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
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.
9 snips
Feb 9, 2026 • 5min
Ep. 3327 - First $1,000: “I dropped off hundreds of orders at the post office…”
Jodi Brough, founder of Dental Lace and creator of a refillable, eco-friendly dental floss, tells how a small idea grew into international retail. She explains designing a lipstick-style dispenser, 3D-printing prototypes with her husband, and hunting suppliers when manufacturers were skeptical. The story traces early silk-floss choices and finding the right refillable container abroad.
7 snips
Feb 8, 2026 • 8min
Ep. 3326 - STORY: Inventor Unclogs Profits With Innovative Drain Solution
A tinkerer turns constant hair clogs into a mushroom-shaped drain catcher. A small Kickstarter crushes its goal and paves the way to big-box retail. Patents and product line extensions fight knockoffs while scaling to seven-figure profits.
4 snips
Feb 7, 2026 • 5min
Ep. 3325 - Q&A: “How can I become a personal finance influencer?”
A wide look at breaking into the crowded personal finance space and why there is room for new voices. Practical ideas for choosing a narrow niche and finding the right audience. Advice on creating content that speaks to who you used to be and the people you want to help.
Feb 6, 2026 • 6min
Ep. 3324 - Failure Friday: “My virtual assistant was a fan of quiet quitting…”
Jack, who runs an advisory side business while working in finance, shares a Failure Friday story about hiring a virtual assistant who ultimately quit. He describes early success, a slow decline he missed, missed appointments and email errors. The conversation, quit, and recovery lead to lessons on onboarding, accountability, and the need for ongoing oversight when delegating.
Feb 5, 2026 • 7min
Ep. 3323 - TBT: English Language Game Throws Down Amazon Gauntlet
Alex Bricker, an English teacher and founder of ESL With Purpose who created the Phrase It game to teach phrasal verbs. He talks about turning teaching into a side income, balancing a full-time job with a growing YouTube channel, a costly $17,000 Amazon mistake, and strategies for long-term audience building like email lists.
7 snips
Feb 4, 2026 • 4min
Ep. 3322 - Q&A: “Can I import rain barrels from the Netherlands?”
A listener found the perfect rain barrel in the Netherlands and wonders if she can bring it to the U.S. The conversation compares distributing imported goods versus manufacturing locally. Practical steps for contacting the maker, running the numbers, and researching manufacturing backups are discussed.
4 snips
Feb 3, 2026 • 5min
Ep. 3321 - Q&A: “Should I start a new business or expand my current one?”
Jenny, a marketing consultant from Iowa who turned a side hustle into a full-time business, calls in about launching trade-show marketing kits for ag exhibitors. The conversation covers whether to expand under her current brand or create a separate identity. Practical factors like market overlap, customer language, income potential, and capacity are discussed.
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.
