"I Thought I Had the Midas Touch": How an $80M Success Led to a Major Failure

Can success create a false sense of invincibility? For Pete, it did—and it cost him millions.

After selling his business for $80 million, Pete felt unstoppable. But his overconfidence led him into a risky venture that didn’t pay off. Determined to prove he wasn’t a one-hit wonder, Pete ignored the warnings, thinking his past success guaranteed future wins. Instead, he faced one of the hardest losses of his career.

In this episode, Pete shares how his upbringing shaped his hunger for security, how overconfidence after a major exit led to a business failure, and how he’s rebuilding emotionally and financially.

This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.

Who is Sam Parr?

Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Pete's Humble Beginnings (01:45)

Early Entrepreneurial Ventures (05:00)

The Big Exit and Its Impact (07:03)

Post-Exit Lifestyle and Spending (09:13)

The New Venture and Its Challenges (10:56)

Realizing the Mistake (22:57)

Financial and Emotional Impact (23:52)

Lessons Learned and Moving Forward (28:17)

Redefining Success (35:31)

Conclusion and Final Thoughts (36:48)

This podcast was produced in partnership with Lower Streetand distributed by Morning Brew.