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

Summary

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

Host: Harry Morton
Guest: Anastasia Koroleva

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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.

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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.

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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:

1. 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)

2. 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)

3. 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)

4. 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.

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3. Navigating Post-Exit Life: Stages and Solutions

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

1. Financial safety
2. Holistic lifestyle upgrades (health, relationships, freedom)
3. 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)

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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)

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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)

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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

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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.

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For more on Anastasia’s work:

• Podcast: Exit Paradox
• Post Exit Academy: Coming soon

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

Transcript

[Harry Morton]

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[Anastasia Koroleva]

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

[Harry Morton]

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]

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]

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

[Anastasia Koroleva]

There is no such thing.

[Harry Morton]

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

[Anastasia Koroleva]

That one was nine digits and we bootstrapped it.

[Harry Morton]

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 [e-mail] 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]

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 the hindsight, but I now understand why.

[Harry Morton]

Do you regret that, though? Is there really any difference between 80 million and 120 or 250?

[Anastasia Koroleva]

You know, I'm okay. I don't regret anything. But I don't regret anything right now because now I've rebuilt a system that gives me that financial safety. But Harry, for a while I was very stressed. Like when I realized that my net worth has gone down, suddenly I was very stressed. Even though you can say, oh, you still were so, so much better off than you were before the exit, of course. But 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.

[Harry Morton]

Okay, great.

[Anastasia Koroleva]

Has nothing to do with how much money we have.

[Harry Morton]

Anastasia came about that calm, logical demeanor the hard way. In the early years after her exit, things looked very different. To put that into perspective, we've got to learn where she started from. As you can tell from her accent, it wasn't America. What was life like growing up in Moscow?

[Anastasia Koroleva]

It was actually amazing because it was the time when the Soviet Union had just collapsed and the country was going through an amazing change. And my parents were very much involved. They are university professors and people like them, you know, former dissidents, they really wanted to be part of everything that was happening. I ended up becoming a journalist, actually, when I was 13, and I went to Berlin and Prague together with my parents. And I reported for the Russian radio about what was happening there. So for me, it was a fantastic time. Looking back, I realized it was very challenging and dangerous in many ways, and hard. And there were times when we had to rely on humanitarian aid for food, but it didn't matter. At the Time, it was exciting, so I wouldn't want any other childhood.

[Harry Morton]

What brought you from there to Silicon Valley?

[Anastasia Koroleva]

Well, at first, when I was a journalist, I realized that I would be a very superficial one if I didn't have proper education. So I went to university in Moscow and I chose law because law was the most exciting thing at the time, because everything was changing. I started working for an American law firm in Moscow and quickly realized that if I wanted to have a real career there, I needed to go and study in the us. So I went to NYU Law School to get an American law degree. Five years later, I ran into this gentleman who just moved from Silicon Valley to New York to open an office for his startup. And we ended up getting married. And he was the one who introduced me to Silicon Valley. And when I first went there, I thought, oh my God, this is so much better than practicing law in New York. This is so much more me. So, in a way, just luck.

[Harry Morton]

So I was going to ask, how did you start your company, your first company, and it sounds like it was your husband to be's company, and you sort of joined. You joined there?

[Anastasia Koroleva]

I joined. Exactly. I joined. And at first I was more involved in what I knew, which was the legal side of things, but then I got involved in other things and also started a new company. When this one became more mature, those.

[Harry Morton]

Two were kind of running in tandem then. These two businesses.

[Anastasia Koroleva]

Yeah, for a while. For a while, yeah. And then the first one got sold, the second one got sold shortly after.

[Harry Morton]

And so these were both bootstrapped businesses. Correct.

[Anastasia Koroleva]

All four of my ventures were bootstrapped. I also started two more, but they didn't work out.

[Harry Morton]

So with that first business or those first two businesses, what period of time were you working on these things for and what did that trajectory kind of look like?

