Does Making $100M Make You Happy?

Does Making $100M Make You Happy?

From Moneywise by Hampton

April 28, 2026 · 38 min · Episode 92

About this episode

Steve Weiss discusses his journey from homelessness to a $100M exit and the impact it had on his happiness and identity.

Chapter Timestamps 00:00 — Homeless at 26, $100M exit at 32 02:22 — Building Mutesix: one of the first productized Facebook ad agencies 09:39 — The 2019 sale and what Steve actually took home 11:52 — The wire hits — at the Western Wall in Israel 14:46 — "The money didn't change my life": post-exit identity crisis 16:31 — How Steve actually spends: the chef, the donations, the Birkin he never bought 19:55 — Why he's obsessed with insurance (and what he tells founders) 23:18 — Post-exit on a Tuesday: the daily search for meaning 25:07 — Did the $100M exit actually make him happy? 32:03 — Looking back 15 years — and what the next 5 look like At 26, Steve Weiss was homeless in Los Angeles, sleeping in his car in a 24 Hour Fitness parking lot with $200 to his name. Six years later, his Facebook ads agency Mutesix sold for $100 million to Dentsu. The day the money hit his account, he was standing at the Western Wall in Israel — and got a phone call that made him realize money doesn't fix what's broken inside you. In this episode of MoneyWise, host Daniel Berk sits down with Steve Weiss to walk through the parts of a nine-figure exit nobody puts in the press release: how much he…

People in this episode

Host: Daniel Berk

Guest: Steve Weiss

Topics covered

  • entrepreneurship
  • personal finance
  • life after exit
  • happiness
  • identity crisis

Keywords

  • $100M exit
  • Mutesix
  • Dentsu
  • happiness
  • identity crisis
  • entrepreneurship
  • personal finance

Mentioned in this episode

Organizations: Mutesix, Dentsu

Places: Los Angeles, Western Wall

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