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

Moneywise

Hampton

Business, Entrepreneurship, Investing

4.8 • 674 Ratings

🗓️ 20 May 2025

⏱️ 60 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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.

Transcript

Click on a timestamp to play from that location

0:00.0	Most of us don't actually look at the big picture, and because of that, we fall into a very predictable trap.
0:11.0	I'm going to be honest, I've never been as engaged in an interview for MoneyWise as I have with this one that we're about to do right now.
0:17.0	We tend to pay for our early mistakes in year five and six. And the idea that
0:23.1	second business is easier is also very naive. We find ourselves overwhelmed with freedom. And we say,
0:30.8	like, what is this freedom for? I just feel confused. You say, oh, now I'll just chase experience
0:37.1	for the rest of my life. A couple
0:38.7	years in, people find themselves in a situation where they feel they're empty. It's basically
0:44.5	a different kind of consumerism, but it's still all about me, me, me, give me more. And if you think
0:51.6	you're the exception to these struggles, you're wrong.
0:54.8	There is no such thing.
0:56.2	Anastasia Coraleva knows this experience very well, because she's been through it.
1:00.8	That one was nine digits and we bootstrapped it.
1:04.7	After her own very intense post-exit period, which included divorce, a business failure, and
1:09.2	an identity crisis, She's found herself
1:11.4	fascinated with the psychology of post-exit founders. And so it's something she's spent the last
1:15.8	13 years diving incredibly deeply into. So in this episode, she's going to lay it all bare.
1:21.2	Her own story, the common traps, and the most important things that you need to do to have a
1:25.8	rewarding and successful post-exit life.
1:28.8	This is MoneyWise and I'm Harry Morton.
1:31.4	We'll talk about it more later,
1:32.6	but just so you know,
1:33.2	this is a podcast made by Hampton for Hampton members.
	...

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