[Anastasia Koroleva]

So for the first company, it took quite a while for it to find its product market fit, but when it did, because at first, I won't bore you with details, but we experimented with all sorts of things. We ended up being one of the first, actually software as a service companies. And now it's such a popular business model, but at the time it wasn't. We ended up selling it to a private equity firm out of Silicon Valley 14 years ago. The private equity firm then resold it for much, much more. And I kept thinking what it is we missed about the potential, but yeah, it's okay.

[Harry Morton]

Yeah, no, cool. And how long were you building that business for before that exit?

[Anastasia Koroleva]

That was six years.

[Harry Morton]

What were you paying yourself during this six year period, were you sort of like classic bootstrappers, paying yourself as little as possible or as little as possible?

[Anastasia Koroleva]

Hardly anything, to be honest. And it was fine. You know, for a while we were just a young couple in New York. I had a bit of money saved from my legal days and then we started having kids. But that was already just a couple of years before we sold.

[Harry Morton]

Okay, wow. So then you, you sold, you sold with toddlers in tow.

[Anastasia Koroleva]

Yeah, yeah.

[Harry Morton]

Okay, so you went from, from basically paying yourself nothing or as close to nothing as you could get away with to suddenly an exit.

[Anastasia Koroleva]

Lots of, lots of zeros. Yeah, that one was, was nine digits. So we did end up with more money that we knew how to handle.

[Harry Morton]

Yeah, I'm sure. And you were just 50, 50 or whatever that split was. Like it was just you as shareholders.

[Anastasia Koroleva]

No, my husband and I had 80% and 20% was basically employee stock options.

[Harry Morton]

But like just a truly life changing sum of money.

[Anastasia Koroleva]

Absolutely.

[Harry Morton]

Going from like base earnings with a couple of kids to suddenly. Okay, we have a lot of optionality at this point.

[Anastasia Koroleva]

Yeah. And that's when all troubles begin.

[Harry Morton]

Well, so firstly, just tell me what did that feel like, how did that impact you emotionally at that moment? Not what occurred later, but how did it feel at the time?

[Anastasia Koroleva]

Yeah, Harry, I was pretty shocked. But at the same time I was really, really busy because first of all, I had two little kids, 1 and 3. And I also had another company to run. And in that company I was involved in seven patent litigations all at the same time in different countries and states. So I was very busy. And I think for my husband it was actually harder because he really, you know, sold this company and he was obviously involved in kids and other things as well. But in a way, being less busy may be harder.

[Harry Morton]

Aha, interesting.

[Anastasia Koroleva]

But gradually, as I started becoming more free and the second company was gone, that's when it really hit me. I was very confused. I was confused also in so many different ways. And also some of my friends were confused about how to deal with me, even though for me nothing really changed. But for them it was a bit of a challenge whether they should be behaving differently around me.

[Harry Morton]

Unfortunately, the struggles that Anastasia and her husband went through took their toll.

[Anastasia Koroleva]

Basically what happened after that. And I really do think that exit had a lot to do with it. My first husband, I'm remarried now and I got divorced. And the divorce was pretty challenging.

[Harry Morton]

And after that is when her business failures happen.

[Anastasia Koroleva]

I immediately jumped into a new venture. Okay, now I understand. I did it for completely wrong reasons. I was actually escaped, escaping the discomfort, escaping my personal problems.

[Harry Morton]

What exactly was it?

[Anastasia Koroleva]

So I got very fascinated by this early trend of health tech. I didn't feel much pressure earning money soon because I felt comfortable personally. Money wasn't really a driver anymore, but I was intellectually fascinated by the trend and the fact that it will change the world. And I still love the industry, but the reason I pretty much shelved the business was just because I couldn't care less at some point about running any business.

[Harry Morton]

You mentioned at the beginning that your parents are academics, you'd started as a journalist, you'd then sort of done law. And I don't want to say you fell into business. I'm sure there was a great deal of decision making, but nevertheless, it was something that maybe wasn't too much.

[Anastasia Koroleva]

Yeah, I was charmed. I was charmed. Didn't you?

[Harry Morton]

Right, you were charmed. I'm just really intrigued as to why you felt a desire to continue on in business and not sort of go great. Well, we've had a nine figure exit. I've got more money than I need to kind of look after myself and my kids and I don't know, go back to academia or law or something else. I'm just really intrigued as to kind of what kept you on that business path, do you think?

