Podcast: Moneywise (LS 54 · TOP 0.5% what is this?)
Episode: The Founder Exit Report: What Happens When You Sell a Company?
Pub date: 2025-11-04

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Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.com

Most exit stories are told in headlines and highlight reels. We wanted the truth. So we surveyed dozens of exited Hampton founders and pulled insights from 100+ interviews to uncover what really happens after the deal closes – from broken earnouts and identity loss to why nearly everyone regrets something they bought.

Here’s what we talk about:

• Why deal structure matters more than the sale price, and how earnouts quietly screw founders
• How 47% of founders said they made less than expected from their deal
• Why having millions in the bank can still feel like financial insecurity
• The surprising trap of feeling “poor” after selling
• Why 92% of exited founders build again – retirement is a myth
• The identity unraveling that hits most founders post-exit
• The most common regret: a house, car, or other “reward” that quickly became a burden
• Why trying to time the market almost always backfires
• The #1 post-sale frustration almost no one talks about: losing control of company culture

Cool Links:

• Hampton joinhampton.com/
• Lower Street lowerstreet.co/
• Hampton Wealth Report joinhampton.com/2024-wealth-report

Sponsors:

• Get a team of AI agents that run compliance for you at delve.co/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise

Chapters:

• (1:21) Deal Structure: Where the Real Money’s Made
• (4:22) Why a Big Payout Can Still Feel Small
• (6:43) The Retirement Myth: You’ll Build Again
• (8:32) Selling Isn’t Just Business, It’s Personal
• (11:33) The Big Purchase Trap
• (13:20) Timing: Stop Waiting for Perfect
• (15:26) Nine Lessons from Founders Who’ve Been There
• (17:00) The Culture Shift Nobody Warns You About

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

The podcast and artwork embedded on this page are from Hampton, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.