PodcastsBusinessSide Hustle School

Side Hustle School

Chris Guillebeau / Onward Project
Side Hustle School
Latest episode

3437 episodes

  • Side Hustle School

    Ep. 3382 - STORY: Cigar Subscription Box Delivers Smoking Returns

    2026-04-05 | 7 mins.
    A software engineer creates a premium subscription box service for savvy cigar smokers.
    Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
    Show notes: SideHustleSchool.com
    Email: [email protected]
    Be on the show: SideHustleSchool.com/questions
    Connect on Instagram: @193countries
    Visit Chris's main site: ChrisGuillebeau.com
    Read A Year of Mental Health: yearofmentalhealth.com
    If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
    See omnystudio.com/listener for privacy information.
  • Side Hustle School

    Ep. 3381 - Q&A: “Driving an RV across the country—can I get sponsored?”

    2026-04-04 | 3 mins.
    Everyone, let’s pack all of our stuff up in an RV and hit the road. We just need a tripod for all those #vanlife photos we’re going to be taking! (Also, our caller wants to know how she can get sponsored for her own RV adventure.)
    Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
    Show notes: SideHustleSchool.com
    Email: [email protected]
    Be on the show: SideHustleSchool.com/questions
    Connect on Instagram: @193countries
    Visit Chris's main site: ChrisGuillebeau.com
    Read A Year of Mental Health: yearofmentalhealth.com
    If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.
  • Side Hustle School

    Ep. 3380 - Failure Friday: “Perfect SAT Score” Tutor Gets Rejected by 100 Publishers

    2026-04-03 | 5 mins.
    In this week’s Failure Friday segment, we hear from the founder of a standardized test prep service. Before he started his business, he earned a perfect score on the SAT—and then pitched a book that was rejected by more than 100 literary agents and publishers.
    Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
    Show notes: SideHustleSchool.com
    Email: [email protected]
    Be on the show: SideHustleSchool.com/questions
    Connect on Instagram: @193countries
    Visit Chris's main site: ChrisGuillebeau.com
    Read A Year of Mental Health: yearofmentalhealth.com
    If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.
  • Side Hustle School

    Ep. 3379 - TBT: These iPad Paintbrushes Never Run Dry

    2026-04-02 | 7 mins.
    In this week’s “Throwback Thursday” segment, we hear from a New Zealand software developer who popularizes iPad lettering brushes, accumulating 300,000 followers and a solid extra income.
    Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
    Show notes: SideHustleSchool.com
    Email: [email protected]
    Be on the show: SideHustleSchool.com/questions
    Connect on Instagram: @193countries
    Visit Chris's main site: ChrisGuillebeau.com
    Read A Year of Mental Health: yearofmentalhealth.com
    If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.
  • Side Hustle School

    Ep. 3378 - Q&A: "Help, my bank said I can't open a business account!"

    2026-04-01 | 3 mins.
    How do you keep your business and personal finances separate? Ideally with a different bank account—but this listener is having trouble opening one.
    Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
    Show notes: SideHustleSchool.com
    Email: [email protected]
    Be on the show: SideHustleSchool.com/questions
    Connect on Instagram: @193countries
    Visit Chris's main site: ChrisGuillebeau.com
    Read A Year of Mental Health: yearofmentalhealth.com
    If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

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About Side Hustle School

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. Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Podcast website

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