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Side Hustle School

Chris Guillebeau
Side Hustle School
Latest episode

3639 episodes

  • Side Hustle School

    Ep. 3582 - TBT: Aussie Sketches Old Homes for New Money

    22/10/2026 | 9 mins.
    In this week’s “Throwback Thursday” segment, we hear from a designer in Australia who sketches and sells illustrations of houses. Her side hustle is now her full-time focus!
    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: team@sidehustleschool.com
    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. 😎 🙏🏼
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle School

    Ep. 3581 - Q&A: “Can you deduct side hustle losses from income taxes?”

    21/10/2026 | 4 mins.
    This listener’s new side hustle lost money this year. Hopefully that will change in the future, but for now—is there a silver lining in being able to deduct losses from his income taxes?
    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: team@sidehustleschool.com
    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. 😎 🙏🏼
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle School

    Ep. 3580 - Q&A: “Is there an easier way to start reselling?”

    20/10/2026 | 4 mins.
    Reselling is quick and simple—but it’s also a lot of work, and today’s caller is looking for a shortcut. Does such a thing exist?
    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: team@sidehustleschool.com
    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. 😎 🙏🏼
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle School

    Ep. 3579 - First $1,000: New Podcaster Sets Up Joint Venture Deals

    19/10/2026 | 7 mins.
    In this week’s First $1,000 segment, we hear from a new podcaster with a business model of setting up joint venture (JV) deals. How does it work and how much money does he make? (Hint: at least $1,000.)
    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: team@sidehustleschool.com
    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. 😎 🙏🏼
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle School

    Ep. 3578 - Un-Tours Of Myanmar Offer Adventure and Unpredictability

    18/10/2026 | 7 mins.
    His friends kept asking him to lead tours of Myanmar, and he finally agreed. But he wasn’t going to stick to the usual sights—his ‘un-tours’ would be anything but typical.
    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: team@sidehustleschool.com
    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. 😎 🙏🏼
    Hosted on Acast. See acast.com/privacy for more 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. Hosted on Acast. See acast.com/privacy for more information.
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