Get the full exit report here: https://joinhampton.com/rich-or-dead-report

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.