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 1, 2026 • 7min
Ep. 3347 - STORY: Trader Joe’s Sign Artist Earns $43,200 Selling Tea-Stained Prints
A Trader Joe’s sign artist turns public-domain art into tea-stained prints sold online. He experiments with quirky animal mashups and adds custom options after a surprise first sale. The hustle scales from a $300 startup to steady monthly profit, long-term growth, and major life changes.
4 snips
Feb 28, 2026 • 4min
Ep. 3346 - Q&A: “I'm being headhunted... for my side hustle!”
Josh, an IT pro who built a popular coding-test side project, shares how a hobby launch on Hacker News snowballed into downloads and an unsolicited interview. He talks about putting projects out into the world, handling unexpected attention, and treating marketing as part of development. Short, surprising outcomes follow taking risks and shipping work.
Feb 27, 2026 • 7min
Ep. 3345 - STORY: Beard Oil Behemoth Expands to 35 Countries
A $46 kitchen-table experiment turned into a beard oil business selling in 35 countries. They talk product tinkering to solve beard itch and smart early marketing on Etsy and social posts. Stories include celebrity fans, scaling production and hiring, and how running a niche brand changed the founder’s life.
Feb 26, 2026 • 6min
Ep. 3344 - TBT: iPhone App Tracks Weight-Loss Progress
A developer builds an iPhone app that tracks measurements and photos to show weight-loss progress. He created the tool while learning iPhone development to reach a personal goal. The story follows slow, steady revenue growth and the challenges of running a one-person product. Learn why coding became the launchpad for this side project.
4 snips
Feb 25, 2026 • 4min
Ep. 3343 - Q&A: “How to break out of a sales slump?”
Elizabeth, a La Habra side-hustler who grew sales with pop-ups and online shops, calls in about a sudden lull. She and Chris explore why outside factors matter. They dig into what drove early growth, which channels to test, and why running big, measurable experiments beats tiny tweaks.
6 snips
Feb 24, 2026 • 4min
Ep. 3342 - Q&A: “What’s the best way to register domains?”
Brad, a listener from Tampa who called in with a practical domain question. Short chat about why owning a domain matters. Tips on registrars, costs, and registering where you build your site. Advice on handling renewals and whether to buy extra extensions.
Feb 23, 2026 • 7min
Ep. 3341 - First $1,000: “Hyperfluent” Language Service Translates Into Profit
Eva Rosales, founder and CEO of Hyperfluent, turned language tutoring into a premium translation and language-acquisition consultancy. She talks about starting with low-rate tutoring, creating diverse service offerings, raising prices for niche work, and landing a high-value client that validated her pricing approach.
Feb 22, 2026 • 8min
Ep. 3340 - STORY: Proud Mainer Brings Whoopie Pies to the World
A Maine baker turns a post-kids hobby into a booming whoopie pie business. She solves shipping puzzles to send treats nationwide. An online store, Amazon and a 5,000+ sq ft storefront help scale production and staff. Sales expand into supermarkets and multiple channels drive rapid growth.
Feb 21, 2026 • 5min
Ep. 3339 - Q&A: “What kind of review platform would be best for online learning?”
Lisa, a graphic and web designer from Merriam, Kansas, pitches a review site for online art and design courses. The conversation explores building a curated review hub first, then opening to user submissions. Practical tips cover leveraging design credentials, recruiting early reviewers, and partnering with creators to build trust and traffic.
5 snips
Feb 20, 2026 • 7min
3338 - Failure Friday: “They just weren’t interested in what we were selling…”
Dale Wilson, co-founder of Married Livestream who builds high-quality wedding livestreams, tells a candid business failure about a COVID pivot to churches. He explains why small budgets, cheaper alternatives, and existing in-house teams killed demand. The story highlights quick testing, knowing your buyer, and returning focus to what already worked.
