

Side Hustle School
Chris Guillebeau / Onward Project
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/
Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Episodes
Mentioned books

Aug 21, 2025 • 6min
Ep. 3155 - TBT: From Abandoned Storage Finds to Museum Artifacts
Discover the journey of a side hustler who transitioned from flipping storage unit finds to providing rare historical artifacts for museums. This transformation emphasizes the importance of knowledge and meaningful sales, moving beyond volume. The episode highlights the preservation of history through entrepreneurship and the significance of finding the right talent for this unique mission, introducing tools like ZipRecruiter to streamline hiring.

Aug 20, 2025 • 8min
Ep. 3154 - STORY: Civil Engineer Sells Hooded Baby Robes on Amazon
A civil engineer in Florida pivoted from selling hooded baby robes on Amazon to living in Bali and creating a groundbreaking app to help others find products. His venture exploded into a business with 80 employees and a user base of 100,000. The journey showcases the challenges of entrepreneurship, innovation, and a commitment to charitable initiatives, inspiring others to carve their own paths in e-commerce.

Aug 19, 2025 • 4min
Ep. 3153 - Q&A: “‘Love spells’ for sale on Etsy … is this real??”
Delve into the fascinating world of online love spells and magic charms! Discover how some entrepreneurs are turning to Etsy to sell these mystical services. Hear about the initial successes and challenges they face due to shifting platform policies. The podcast examines the intriguing market for digital spellwork and offers creative strategies for navigating this quirky niche.

6 snips
Aug 18, 2025 • 6min
Ep. 3152 - First $1,000: Book Summary Subscription Breaks Out
Discover how a side hustler launched a thriving paid book summary subscription, merging AI tools with personal touches to capture attention. Explore the creative strategies for engaging busy professionals and building trust with subscribers. The discussion highlights the power of personal branding in a competitive market and the growing popularity of subscription services among business enthusiasts. This inspiring story encourages listeners to embark on their own projects and monetize their unique ideas.

Aug 17, 2025 • 7min
Ep. 3151 - Weekend Workshop: Emotional Products Command Premium Prices
Discover how emotional connections to products can boost their value significantly. An industrial engineer shares his journey of creating nostalgia-themed slate carvings that resonate with both locals and expats. Learn the power of regional identity in crafting unique items that command premium prices. This insightful discussion offers actionable steps for turning hobbies into profitable ventures by tapping into community ties. Explore how to create meaningful products that evoke strong emotions and resonate with diverse audiences.

Aug 16, 2025 • 4min
Ep. 3150 - Q&A: “Do I need to worry about international taxes on digital products?”
Selling digital products can get tricky when international taxes come into play. This discussion breaks down the complexities of VAT and provides crucial compliance tips for creators. Learn how to navigate tax obligations without feeling overwhelmed. Discover the importance of using sales platforms to simplify tax collection. These insights empower small business owners to sell globally while staying compliant!

Aug 15, 2025 • 5min
Ep. 3149 - Q&A: “Can you still make money flipping domain names?”
Discover the potential of flipping domain names as a viable side hustle in today's market. Explore the origins of this trend and whether it's still profitable for newcomers. Dive into strategies for success, including targeting niche markets and staying aware of current trends. Learn about common pitfalls, such as trademark issues, that can derail budding domain flippers. Get ready to uncover the secrets of making money online in this intriguing conversation!

10 snips
Aug 14, 2025 • 5min
Ep. 3148 - TBT: How I Knew It Was Time to Quit My Side Hustle
A side hustler shares the ups and downs of running a successful online stationery shop. The story dives into the thrill of starting out, and how it eventually led to stress and burnout. The speaker reflects on the hard decision to shut it down, highlighting the importance of reassessing personal goals. It emphasizes that quitting can be a vital step toward new opportunities and explores the emotional process of letting go. Effective time management plays a crucial role in this journey of transition.

Aug 13, 2025 • 8min
Ep. 3147 - STORY: Coffee Lovers Brew Quick Fix Into $1 Million Hustle
Discover the journey of a General Mills employee who transformed his passion for cold brew coffee into a thriving business. While training for a grueling obstacle course and juggling a full-time job, he and his partner launched Busy Coffee. This fascinating story delves into their challenges in sourcing and marketing, leading to over a million dollars in sales. They share valuable insights on risk management, timing, and the motivation to inspire aspiring entrepreneurs looking to turn their hobbies into profitable ventures.

Aug 12, 2025 • 5min
Ep. 3146 - Q&A: “Can you buy or sell Instacart accounts as a side hustle?”
Curious about buying and selling Instacart accounts? Dive into the controversial gray market as the hosts explore potential profits and the serious risks involved, like account bans. Discover the journey of a former Instacart shopper who navigates this hustling world. The discussion doesn't just highlight this risky venture; it also teases safer side hustle alternatives for those looking to earn extra cash. Tune in for insights that could steer your side hustle path in an unexpected direction!


