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 15, 2026 • 8min
Ep. 3361 - STORY: Designer Earns $1 Million Giving It The Old College Try
A designer missing his Southern roots builds a nostalgic line of pennants and tees celebrating hometown pride. A viral blog feature and social buzz send waves of orders and fuel rapid growth. He scales with low upfront cost, packing parties, and customer-driven designs while keeping his day job.
5 snips
Mar 14, 2026 • 6min
Ep. 3360 - Q&A: “How to start a meal prep side hustle?”
Bryce, a listener who meal-preps weekly and wants to monetize that skill. He explores positioning as an athlete-friendly, macro-aware meal planner. Ideas include a paid weekly prep kit with grocery lists and macros, a four-week high-touch cohort, and a fast seven-day paid pilot to test and gather testimonials.
Mar 13, 2026 • 8min
Ep. 3359 - STORY: Working Mother Sells Coats to Buckle in Babies
A working mother redesigns winter coats so babies can be buckled safely without removing bulky outerwear. The story follows her side-opening zipper idea, prototyping and safety testing, and early manufacturing setbacks. A viral demo and Kickstarter validate demand, leading to production pivots, community updates during delays, and steady sales growth.
Mar 12, 2026 • 7min
Ep. 3358 - TBT: Rosary Beads Count Off Extra Income
Maria Lauren, Chicago-based maker behind Willow and Bee who crafts faith-based jewelry like rosaries and First Communion pieces. She recounts starting on Etsy, landing boutique and Amazon Handmade placements, and expanding with subscriptions. She talks about outsourcing challenges, inventory testing, and focusing on serving repeat customers to grow income.
Mar 11, 2026 • 6min
Ep. 3357 - Q&A: “How can I get paid to help resellers?”
Joe from Atlanta, a listener who scouts products for resellers. He asks what resellers truly need and whether he can get paid to source items. The conversation covers where resellers find products, the markets they serve, and how to build a competitive advantage when supplying them.
Mar 10, 2026 • 5min
Ep. 3356 - Q&A: “I’m a professional speed skater. How can I fundraise?”
Justin, an amateur-to-pro speed skater from St. Paul pursuing Olympic dreams. He asks how to fund training and build support. The conversation covers focusing priorities, why Patreon is risky without an audience, creating products for sustainable income, improving social presence on one or two platforms, and pursuing brand deals and sponsorships for bigger payout.
6 snips
Mar 9, 2026 • 6min
Ep. 3355 - First $1,000: Camping YouTuber Earns Affiliate Income
A camper turns smartphone reviews into a YouTube channel showcasing gear and tips. He uses affiliate programs and adds purchase links to earn when viewers buy. Short listicle videos, SEO keywords, and analytics shape his content strategy. Patience and data-driven pivots lead to the first $1,000 in earnings.
12 snips
Mar 8, 2026 • 7min
Ep. 3354 - STORY: “Productivity Nannies” Dig Co-Working Caves for Modern Workers
A team creates daylong distraction-free "caves" where people disappear to finish important work. They sold out a first public event with simple promotion and turned it into memberships, virtual days, and corporate offerings. The founders learned to define roles early and scaled with low-cost operations and thoughtful product additions.
Mar 7, 2026 • 5min
Ep. 3353 - Q&A: “One-page business plan: what is the essential info?”
A short Q&A on what belongs in a one-page business plan and where to find the original template. They highlight the two core questions: what you will sell and who will buy it. Practical choices about pricing and payment methods get attention. The conversation stresses action steps, defining success, and why a concise plan can propel your side hustle.
6 snips
Mar 6, 2026 • 8min
Ep. 3352 - Failure Friday: “Our first trade show was canceled with no refund…”
Chris Cavallari, founder and lead craftsman at The Acadian who makes handmade luxury pens and leather goods. He recounts preparing for his first wholesale trade show and then losing booth fees when COVID-19 canceled it. He talks about writing an emergency continuity plan, building local support through a Facebook peer group and Zooms, and diversifying income to survive the shutdown.
