I Sold for $100M and Now I Spend $1M/Yea...

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.

Inspired by real conversations happening in the Hampton community.

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Dan Berger sold his company Social Tables for $100 million in 2018. But his net worth today hasn’t moved at all. Why?

Here's what we talk about:

• How Dan went from bootstrapping websites to an eight-figure exit
• Why his net worth hasn’t grown in seven years (and he’s totally fine with that)
• His biggest post-exit financial mistakes: angel investing, dumb NFTs, and a $7.5M NYC apartment
• The hidden struggles of founders post-exit—why selling doesn’t solve your problems
• How Dan’s early-life struggles led to a lifelong search for belonging
• What entrepreneurs get wrong about identity, success, and relationships
• His perspective on the Die With Zero philosophy—and how he’s ACTUALLY living by it.
• How he rebuilt his sense of purpose

Your Hosts:

Sam Parr

• Founder of Hampton, a private community for CEOs.
• Sold his last company, The Hustle, for tens of millions.
• Big fan of first-class flights (unlike Dan).

Harry Morton

• Founded and runs Lower Street, the leading branded podcast production service in the world.
• Hampton Member.

Cool Links:

• Hampton – Join the Founder Community https://www.joinhampton.com/
• Lower Street – Podcast Production https://www.lowerstreet.co/
• The Quest by Dan Berger – A book on belonging and identity. https://www.belongingquest.com/
• Die With Zero by Bill Perkins – The book that inspired Dan’s financial philosophy. https://www.diewithzerobook.com/welcome

Chapters:

Meet Dan Berger: The $100 Million Exit (01:08)

The Journey of Social Tables (01:49)

Life After the Big Sale (03:47)

Financial Transparency and Mistakes (08:10)

Living the Die With Zero Philosophy (18:01)

Rediscovering Success (22:39)

Financial Insights: Investments and Income Sources (23:40)

The Belonging Crisis: A Personal Journey (24:21)

Adoption, Abandonment, and Immigration: Early Life Struggles (24:45)

Building Belonging: From Company Culture to Personal Connections (26:02)

Addiction and Recovery: A Path to Belonging (30:01)

Men in Crisis: Addressing Modern Masculinity (36:58)

Post-Exit Reflections: Investing and Finding Purpose (40:51)

Creating Community: The Birth of Hampton (45:44)