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
Dec 4, 2025 • 5min
Ep. 3260 - TBT: Campaign Scheduling Tool Turns Out Voters
Learn how a chaotic volunteer scheduling tool evolved into a licensed software product for multiple counties. Hear about the creative use of Google Forms to streamline campaign organization. Discover the transformation to CanvasPal, with features like tiered pricing and Stripe payments. Find out how word-of-mouth helped grow modest earnings of around $18,000. This tale emphasizes that solving small chaotic problems can lead to significant opportunities.
Dec 3, 2025 • 8min
Ep. 3259 - STORY: Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers
After feeling burnt out as a CPA, Janet LeBlanc shifted gears to launch a successful Etsy shop. She faced new challenges as a parent, leading her to pivot towards creating spreadsheets for fellow Etsy sellers. Her digital products quickly gained traction, earning her over $10,000 in the first year and eventually surpassing her CPA salary. Now on track for six-figure earnings, Janet is exploring future ventures like courses and live events, showcasing the power of blending skills for a profitable side hustle.
Dec 2, 2025 • 5min
Ep. 3258 - Q&A: “Can I profit from flipping open-box customer returns?”
Turning store returns into cash is the main focus, with tips on evaluating pallets and ensuring profitability. Learn how to buy manifest-listed pallets for better returns and the importance of specializing in one product category. Expect discounts of 25-40% and be conservative when estimating resale prices. Get creative with unsellable items by donating them for tax write-offs. The episode encourages disciplined sourcing and starting small before scaling your side hustle.
Dec 1, 2025 • 5min
Ep. 3257 - First $1,000: DIY Headshot Stations for University Job Fairs
Discover how a clever grad spotted a need for professional LinkedIn photos at university job fairs. He crafted a simple headshot booth, earning his first $1,000 without lifting a camera! With a minimal setup and zero hands-on work, he secured multiple bookings from nearby campuses. Learn about his pitch to career services and how seasonal demand can drive profits. This inspiring story highlights the potential of side hustles that require minimal effort while addressing a real demand.
6 snips
Nov 30, 2025 • 8min
Ep. 3256 - Weekend Workshop: Building Teams Without Hiring Employees
Discover how an unexpected layoff turned into a successful side hustle for Erica, who launched a transcription service from home. Initially aiming for live-event transcription, she faced challenges but pivoted to fill a market gap with her unique formatting service. Instead of hiring employees, she opted to scale using contractors, allowing flexibility. Learn how her journey emphasizes solving complete problems and doing ordinary work better, providing valuable insights for aspiring side hustlers.
Nov 29, 2025 • 5min
Ep. 3255 - Q&A: “When is uneven side-hustle income safe to rely on?”
A caller reveals they earn more from their weekend pen business than their day job, sparking a discussion on income stability. The host shares tips on assessing revenue against fixed expenses before making a leap. They explore strategies for smoothing out seasonal income, like deposits and subscriptions. Transitioning to fewer workdays or consulting is suggested as a safe bridge. Finally, the episode outlines key signals for quitting, stressing the importance of financial cushioning.
Nov 28, 2025 • 4min
Ep. 3254 - Q&A: “How do I price my VA work for true value?”
Elise, a virtual assistant from Spokane, seeks advice on pricing her services. She learns why hourly rates can limit her potential and how to package her offerings for higher value. Chris shares strategies to justify increased rates, emphasizing results over time-tracking. He suggests shifting to retainer packages and communicating these changes effectively to clients. Through this conversation, listeners discover that focusing on outcomes can elevate their worth and build loyal client relationships.
Nov 27, 2025 • 6min
Ep. 3253 - TBT: Scarce Lego Sets Build Value Over Time
Discover how a savvy side hustler turned retired LEGO sets into a lucrative business. He shares insights on predicting which sets will appreciate in value using market data. With successful buys like the Saturn V and UCS snowspeeder, he's made impressive profits. Learn about his meticulous tracking strategies and how he reinvests earnings into other collectibles. Brandon emphasizes patience and smart buying tactics, showcasing a unique way to grow wealth through childhood nostalgia.
Nov 26, 2025 • 8min
Ep. 3252 - STORY: Frenchman Says Bonjour to $35,000/Month Foodie Hustle
After moving from France to Quebec, Cédric Fontaine missed the flavors of his homeland, leading him to create Terroir Quebec, a directory of local artisans. Starting with just ten products, he expanded to around 400, crafting a unique e-commerce platform. Navigating seasonal sales, he faced shipping hurdles but adapted with better packing strategies. With a focus on customer feedback and reinvestment, Cédric aims to grow while maintaining his culinary roots, embodying the spirit of a passionate food ambassador.
Nov 25, 2025 • 5min
Ep. 3251 - Q&A: “Is my burnout a signal to pivot?”
A listener grapples with burnout from her calligraphy side hustle, realizing she dreads her once-loved orders. The host helps evaluate if it's time for a break or a significant pivot. They discuss pinpointing operational stressors like logistics and communication. Additionally, there's reassurance that side hustles aren't permanent; they can lead to personal evolution and new opportunities. The emphasis is on prioritizing enjoyable and meaningful work.
