
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

Apr 17, 2025 • 6min
Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse
Discover how a travel blog transformed into a spring break revenue powerhouse, generating up to $8,000 in peak months. Learn about the clever integration of ad networks and AI-generated content to overcome monetization hurdles. This side hustler shares actionable insights for anyone looking to boost their earnings while juggling a full-time job. Tune in for inspiration on automating your side hustle successfully!

Apr 16, 2025 • 8min
Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle
A college student transforms his financial struggles into a $40,000 a month side hustle through ethical hacking. Starting from a simple $40 investment, he created engaging online courses that resonated with thousands. The discussion highlights the power of finding your niche and delivering real value in the online education space. It serves as an inspiring reminder that success often comes from adapting and maximizing your unique skills.

Apr 15, 2025 • 6min
Ep. 3027 - Q&A: “How do side hustle ‘power laws’ work?”
Why do some efforts yield most results in side hustles? The discussion unveils power laws and their significance in maximizing impact. Focusing on a few key elements can drastically improve success rates. Listeners learn to identify high-impact areas to streamline their efforts. Plus, tips for effective time management are shared, linking it to entrepreneurial strategies. It's all about working smarter, not harder!

Apr 14, 2025 • 6min
Ep. 3026 - First $1,000: From Text Messages to Digital Concierge
Discover the journey of a meticulous organizer who turned a personal passion into a thriving digital concierge service. This innovative business offers tiered subscriptions for handling routine tasks and providing real-time support. Learn how the transition from helping friends to launching an online platform created a sustainable business model. Tune in for insights on transforming skills into income while balancing your regular job!

Apr 13, 2025 • 7min
Ep. 3025 - Weekend Workshop: Making Time for What Matters
Discover effective ways to maximize your time for business growth by prioritizing essential tasks. Hear a captivating story of a photographer who focused on activities that boosted revenue and customer satisfaction. Learn how to carve out time for your most important endeavors and reduce distractions. This engaging episode guides you through practical steps to enhance your side hustle without overwhelming your schedule.

Apr 12, 2025 • 5min
Ep. 3024 - Q&A: “What’s the ROI of renting out equipment or tools?”
Discover the profitable potential of running a tool rental business. Dive into managing inventory, minimizing risks, and maximizing profits. Learn which high-demand items, like photography gear and power tools, can boost your earnings. Explore the importance of starting small to gauge market demand and test the waters. This engaging discussion offers practical insights for anyone looking to earn extra income without giving up their day job.

Apr 11, 2025 • 5min
Ep. 3023 - Q&A: “Could selling templates for AI tools be a business?”
As AI tools like ChatGPT soar in popularity, the potential for selling templates tailored for these applications emerges as an intriguing side hustle. The discussion delves into marketing strategies, pricing models, and how to navigate the competitive landscape. Opportunities abound, but so do challenges, making it essential to stay adaptable and innovative. This exploration of a trending business idea is both timely and relevant for aspiring entrepreneurs.

Apr 10, 2025 • 6min
Ep. 3022 - TBT: When Selling Prints Wasn’t Enough
Discover how a digital artist transformed their side hustle by shifting from selling art prints to creating sought-after mock-ups for e-commerce platforms. This inspiring journey emphasizes the importance of adaptability in entrepreneurship. By addressing a key need for visually attractive product presentations, they found both financial success and renewed creative fulfillment. Tune in to ignite your own imagination and learn valuable strategies for reassessing and evolving your business!

Apr 9, 2025 • 7min
Ep. 3021 - STORY: Immigrant Couple Translates Heritage Into Children’s Flash Cards
Discover the inspiring story of an immigrant couple who turned their passion for language into a thriving business. They created dual-language flash cards celebrating their heritage, generating over $50,000 in sales within a year. Learn how they targeted a specific audience, turning a simple idea into a successful venture. Their journey highlights the power of cultural connection and community impact, proving that with creativity and strategy, anyone can transform their side hustle dreams into reality.

Apr 8, 2025 • 5min
Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?”
This discussion focuses on how freelancers can effectively manage last-minute client requests while avoiding burnout. Strategies like incorporating buffer time into schedules and setting clear project boundaries are emphasized. Communication and structured workflows play key roles in managing client expectations and maintaining a healthy work-life balance. Learn to navigate the chaos of urgent demands without sacrificing quality or your sanity.
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.