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

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

May 20, 20251 hrEp. 53
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Episode description

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

After a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.

Here’s what we talk about:

  • Anastasia’s journey from a bootstrapped nine-figure success to divorce, burnout, and identity loss
  • Why second businesses often fail, and how success the first time around can actually work against you
  • The four biggest traps post-exit founders fall into: rushing into something new, chasing unfamiliar industries, losing self-awareness, and falling into “Sudden Wealth Syndrome”
  • How to rebuild your life after selling a company using frameworks like Maslow’s hierarchy and cognitive dissonance theory
  • Why wealth alone doesn’t create fulfillment, and what actually does
  • Anastasia’s personal portfolio strategy: no wealth manager, heavy in private credit, designed for low stress and high flexibility
  • A real look at her post-exit lifestyle, including two homes and $650K to $1M in annual spending
  • How long it truly takes to feel whole again after an exit, and why slowing down might be the smartest move
  • Why she now spends her time helping other founders avoid the same mistakes


Cool Links:

Chapters:

  • (00:00) Introduction: The Big Picture Trap
  • (00:56) Meet Anastasia's Net Worth
  • (03:14) Anastasia's Early Life and Career Beginnings
  • (04:19) The Silicon Valley Leap and First Ventures
  • (07:25) The Emotional Rollercoaster of Success
  • (09:25) Post-Exit Challenges and Personal Struggles
  • (17:55) The Psychology of Second Ventures
  • (24:26) Understanding Sudden Wealth Syndrome
  • (28:20) Minimizing Psychological Discomfort Post-Exit
  • (29:37) The Paradox of Wealth and Freedom
  • (31:30) Confronting Financial Freedom
  • (32:48) The Third Level of Wealth
  • (33:30) Emotional Challenges and Evolution Post-Exit
  • (34:49) Rebuilding the Basics: The Maslow Pyramid
  • (35:44) The Goldilocks Approach to Post-Exit Life
  • (48:07) Managing Wealth Post-Exit


This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.


Inspired by real conversations happening in the Hampton community.


Your Host: Harry Morton

  • Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
  • Co-parents a cow named Eliza.
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+$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too. | Moneywise podcast - Listen or read transcript on Metacast