Harry Morton
Guest: Anastasia Koroleva

Episode Overview

This episode features Anastasia Koroleva, multi-exit founder and host of the Exit Paradox podcast, as she shares her personal and financial journey after a nine-figure startup exit. Anastasia discusses the counterintuitive reality that 70% of second-time founders fail, explores the psychological traps of post-exit life, and offers unique insights into what true wealth, fulfillment, and success mean for high-net-worth entrepreneurs.

Key Discussion Points & Insights

1. Anastasia's Background and Numbers (03:01 – 08:28)

Anastasia Koroleva made a nine-digit exit from her first company, which was fully bootstrapped. Due to her divorce and “very stupid decisions,” her current net worth is in the high eight figures.
- Quote: “I'm no longer in nine figures because of my divorce, but I'm in high eight figures, not only because of the divorce, by the way. I made quite a lot of very stupid decisions in hindsight, but I now understand why.” (03:01, Anastasia)
She and her then-husband owned 80% of the company; 20% was employee stock options.
Her early years: Born in Moscow post-Soviet era, began as a journalist at 13, studied law at NYU, married a Silicon Valley entrepreneur, and joined his startup, later launching other companies herself.
All her ventures were bootstrapped: “All four of my ventures were bootstrapped. I also started two more, but they didn't work out.” (06:58, Anastasia)

Emotional Reaction to Exit

After years of scraping by, the massive payout was life-changing—but not straightforward:
- “When I realized that my net worth has gone down, suddenly I was very stressed… That's not how human psychology works, right? There is this famous research that when our net worth goes down 10%, our body has a similar reaction to a heart attack.” (03:23 – 04:02, Anastasia)
She was “shocked but busy” after the exit; confusion and social awkwardness followed once things slowed down.

2. Post-Exit Trap: Why 70% of Second-Time Founders Fail (10:48 – 20:10, 22:14 – 29:43)

A Personal Account of Failure

Jumped into a new health tech company after her first exit, but admits: “I did it for completely wrong reasons. I was actually escaping the discomfort, escaping my personal problems.” (10:48, Anastasia)
She struggled with loneliness, loss of identity, and a craving for the founder/CEO role as a source of self-worth.

The Four Failure Traps (20:10 – 29:43)

Anastasia’s research and personal experience point to four main reasons second-time founders fail:

Timing—Starting too soon or too late
- Jumping in too early, out of momentum or discomfort, leads to loss of motivation when things get tough. Many continue throwing good money after bad, sometimes “tens of millions” before walking away.
- Example: “A very good friend of mine… almost $30 million invested in the company. He just walked away.” (21:57, Anastasia)
Naivety—Switching industries with no advantage
- “We get bored and we jump into a completely different industry which we don't understand… and then we realize that we have no competitive advantages whatsoever.” (22:14, Anastasia)
Lack of Self-Understanding
- Many founders don’t recognize whether their strengths are as creators, operators, or investors—leading to wrong roles and unbalanced partnerships.
- The importance of honest introspection and soliciting feedback: “Success usually comes to people who are very honest about their strengths.” (25:18, Anastasia)
Sudden Wealth Syndrome (SWS)
- The psychological impact of newfound wealth induces stress, impulsiveness, and risk aversion.
- “After an exit, lots of people… feel this emotional rollercoaster and confusion… We get very stressed about the wealth, and we start focusing on it a lot and panicking. It's called sudden wealth syndrome in psychology.” (26:43, Anastasia)
- Most rush back into work to minimize discomfort.

Cognitive Dissonance and the Trap of "Resolution"

The urge to resolve internal discomfort leads to premature or shallow new ventures.
- “We want to say, ‘Oh, all this psychological discomfort is not important. I'll just jump back into the business. I'll be fine.’”
- Simple “experience chasing” (travel, pleasure) also leads to emptiness.

3. Navigating Post-Exit Life: Stages and Solutions

Three Levels of Wealth (33:50 – 36:10)

Financial safety
Holistic lifestyle upgrades (health, relationships, freedom)
Wealth-as-leverage for purpose

“When we get to financial freedom, this is when we naturally switch to the desire to upgrade our life holistically… But that's just the first stage.” (35:00, Anastasia)

Recognizing Gains & Losses After Exit (36:17)

Think of a new “P&L” — not just profit and loss, but gains (freedom, time, money, reputation) and losses (social circle, identity, daily purpose). Use frameworks like the Maslow Pyramid to rebuild fundamentals.

