
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/
Latest episodes

9 snips
May 4, 2025 • 7min
Ep. 3046 - Weekend Workshop: Ask 10 People for Help
Discover the art of building a powerful support network for your side hustle. Learn how asking for help can open doors to mentorship and collaborations. Hear a young entrepreneur's journey, showcasing how specific requests can transform their business. Gain insights on who to approach and how to make effective requests that respect others' time. These tips not only enhance your relationships but also help you thrive in your hustle.

4 snips
May 3, 2025 • 5min
Ep. 3045 - Q&A: “Should I switch my business to a subscription model?”
Is a subscription model right for your business? Explore the advantages and challenges of this trend, including a deep dive into a real entrepreneur's shift from individual sales to a subscription service. Discover key strategies to make the transition smoothly while keeping customers engaged. Learn about customer preferences and the risks involved, ensuring your business grows while maintaining strong relationships with your audience.

May 2, 2025 • 6min
Ep. 3044 - Q&A: “Why do authors offer pre-order bonuses?”
Curious about pre-order bonuses for books? This discussion uncovers whether they truly boost sales or just add more tasks for authors. Discover strategies to craft compelling offers and tackle the challenge of reader fatigue. The conversation emphasizes the importance of meaningful bonuses that enrich the reading experience. Tune in to explore how to make your book launch successful!

May 1, 2025 • 6min
Ep. 3043 - TBT: From Cracked Screens to Tech Buyback Business
A college student turned their passion for fixing cracked screens into a thriving tech buyback platform. By identifying market needs and strategic partnerships, they achieved monthly inventories exceeding $20,000. The journey highlights the evolution from a small repair venture to scalable success, showcasing the importance of business identity and adaptation in a competitive market.

Apr 30, 2025 • 6min
Ep. 3042 - STORY: Fashion Buyer Creates Quirky Comfort Craze
Kyle Bergman shares his journey from a unique fashion buyer to the creator of Swoveralls, a quirky blend of sweatpants and overalls. The story highlights the role of viral marketing and personal connections in launching a trend. Listeners get insights into the challenges of sourcing materials and building a brand. It’s a testament to how a single idea can transform into a successful venture, appealing to those with a taste for comfort and creativity.

Apr 29, 2025 • 5min
Ep. 3041 - Q&A: “Should I expand the services I offer?”
Ever wondered how to grow your business without feeling overwhelmed? This discussion offers strategic insights into managing expansion while keeping your priorities straight. The focus is on evaluating personal capacity and aligning new services with your core skills. A listener explores challenges in enhancing a video editing business, emphasizing the importance of maintaining clarity on business goals. Tune in for practical advice on juggling growth and staying focused!

Apr 28, 2025 • 6min
Ep. 3040 - First $1,000: Flipping Phones and Tablets for Fun and Profit
Discover how one tech-savvy entrepreneur turned old phones and tablets into a lucrative side hustle. They offer secure data wiping and refurbishment, meeting a growing demand. The episode showcases the thrill of reviving forgotten electronics and making a profit. Gain insights on transforming a simple idea into a flourishing business, and learn how you too can tap into the value of outdated tech. It's an inspiring journey of innovation and entrepreneurship!

9 snips
Apr 27, 2025 • 6min
Ep. 3039 - Weekend Workshop: Sell Like a Girl Scout
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: the art of natural selling! 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.

Apr 26, 2025 • 6min
Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?”
When is it time to start spending real money on your side hustle? In this episode, we explore how to balance scrappiness with strategic investments to fuel growth. 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.

Apr 25, 2025 • 4min
Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?”
How do you turn being an industry outsider into a strength? In this episode, we explore how to practice creativity while building trust and credibility with customers. 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.