How Buying an Oil Tanker Became My Favorite Mistake — Kevin Hipes

What happens when a business deal looks solid on paper—but falls apart in real life?

Episode page with video, links, and more

My guest for Episode #335 of the My Favorite Mistake podcast is Kevin Hipes, an entrepreneur, author, and former city commissioner who’s been called the “New York Forrest Gump” because of the many lives he’s lived.

Kevin shares the story of one of his biggest—and most unforgettable—business mistakes: buying an oil tanker in the Caribbean. What began as a seemingly foolproof investment with a strong pro forma turned into a cascade of unexpected challenges, including regulatory changes, ethical dilemmas, geopolitical risk, and international drama.

In this episode, we talk about:

• Why smart people still make big business mistakes

• How external forces can derail even the best plans

• Learning from failure instead of hiding from it

• Resilience after financial and emotional setbacks

• The importance of mental health awareness for leaders and entrepreneurs

Kevin’s story is funny, sobering, and deeply human—and a powerful reminder that mistakes don’t define us unless we refuse to learn from them.