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Side Hustle School

by Chris Guillebeau
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Latest episodes

  • Ep. 3571 - STORY: Guitar Player Chalks Up Success By Enjoying The Process

    October 11, 2026 · 8 min

    A systems administrator and lifelong guitar player generates thousands per month writing about his musical hobby.  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without…

  • Ep. 3570 - Q&A: “Can I offer a permanent price discount?”

    October 10, 2026 · 4 min

    Our listener has seen furniture stores offer non-stop sales. Is there any reason they can’t have a sale that never ends in their business?  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who…

  • Ep. 3569 - STORY: Hand Lettering Artist Upgrades Photo Booth Props

    October 9, 2026 · 8 min

    An illustrator gives boring wedding photo booth props a much-needed upgrade, creating an alternative to greeting cards at the same time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who…

  • Ep. 3568 - TBT: Physician Designs Plush Toys to Teach Anatomy

    October 8, 2026 · 7 min

    In this week’s “Throwback Thursday” segment, we hear from a doctor who makes plush toys in the shape of human organs to teach kids about the body.  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…

  • Ep. 3567 - Q&A: “Can I resell items I get for free?"

    October 7, 2026 · 4 min

    Today’s listener received some free display equipment at a trade show. Can he resell it without worrying, or does this create an ethical dilemma?  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…

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About the show

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books. Hosted on Acast. See acast.com/privacy for more information.