Warning: distressing content.
From Bloomberg, September 11:
A growing post-exit ecosystem is helping founders deal with the unexpected difficulties of becoming extremely wealthy.
It was the kind of exit every entrepreneur dreams about. After bootstrapping a software startup together, Anastasia Koroleva and her husband sold for nine figures: 100% cash on Day 1, zero earnouts, no strings attached. But what followed blindsided the founder and former Skadden Arps M&A lawyer. Instead of the soft life she’d expected, Koroleva found herself dealing with years of unease and a painful divorce.
“Everything was very different from what we expected, and that was shocking for me,” she says. “I went through quite a difficult adjustment to that new reality.”
Today, 16 years after her payout and nearly three years into hosting her podcast, Exit Paradox, Koroleva explores what happens when net worth removes the need to work. Her interviews with the extraordinarily wealthy have uncovered a recurring theme: For many, the exit does not feel like a crowning achievement — or, at least, not for long. It can feel more like an existential rupture. Guests describe becoming staggeringly rich using the language of trauma: “recovering from a $500 million sale,” “thrashing about for a decade” or drifting in a state of aimless ennui.
Koroleva’s podcast is one piece of a growing ecosystem of content, coaches, therapists and communities giving people who’ve amassed more money than they’ll ever need somewhere to talk freely — a gap traditional wealth advisers and founder networks don’t fill. Its rise reflects two shifts: a tech sector generating wealth at breakneck pace and a post-Covid culture far more willing to talk about mental health.
“There’s been a tremendous softening of conversations around mental health and well-being among entrepreneurs,” says Sherry Walling, a clinical psychologist who specializes in founders. She credits that partly to the shock of Zappos founder Tony Hsieh’s death in 2020. “I do think that we’ve moved on from it as the world’s tiniest violin.”
Last November, Walling co-authored a playbook on the subject, Exit Strategy. She’d seen too many clients who’d done everything they set out to do, achieved the big exit — and were miserable. “There were some really dramatic stories,” she says. “People being suicidal, just really, really lost in their post-exit experience.”....
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