[Anastasia Koroleva]

I think there were several things. One, I had this incredible momentum from years and years of working very hard and being very ambitious and being very busy, and the momentum was just carrying me forward. I didn't quite know how to stop and smell the roses. I also didn't want to because I loved the excitement. But also, as I realized much, much later, I really did not like the emptiness and the fact that I needed to deal with some kind of psychological discomfort on top of dealing with family issues. So it was really an escape into something that felt familiar and exciting. And then there was another reason which also I didn't realized right away. I could not stand being nobody. I really wanted to have that title in LinkedIn and to be able to say, you know, I'm a founder or CEO now. For me it actually sounds very funny because I, I can't quite feel it anymore, but I remember it very, very well that it really mattered. I wanted to go back.

[Harry Morton]

It's really interesting because, you know, you could have chosen to still fulfill some of that by, I don't know, writing a book or, you know, something more cerebral or whatever.

[Anastasia Koroleva]

Yeah. But there was a fourth reason, which is loneliness.

[Harry Morton]

Okay.

[Anastasia Koroleva]

And I felt very lonely. I felt very disconnected from my friends in a way, from both sides. As I mentioned before, I felt that they were a bit awkward around me. But I also felt that my social needs have changed in a way that I don't fully understand. And I felt very lonely. And I felt only by going back to having the kind of social environment I was used to would help me. What happened actually is that it didn't help me because what I was going back to was very transactional employer relationship. But what I craved really was finding peers who could relate to my problems. So one of the many reasons I closed that business was that it actually did not satisfy those needs that changed and evolved into something different.

[Harry Morton]

Yep. Sounds like you needed a community like Hampton at the time. I can't help myself.

[Anastasia Koroleva]

Absolutely. I wish I did.

[Harry Morton]

Hi. Usually in this moment I break in to tell you myself about how great the Hampton community is, which, if you're new here by the way, is Sam Parr's highly vetted community community for high net worth founders doing at least 3 million in ARR. The reason I always talk about it is one, they make this podcast and two, it's an incredibly valuable resource to me. It's why I'm even hosting this podcast at all. And I truly believe it will also be just as important in your life. But because community came up so naturally in this conversation, I'll actually let Anastasia explain the benefits for this episode. Hampton Plug Specifically why a large and diverse community like Hampton is crucial.

[Anastasia Koroleva]

I think it's actually the most important thing. Over time, I appreciate it more and more and more and more because in the beginning it's more about feeling better. Later we learn from others. But today for me, it's more about having these people around me who are where I am and they're pursuing their purpose and their mission for reasons other than money. And it's very hard to tell the world that this is the case because the world is very skeptical for that. You do need a community of people who are in a similar place. There's only one caveat though, that I have to mention. You know how we talked about how most exited founders we talk to today sold their companies in 2021.

[Harry Morton]

That's coming in a second.

[Anastasia Koroleva]

By the way, what I see happen a lot is that sometimes if one person's community is just those people who also exited in 2021, which tends to be the case because that helps us normalize our situation, we all feel the same way at that stage. The danger, however, is that we amplify each other's mistakes. So I love communities that are more diverse. There are enough people that are exactly where you are, but then there are people who are ahead of you or behind you on the journey.

[Harry Morton]

Okay, back to it.

[Anastasia Koroleva]

Closing that company was really, really painful for me, even though I did it voluntarily. It also felt like I was burying a baby and I was failing, and I literally cried for two months. So after that, I became really fascinated by the whole reason, like why I had all the ingredients to make that business a success, and yet I didn't want to or I failed again. For a while, I felt something was horribly wrong with me. And then sometime later, I came across this Harvard Business School study that said that 70% of second businesses fail. And then that really piqued my interest. I thought, okay, if it's not just me, maybe there are other reasons that I don't understand.

[Harry Morton]

That sounds completely counter narrative, because I feel like everyone that's like the narrative seems to be that, you know, successful founder has the network, has the tools, has the experience, exactly all of this to then go and succeed. And it feels like everything I see on Social is exited founders succeeding. I guess that's confirmation bias and not the truth.

