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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. 3291 - STORY: Dachshund-Loving Duo Designs Doxie Apparel Jan 04, 2026
    Show notes

    Two dog lovers create and grow a wiener-dog themed brand that now provides a six-figure income.

    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. 3290 - Q&A: “What if you don't want to use social media?” Jan 03, 2026
    Show notes

    This listener makes motion videos and backgrounds for churches, but he dislikes social media (#notafan). Should he just get over his resistance, or can his business succeed in another way?

    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. 3289 - STORY: Rent the Chicken! An Egg-Cellent Idea Clucks Into Cash Jan 02, 2026
    Show notes

    This Pennsylvania couple rents out 2,000 chickens to people interested in urban homesteading. It’s a side hustle worth clucking about!

    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. 3288 - Side Hustle School Season 10 Starts TODAY Jan 01, 2026
    Show notes

    We’re back with an all-new season! Here’s how year ten (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of 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. 😎 🙏🏼


    See omnystudio.com/listener for privacy information.

    Ep. 3287 - STORY: Military-Themed Teddy Bears Help Kids Hibernate Dec 31, 2025
    Show notes

    An in-house ad executive turned teddy bear manufacturer creates a military-grade sleep system for children, earning six figures in sales and making a lot of people beary happy.

    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. 3286 - Q&A: “After nine years of daily episodes, what’s next?” Dec 30, 2025
    Show notes

    A longtime listener inquires about the future of Side Hustle School. Don’t worry, we’re not done!

    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. 3285 - First $1,000: A Discord Server That Pays the Rent Dec 29, 2025
    Show notes

    In this week’s Throwback Thursday segment, discover how one creative learner built a thriving online community—and why most of its value has nothing to do with algorithms or ads.

    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. 3284 - Weekend Workshop: From Wedding Dresses to State Legislature Dec 28, 2025
    Show notes

    This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: a young entrepreneur builds her way to the Nebraska State Legislature.

    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. 3283 - Q&A: “How can I keep from negotiating against myself?” Dec 27, 2025
    Show notes

    Today’s caller undercuts her own price before the client even speaks. Let’s help her overcome this pattern of self-sabotage!

    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. 3282 - Q&A: “I’m ready to raise prices … but how?” Dec 26, 2025
    Show notes

    Inflation climbs and workload grows, but rates stay frozen—sound familiar? Today we’ll run a quick value check, set a price-rise timeline, and craft a client email that keeps loyalty high.

    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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