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
Apr 5, 2026 • 7min
Ep. 3382 - STORY: Cigar Subscription Box Delivers Smoking Returns
A college student turns a poolside idea into a premium cigar subscription service. The story covers niche research, sourcing and humidified fulfillment from an apartment. It explains growth without paid ads, startup costs and steady recurring revenue. There's also a quirky regulatory anecdote and a pivot into a second complementary venture.
Apr 4, 2026 • 4min
Ep. 3381 - Q&A: “Driving an RV across the country—can I get sponsored?”
Lauren, a listener from Omaha planning a family RV trip while working remotely. She asks about getting sponsors for her cross-country adventure. The conversation covers what sponsors actually want, realistic timelines for building an audience, and practical choices: enjoy the trip or build an offer and following first.
Apr 3, 2026 • 6min
Ep. 3380 - Failure Friday: “Perfect SAT Score” Tutor Gets Rejected by 100 Publishers
Sean Patel, founder of Prep Expert and a perfect SAT scorer turned test-prep entrepreneur. He recounts pitching a book to over 100 publishers and getting rejected. He then built a pilot SAT course with big score gains. After proving results, a major publisher signed him and his book climbed the charts.
Apr 2, 2026 • 7min
Ep. 3379 - TBT: These iPad Paintbrushes Never Run Dry
Karen Newport, a New Zealand software developer behind iPad Lettering (KiwiCoder). She explains how the iPad transformed her art and how she created and sold Procreate brushes. She shares stories about early growth, balancing a day job with a creative side income, adapting in a crowded market, and using accountability to stay focused.
Apr 1, 2026 • 4min
Ep. 3378 - Q&A: "Help, my bank said I can't open a business account!"
Ben from Montauk, a part-time side hustler, calls in about being denied a business bank account. He recounts the bank saying his business was not properly registered. The conversation covers trying another bank, quick and cheap registration options, and interim bookkeeping tactics to keep finances separate.
Mar 31, 2026 • 6min
Ep. 3377 - Q&A: “Should I create a website for medical coders?”
Tricia, a Cleveland-based medical coding professional, is building a site listing free continuing education credits for coders. The conversation covers monetization worries, why ads may underperform, partnering with CE providers for referrals, handling signups as traffic grows, and the long-term option of creating accredited training.
5 snips
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.
