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
5 snips
Mar 25, 2026 • 6min
Ep. 3371 - Q&A: “Any tips for buying stuff at flea markets to resell?”
Allison, a listener from Kansas City getting into flea market reselling, asks how to start and avoid bad inventory. The conversation covers checking completed listings to confirm demand, specializing in a category to get faster and sell more, and treating early sales as learning investments. Practical tips for finding and validating items at flea markets, yard sales, and thrift shops are highlighted.
4 snips
Mar 24, 2026 • 4min
Ep. 3370 - Q&A: “Can I tell people where to find fake luxury goods?”
Kim, a listener who called in with a real-world question about selling info on replica luxury items. The conversation probes demand for knockoffs and whether connecting buyers to sellers without handling inventory is wise. Legal gray areas and enforcement risks come up. Practical alternatives and smart side-hustle ideas are suggested.
5 snips
Mar 23, 2026 • 6min
Ep. 3369 - First $1,000: City Government Staffer Leads Virtual Events
A city government staffer turned virtual events planner shares how a pandemic birthday gig sparked a new income stream. She walked through tech setup, creating engaging online atmospheres, and landing a first paid networking event. Stories include a hilarious virtual baby shower moment and practical advice about starting small and testing ideas.
6 snips
Mar 22, 2026 • 8min
Ep. 3368 - STORY: Veteran Turns Sweet Compulsion Into Obsessive Candy Hustle
A veteran channels obsessive routines into a candy business with carefully arranged, OCD-friendly packaging. She opens a Tacoma storefront after turning a counting compulsion into product design. The shop attracts autistic customers and sparks charitable giving. The venture becomes a purposeful, income-generating project during retirement planning.
5 snips
Mar 21, 2026 • 5min
Ep. 3367 - Q&A: “I’m ready for more passive income—what should I do?”
A listener shares he earns over $50,000 from three side projects and wants income to be more passive. The conversation covers designing projects with automation and fewer touch points. The host outlines a two-step path to true passive income and stresses balancing customer value with better quality of life. A one-year challenge to apply these ideas is proposed.
4 snips
Mar 20, 2026 • 8min
Ep. 3366 - Failure Friday: “A $300 mistake cost me $100,000”
Joel Runyon, founder of the Impossible brand and endurance entrepreneur, shares a trademark nightmare that spiraled into years of legal drama. He recounts early cost-cutting mistakes, the turnaround after hiring top IP counsel, and the $300 registration that would have prevented nearly $100,000 in costs. He urges timely legal protection for growing side businesses.
Mar 19, 2026 • 9min
Ep. 3365 - TBT: YouTube Tutorials Help Immigrants Gain Citizenship
Danielle Fang, an educator who teaches citizenship and ESOL and posts civics lessons on YouTube. She explains why she started uploading lessons for students who missed class. She talks about turning lessons into a global channel, simplifying intimidating government processes, and building a support network to help viewers locally. She also covers rapid subscriber and income growth and daily community management.
Mar 18, 2026 • 4min
Ep. 3364 - Q&A: “Can I use other people's recipes in my children’s ebook?”
Cal Grant-Smith, a Sydney-based creator behind a YouTube channel called Foodie Phonics. He asks about using and renaming online recipes in a children’s ebook. The conversation covers when to seek permission and when simple, common recipes can be adapted. Fun renaming and personalization ideas are offered to make recipes uniquely his.
Mar 17, 2026 • 4min
Ep. 3363 - Q&A: “Should I start a podcast or a YouTube channel?”
A listener asks whether to start a podcast or a YouTube channel. The discussion contrasts starting with a topic versus a format. Trade offs of audio, video, and multi-format publishing are explored. Practical guidance on when to stick with audio and when to publish both is covered.
Mar 16, 2026 • 5min
Ep. 3362 - First $1,000: The Canadian Wilderness Experience Curator
A Canadian entrepreneur turns wilderness hikes into immersive tours that blend stunning scenery with indigenous stories. He explains pricing, cost planning, and marketing on a shoestring. Learn how collaborations with local indigenous communities shaped the experiences and how winter treks, survival workshops, and northern lights trips expanded the offering.
