

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 22, 2025 • 7min
Ep. 3278 - First $1,000: Helping Creators Migrate Course Content
In this week’s First $1,000 segment, four course creators feared ripping their content out of their current system. One weekend migration specialist moved every video and quiz to Kajabi—pocketing a paycheck while their students never missed a lecture. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 See omnystudio.com/listener for privacy information.

Dec 21, 2025 • 6min
Ep. 3277 - Weekend Workshop: The Sculptor Who Thrived on Disaster
Discover how New York sculptor Rachel K. Vargas turned disasters into triumphs! From a studio collapse that sparked a lucrative commission to a job loss that pushed her to fully embrace her art, her journey is inspiring. A dramatic robbery reshaped her risk tolerance and priorities. Learn how she sold over 2,200 custom fire bowls to clients globally, including notable installations. The episode highlights the power of resilience, authenticity, and creativity in building a successful side hustle.

Dec 20, 2025 • 4min
Ep. 3276 - Q&A: “Can I I force myself to ship something every two weeks?”
A listener grapples with endless learning but struggles to launch their side hustle. To break the cycle, Chris recommends a 30% learning and 70% doing approach. Setting a bi-weekly launch checkpoint can ensure visible progress. He emphasizes turning notes into actionable tasks and suggests pausing new learning until goals are met. Chris's tips empower listeners to shift focus from theory to practice, proving that taking action is the key to success.

5 snips
Dec 19, 2025 • 5min
Ep. 3275 - Q&A: “How do I talk about pricing when it feels impolite?”
Discussing pricing can often feel uncomfortable, but reframing it as offering a structured service can ease the tension. Learn practical tips for confidently quoting rates, like using a standard package and a prepared script. The conversation highlights cultural factors that make discussing money feel rude. Plus, discover how to view fees as commitments that help clients achieve their goals. With practice, anyone can become more comfortable when it comes to pricing!

5 snips
Dec 18, 2025 • 6min
Ep. 3274 - TBT: I Reverse-Engineered Google-Form Hacks
Explore the creative world of Google Forms, where one individual transformed a mundane tool into a money-making machine. By implementing timers and custom branding, he charged over a thousand dollars through innovative Zoom sessions. Hear about his journey from a $200 demo to landing substantial clients via LinkedIn. Discover how a university quiz project turned into a weekend earning spree. He highlights the importance of limiting scope to scale effectively, making every feature count.

5 snips
Dec 17, 2025 • 8min
Ep. 3273 - STORY: London Photographer Rents Camera Gear 1,100 Times
A London receptionist turns his love for photography into a thriving side hustle by renting out his gear. He discovers a peer-to-peer platform that saves him from expensive traditional rentals. Nervous at first, he quickly overcomes his fears and maximizes his bookings through efficient systems. As demand grows, he reinvests his profits into more equipment and even manages to buy an apartment. This story showcases the potential of side hustles to create financial independence while maintaining a full-time job.

Dec 16, 2025 • 4min
Ep. 3272 - Q&A: “How do I avoid a bad review on my first client job?”
Facing your first client is nerve-wracking, especially with the fear of a bad review. Setting clear expectations in writing can prevent misunderstandings. A midpoint walkthrough helps ensure everything is on track. Chris emphasizes the importance of confidence and reminds listeners that some anxiety is natural. Following up with clients shortly after the job finishes can catch any issues early and secure positive feedback. These practical tips can turn a daunting first experience into a successful one.

Dec 15, 2025 • 6min
Ep. 3271 - The Ski-Lodge Lost-and-Found Hustle
A ski bum turned entrepreneur uncovers a goldmine in a ski lodge's lost-and-found. After negotiating to buy two bags of unclaimed gear for just $50 each, he cleans and resells the items for a whopping profit. Using platforms like Poshmark and Facebook Marketplace, he quickly turns trash into treasure. With initial sales bringing in over $685 and a total profit of $1,080 in just three weeks, he shares the ups and downs of this chilly side hustle, highlighting both its potential and its limitations.

7 snips
Dec 14, 2025 • 7min
Ep. 3270 - Weekend Workshop: From Rock Bottom to Business Empire
A British woman transforms her life from a homeless shelter to a million-dollar business. She launches IttyBiz with a focus on effective marketing sessions, charging clients $250 for actionable advice. Naomi's straightforward approach emphasizes profit over popularity, helping business owners succeed. She expands her services into courses and products, maintaining a strict rule of keeping only revenue-generating activities. The podcast highlights practical lessons that listeners can implement immediately to start their own side hustles.

5 snips
Dec 13, 2025 • 5min
Ep. 3269 - Q&A: “What do I do if my partner doesn’t believe in my business?”
A listener grapples with a partner's skepticism about their business dream. The discussion emphasizes the importance of safety, trust, and respect in relationships. Suggestions include using an empathy-first approach to ease fears and proposing a trial period for the side hustle. Chris also recommends setting non-negotiable boundaries and having regular check-ins to evaluate progress. Tune in for practical advice on pursuing your passion while maintaining harmony at home!


