$60M Exit, 25+ Deals, and Why Angel Inve...

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

Auren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.

Here’s what we talk about:

• Auren Hoffman made $60M—and then became an angel investor.
• He shares why angel investing isn’t as sexy as it sounds.
• The truth about money: yes, it did make him happier.
• How he tracks spending (only big and small stuff—never the middle).
• Why he never sets goals and doesn’t chase happiness.
• His step-by-step guide to being unhappy (for real).
• How trash-talking saved LiveRamp from a PR meltdown.
• The right way to invest after a big exit (hint: take it slow).
• Why most people shouldn’t even think about investing before hitting $3M.
• Sam and Auren go deep on process vs. planning—and what really drives success.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Auren’s Twitter https://x.com/auren

Chapters:
(00:00) Auren Hoffman's Big Exit
(00:17) The Reality of Angel Investing
(00:53) Introducing Moneywise
(01:02) The Hampton Community
(02:23) Auren's Early Entrepreneurial Journey
(03:39) First Million in the Twenties
(06:47) LiveRamp and the $60 Million Exit
(07:52) Handling Wealth and Lifestyle Changes
(12:00) Navigating Business Challenges
(13:56) Entrepreneurial Mindset and Resilience
(15:33) The Importance of Community for Founders
(17:17) Navigating Uncertainty in Business
(17:40) Insights from Successful Founders
(18:26) Auren's Journey Post-Big Exit
(19:44) Balancing Work and Personal Fulfillment
(21:05) The Philosophy of Happiness and Success
(28:52) Advice on Angel Investing

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: Sam Parr

• Founder of Hampton, a private community for CEOs.
• Sold his last company, The Hustle, for tens of millions.