
Side Hustle School
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/
Latest episodes

May 14, 2025 • 9min
Ep. 3056 - STORY: Architect Creates Mini-Blind Repair Too
An architect shares his journey of creating a mini-blind repair tool that now adds an extra $15,000 to his income. The discussion reveals the challenges he faced in patenting and manufacturing. It also highlights the intricate world of product development and the risks of imitation. Perseverance in side hustles is emphasized, showing that innovation can lead to success while balancing life's complexities.

May 13, 2025 • 5min
Ep. 3055 - Q&A: “Can you really publish a book in a week?”
Can you truly publish a book in just a week? This discussion dives into the intriguing realm of speed-publishing, weighing the benefits against potential pitfalls. The emphasis is on the battle between quality and quickness in writing. Is it worth sacrificing depth for speed, or can a meaningful work emerge from such haste? Tune in to unravel these questions and more!

May 12, 2025 • 6min
Ep. 3054 - First $1,000: Community Host Boosts Engagement and Retention
Discover how a community manager turned her passion into profit by focusing on personal connections and engaging virtual events. She created a supportive environment for solopreneurs to thrive. This inspiring success story highlights the importance of community dynamics in boosting engagement and retention, showcasing how dedicated efforts can lead to surpassing the $1,000 milestone. Tune in for insights on transforming engagement into income while maintaining that personal touch.

May 11, 2025 • 7min
Ep. 3053 - Weekend Workshop: Test, Test, and Test Again
Discover the essential role of testing in launching a successful side hustle. Learn practical strategies, including A-B testing, to refine your approach. Hear a fascinating success story of how a simple hobby evolved into a profitable venture. Get inspired to track your progress and experiment for optimal results. This week’s focus is on building a solid foundation for your side hustle journey.

7 snips
May 10, 2025 • 5min
Ep. 3052 - Q&A: “How can I push past hesitation and market my creative work?”
A creative entrepreneur shares their struggle with self-doubt while trying to market unique hair accessories. The discussion offers actionable strategies to overcome hesitation and connect with the right audience. Listeners are encouraged to embrace authenticity and storytelling in their ventures. The importance of taking risks in creativity is highlighted, fueling confidence in launching a business. Inspiring anecdotes illustrate the journey of turning passions into profit, making it relatable for anyone with creative ambitions.

May 9, 2025 • 4min
Ep. 3051 - Q&A: “How do I balance what I love with what the market wants?”
Discover the tension between pursuing personal passion and meeting market demand in product-based businesses. A listener shares their journey creating custom wooden desk organizers, wrestling with artistic integrity and financial success. The discussion offers practical strategies, like introducing a dual-tier product line, to strike the right balance. Tune in for insights that empower creators to sustain their inspiration while thriving commercially.

May 8, 2025 • 5min
Ep. 3050 - TBT: Lawn Sign Biz Expands to Wedding Décor Rentals
A third-grade teacher turned her creative lawn sign business into a sought-after wedding décor rental service. Discover her inspiring transformation and how she navigated challenges during the pandemic. The podcast showcases the strategic decisions and client relationships that helped her thrive in the side hustle world.

May 7, 2025 • 7min
Ep. 3049 - STORY: Internet Trolls Eat Their Words In This Comedic Cake Hustle
A woman takes a jab at internet trolls by converting their negative comments into witty cake designs. Her absurd and comedic approach leads to a surprising and successful side hustle. This journey not only showcases creativity but also serves as a clever commentary on online negativity, reminding us that even the harshest critiques can be turned into something delightful.

May 6, 2025 • 5min
Ep. 3048 - Q&A: “Best practices for Meta ads?”
Discover the secrets to running profitable Meta ad campaigns on Facebook and Instagram. Learn about the importance of effective budget setting and audience targeting. Find out how video content can significantly boost your ad performance and ROI. With real listener feedback, this discussion unveils best practices to maximize your returns and make the most of your investment in social media advertising.

May 5, 2025 • 7min
Ep. 3047 - First $1,000: Pop-Up Cosplay Salon Takes Con-Goers by Surprise
A Seattle hairstylist transforms a love for wigs into a thriving pop-up salon at comic conventions. Tackling last-minute hair emergencies for cosplayers, they capitalize on social media to boost visibility. The journey emphasizes embracing creative risks and unconventional strategies for business success. With increasing demand, future expansion plans are on the horizon, showcasing how a side hustle can turn into something much bigger.