
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 24, 2025 • 6min
Ep. 2977 - First $1,000: Social Media Captions Turn Into Passive Income
An Arizona writer transforms her love for social media into a thriving business by crafting engaging captions for busy freelancers. Her journey showcases the power of turning creative skills into extra income. Strategies for attracting clients and understanding their needs are discussed, emphasizing profitable growth through innovative content solutions. This inspiring tale highlights the potential for anyone to embark on their own entrepreneurial venture.

8 snips
Feb 23, 2025 • 7min
Ep. 2976 - Weekend Workshop: Crafting a Compelling Offer
Get ready to learn how to craft a compelling offer that captivates customers! This segment is packed with practical examples to help transform your business idea into something irresistible. Discover the critical components like value, engaging pitches, and clear pricing. Plus, there’s an actionable exercise to guide you in developing your own offer. It's a must-listen for anyone eager to kickstart their side hustle and make 2025 their year of success!

Feb 22, 2025 • 5min
Ep. 2975 - Q&A: “How do I handle blog questions without feeling overwhelmed?”
This discussion dives into strategies for health bloggers overwhelmed by reader questions. It emphasizes the importance of batching tasks for efficiency. Listeners learn how to balance audience interaction while maintaining content quality. The conversation also highlights setting boundaries to prioritize responses and encourage community engagement. Perfect for anyone looking to enhance their blogging experience!

Feb 21, 2025 • 6min
Ep. 2974 - Q&A: “Where should I host my online course?”
A history professor grapples with the decision of where to host his online course. The discussion reveals the trade-offs between popular platforms like Udemy and independent hosting options. Insights on attracting an audience for niche topics unfold, highlighting the delicate balance of reach versus control. Listeners are treated to valuable advice on maximizing revenue potential while maintaining creative control over their course content.

Feb 20, 2025 • 7min
Ep. 2973 - TBT: Turning Late-Night Edits into a Niche Agency
Explore the journey of a Toronto freelancer who transformed scattered editing gigs into a thriving niche agency for fitness creators. Learn how they identified a market opportunity and successfully implemented a subscription model. The discussion dives into refining service offerings and enhancing client relationships for steady income. Discover practical strategies for scaling operations and maintaining a casual work culture while achieving sustainable success.

Feb 19, 2025 • 7min
Ep. 2972 - STORY: 13-Year-Old Australian Creates Schoolyard Lollipop Fortune
A 13-year-old from rural North Queensland is turning heads—and earning a fortune—by selling lollipops at school. With a stunning 100% profit margin, she attracts a crowd with the jangling of her pockets full of sweets. Her story not only showcases her entrepreneurial spirit but also highlights the confidence she gains through this sweet side hustle. Discover how this young innovator is making her mark, one lollipop at a time!

Feb 18, 2025 • 5min
Ep. 2971 - Q&A: “Should I keep offering a service that’s profitable but draining?”
A graphic designer grapples with the challenge of a lucrative but exhausting service. The discussion focuses on balancing financial success with personal well-being. Strategies to combat burnout are explored, including the use of AI tools. Tips on finding more fulfilling work alternatives are also shared, emphasizing the importance of aligning one's passion with profit. It's an insightful look at how to navigate the complexities of freelance life.

Feb 17, 2025 • 6min
Ep. 2970 - First $1,000: Mystery Gift Bundles for the Indecisive Shopper
Discover the creative journey behind the success of mystery gift bundles designed for indecisive shoppers. Dive into the entrepreneurial process, from market research to sourcing products, and explore the effective marketing strategies that made these bundles a hit. Hear how the element of surprise adds excitement for customers, proving that sometimes the unknown can lead to remarkable success in the world of side hustles.

5 snips
Feb 16, 2025 • 8min
Ep. 2969 - Weekend Workshop: Finding Your Ideal Customer
Discover the essentials of identifying your ideal customer and why it’s crucial for your side hustle. The podcast guides you through creating a customer avatar and understanding their needs and pain points. Engage in practical exercises to enhance your commitment to serving this specific audience. Plus, enjoy daily insights and real-life case studies of people earning extra income while keeping their day jobs!

Feb 15, 2025 • 6min
Ep. 2968 - Q&A: “How do I handle customer refunds without ruining my cash flow?”
An online shop owner learns to balance customer satisfaction with financial health while handling refund requests. Discover practical strategies like clear refund policies to maintain cash flow. The discussion encourages a growth mindset, transforming challenges into opportunities for success. Tune in for insights that help navigate the complexities of running a small business while keeping customers happy.