
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

5 snips
May 23, 2025 • 6min
Ep. 3065 - Q&A: “How do I take a break from my hustle without losing momentum?”
Can you really pause your side hustle without losing your vibe? Discover essential strategies to take a break while keeping your momentum intact. Hear a relatable story of burnout and learn how to recharge effectively. Find out how to maintain customer engagement and ensure operational continuity during your downtime. Planning transparency is key to making a smooth return stronger than ever!

May 22, 2025 • 5min
Ep. 3064 - TBT: Turning Plastic into High-End Interior Pieces
Discover how a 3D printing enthusiast transformed her hobby into a thriving business by creating high-end interior decor. She shares insights on adapting designs for upscale markets and collaborating with interior designers. The podcast also tackles the complexities of e-commerce, highlighting innovative solutions for shipping challenges and the surge in client orders. Listeners are encouraged to share their own experiences in navigating the booming world of 3D printed decor.

May 21, 2025 • 8min
Ep. 3063 - STORY: Golfer Takes Swing At Content Website
A sales manager channels his frustration with poor online golf advice into a successful niche website, raking in $5,000 a month. He shares how optimizing search engine traffic and attracting organic visitors turned his passion into profit. The story highlights practical tips on SEO and monetization strategies for aspiring content creators. Tune in for insights on transforming discontent into a thriving online business!

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.