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    Business

    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/  

    Advertise

    Copyright: © 588793

    • Apple Podcasts
    • Google Play
    • Spotify
    Latest Episodes:
    Ep. 3411 - First $1,000: Software Engineer Crafts Balloon Sculptures May 04, 2026
    Show notes

    In this week’s First $1,000 segment, we hear from an engineer who takes out his daytime frustrations on a series of side hustle balloon sculptures.


    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.

    Ep. 3410 - STORY: Athletes Create “Chewable Energy” Gum May 03, 2026
    Show notes

    Searching for energy on-the-go without a nasty crash or sugar rush, these two friends and high-performing athletes chew on the idea until inspiration strikes.


    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.

    Ep. 3409 - Q&A: “I bought and sold 75 Peloton bikes…” May 02, 2026
    Show notes

    Today’s caller took advantage of the “pandemic Peloton” trend and resold dozens of them! He’s got a story for us, and he’s also wondering how to figure out what comes next.


    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.

    Ep. 3408 - Failure Friday: “My Facebook page was taken over by hackers…” May 01, 2026
    Show notes

    In this week’s Failure Friday segment, we hear from the world’s leading expert on tailgating. When his popular Facebook page got hacked, he lost thousands of followers and it took more than a month to resolve.



    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.

    EP. 3407 - TBT: Kindle Books Produce Passive Income for Aussie Novelist Apr 30, 2026
    Show notes

    In this week’s “Throwback Thursday” segment, we hear from Kyla Gardner in Melbourne, Australia. She’s created passive income from a series of self-published nonfiction books—and now she’s jumping into fiction.


    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.

    Ep. 3406 - Q&A: “I want to make an asexual dating app…” Apr 29, 2026
    Show notes

    Today’s caller has an idea to start her own app for people who identify as asexual (where you don’t feel much sexual attraction to anyone). What’s the best path forward?


    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.

    Ep. 3405 - Q&A: “The alarm clock that costs money if you oversleep…” Apr 28, 2026
    Show notes

    That’s right, this alarm clock debits your bank account if you don’t get up in time. It’s sure to be a hit! The only problem: our caller isn’t sure how to make it.


    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. 😎 🙏🏼

    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.

    Ep. 3404 - First $1,000: Digital Art Reaches Physical Homes Worldwide Apr 27, 2026
    Show notes

    In this week’s First $1,000 segment, we hear from the co-founders of Wandercolors. Together, they produce digital art of iconic travel destinations.


    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.

    Ep. 3403 - STORY: Shoe Designer Runs After $1 Million Challenge Apr 26, 2026
    Show notes

    “Why can’t dress shoes look great and perform well at the same time?” This runner and industrial designer was irritated, so he set out to find the sole solution.

    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.

    Ep. 3402 - Q&A: “Need to increase income as an adjunct professor…” Apr 25, 2026
    Show notes

    Today we hear from a professor of sociology who wants to make more money. Nothing wrong with that! Let’s see if we can help.


    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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