In this episode of Burning the Ships, I sit down with my friend and one of the most encouraging humans I know, Chuck Glover—a former school teacher and administrator who didn’t find his true calling in real estate and private lending until his late 60s.

Chuck spent decades doing things “the right way”: 27 years in education, a handful of “solid but stagnant” businesses, and a consulting career that never quite broke through. Then, at around 69–70 years old, everything came crashing down. He had mounting debt, dwindling income, and a marriage that ultimately ended in divorce. Chuck found himself at 70 years old with the financial outlook of a 20-year-old and the weight of starting over when most people are winding down.

Instead of quitting, Chuck rebuilt from rock bottom to financial freedom using mindset, connection, and a very specif ...