[Anastasia Koroleva]

Well, first of all, people don't like to talk about their failures, right? So we don't hear those stories where people failed. But even more relevant is the fact that it takes a while to fail. So there was a huge wave of exits in 2021. So most people you and I talk to today, they are three, four years after they exit. The pattern I see is that we tend to pay for our early mistakes in year five and six. And I'm very curious to see what happens in this wave. Year 3, 4 is usually when people are very busy doing whatever they chose to do early on. So they may be still angel investing, something that almost everyone regrets. When they look back after 10 years, they may be very, very busy trying to make their business, second business, a success. But 70% statistically will fail. But those failures happen a bit later.

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[Harry Morton]

Like Anastasia said, there are many reasons why those second time founders fail. She's put them into four high level categories. So let's go through them starting with number one, timing.

[Anastasia Koroleva]

The first group is when people start a business either too early or too late. Too early is quite obvious when we jump into a business like I did, usually for your own reason. Because we just follow this momentum because everybody else is doing it, because we want our found identity back. We escape from dealing with psychological discomfort, whatever it is, we jump into a new business too early, then what happens often is that we run out of motivation. Especially if the first exit was successful and we are financially set. There is a point in any startup when it becomes very difficult and we start being disappointed and we are no longer naive and we're disillusioned. So at that point we need all the resilience and motivation we can get. But we can't find it because this thought comes to our head like why am I working so hard? I have all this money, I can do whatever I want. What am I doing in the startup? So people often quit or actually this is the most dangerous thing. They don't quit and they start throwing good money after bad because second ventures are often self financed and then it's year six, seven and often tens of millions in when they finally said, you know what, that's it. A very good friend of mine just last week was in exactly that situation. Almost 30 million invested in the company. He just walked away. He said I just have no motivation. But his motivation was over about three years in.

[Harry Morton]

So he's just grinding for Another three?

[Anastasia Koroleva]

Yeah, yeah. Just also because in his case, for example, he couldn't face telling people that he failed.

[Harry Morton]

Group two, the naive.

[Anastasia Koroleva]

We get bored and we jump into a completely different industry which we don't understand. And for a while it's okay, it's very exciting. And then we realize that we have no competitive advantages whatsoever.

[Harry Morton]

Sure.

[Anastasia Koroleva]

And the idea that second business is easier is also very naive. So the combination of our illusion about the second business being easier and the fact that we are in a new industry is usually not very helpful.

[Harry Morton]

The next one is a bit more personal. Group three is those lacking crucial self understanding.

[Anastasia Koroleva]

Everybody who had a successful exit and built a business is relatively good at being a creator, being an operator, and being an investor. But oftentimes we don't quite know which of these functions we became good at because we had to, and which of these functions we are naturally good at. And I found that it's extremely important to understand because we are much more likely to keep pushing, keep grinding if we positioned ourselves doing work that we are naturally good at, even if we've learned to be really good at something else. And it's interesting because in a way it seems so obvious, but I see it all the time when a few years in, people find themselves with partners that are not actually complementary because they themselves did not understand that they were more, say, creatives than operators.

[Harry Morton]

This may feel like a completely base level, stupid question, but like, how do we find out what it is that we're naturally good at? Because I think a lot of time we're just busy doing, right? You're just like, heads down, grinding away. It's actually quite hard to separate yourself from that process and go, that's where I get my energy, that's where I'm naturally good. And this is what I've trained myself to be good at.

[Anastasia Koroleva]

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.

[Harry Morton]

And now we get to the deepest layer. Group four is about sudden wealth syndrome.

[Anastasia Koroleva]

It's basically not understanding how our emotions mess up with our brain and how cognitive biases that we don't fully appreciate make us make decisions that are not very rational. So, for example, after an exit, lots of people on your podcast shared that they feel this emotional rollercoaster and confusion, and they feel overwhelmed. One of very dangerous things that happen, especially for people with sudden wealth, is that we get very emotional about the wealth, we get very stressed about it, and we start focusing on it a lot and panicking. It's called sudden wealth syndrome. In psychology. We have this irrational fear of losing money. And that irrational fear makes us, for example, rush to start a new business because we realized that through investing, it's very hard to create wealth, at least to create bigger wealth than we did in the first venture. What they need to do instead is actually take some time to create financial safety. That's also one of the Mistakes I made. I wish I knew that earlier. Looking back, I couldn't understand why I made such stupid decisions.

