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:

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.

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)

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

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