
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

Jun 22, 2025 • 8min
Ep. 3095 - Weekend Workshop: Creating Business Systems
Learn how to turn your ideas into action by establishing effective business systems for your side hustle. Discover the significance of documenting processes to enhance efficiency and reduce stress. Explore practical strategies for transforming informal knowledge into systematic workflows. Gain insights on documenting essential business operations, from sales to delivery, to create smoother and more successful ventures. This journey not only boosts organization but also sets the stage for scalability and long-term success.

Jun 21, 2025 • 6min
Ep. 3094 - Q&A: “Can organizing someone’s email become a real side hustle?”
Exploring the niche of email organization as a side hustle, this podcast delves into the growing demand for inbox cleanup services. It tackles the challenges of marketing these services as productivity boosters and the importance of building trust with clients. Tips for effective communication and privacy measures are shared to help entrepreneurs attract high-value clients and avoid inbox overwhelm.

Jun 20, 2025 • 5min
Ep. 3093 - Q&A: “Is there a market for professional home inventory services?”
Could a home inventory service become a lucrative side hustle? The discussion dives into market demand and identifying potential clients. Listeners learn about the unique challenges of promoting this service and the importance of building strategic partnerships with insurance agents. Emotional connections through testimonials can greatly enhance credibility. Plus, practical tips for navigating the complexities of launching this venture are shared, making it insightful for anyone considering this path.

Jun 19, 2025 • 6min
Ep. 3092 - TBT: Digital Sticker Sales Skyrocket to $500K
Discover the incredible journey of a graphic designer who transformed her humble digital sticker sales into a $500,000 success story. The podcast explores the evolution of her business, navigating from Etsy to platforms like Shopify. Learn about effective marketing strategies and the advantages of digital products. The discussion also touches on the chaos of managing a creative business amidst other responsibilities, highlighting tools to streamline operations. It's a tale of creativity, growth, and finding balance in entrepreneurship.

Jun 18, 2025 • 7min
Ep. 3091 - STORY: Faux Taxidermy Turns Heads on Home Decor
A Pennsylvania couple turned their differing tastes in home decor into a thriving faux taxidermy business. Their creative journey showcases teamwork and innovation, leading to success across various online platforms. They share valuable insights on overcoming challenges and the benefits of pursuing side hustles for financial independence. This unique niche in home decor highlights how passion can evolve into a profitable enterprise.

Jun 17, 2025 • 5min
Ep. 3090 - Q&A: “Can renting your car on Turo actually make money?”
Is renting your car on Turo a smart move or just a hassle? Delve into the numbers and risks involved in this side hustle. The discussion covers profitability and how factors like vehicle type and location influence earnings. It's a revealing look at whether one car can really generate extra income or just lead to wear and tear. Tune in for insights from real case studies and listener questions.

Jun 16, 2025 • 6min
Ep. 3089 - First $1,000: Custom Trekking Gear from a Home Printer
A weekend hiker turned passion into profit by using a 3D printer to create custom trekking pole grips. This innovative side hustle combines a love for the outdoors with technology, resulting in products that fit perfectly for users. The journey from personal projects to online sales showcases both the creativity in design and the potential for financial success. Listeners are encouraged to explore their own entrepreneurial dreams, proving that with the right tools, anyone can carve out a niche!

Jun 15, 2025 • 8min
Ep. 3088 - Weekend Workshop: Look for Money Lying Under a Rock
Discover how to spot hidden financial opportunities and make money with minimal effort. Learn key strategies for streamlining your operations during hectic times, especially for entrepreneurs. Explore ways to expand your side hustle by identifying natural growth opportunities that you may not have considered. Each segment is packed with practical examples and activities to help you take steps towards your financial goals in 2025.

Jun 14, 2025 • 5min
Ep. 3087 - Q&A: “Should I create a free course before launching a paid one?”
Is a free course a gateway to sales or just a magnet for freeloaders? This discussion dives into when offering free content can successfully transition users to paid courses. Learn strategies for crafting engaging free courses that build trust and showcase value. Tips include using webinars and downloadable resources to create a smooth shift to paid offerings while ensuring that simplicity stays at the forefront. Discover the nuances of balancing valuable content with the desire for financial return!

Jun 13, 2025 • 5min
Ep. 3086 - Q&A: “Should I monetize my free Facebook group?”
Can you turn a free Facebook group into a money-maker? Discover ethical strategies that keep your community engaged while generating revenue. Learn the importance of relying on efficient solutions to manage life's chaos. Plus, explore innovative ideas like paid memberships and product sales to sustain a thriving online space without compromising connections.