[Harry Morton]

So, yeah, what are the emotional patterns that you see show up in post exit founders?

[Anastasia Koroleva]

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.

[Harry Morton]

On. Money wise. We've spoken to a ton of post exit founders, and while most of them aren't at that 10 year post exit mark, a lot of them have already run headfirst into many of these challenges, which is why we've talked about them and learned from them. The ones who haven't. Now I'm thinking more deeply about the challenges they don't even realize they have coming. The thing is, it's hard to look five years out, let alone 10. It's overwhelming. But zooming out and thinking about this psychologically, there is one move that sets the whole game up right from the start. You need to confront the money. This is what I mean.

[Anastasia Koroleva]

It takes a bit of time to just get to financial freedom. We don't get it regardless how much money we get from our exit. And of course, the content attached to the fact that we feel financially safe, it's very, very important to get there. But when we get to financial freedom, this is when we naturally switch to the desire to upgrade our life holistically. We focus on health and relationships and freedom. But lots of people start doing that before they actually created financial safety. So they still want to chase money because they don't feel financially content, or they're nervous and stressful, so they can't find this fulfillment. But what happens is that lots of people just settle for that sort of comfortable life and think that's all it is. When I look at people who successfully kind of completed the long journey and build lives that are deeply fulfilling in a holistical sense, they don't stay at that level. They take care of their health and families and lifestyle, and then they move to the third level. And the third level of wealth is when we use wealth as leverage for our purpose. But that also happens years later. Unfortunately, if we don't understand the whole picture, how our relationship with wealth changes, we think that the first level is sufficient. We say, oh, I have financial freedom, I do whatever I want. But that's just the first stage. And of course, our motivation also changes during those 10 years dramatically. And if we don't understand that, we will want naturally something very different two years from now. It's very hard to make decisions. So you asked me about emotional challenges post exit, and I think a lot of those emotional challenges actually come from the fact that we don't understand how we naturally evolve post exit in terms of motivations, in terms of our understanding what success and wealth actually means, and the appreciation that we will want different things later on. And that's okay.

[Harry Morton]

That confrontation period also involves recognizing the things the exit has added to your life, as well as the things it's taken away.

[Anastasia Koroleva]

When we sell a company, we have a new kind of P and L. Not the profit and loss P and L, but the P and L with respect to all areas of our lives. So we lose certain things. We lose our business, our basic needs are no longer satisfied. We lose our social circle. We lose the world as we know it. But we also gain a lot of great things. We gain freedom, we gain time, energy, money, reputation, which is often underestimated. So the most helpful framework, I think, is to think, how can I get the most out of these post exit assets that I got while recovering all these post exit losses? So for losses, I really like the Maslow pyramid framework, I think it works and it's time tested and for the gains, it's also very important to understand that each of them we need to get the most out of. So if you just jump into the next business, it doesn't mean that you got the most out of the freedom, energy and all these other things that you go through the exit. And the tragedy is that 10, 20, 30 years later, people look back and they say, oh, I had these amazing gifts given to me and I just wasted them because I thought I just needed to identify that specific activity I needed to do right away.

[Harry Morton]

It's a lot to think about and while you're thinking about all that stuff, there's likely a part of you that's itching to get to the next thing because, well, we have a lot of energy and it's got to go somewhere. So how do you know when it's actually time to expel that energy onto your next thing? To find out, I'm going to steal the structure of one of the wisest stories ever. Goldilocks. We already covered the papa bear bit. Being eager and starting your business too quickly, but you can also pull a mama bear and wait too long.

