Mike Cobb: What Raising Kids Overseas Does to How They See the World

Mike Cobb: What Raising Kids Overseas Does to How They See the World

From Burning The Ships by The Boat Crew

June 7, 2026 · 43 min · Season 1 · Episode 225

About this episode

Mike Cobb shares his journey of building businesses overseas and the impact on his worldview and leadership style.

Mike Cobb didn't find his path — he built it from scratch in a country most people couldn't locate on a map. In the mid-90s, a trip to Belize with a lawyer buddy turned into a mortgage company, which turned into a bank, which turned into a 2,500-acre development on the Pacific coast of Nicaragua, which turned into a teak timber operation planted in 1999 that's only now coming to harvest. Three businesses, three countries, and thirty-plus years of building things designed to outlive him. This episode isn't about the deals or the developments. It's about the mindset behind someone who has spent his entire adult life saying yes when most people would have walked away, and who now spends his time building leaders the same way he planted teak trees — knowing full well he may never sit in the shade. Key Talking Points of the Episode [00:37] How Mike and Jason first connected at a Dealmaker event in Richmond through Jim Ingersoll [02:49] The mid-90s trip to Belize that accidentally launched a mortgage company [03:51] Finding the gap: no mortgage money existed for North Americans buying in Belize [04:36] Growing the mortgage company into a full bank — a process that took from 1998 to…

People in this episode

Guest: Mike Cobb

Topics covered

  • entrepreneurship
  • international business
  • leadership development
  • risk management
  • expat life
  • mindset

Keywords

  • entrepreneurship
  • Belize
  • Nicaragua
  • leadership
  • risk
  • expat
  • mortgage
  • banking
  • teak timber

Mentioned in this episode

Places: Belize, Nicaragua

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