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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. 3316 - TBT: Designer Scales Personalized Wedding Products to $1M+ Jan 29, 2026
    Show notes

    In this week’s “Throwback Thursday” segment, we hear from a graphic designer who does custom illustrations for weddings and other events. It’s now a seven-figure business!

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3315 - Q&A: “How do I transition from Etsy to Shopify?” Jan 28, 2026
    Show notes

    A listener has been selling on Etsy and wants to make the switch to Shopify. What’s the best way to do this?

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3314 - Q&A: “What's the best software to write a non-fiction book?” Jan 27, 2026
    Show notes

    Today’s caller wants to know about the easiest and most helpful tools to write a non-fiction book. Unfortunately, books do not write themselves, but we’ll give him three resources that might make it easier.

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3313 - First $1,000: “I still remember the day I hit the goal…” Jan 26, 2026
    Show notes

    In this week’s First $1,000 segment, we hear from Jodi Carlson, who sells resources and materials for Girl Scout troop leaders.

    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. 😎 🙏🏼

    See omnystudio.com/listener for privacy information.

    Ep. 3312 - STORY: The Clothes Dryer That Changed a Family Forever Jan 25, 2026
    Show notes

    When this government employee is let go from his job, he stumbles upon a reselling opportunity that would end up helping his family ride the coming recession—and eventually earn six figures in a single year.

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3311 - Q&A: “Get paid to help brands with their Terms & Conditions?” Jan 24, 2026
    Show notes

    Today’s caller wants to help brands improve their Terms & Conditions, also known as T&C. Can she design and license a template that companies will pay 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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3310 - Failure Friday: “We were incredibly disappointed…” Jan 23, 2026
    Show notes

    In this week’s Failure Friday segment, we hear from the founder of Kettlebell Kings, an ecommerce shop. When a big early order from a supplier went terribly wrong, he had to regroup and learn resilience.

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3309 - TBT: “MomBox” Expands to Popular Subscription Box Service Jan 22, 2026
    Show notes

    In this week’s “Throwback Thursday” segment, we hear from Kate Westervelt, the founder of MomBox. She’s gone from frustrated new mom to CEO of a growing startup!

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3308 - Q&A: “What are the ethics of paid referrals to therapists?” Jan 21, 2026
    Show notes

    A listener with a YouTube channel about quitting smoking wants to earn commissions by referring viewers to therapists. What are the ethical and practical concerns of this idea?

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3307 - Q&A: “Should I charge a flat fee or percentage?” Jan 20, 2026
    Show notes

    A listener and her teenager have been getting off to a good start selling on Facebook Marketplace. They now have the chance to sell for others, and are wondering about some best practices.

    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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

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