[Anastasia Koroleva]

If we allow ourselves to just have this very comfortable life, say chasing experiences for a while and then just having this, we stop to smell the roses for too long. What happens is that we build a whole external scaffolding around us, a new system supporting this kind of self indulgent life. And then at some point we feel very empty because we have no purpose. So we start thinking, oh, I miss those days when I built the business with the most amazing people and I solved difficult problems. I really, really want to do it again. So people start a business again. But that's years after their previous business and loss of the skills have atrophied. Loss of relationships are no longer there and maybe relationships that they need are not there because their new relationships are supporting the self indulgent life. I see it all the time among those who exited 10 years ago or seven years ago.

[Harry Morton]

So what's the baby bear solution?

[Anastasia Koroleva]

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.

[Harry Morton]

Okay. So Sam has said on episodes of Money Wise before that what you should do is just put your money aside and just wait for a year and just, you know, do nothing for a year. I don't think he ever did nothing. I don't know if that's true. I don't know if he did nothing or not. But like he didn't do anything with his money and that was to sort of avoid some of these cock ups basically of just doing something too quickly.

[Anastasia Koroleva]

I think it's a great advice. But I also think that if you just wait for a year and then you start doing something else, chances are that you will still not be in this deeply fulfilling place. Right, sure. Because oftentimes I read somebody sharing their post exit experience. So I talk to people doing that and they think that the problem is so solved once they've decided what to do next.

[Harry Morton]

Sure.

[Anastasia Koroleva]

And to me it's completely ridiculous because just because you decided what you do next doesn't mean it's the right decision.

[Harry Morton]

Sure.

[Anastasia Koroleva]

And more often than not, it actually is not.

[Harry Morton]

This has been a ton of focus on you, the founder. This is still money wise, so don't worry. We've got more on Anastasia's personal finances and spending coming up. But to round out our focus on you and me, I had a pressing question. What type of personality or founder profile do you think struggles post exit?

[Anastasia Koroleva]

The most sensitive creators.

[Harry Morton]

Okay.

[Anastasia Koroleva]

People who are naturally very creative, they saw a business as a form of art. And as one of my guests puts it very beautifully, he suffers most from knowing that his vision will never be realized. And he was actually telling me that he didn't think that that would be a problem. But he can't get over the fact that he had this piece of art he was building and then somebody took it away and he cannot realize his creative vision. These people suffer quite a bit.

[Harry Morton]

Okay, so that's me. I don't know if I have a creative vision specifically, but I am the creative, thoughtful type. So you've got my interest. What do I do?

[Anastasia Koroleva]

Don't sell.

[Harry Morton]

Yeah, okay, great.

[Anastasia Koroleva]

Or sell when you feel your vision has been realized. But the reason I think it's very difficult for this type is that we often don't realize how our motivation evolves while we are building a business. I talked to so many people who are telling me after their exit that they were motivated in the first business by money. But what I found is that I've still to meet a successfully exited founder who was motivated by money later on in the business. But most of us, we don't realize we're too busy. So say somebody starts a business with because of some combination of desire for money and financial freedom and a chip on their shoulder. The most typical situation. Of course there are also other reasons, like they don't feel they fit anywhere, they don't like any job, all of it. But they registered in their mind that they wanted financial freedom and they wanted to prove themselves to somebody else. Ten years later they sell a business for half a billion and they say, oh, in the first business, that was my motivation. They remember it that way. Now I want to be motivated by something else. But then when I talk to them and I ask them, okay, so did you care about your employees? Oh, of course I cared about my employees. Did you care about your customers? Of course I cared about my customers, partners and everybody else. And it becomes very clear through a set of questions that their motivation evolved into genuinely caring about other people. They just never registered it.

[Harry Morton]

Sure.

[Anastasia Koroleva]

If you think about any successful company, that company at some point became customer centric. And that company did a very good job attracting and motivating employees. I don't think a founder can continue being motivated by just money and the chip on their shoulder and succeeding in doing this. I think when a founder's motivation doesn't evolve, then the business either fails or stagnates. They don't have a super successful exit. But the reason it's very important for our emotional state is that lots of us feel imposter syndrome or we feel self doubt after an exit. We are not sure we actually deserve it. But if we realize that we are not that greedy, insecure person we thought we were when we started the journey, but actually we evolved into this beautiful caring person who solves problems for others that heals our imposter syndrome and the self doubt that we have, and I see it all the time through these conversations that people are surprised that they're much better people than they thought they were.

