
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

Feb 4, 2025 • 4min
Ep. 2957 - Q&A: “How can I make a slow month more productive?”
Discover strategies to boost productivity during slow business months. Learn how to turn quiet times into opportunities for skill development and future growth. A freelance photographer shares their challenges and insights on balancing business efforts with necessary downtime. This engaging discussion provides practical tips to make off-peak seasons more rewarding.

Feb 3, 2025 • 7min
Ep. 2956 - First $1,000: Temporary Tattoo Artist for Events
Discover how a Mississippi artist turned their design passion into a booming event business by offering custom temporary tattoos. This fun venture caters to weddings, parties, and corporate events, tapping into a unique niche. Learn about the strategies that helped this creative entrepreneur achieve their first $1,000 in profit. Temporary tattoos are gaining popularity, making this an inspiring and accessible side hustle idea for aspiring creators.

14 snips
Feb 2, 2025 • 8min
Ep. 2955 - Weekend Workshop: Choosing Your Best Idea
Discover how to choose your best side hustle idea with practical tools and activities. Learn the importance of evaluating your business concepts through a systematic approach, applying five essential criteria to make informed decisions. Enjoy real-life examples, including a deep dive into cooking business ideas, to inspire your entrepreneurial journey. This segment is packed with guidance to help you thrive in your side hustle without quitting your day job.

Feb 1, 2025 • 5min
Ep. 2954 - Q&A: “Is a subscription box for indie comics the right idea?”
A comic enthusiast debates the best way to promote indie creators through a potential subscription box. The discussion reveals challenges such as maintaining a steady content supply and keeping subscribers engaged. Instead of a rigid subscription model, alternatives like one-time collections or digital offerings are suggested. This approach could provide more flexibility and cost-effectiveness, making it easier for indie creators to thrive.

Jan 31, 2025 • 5min
Ep. 2953 - Q&A: “How can I negotiate better terms with my suppliers?”
Explore the art of negotiating with suppliers in the food industry. Discover how a bakery owner can improve payment terms and reduce costs, all while fostering strong business relationships. The discussion highlights collaborative strategies that go beyond just haggling over prices. Learn tips for navigating the complexities of supplier negotiations and consider alternative market options to enhance your business. It's a treasure trove of insights for anyone looking to save money and strengthen their vendor partnerships!

Jan 30, 2025 • 6min
Ep. 2952 - TBT: Microbrewery Tours Expand to Hops and Brewing Classes
Discover how a Chicago microbrewery tour guide transformed a love for craft beer into a profitable business, turning passion into profit. The journey not only involved tours but evolved into hands-on brewing classes and hops growing kits. Learn about the transition from simple tours to interactive experiences that captivated audiences. This inspiring story showcases the potential for pursuing personal interests and monetizing them creatively.

Jan 29, 2025 • 8min
Ep. 2951 - Lifelong Girl Scout Earns Her Side Hustle Badge
A lifelong Girl Scout turned her passion into a thriving side hustle. She launched a resource website for troop leaders, showcasing her expertise and creativity. With savvy social media and content marketing strategies, she built a strong community around her initiative. Her journey is not just about profits, but also about connection and support among fellow leaders.

Jan 28, 2025 • 5min
Ep. 2950 - Q&A: “How much time should I spend on social media each week?”
A handmade pottery business owner grapples with the tricky question of social media time management. Discover effective strategies to reduce anxiety and boost online presence without burning out. Learn how to prioritize impactful actions and focus on a few key platforms. Gain insights into utilizing analytics and scheduling tools to enhance content creation and audience engagement. It's all about working smarter, not harder!

Jan 27, 2025 • 6min
Ep. 2949 - First $1,000: Career Transition Guides Quickly Earn $25,000
Discover the inspiring journey of a former HR professional who pivoted to creating career transition guides. Learn how her niche marketing strategies helped her earn over $25,000 while balancing her day job. The discussion highlights her innovative workshops and how she effectively aids professionals, particularly teachers moving into tech. This tale showcases the potential of side hustles to transform passion into profit, emphasizing the power of focused expertise.

Jan 26, 2025 • 7min
Ep. 2948 - Weekend Workshop: Money Math Made Simple
This segment introduces a workshop series designed to simplify launching side hustles in 2025. Listeners learn basic math to make smart profit projections, using relatable examples like car rentals and dog walking services. The conversation emphasizes understanding financial projections through conservative and optimistic estimates. It's all about empowering entrepreneurs to forecast their potential earnings and assess the viability of their ideas, making money math approachable and practical for everyone.