
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 20, 2025 • 4min
Ep. 3062 - Q&A: “Are there any ‘good’ MLMs?”
The discussion tackles the controversial world of multi-level marketing (MLM). It examines the ethical issues and risks posed by MLM structures. Sobering statistics reveal how many participants lose money. The conversation advocates for seeking more empowering and sustainable entrepreneurial opportunities instead. Tune in for insights on making smarter side hustle choices!

May 19, 2025 • 7min
Ep. 3061 -First $1,000: Coffee Gear Affiliate Site Brews Profits
Discover how a coffee enthusiast turned passion into profit with an SEO-driven affiliate website. Dive into strategies for attracting coffee lovers and optimizing content to drive conversions. Learn practical tips on starting small to earn that first $1,000. Explore how seasonal trends can impact earnings and gather insights to craft your own successful niche site. This journey showcases the power of blending hobbies with smart marketing techniques for financial gain.

May 18, 2025 • 7min
Ep. 3060 - Weekend Workshop: Burn Down the Furniture Store
Discover the art of compelling promotions with creative strategies that ignite urgency. Learn how special offers can dramatically enhance customer engagement, using real-world examples like a slate artist's successful discount campaign. Explore practical planning tips for launching your own flash sales and holiday specials. This engaging discussion emphasizes taking action and embracing the power of scarcity to boost your side hustle's profits.

May 17, 2025 • 5min
Ep. 3059 - Q&A: “How can I wireframe a website?”
Discover how to wireframe a website without getting overwhelmed. The hosts share essential tools and strategies to outline your vision, emphasizing the importance of core pages for user experience. Learn how a well-structured wireframe serves as a blueprint for design, especially for projects like subscription boxes. Ideal for anyone looking to refine their web development skills and enhance digital presence.

May 16, 2025 • 5min
Ep. 3058 - Q&A: “Is it a good time to launch a meme coin?”
Is launching a meme coin a smart side hustle? The discussion dives into the evolving landscape of these crypto coins, unpacking their risks and rewards. With market volatility in mind, the need for strong branding and storytelling emerges as a key to success. It’s not just about profit; the conversation urges aspiring creators to focus on genuine value and sustainability in a crowded market. Tune in to learn how to navigate the challenges of this intriguing and unpredictable arena!

May 15, 2025 • 7min
Ep. 3057 -TBT: Crossing Borders, Boosting Orders
Discover how a Canadian e-commerce expert transformed his Amazon experience into a successful consulting business. He reveals key strategies for fellow Canadians to access the thriving U.S. market, tackling logistics and legal hurdles. Plus, learn about his plans for a digital course and coaching program that aims to empower others in the e-commerce space. Streamlining fulfillment processes is also a focus, providing valuable insights for online sellers.

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.