Goldilocks Timing: Not Too Fast, Not Too Slow (37:47 – 43:34)

Start too soon = burn out, wrong motivation
Wait too long = loss of skills, relationships, sense of purpose
Healthy path: Take a break and rebuild basics (social/emotional/financial safety), give yourself permission to not know, and rediscover motivation organically.
- “When we build a business, we really build our customized Maslow pyramid… We sell it, everything collapses. So it's very important to appreciate how fundamental that problem is. So we need to spend some time rebuilding the basics.” (41:00 – 41:52, Anastasia)
“When people are feeling very rational and very good about it, it takes between a year and two years to be in a very good place.” (43:13, Anastasia)

Dealing with Founder Types post-Exit (44:55 – 47:41)

Creators/artists struggle most—feel pain over “losing their art” or not realizing the full vision.
Most founders start for money or to prove themselves, but over years, genuine care for people and impact emerges. Not recognizing this evolution leads to imposter syndrome or dissatisfaction.
- “We evolve into this beautiful caring person who solves problems for others—that heals our imposter syndrome.” (48:24, Anastasia)
Nobody escapes struggle: “Everybody struggles, okay? There is no such thing that people don't struggle.” (49:07, Anastasia)

4. Anastasia's Approach to Wealth, Portfolio, and Spending (52:01 – 57:42)

Portfolio Structure

No wealth manager; prefers total control.
65%: Public equities and cash/cash equivalents (“relatively liquid”)
25%: Private credit (uncorrelated, low/no leverage, 12%+ returns; e.g. Chicago Atlantic in the cannabis sector, yielding 16–20%)
10%: Private equity (“potentially high growth, but if I lose it, I don't care”)
Avoids real estate—moved capital from property to private credit to simplify her life.
- “Cash flow is so much more important than any theoretical net worth number.” (54:42, Anastasia)
- Private credit is intentionally “locked up” as a safeguard against impulsive moves: “I'm so dangerous to my money that I should be locked up!” (55:15, Anastasia)

Spending & Lifestyle

Family annual spend: $650,000 – $1 million
Two homes: south of France (beachfront, 3 months a year) and London (main base); splits time between London and Miami but doesn’t own in Miami.
Difference in annual spend tied to travel frequency.
Three sons, noisy household, lots of family time.
Second home in France is a legacy of “what else can I buy?” phase post-exit; not a must-have for everyone.
- “I would never tell anyone that you need to have a second home… It was one of those purchases that I made early on after an exit when I was going through this kind of what else can I buy stage.” (57:42, Anastasia)

Notable Quotes & Memorable Moments

“The idea that a second business is easier is very naive. We find ourselves overwhelmed with freedom and we say, ‘What is this freedom for? I just feel confused.’”
– Anastasia Koroleva (01:21, recurring theme)

“I immediately jumped into a new venture. Okay, now I understand. I did it for completely wrong reasons… escaping discomfort, escaping my personal problems.”
– Anastasia Koroleva (10:48)

“We tend to pay for our early mistakes in year five and six… 70% of second businesses fail.”
– Anastasia Koroleva (01:15, 16:04, and 17:54)

“We evolve into this beautiful caring person who solves problems for others. That heals our imposter syndrome.”
– Anastasia Koroleva (48:24)

“Cash flow is so much more important than any theoretical net worth number.”
– Anastasia Koroleva (54:42)

Important Segments & Timestamps

Anastasia’s Exit & Early Reaction: 03:01 – 10:29
Struggles of Wealth & Second Ventures: 10:48 – 15:13
Community & Peer Support’s Importance: 15:13 – 16:38
Why 70% of Second-Time Founders Fail: 16:44 – 29:43
Sudden Wealth Syndrome & Cognitive Dissonance: 26:43 – 33:17
Three Levels of Wealth: 33:50 – 36:10
Timing Your Next Move (Goldilocks Principle): 37:47 – 43:34
Founder Psychology & Motivation Over Time: 44:55 – 49:02
Anastasia’s Wealth Strategy: 52:01 – 56:07
Lifestyle, Family, and Homes: 56:13 – 57:42
From Me-Focus to Mission: 58:04 – 60:32

Conclusion

This episode provides radical transparency about life before and after a massive startup exit. Anastasia’s candor demystifies the financial, psychological, and social hurdles that exist behind the headline numbers. She urges listeners to anticipate the emotional rollercoasters, invest in community, and recognize how both wealth and motivation transform over time. Her message is a clarion call for high-net-worth founders to avoid “post-exit traps” and thoughtfully design their next chapters for meaning and fulfillment—not just more zeros in the bank.

