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

131 snips

May 20, 2025

Anastasia Koroleva, who navigated the tumultuous aftermath of a nine-figure exit, shares her journey through divorce, burnout, and identity loss. She discusses the traps many second-time founders fall into, including rushing into new ventures and losing self-awareness. Anastasia emphasizes that wealth alone doesn’t guarantee fulfillment and offers her personal portfolio strategies focused on flexibility. With insights into rebuilding life post-exit and the emotional challenges faced, she aims to guide others in avoiding similar pitfalls.

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00:00 / 00:00

Loneliness After Exit

Anastasia faced intense confusion and loneliness after her exit and divorce.
Returning to business did not fulfill her need for meaningful social connection.

00:00 / 00:00

Don't Rush Second Ventures

Avoid jumping into a new business too early after exit driven by momentum or escape.
Lack of motivation often causes failure even if you have financial security.

00:00 / 00:00

Know Your Natural Role

Identify if you're naturally a creator, operator, or investor before starting again.
Align your new venture to your true strengths to sustain motivation and success.

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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.