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 investment decisions. "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."

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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."

Instead of self-destruction, Altucher created himself anew. He dedicated himself to learning about finance, reading over a hundred books about investing. He built a new career as a hedge fund manager, earning writing gigs at TheStreet.com and The Financial Times.

The real estate crisis of 2008 wiped the slate clean. Finding himself with nothing to lose yet again, Altucher began blogging about his riches-to-rags-to-riches-again life story, eventually writing books—18 of them so far—for an audience that had felt the sting of the recession.

Crawling out of the abyss a few times has made Altucher wary of the American Dream. A Cornell and Carnegie Mellon graduate, he scorns higher education as an overpriced luxury. Home ownership is great for the banks, but a lousy deal for home owners. Hedge funds are a scam. He's never had credit card debt because he's never had a credit card.

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.

Altucher's self-published book about the art of self-creation, Choose Yourself! Be Happy, Make Millions, Live the Dream, charts his life story, detailing how he bounced back, time and again, from disasters personal and financial. Equal parts self-help manual, cautionary tale, and tell-all autobiography, Choose Yourself! challenges us to create the best version of ourselves through a constant process of optimism, authenticity, and hard work.

Edited by Todd Krainin. Hosted by Nick Gillespie. Cameras by Jim Epstein and Krainin.