
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

4 snips
Jun 2, 2025 • 6min
Ep. 3075 - First $1,000: Marketing Pro Builds GPT Bots—No Code Needed
A marketer transitioned from consulting to creating custom GPT chatbots without any coding skills. Discover how they identified client needs, effectively engaged customers, and priced their services. Learn valuable insights about scaling a business in the tech space while keeping it simple. This story showcases the potential of side hustles, proving anyone can turn an idea into income with the right approach.

Jun 1, 2025 • 8min
Ep. 3074 - Weekend Workshop: Measure What Matters
Discover how to effectively measure what matters in your side hustle! Learn the importance of tracking key metrics for smarter business decisions. A practical example of a resume design business illustrates what numbers to focus on to adapt your strategy. Get ready to transform your side hustle in 2025 with actionable insights and free lessons that will guide you every step of the way!

May 31, 2025 • 6min
Ep. 3073 - Q&A: “What’s the purpose of more than one business bank account?”
Explore the benefits of having multiple business bank accounts in this discussion. Discover how separating personal and business finances can streamline cash flow and improve financial stability. Two key financial models are introduced to enhance your financial discipline. Managing your money better could mean paying yourself more effectively and setting a strong foundation for future growth!

May 30, 2025 • 5min
Ep. 3072 - Q&A: “Why do struggling businesses keep their doors open?”
How do some failing retail stores manage to keep their doors open? Discover the surprising factors that contribute to their longevity, including external funding and tax benefits. Explore the complexities of unprofitable businesses that persist due to loss leadership or personal passion. This discussion sheds light on the resilience required to navigate challenging environments while maintaining a business, revealing the intricate reasons behind keeping ventures alive despite financial struggles.

4 snips
May 29, 2025 • 6min
Ep. 3071 - TBT: From DIY Pet Tributes to Six-Figure Etsy Shop
A maker transformed grief into profit by turning a small Etsy shop for custom pet memorials into a six-figure success story. They expanded their product line to help grieving pet owners celebrate their companions. The journey highlights the importance of emotional connections with customers and efficient order fulfillment. Discover how strategic improvements and tools, like ShipStation, boosted their e-commerce management for enhanced satisfaction.

May 28, 2025 • 7min
Ep. 3070 - STORY: High School Student Earns $20,000 Making Wooden Bow Ties
A high school student transforms an unimpressive gift into a thriving business by crafting wooden bow ties. He capitalizes on his woodworking hobby, showcasing how passion can lead to profitability. Through challenges and successes, he learns about the importance of quality and standing out in the market. Remarkably, he earns $20,000 in just a year, proving that young entrepreneurs can make big waves with creativity and determination.

4 snips
May 27, 2025 • 6min
Ep. 3069 - Q&A: “I’m ready to sell my side hustle—how do I do it?”
Wondering how to sell your side hustle and not get shortchanged? Learn valuable tips on business valuation, finding the right buyer, and ensuring a smooth transition. The discussion includes real-life inquiries and expert strategies for a successful sale. Whether you're ready to cash in or just curious about the process, this insightful breakdown offers fresh perspectives and actionable advice.

4 snips
May 26, 2025 • 6min
Ep. 3068 -First $1,000: Real Estate Office Rents Out Podcast Studio
A small real estate office in Del Mar cleverly turns an unused conference room into a profitable podcast studio. This innovative side hustle generates steady income with minimal effort and showcases the potential of leveraging existing spaces. The podcast emphasizes the financial benefits and community connections that come from renting space creatively, offering inspiration for anyone looking to monetize what they already have.

May 25, 2025 • 6min
Ep. 3067 - Weekend Workshop: Frame Your First Dollar
Discover the key to success in side hustling by celebrating milestones! This segment explores the emotional boost that comes from earning your first dollar and how it can ignite your motivation. Through inspiring stories, like a blogger who made his first $200, you'll learn the power of recognizing achievements, no matter how small. Embrace these moments to build momentum and set future goals. Get ready to kickstart your side hustle journey with practical insights and encouraging examples!

8 snips
May 24, 2025 • 5min
Ep. 3066 - Q&A: “Is YouTube really ‘top of funnel’ for educational creators?”
Is YouTube truly the best way for educational creators to convert viewers into paying customers? The discussion dives into whether the platform serves as a genuine sales funnel or just a free content hub. Creators are encouraged to strategically balance free offerings with monetization strategies. There's a focus on structured content and effective marketing tactics that can enhance viewer engagement. Discover how to maximize YouTube's potential while navigating the challenges of the educational landscape!