For more on Anastasia’s work:

Podcast: Exit Paradox
Post Exit Academy: Coming soon

[End summary. Skip ad spots, intros, outros. For questions or more deep dives, reach out on Moneywise’s community channels.]

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Transcript

Harry Morton (0:00)

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Anastasia Koroleva (1:06)

Most of us don't actually look at the big picture and because of that we fall into a very predictable trap.

Harry Morton (1:15)

I'm going to be honest, I've never been as engaged in an interview for Money wise as I have with this one that we're about to do right now.

Anastasia Koroleva (1:21)

We tend to pay for our early mistakes in year five and six. And the idea that second business is easier is also very naive. We find ourselves overwhelmed with freedom and we say like, what is this freedom for? I just feel confused. You say, oh, now I'll just chase experience for the rest of my life. A couple years in, people find themselves in a situation where they feel very empty. It's basically a different kind of consumerism. But it's still all about me, me, me, give me more.

Harry Morton (1:54)

And if you think you're the exception to these struggles, you're wrong.

Anastasia Koroleva (1:58)

There is no such thing.

Harry Morton (2:00)

Anastasia Koroleva knows this experience very well because she's been through it.

Anastasia Koroleva (2:04)

That one was nine digits and we bootstrapped it.

Harry Morton (2:08)

After her own very intense post exit period, which included divorce, a business failure and an identity crisis, she's found herself fascinated with the psychology of post exit founders. And so it's something she's spent the last 13 years diving incredibly deeply into. So in this episode she's going to lay it all bare. Her own story, the common traps and the most important things that you need to do to have a rewarding and successful post exit life. This is money wise and I'm Harry Morton and we'll talk about it more later. But just so you know, this is a podcast made by Hampton for Hampton members. So if you're a founder, go and check it out@joinhampton.com and if you end up liking what Anastasia has to say, definitely go and check out her podcast. It's called Exit Paradox and it goes super deep into post exit founder psychology. Okay, let's start where we love to start. Why the hell should you listen to Anastasia, AKA what are her numbers?

Anastasia Koroleva (24:09)

Harry, we have to channel our focus and energy into that question, right? Otherwise nobody will answer it for us. So it does take a little bit of time to go back and think about the process, the experience of us doing that business and also maybe talking to other people, because again, another good friend of mine shared with me a few days ago actually that it wasn't until he talked to his former partner and that former partner told him that, you know, you were very, very useful in the beginning, but you were pretty useless after three years because you're so creative that we wouldn't have started this business without you. But then you were kind of, you know, annoying later on because you were too creative and I needed to Build systems. And I'm good at that, right? And I thought it was very interesting. They spent seven years building that business, and it was only after the exit that they had that conversation when the partner was comfortable sharing that. But it's very useful sometimes to ask other people to share their own view, because some people are very like. In my podcast, I also often ask people this question, do you think you are a creative or you're an operator? And many people are confused. Or they say, oh, I'm good at both. And I'm like, probably you're better in one of these things because they're very, very different. But what I did notice, because I look at so many stories of success, I can see that success usually comes to people who are very honest about their strengths. And for example, lots of exited founders would love to not work as hard and just not be operators anymore and only share big ideas. But if your strength is an operator, then this is your strength, and then you have to design that new business very differently. And maybe, okay, you don't want to be an operator all day long, but you still need to find a partner who compliments you on the creative side, because actually it's not your thing. Most importantly, I think, is to understand that our exit gives us this opportunity to take the time and to channel our focus and energy to things like that. And they actually don't take that long. We don't need to spend years figuring these things out. We just need to know that these are the things we need to do and then we can do them quite efficiently.

Anastasia Koroleva (28:07)

