

Side Hustle School
Chris Guillebeau / Onward Project
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/
Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Episodes
Mentioned books

Oct 17, 2025 • 5min
Ep. 3212 - Q&A: “Will people pay for AI-optimized resumés?”
Cheap resumé bots and pricey human writers leave a gap. We’ll show how an AI-plus-expert service can fill it, both profitably and credibly. 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.

Oct 16, 2025 • 5min
Ep. 3211 - TBT: Built in a Weekend, Used by Thousands
In a captivating Throwback Thursday segment, discover how a simple Chrome extension, built in just a weekend, attracted 5,000 loyal users. Brian shares his inspiration for creating Quick Highlight to save key points from articles, despite its clunky design. He details how he monetized the tool with affordable subscription options and the surprising demand from edtech companies for white-labeled versions. The key takeaway? Focus on creating something useful rather than perfect, and you'll find your audience!

Oct 15, 2025 • 8min
Ep. 3210 - STORY: Canadian Bidets Modernize Bathroom Life
Bidets aren't just for Europe—one Canadian entrepreneur is on a mission to change bathroom habits in Canada. By testing demand online before investing in inventory, he created a successful business selling handheld bidets. With clever marketing strategies spanning social media and local ads, sales skyrocketed. Key takeaways include validating ideas and targeting your audience effectively. Plus, customers are buying multiple bidets per household, revealing unexpected market potential.

Oct 14, 2025 • 5min
Ep. 3209 - Q&A: “How do I use exit pop-ups?”
A well-timed nudge can rescue sales, but only if it feels like service, not a race to the bottom. Let’s design a polite “please stay” offer that boosts revenue without creating coupon addicts. 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.

Oct 13, 2025 • 5min
Ep. 3208 - First $1,000: Vintage Sewing Machine Rehab Workshops
Discover how a creative soul turns thrift-store treasures into thriving workshops. By purchasing vintage Singer sewing machines for just twenty bucks, she teaches students to restore them while adding personal flair. Participants walk away with fully functional machines, creating a hands-on experience that nets her the first $1,000. Plus, get key tips on pricing and ensuring everyone leaves with a sense of accomplishment. It's a delightful exploration of blending skills and passion for profit!

Oct 12, 2025 • 7min
Ep. 3207 - Weekend Workshop: The Global Photography Pivot
Discover how a truck accident sparked a six-figure travel photography business! Learn about the power of building relationships with clients, as Kyle Hepp shares her strategy for turning couples into advocates. The podcast explores how this relationship-first approach can apply to various service industries. Plus, find out how personal setbacks can lead to incredible opportunities for freedom and financial independence. Get ready for inspiring insights and practical steps to kickstart your own side hustle!

Oct 11, 2025 • 5min
Ep. 3206 - Q&A: “How do I fight piracy without hurting buyers?”
Chris tackles the challenge of digital piracy while keeping customers happy. He discusses low-cost deterrents like metadata stamping and re-download portals. The importance of focusing on customer satisfaction over complex tech solutions is highlighted. Practical advice includes leveraging DMCA takedowns and staying product-focused. This episode is filled with insights on balancing security and customer experience for sellers in the digital space.

Oct 10, 2025 • 5min
Ep. 3205 - Q&A: “How do I license calming coloring pages to wellness apps?”
Transforming $2 art sales into lucrative B2B licensing deals is the focus here. A listener seeks advice on offering coloring bundles to wellness apps. Detailed strategies on packaging art for easy integration are discussed. The importance of connecting with the right contacts on LinkedIn for successful pitches is emphasized. Plus, valuable resources for listeners looking to monetize their creativity are shared. This conversation is packed with practical tips for aspiring side hustlers!

Oct 9, 2025 • 5min
Ep. 3204 - TBT: The Secret Author Behind Your Favorite Romance Novel
Discover how a fanfiction writer transformed her passion into a lucrative ghostwriting career. Earning five figures per project, she now pens bestselling romance novels under various pen names. Learn about her journey from a $5,000 co-write to earning $10,000 for full-length novels. She shares insights on payment structures, working with multiple romance subgenres, and the tools that support her thriving business. It's a fascinating look at balancing creativity with the demands of a fast-paced publishing world.

Oct 8, 2025 • 7min
Ep. 3203 - STORY: Underwear Side Hustle Turns Into $500,000/Month Business
Two women turned a side hustle into a $500,000/month underwear brand. They thrived after a successful Kickstarter campaign, focusing on inclusive designs. With no fashion background, they researched and tested products diligently. Adapting their advertising and building an Instagram community helped them connect with customers. Their journey exemplifies how a simple idea can evolve into a multi-million dollar business, showcasing the diverse outcomes that side hustles can achieve.


