

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 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.

Sep 2, 2025 • 6min
Ep. 3167 - Q&A: “How to handle customer service without burning out?”
Struggling with customer emails? Learn how to automate 60% of your support while keeping your customers satisfied. Discover practical tools like FAQs and canned responses to streamline inquiries. Plus, find out how to set boundaries that help you avoid burnout and reclaim your weekends. These strategies are tailored for solo founders looking to manage customer service efficiently.

Sep 1, 2025 • 6min
Ep. 3166 - First $1,000: Language Nerd Builds “Fake Language” Creation Kit
A linguistics grad transforms a passion for invented languages into a thriving side hustle. They create a digital toolkit for writers and gamers, generating $1,000 in just five weeks. The journey emphasizes the power of turning curiosity into profit through effective marketing and community engagement. Discover the creative process behind crafting a Conlang Creation Kit and learn how personal passions can lead to unexpected financial success.

6 snips
Aug 31, 2025 • 8min
Ep. 3165 - Weekend Workshop: How Makeup Videos Built a Million-Dollar Brand
Dive into the compelling world of transforming passion into profit through makeup tutorials! Discover how one creator turned her videos into a million-dollar cosmetics brand. Learn about the importance of authenticity and building a genuine connection with your audience. Get inspired by practical strategies and real-life examples, perfect for anyone looking to launch their own side hustle. Plus, uncover key insights that could spark your entrepreneurial journey in 2025!

Aug 30, 2025 • 5min
Ep. 3164 - Q&A: “Is there a market for fancy cookware rentals?”
Could renting out luxury kitchen gear be a profitable sideline? The discussion delves into the potential market for high-end cookware rentals, highlighting the importance of assessing local demand. Listeners learn about the logistical challenges that come with this venture, including risks of damages and liability. It's a thought-provoking exploration of turning a passion for cooking into a money-making opportunity!


