

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

Sep 12, 2025 • 4min
Ep. 3177 - Q&A: “How can I make money by renting out houseplants?”
Can houseplants become a source of income? Discover the innovative concept of renting out indoor plants for styling and events. One hobbyist shares their journey of turning a rare plant collection into a profitable venture. Learn about market demand, pricing strategies, and how to manage plant rentals. This burgeoning trend highlights a unique way to turn a passion for greenery into a thriving side business.

Sep 11, 2025 • 6min
Ep. 3176 - TBT: Helping High School Dropouts Start Plumbing Careers
Discover how a unique program is helping high school dropouts kickstart rewarding careers in plumbing by providing essential skills and paid apprenticeships. Learn about the innovative business model bridging the skills gap between eager students and employers. Delve into the traits that make side hustlers successful, focusing on the importance of curiosity and proactive choices. Also, find out how platforms like ShipStation can streamline operations for small business owners. This engaging discussion offers both inspiration and practical insights!

Sep 10, 2025 • 7min
Ep. 3175 - STORY: Movie Industry Friends Rewrite the Credits, Earn $20,000/Month
In a fascinating twist, two friends modify the tedious process of movie credits, leading to a successful side hustle. Their innovative software, InCrawl, changes the game for film producers. It streamlines credit sequences and boosts efficiency. This venture generates an impressive $20,000 each month, showcasing how creativity can transform mundane tasks into lucrative opportunities.

Sep 9, 2025 • 5min
Ep. 3174 - Q&A: “How can a first-time author stand out in a market of 4,500 books per day?”
Navigating the book market is a challenge for first-time authors, with thousands of titles released daily. Effective marketing is crucial for standing out amid the competition. The discussion emphasizes the importance of engaging with audiences and building a strong platform. Concrete strategies are provided to help authors gain visibility and achieve success in a crowded landscape.

Sep 8, 2025 • 6min
Ep. 3173 - First $1,000: Houston Homeowner Turns Studio Into Weekend Venue
A Houston homeowner turned a backyard shed into a thriving rental studio for events and photos. The journey showcases a creative transformation with practical tips for maximizing space and enhancing aesthetics. Listeners discover effective marketing strategies and the importance of a seamless booking process. This tale encourages others to explore their entrepreneurial sparks and develop side hustles from underutilized spaces.

7 snips
Sep 7, 2025 • 7min
Ep. 3172 - Weekend Workshop: The Seasonal Business Goldmine
Discover how a marketing pro turned a seasonal custom candy hearts business into a six-figure success. Learn strategic insights for spotting market gaps and optimizing sales during peak seasons. The episode covers essential qualities of thriving side hustlers and the importance of efficient partnerships. Hear the empowering journey of entrepreneurs seizing seasonal business opportunities, with nuggets of wisdom on niche marketing and product development. Perfect inspiration for anyone looking to launch their own side hustle!

Sep 6, 2025 • 5min
Ep. 3171 - Q&A: “Managing cash flow across PayPal, Stripe, Venmo, and Etsy…”
Navigating multiple payment platforms can feel chaotic, but there's a streamlined approach to manage cash flow effectively. Discover a four-step system that makes bookkeeping less of a hassle and tax time smoother. Learn practical tips for leveraging automation in financial tracking. Entrepreneurs are also encouraged to embrace traits like curiosity and persistence, essential for overcoming challenges in managing their finances. Tune in for valuable insights to keep your side hustle thriving!

Sep 5, 2025 • 6min
Ep. 3170 - Q&A: “Do followers still matter in the age of algorithms?”
In this discussion, the focus is on the evolving landscape of social media where algorithms dictate content visibility. The episode delves into the fading significance of follower counts, emphasizing the value of a loyal and engaged subscriber base. It's a reminder that quality interactions can still give creators a competitive edge, even amidst algorithmic challenges. Insights into maximizing reach and conversion in this new environment provide practical takeaways for aspiring side hustlers.

Sep 4, 2025 • 5min
Ep. 3169 - TBT: Selling Ads for Medical Conferences on Commission
Discover the intriguing story of a freelance marketer who carved out a side hustle selling ad placements for medical conferences purely on commission. Learn how networking and persistence played crucial roles in his journey to success. Explore the value of maintaining relationships in side hustles and how technology enhances productivity. This episode reveals how you can earn extra income without owning a product, highlighting insightful strategies for leveraging connections effectively.

Sep 3, 2025 • 7min
Ep. 3168 - STORY: IT Guy Earns Extra $50,000/Year Restoring Vintage Radios
An IT professional taps into his engineering background to revive vintage 1950s radios, creating a profitable side hustle. By dedicating just a few hours each week, he discovers a lucrative niche that could net him an extra $50,000 annually. This journey highlights the idea that with the right passion and skills, turning personal interests into a thriving business is not only feasible but also rewarding.


