

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 24, 2025 • 8min
Ep. 3280 - STORY: The Rise and Fall of BirdSupplies.com
A passionate bird lover turned entrepreneur, Diane Burroughs launched BirdSupplies.com to fill a gap in quality parrot products back in 1998. With a $12,000 investment, she soared to $250,000 in sales, but faced a setback when Google penalized her SEO efforts. After an 18-month battle to recover, Diane diversified her marketing strategies, embracing social media and crafting unique products like fleece collars for feather-plucking. Her journey offers valuable lessons on resilience and adapting in a changing landscape.

Dec 23, 2025 • 5min
Ep. 3279 - Q&A: “Do I have to be loud to sell my service?”
A caller seeks clients without the need for loud self-promotion. The host shares low-key tactics for marketing, emphasizing the importance of systematic referrals. Monthly evergreen tutorials can attract traffic without the noise of daily social media presence. Analyzing past client sources helps identify effective channels. For introverts, success lies in comfortable, non-salesy approaches, making the process easier and more effective over time.

6 snips
Dec 22, 2025 • 7min
Ep. 3278 - First $1,000: Helping Creators Migrate Course Content
The Weekend Migration Specialist, a marketing consultant and course migration expert, delves into the challenges course creators face when shifting content. He shares insights on his streamlined process, which includes a guaranteed minimal downtime migration to Kajabi for a flat fee. Discover how he effectively markets his services through testimonials and weekend sprints. He highlights the importance of understanding both platforms, turning the fear of migration into opportunities for creators. Tune in for practical takeaways to boost your side hustle!

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.

6 snips
Dec 17, 2025 • 7min
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.


