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Mar 2025
47m 57s

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

Hampton
About this episode

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:


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)

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