+$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too.
Update: 2025-05-20
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:
- Hampton https://www.joinhampton.com/
- Lower Street https://www.lowerstreet.co/
- Anastasia’s Podcast https://www.exitparadox.com/
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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