How Losing $28 Million Taught Me the Most Valuable Business Lesson

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In this episode, I share a deeply personal story about how I thought I had everything figured out with my first business—until one critical mistake cost me everything. At 27 years old, I secured $28 million, feeling invincible, but by July 2001, I was out of a job, and my business was sold.

I reflect on how overconfidence and believing I had "cracked the code" led me to overlook one tiny yet critical detail in my agreement that allowed my private equity group to liquidate my company. I explain how this painful experience taught me the importance of never assuming you’ve got it all figured out. It’s vital to constantly ask yourself how you can improve and be willing to adapt.

Historical accomplishments are not a guarantee of future success, and a lack of curiosity or failure to ask the right questions is often the first sign of future failure. This lesson is crucial for every business owner: stay humble, keep evolving, and never stop questioning.

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