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
Feb 19, 2026 • 8min
Ep. 3337 - TBT: The Mushroom Kingdom of North Carolina
Shannon Barrett, business manager and C-suite partner at Phenomenal Fungi, who helped pivot the company from growing mushrooms to supplying equipment, cultures, and tinctures. They talk about launching an Etsy supply business, inventing a laminar flow hood, rapid pandemic-driven growth to $20K/month, and ongoing supply chain and shipping challenges.
Feb 18, 2026 • 5min
Ep. 3336 - Q&A: “Is there a way to trade plane tickets for profit?”
Jazlyn, a listener who called in with a travel idea, asks about trading or reselling unused plane tickets. The conversation covers how airline name/ID rules limit transfers. A marketplace that handles transferable tickets is mentioned. Other travel-related side-hustles and changing refund policies are discussed.
Feb 17, 2026 • 5min
Ep. 3335 - Q&A: “What separates small earners from big ones?”
A Q&A dives into what separates modest earners from high earners in side hustles. They discuss how different goals and effort levels shape outcomes. The conversation highlights idea choice, pricing strategy, and the need to iterate and adapt. Marketing gets called out as critical, and taking more chances to increase luck rounds out the themes.
Feb 16, 2026 • 5min
Ep. 3334 - First $1,000: “I started by setting up a booth at the farmer's market…”
A maker turns a love of natural remedies into a profitable product line. She tests recipes, offers samples at a farmers market booth, and crafts on-the-spot custom blends. One weekend brought her first $1,000 in sales. The story highlights adapting products to customer needs and plans to grow the business.
Feb 15, 2026 • 7min
Ep. 3333 - STORY: Game of Cones: Two Women Make Architecturally-Inspired Ice Cream
Two women turn architecture class ideas into sculptural ice cream and desserts. They test treats at farmers markets, Whole Foods, and a major festival launch that sparks viral attention. The story tracks branding, frugal scaling, product expansion, and an eventual acquisition.
5 snips
Feb 14, 2026 • 5min
Ep. 3332 - Q&A: “How to sell a reusable fork…”
Sharice, creator of an eco-friendly foldable tote with attached utensils, seeks customers for her souvenir-style product. The conversation explores whether zoos and parks are good buyers. It discusses product naming, small-batch manufacturing limits, choosing between direct sales or wholesale, and practical outreach tactics like regional retail and trade-show strategies.
5 snips
Feb 13, 2026 • 8min
Ep. 3331 - STORY: Dog Stocking Hustle Earns Husky Payoff
A marketer spots a niche in dog Christmas stockings and pivots into a seasonal product play. He uses SEO and breed-specific searches to uncover demand and ranks pages for early sales. He launches with dropshipping to minimize risk and scales rapidly the next year. The story highlights why seasonal side projects can explode with the right timing and execution.
Feb 12, 2026 • 8min
Ep. 3330 - TBT: The Accountant Who Sold Spreadsheets to Etsy Sellers
Janet LeBlanc, a financial educator for makers who runs Paper and Spark, built bookkeeping spreadsheets and courses for creatives. She tells how an Etsy jewelry shop led to a bestselling bookkeeping template. She explains blending accounting with visual design, automating products, and scaling into courses that support her family.
4 snips
Feb 11, 2026 • 4min
Ep. 3329 - Q&A: “Should I pay a publicist to book me as a podcast guest?”
A caller asks whether hiring a publicist to book podcast appearances is worth it. The conversation covers why paid publicists often deliver poor ROI and low-impact bookings. Alternative strategies are explored, like building genuine relationships, attending events, and pitching yourself to save budget. Practical encouragement to invest time in direct outreach rather than outsourcing.
5 snips
Feb 10, 2026 • 5min
Ep. 3328 - Q&A: “Why do online courses cost so much—or so little?”
Discussion about why online course prices range from inexpensive to very expensive. Short breakdown of how your target audience influences pricing. Talk about linking price to clear, measurable outcomes and credentials. Comparison with free resources like YouTube and guidance to price slightly above free alternatives.
