PodcastsBusinessSide Hustle School

Side Hustle School

Chris Guillebeau
Side Hustle School
Latest episode

3533 episodes

  • Side Hustle School

    Ep. 3471 - STORY: Tinder Matched Couple Swipes Right to Sell Cupcakes

    03/07/2026 | 8 mins.
    After meeting on Tinder, a couple takes a long walk through Central Park and decides to sell cupcakes for $20 each. Surprise: it works.

    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. 3470 - TBT: Comfy Pillow Provides Seatbelt Support for Cancer Patients

    02/07/2026 | 7 mins.
    In this week’s “Throwback Thursday” segment, we hear from the creator of the ParkPuff, a “go anywhere” seat belt pillow for cancer and surgery patients.

    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. 3469 - Q&A: “Where's the best place to hire contractors?”

    01/07/2026 | 5 mins.
    Today’s caller is starting a *second* side hustle and wants to know where to find the best virtual assistants and other contractors.

    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. 3468 - Q&A: “How do you determine a customer’s emotional needs?”

    30/06/2026 | 5 mins.
    Today’s listener is inspired to learn more about the “core emotional needs” of a potential customer, but isn’t sure how to do it or what to do with the info. Are these needs always the same, or do they vary?

    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. 3467 - First $1,000: “Clients don’t want Wordpress, they want a website…”

    29/06/2026 | 4 mins.
    In this week’s First $1,000 segment, we hear from the self-described “Wordpress Girl,” who starts a service helping female entrepreneurs get set up with a website.

    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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