James Altucher has rebounded from personal catastrophe so many times in his 49 years, it's hard to imagine a more qualified evangelist for personal reinvention. During the dot-com boom of the 1990s, Altucher made millions designing corporate websites, only to squander it all on gambling and a string of disastrous investments. "I was probably losing about a million [dollars] a week for an entire summer," he tells Reason's Nick Gillespie. "I just made every stupid decision in the book."

With $143 left in his bank account, Altucher contemplated suicide. "I equated my self-worth with my net worth," he says, "and I just figured there's no way I'm going to dig myself out of this hole."

In keeping with his philosophy of radical self-creation, Altucher's latest identity is a 21st century urban ascetic. He has pared down his possessions, discarding every item he doesn't need. He is determined that nothing get in the way of his chosen life, his best self. Today, he lives in AirBnB rentals and owns fifteen things that he carries in a small canvas bag.

Edited by Todd Krainin. Hosted by Nick Gillespie.