[Harry Morton]

The ones that don't struggle, like what do they have in common?

[Anastasia Koroleva]

Everybody struggles, okay? There is no such thing that people don't struggle. Some people don't struggle at first because they usually already had a plan before. For example, they were waiting for that exit so they could go with their loved ones and travel the world. And that's exactly what they do. And it's very exciting and it's beautiful to watch. But the problem is that all this traveling around the world, which I also did, is absolutely wonderful. For a maximum of two years, sure. And then you really want to do something that's useful, you want to matter for the world, you want to be engaged and you want challenges. And then everybody struggles at that point. So even the luckiest ones that seem to have it all in the beginning, they will struggle. And that's okay, because that's so beautiful, isn't it? It's how we grow. It's exactly why our exits are these incredible opportunities to go to a completely different level in our personal growth.

[Harry Morton]

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[Harry Morton]

But the emotional stuff. Now let's get into what you really want to know. How does someone with a high eight figure Net worth actually manage their money. Here's how Anastasia does it.

[Anastasia Koroleva]

So at some point I simplified everything because I tried so many different things. I overcomplicated things. Right now I don't have any wealth manager. I didn't like working with any of them for a number of reasons. The way I think about my portfolio is that 65% of my assets belong to the category which is relatively liquid and low risk. So these are public equities and cash and cash equivalents. The reason they're only relatively liquid is because when the market goes down like now, my equity pretty much becomes illiquid because I don't want to sell. But that's okay because 25% of my portfolio generates cash. And at the moment, it's all in private credit. The way I look at private credit is that I only pick things that are completely not correlated with the equity market that use either. No leverage. But that's super hard to find, sometimes low leverage, because this is how I make sure it's actually low risk. That's my definition of low risk. Zero correlation with the equity market and no leverage or very low leverage. And then I want those assets to generate at least 12% return per year. So right now, for example, my biggest holding is this company, Chicago Atlantic, which is the largest credit organization for the cannabis industry. So cannabis industry is not correlated with anything else I have on the equity market. They use zero leverage. They pay me 3% per quarter in cash. But I also have equity kickers. So in reality I get between 16 and 20% a year return.

[Harry Morton]

Wow.

[Anastasia Koroleva]

So I have this very, very reliable stable cash flow which covers me when equity markets are down. Because the whole structure of my portfolio is to reduce my stress and to make sure that my motivation is free and I can pursue my mission to help exited founders.

[Harry Morton]

And does it work, by the way? So when the tariff mayhem kicks off and everyone's portfolio drops by that 10% you just mentioned, are you okay? Do you get that heart attack response or no?

[Anastasia Koroleva]

No, no. Because the whole portfolio is fine. Right. And also this is the lesson that I learned the hard way, that cash flow is so much more important than any theoretical net worth number.

[Harry Morton]

Sure.

[Anastasia Koroleva]

And if I know that I have cash coming from different sources, I feel very comfortable. Also, I personally completely exited real estate market some time ago. I decided that I don't want it. I switched to private credit. I also wanted to simplify things. So the remaining 10% are I have in private equity. But the way I think about it is that, okay, this is potentially High growth. But if I lose it, I don't care.

[Harry Morton]

Okay. Yep.

[Anastasia Koroleva]

And this allows me to sleep well at night. My kind of three buckets, relatively liquid. Then my private credit is relatively illiquid because when I just start the relationship, usually they lock you up. Which I learned to appreciate in the beginning of my investor career. I didn't want to invest in anything where I would be locked up. And then later I realized that I'm so dangerous to my money that I should be locked up. And it's actually the source of sense of safety for me today. I don't mind it at all. Also, if I choose my investments carefully, I don't want to jump in and out all the time. And then of course, private equity is illiquid. So relatively liquid. Relatively illiquid. And then illiquid.

