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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. 3431 - STORY: Delaware College Students Place Ads on 450,000 Cars May 24, 2026
    Show notes

    Two enterprising students start a business that connects advertisers with car owners. They now pay thousands of drivers up to $500/month, and are on track to earn $5 million in revenue.

    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. 3430 - Q&A: “How many income streams is best?” May 23, 2026
    Show notes

    Today’s caller is diving into the world of side hustling, already earning money from one or two sources with plans to add more. Is there an optimal number to aim for?


    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. 3429 - STORY: Art School Model Starts Sexually Stimulating Side Hustle May 22, 2026
    Show notes

    This biology student-turned model had a penchant for writing about sexual wellness. She just had to find a way to make money with it—and she did.



    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. 3428 - TBT: Luxury Buttercream Cakes Make Life Batter May 21, 2026
    Show notes

    In this week’s “Throwback Thursday” segment, we hear from the owner of Sweet Afternoon Bakeshop. Have your cake and listen to it too!


    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. 3427 - Q&A: “Is there a template to make an app or other software?” May 20, 2026
    Show notes

    Today’s listener is looking for a template to make a website that has some specific functionality—in her case, a combination of Craigslist and Airbnb.


    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. 3426 - Q&A: “Should I provide a guarantee for my real estate photography service?” May 19, 2026
    Show notes

    Today’s listener is starting to get paid for real estate photography. Should she offer a money-back guarantee in case a client is unsatisfied?



    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. 3425 - First $1,000: The Med School “Decision Doctor” May 18, 2026
    Show notes

    In this week’s First $1,000 segment, we hear from a medical resident working in Chicago who has a side hustle as the med school “decision doctor,” helping students and interns navigate crucial decisions.

    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. 3424 - STORY: Fire in the Hole! Handcrafted Drumsticks Ignite Into Profits May 17, 2026
    Show notes

    The podcast is on fire! A woman creates an Etsy store to market her wood-burned artistry wares, specializing in custom, handcrafted drumsticks.


    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. 3423 - Q&A: “How can I compete with unfair Etsy sellers?” May 16, 2026
    Show notes

    We had an episode recently with an Amazon seller who had a competitor posting lots of fake reviews. Today’s caller has been dealing with a similar problem: unfair Etsy sellers who mass-manufacture their products, contrary to the platform’s seller policy.


    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. 3422 - Failure Friday: “We tried to be everything to everyone…” May 15, 2026
    Show notes

    In this week’s Failure Friday segment, we hear from the founder of Cleanlots, a parking lot cleanup service that’s been operating for decades. In its early years, Cleanlots expanded too quickly, learning a valuable lesson before pulling back to its core competency.


    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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