Nassim Nicholas Taleb is a former trader and hedge fund manager, a bestselling author, and a groundbreaking theorist on risk and resilience. A finance professor at New York University and a research scholar at Oxford, Taleb drew wide attention after the 2007 publication of The Black Swan: The Impact of the Highly Improbable, which warned that our institutions and risk models are not designed to account for rare and catastrophic events. Among other things, the book presciently cautioned that oversized and unaccountable banks using flawed investment models could trigger a financial crisis. He also warned that the government-sanctioned housing finance agencies, Fannie Mae and Freddie Mac, were sitting on a “barrel of dynamite.” One year after The Black Swan was published, Taleb’s predictions came to pass. Taleb doesn’t identify as a libertarian, but he often sounds like one. Taleb’s new book, Antifragile: Things that Gain with Disorder, argues that in order to create robust institutions we must allow them to build resilience through adversity. The essence of capitalism, he argues, is encouraging failure, not rewarding success.

Reason TV Editor in Chief Nick Gillespie sat down with Taleb in January for a wide-ranging discussion about debt, technology, the banking system, capitalism, and why he’ll never take writing advice from “some academic at Cambridge who sold 2,200 copies.”