328. Chris Guillebeau: Finding New Pathways to Prosperity

If you consider yourself a Millennial or part of Generation Z, chances are you’ve felt a little jaded by the usual dusty office job. According to bestselling author and Town Hall veteran Chris Guillebeau, you’re not alone. Many of the post-Baby Boomer generations are choosing to rewrite the rules of capitalism.

In his latest book, Gonzo Capitalism: How to Make Money in An Economy That Hates You, Guillebeau details how many of today’s young people are burdened with debt, stagnant wages, and the ever-rising cost of living. Disillusioned with traditional, draining work models, they eschew more conventional ways of earning a living, instead opting to pursue new and creative ways to make money — alternate options to the 9-to-5 lifestyle inherited more readily by generations before.

Enter a new world where creativity is currency and creators have control. Anything goes: from communities of gamers getting paid to play; to armchair pundits betting against bookies in online markets; to TikTok “Sleepfluencers,” AI artists, and others upending rules. As we explore these realms of novelty and innovation, Guillebeau offers wisdom on how others can capitalize on the new tools and platforms at our disposal, discovering our own unconventional ways to turn time and talent — on our own terms — into income.

Chris Guillebeau is the New York Times bestselling author of The $100 Startup, Side Hustle, The Happiness of Pursuit, and other books. He is a serial entrepreneur, the host of the Side Hustle School podcast and the founder of the World Domination Summit, an event for cultural creatives that has, for the past decade, attracted thousands of attendees to Portland, Oregon every summer.