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:
Sponsors:
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.
