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 2, 2026 • 6min
Ep. 3320 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer
An accountant turns a wedding favor into paid engagement photography and navigates first-session nerves. She describes charging for early shoots, finding clients through friends, ads, and directories. Pricing climbs as she refines marketing and grows the side business.
7 snips
Feb 1, 2026 • 7min
Ep. 3319 - STORY: Physician Designs Plush Toys to Teach Anatomy
A physician turned toy designer creates plush human organs to teach anatomy and comfort hospital patients. The story covers prototyping costs, manufacturing hurdles overseas, and choosing third-party fulfillment. It follows a Shopify launch fueled by ads, partnerships with hospitals, and lessons about quality control and outsourcing.
Jan 31, 2026 • 4min
Ep. 3318 - Q&A: “How can I sell on a platform like NextDoor?”
Tara, a listener who asked about selling locally on Nextdoor. The conversation covers when neighborhood apps work best, practical tips like clear photos and detailed listings, and how Nextdoor compares to Craigslist and Marketplace. Short, actionable advice for hyper-local pickup sales.
Jan 30, 2026 • 7min
Ep. 3317 - STORY: Jiu-Jitsu Instructor Pins Down Mobile Workout Tool
A DIY training tool idea grows from backyard tinkering into a production-ready fitness product. The creator uses Kickstarter to validate demand and secures major funding. He navigates factory sourcing, travel to inspect samples, and scales to steady monthly sales. Lessons focus on prototyping, manufacturing vigilance, and fulfillment challenges.
6 snips
Jan 29, 2026 • 6min
Ep. 3316 - TBT: Designer Scales Personalized Wedding Products to $1M+
Kristen Barry Massoris, a graphic designer who built Miss Design Barry into a seven-figure custom wedding-illustration brand. She shares how she launched on Etsy, raised prices and moved to a direct site, and used niching and coaching to reach high-value clients. She also discusses scaling beyond Etsy, building new product lines, and partnering with charity.
Jan 28, 2026 • 5min
Ep. 3315 - Q&A: “How do I transition from Etsy to Shopify?”
Elsa, an Etsy seller from Seattle, calls in seeking a Shopify transition. The conversation covers why Shopify offers flexibility while Etsy provides built-in traffic. Tips include keeping Etsy open during the switch, learning Shopify hands-on, and avoiding dependence on others for simple site changes.
Jan 27, 2026 • 5min
Ep. 3314 - Q&A: “What's the best software to write a non-fiction book?”
Alonzo, a listener from Pensacola, calls in seeking the best tools to write a nonfiction book. They discuss why outlining first helps, how Scrivener organizes sections and manuscripts, and other options like Google Docs, Notion, Ulysses, or even longhand. There is also a reminder to limit distractions from social media while writing.
4 snips
Jan 26, 2026 • 8min
Ep. 3313 - First $1,000: “I still remember the day I hit the goal…”
Jodi Carlson, creator of Leader Connecting Leaders who makes resources for Girl Scout troop leaders. She turned a hobby into income by selling printable badge programs. The conversation covers how she found buyers, built an email list and social channels, added direct sales to her site, and the moment a bulk purchase pushed monthly revenue past $1,000.
Jan 25, 2026 • 8min
Ep. 3312 - STORY: The Clothes Dryer That Changed a Family Forever
A laid-off government worker turns a free clothes dryer into a repeatable reselling system. The story follows discovering Craigslist, quick listing tactics, and cleaning and photo tricks that speed sales. Strategies for scaling from small flips to five-figure months and beyond are highlighted.
Jan 24, 2026 • 5min
Ep. 3311 - Q&A: “Get paid to help brands with their Terms & Conditions?”
A Q&A about turning legal fine print into a paying side project. Discussion covers why people ignore T&C and how companies craft them. Ideas include designing reusable T&C templates, pricing and marketing that product, and whether brands would pay for simplified clauses. Alternatives explore educating consumers and focusing on clear customer demand.
