<p>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</p><p>After a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.</p><p><strong>Here’s what we talk about:</strong></p><ul><li>Anastasia’s journey from a bootstrapped nine-figure success to divorce, burnout, and identity loss</li><li>Why second businesses often fail, and how success the first time around can actually work against you</li><li>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”</li><li>How to rebuild your life after selling a company using frameworks like Maslow’s hierarchy and cognitive dissonance theory</li><li>Why wealth alone doesn’t create fulfillment, and what actually does</li><li>Anastasia’s personal portfolio strategy: no wealth manager, heavy in private credit, designed for low stress and high flexibility</li><li>A real look at her post-exit lifestyle, including two homes and $650K to $1M in annual spending</li><li>How long it truly takes to feel whole again after an exit, and why slowing down might be the smartest move</li><li>Why she now spends her time helping other founders avoid the same mistakes</li></ul><p><strong><br>Cool Links:</strong></p><ul><li>Hampton https://www.joinhampton.com/</li><li>Lower Street <a href="https://www.lowerstreet.co/">https://www.lowerstreet.co/</a></li><li>Anastasia’s Podcast <a href="https://www.exitparadox.com/">https://www.exitparadox.com/<br></a><br></li></ul><p><strong>Chapters:</strong></p><ul><li>(00:00) Introduction: The Big Picture Trap</li><li>(00:56) Meet Anastasia's Net Worth</li><li>(03:14) Anastasia's Early Life and Career Beginnings</li><li>(04:19) The Silicon Valley Leap and First Ventures</li><li>(07:25) The Emotional Rollercoaster of Success</li><li>(09:25) Post-Exit Challenges and Personal Struggles</li><li>(17:55) The Psychology of Second Ventures</li><li>(24:26) Understanding Sudden Wealth Syndrome</li><li>(28:20) Minimizing Psychological Discomfort Post-Exit</li><li>(29:37) The Paradox of Wealth and Freedom</li><li>(31:30) Confronting Financial Freedom</li><li>(32:48) The Third Level of Wealth</li><li>(33:30) Emotional Challenges and Evolution Post-Exit</li><li>(34:49) Rebuilding the Basics: The Maslow Pyramid</li><li>(35:44) The Goldilocks Approach to Post-Exit Life</li><li>(48:07) Managing Wealth Post-Exit</li></ul><p><br>This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.</p><p><br>Inspired by real conversations happening in the Hampton community.</p><p><br></p><p><strong>Your Host: Harry Morton</strong></p><ul><li>Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.</li><li>Co-parents a cow named Eliza.</li></ul>

Moneywise

Hampton

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

MAY 20, 202560 MIN
Moneywise

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

MAY 20, 202560 MIN

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.