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
Mar 30, 2026 • 5min
Ep. 3376 - First $1,000: “I went door-to-door selling home alarms…”
A real-life door-to-door alarm salesperson shares why he tried sales and how a friend’s success inspired him. He talks about two weeks of training and the fear of repeated rejection. Low conversion rates, commission math, and the payoff of a big sale are discussed. The story highlights personality fit and why this hustle is not for everyone.
6 snips
Mar 29, 2026 • 6min
Ep. 3375 - STORY: Firefighter Uses Chainsaw for Jumbo-Sized Woodworking
A firefighter turns downtime into jumbo-sized chainsaw carvings, creating life-size wooden bears and moai from large logs. He lands commissions from universities, restaurants, and local festivals. Marketing pivots from Instagram to YouTube and clever pitches to designers and lumberyards help grow sales. He charges by project and plans ambitious builds like a documented log cabin.
Mar 28, 2026 • 5min
Ep. 3374 - Q&A: “Should I offer a pay-what-you-will price?”
Nikki, founder of the XO Project who sends calligraphed greeting cards by snail mail, joins to discuss scaling a handcrafted pen-to-paper business. She asks about target audience and whether pay-what-you-will pricing works. The conversation covers growth strategies, fixed pricing alternatives, and ways to sell non-handmade items while keeping personalized offerings.
Mar 27, 2026 • 7min
Ep. 3373 - STORY: Savvy Stationery Site Offers Cards for Divorce & Diwali
A director builds an e-commerce stationery brand offering modern, underrepresented occasions like Diwali, Ramadan, same-sex weddings and even divorce cards. She recruits local female artists to create unique designs and navigates consumer launches, a pivot into wholesale, pricing and seasonality. The story ends with growth plans, balancing a day job, and an eventual business sale.
Mar 26, 2026 • 7min
Ep. 3372 - TBT: Frozen Yogurt Dog Treats Are No Barking Matter
Matt Meyer, co-founder and co-owner of The Bear and the Rat, makes prebiotic frozen yogurt treats for dogs. He tells the origin story from kitchen tests to farmer's markets. He outlines simple, real ingredients and why the pet industry is ripe for growth. He talks about scaling distribution and the challenge of keeping independent pet stores visible as the brand expands.
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.