[Harry Morton]

Okay, got it. That amazing. And what's your monthly burn, do you think? What do you spend on a monthly basis?

[Anastasia Koroleva]

Well, so I prefer to think annually. So if you don't mind. So I basically spend between 650,000 and the million per year on the family, as a family.

[Harry Morton]

Okay. And how many kids now do you have?

[Anastasia Koroleva]

Three. I have three kids.

[Harry Morton]

Awesome. I'd love to just know what you know with that. 650 to a million. What does your lifestyle look like?

[Anastasia Koroleva]

Well, I have two homes. I'm very comfortable with my two homes. One is in the south of France on the beach. That's where we spend three months a year as a family. And another home I own is in London. I share my time between London and Miami. Really?

[Harry Morton]

Okay.

[Anastasia Koroleva]

But I'm in London more and I don't own anything in Miami. And so in terms of the properties I own, they're in Europe.

[Harry Morton]

Okay.

[Anastasia Koroleva]

The difference between 650 and the million has to do with how much we travel.

[Harry Morton]

Okay.

[Anastasia Koroleva]

That's the difference. Sometimes we travel more, sometimes we travel less. We spend a lot of time together as a family. I have three boys. I live with four men in the house. A lot of testosterone, especially given that two are teenagers. And then I have a six year old.

[Harry Morton]

Wow.

[Anastasia Koroleva]

It's a very busy, fun, noisy home.

[Harry Morton]

Are you glad that you own the second home in France? Would you like? Because I'm often. I'm just personally interested in this because I just wonder if it's worth the extra effort of owning versus just renting when you go there, you know, Harry.

[Anastasia Koroleva]

I go back and forth on that one. But I think when you have three kids, it's good to have a second home where they all love to go.

[Harry Morton]

Sure.

[Anastasia Koroleva]

But I would never tell anyone that you need to have a second home. Absolutely not. 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.

[Harry Morton]

It's been nearly 15 years since Anastasia's exit. Plenty of time to figure out what life looks like on the other side. So here's how things have changed for her.

[Anastasia Koroleva]

When I sold my business, it was all about me, me, me. I felt so much pain from losing that world. I loved losing the relationships, all my basic needs, being not satisfied anymore. I was very focused on myself. Today I'm really genuinely driven by how I can give my very, very best to the world. And when I can, that's when I'm happy and satisfied. But I needed to get to the point where I really, genuinely feel it. You can't fake it. You cannot decide that this is what's going to motivate you today.

[Harry Morton]

And is that your full time gig now?

[Anastasia Koroleva]

Yeah. I love it. I really, really care about exited founders. I think exited founders are some of the most consequential people on the planet, some of the most capable people on the planet. And when I see people like that get stuck for 10 years, first of all, it's very unfair to them because they worked so hard, they gave so much to the world disproportionately through building those really valuable businesses. But I also feel, and this is becoming more and more important for me over time, that the society is missing so much because these talented people are stuck in these psychological traps for a decade or more. So it drives me like I wake up in the morning. This is what I really care about more than anything else. So today I have basically three ways of pursuing that mission. I have a Post Exit playbook, which is basically a program where I take people step by step and walk them around those traps to make sure whatever path they choose, they don't get stuck in predictable places. I'm building Post Exit Academy where I want to bring everything that people should learn, not only from me, but from everybody else in one place, like a hub. And then I have my Exit Paradox podcast, which is basically for me a way to share the stories of people who otherwise don't share their stories and to ask them the questions that most people don't ask them about how they dealt with this Post Exit challenge.

[Harry Morton]

Anastasia had a ton of amazing insight and to be honest, we've only really scratched the surface. So if you want her back, let me know. Let me know in the comments. On YouTube or on Spotify, or tweet at me, I'm HarryMorton or find me on LinkedIn Harry Morton over there. Wherever you want, but just let me know. And if you want to get loads more diverse perspectives from other post exit founders or also the founders who didn't and have no plans to exit, definitely go and check out joinhampton.com and if you want a podcast like this one, you can check out my company Lower Street. Go to Lowestreet co I'm Harry Morton and this is money wise. We'll see you next week.