It's interesting that you said emotional patterns because I think there are patterns that people like to talk about, which are what people tend to do post exit. For me, to be honest, it's not very interesting. I think first of all, it's a bit superficial, but also people often change what they do over time. What's interesting is why we do what we do. And in the beginning, most of the mistakes we make are because we don't handle our emotions very well. And I remember I was really shocked when I came across another statistics, which is that on average it takes us 10 years to adjust to an exit. So I was very curious to understand why it takes a whole decade and then most people don't do it very well. So I started interviewing people specifically who exited more than 10 years ago so we could see the whole pattern. And this is where I found, I think the key to the problem, the root cause. Most of us don't actually look at the big picture. So we expect that within a few months, maybe a year, we'll be fine. And because of that, we fall into a very predictable trap. And the trap is that we find some easy solution. And it's very interesting where it comes from psychologically. When we exit a company, we find ourselves in a situation where our reality conflicts with what we expected and conflicts with some of our very basic beliefs, like what success is, what freedom is, what wealth is. And there is this very interesting American psychologist called Leon Festinger, who wrote a book in 1957 which is called the Theory of Cognitive Dissonance. So if you apply his theory to an exit situation, it explains a lot. We basically go through not just a simple cognitive dissonance, but an overwhelming cognitive dissonance where lots of things don't match, lots of our ideas don't match the reality. But the reason this theory is very helpful is because Leon Festinger found that humans naturally want to minimize the importance of cognitive dissonance. It feels very uncomfortable. So there are two ways to deal with it. Either resolve it or minimize the importance. And most of us want to minimize the importance. And we do it in the post exit scenario by, for example, jumping back into business the way I did it and I see lots of people doing it. We want to say, oh, all this psychological discomfort is not important. I'll just jump back into the business. I'll be Fine. But we also often try to resolve it in ways that don't actually resolve it. For example, people say, oh, wealth didn't make me happy, so now I'll be chasing experiences. We read books like Die with Zero, which is a brilliant book, but if you take it too far and you say, oh, now I'll just chase experience for the rest of my life, what happens is that a couple years in, people find themselves in a situation where they feel very empty because they are not contributing anything to the world. It's basically a different kind of consumerism. Now. Instead of buying material things, we get experiences and different type of pleasure from the world. But it's still all about you, me, me, me, give me more. I want to experience more, I want to have more. What happens is that people try to resolve this cognitive dissonance in a way that is oversimplified. So I found that people who actually resolved cognitive dissonance, well, they apply paradox to it and they say, you know what? I'm okay with two conflicting truths. I'll reconcile them. And the simplest example is when people say, okay, wealth didn't bring me happiness, but wealth is very important and is very helpful and I want to continue creating more wealth. I just also will make sure that I have other things in my life that bring me fulfillment. A similar situation with freedom. Freedom is even more important than wealth as a motivator for entrepreneurs. But when we successfully exit, we find ourselves overwhelmed with freedom. We find ourselves in a decision paralysis and we say, like, what is this freedom for? I just feel confused. So if we apply the tool of paradox to this situation, we can also say, no, no, freedom was still worth it as a goal. But now that I have freedom, I simply need to take a few more steps to build the life that I want to build.

Anastasia Koroleva (39:29)

The healthiest way to deal with a post exit journey is first to give yourself a bit of time to just let go and let that momentum go away. I see all the time people, especially younger exited founders, clinging onto that momentum in fear that it will not come back. They say, I cannot stop because then I relax, I'm not going to want to do it again. And in a way they're right because it may happen but it doesn't have to happen. So I think it's extremely important to let go and just recover and relax and let the emotions do their job. And then after that, lots of people need to go and expand life experiences because I see so many people who started a business very young in their lives and haven't actually seen the world or experienced anything other than doing a business. So they may rest and recover and then they say, oh, the only thing I know is how to build a business. And that's not necessarily healthy for them because then they jump into a new business and they never do all these things they could do because they just don't know what they don't know. So when I look at very successful cases, usually people give themselves permission to not know and not do anything and they relax and then they go and they experience lots of things they never experienced. But they don't worry about the fact that their motivation may not be there. They believe it will come back, which it should, if they do things right. And then the next thing, Harry, I think is extremely important because that has to do with rebuilding the basics. When we build a business, we really build our customized Maslow pyramid. The business is our whole world. The safety comes from our business. The self esteem comes from our business. Love and belonging comes from our business. Self realization comes from our business. Everything comes from our business. We sell it, everything collapses. So it's very important to appreciate how fundamental that problem is. So we need to spend some time rebuilding the basics. Because if you think about it, the whole idea of Maslow Pyramid is that it shows how our motivation naturally flows. And what Maslow discovered is that until we have safety, not just physical safety at the bottom of the pyramid, but safety in terms of love and belonging, safety in terms of self esteem, knowing who we are and why we're here, until we have that safety, we cannot actually start contributing our very best to the world. It's interesting that Maslow, shortly before his, his death, added another level to his pyramids which most people don't know about, which is actually the spiritual level, which is all about giving our best to the world. But it can only happen if we have safety. Financial safety, social safety, emotional safety. But it's so boring for most of us to be building it right. But we have to, because if we don't, this is exactly why we fail. We fail in our investments, we fail in our new businesses. Relationships, divorces, they basically come from our failure to reluctance to do the boring job of rebuilding that pyramid with something else. Yeah, so Going back to your question, how much time it takes, I think when people are feeling very rational and very good about it, it takes between a year and two years to be in a very good place.