

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

Oct 30, 2025 • 6min
Ep. 3225 - TBT: A Guided Journal, a Friend in Need, and 1,000+ Sales
 Discover how a creative project for a friend in recovery transformed into a thriving business. A 30-day guided journal was crafted to offer personal support, leading to a successful Etsy launch. Growth exploded thanks to influencer collaborations and savvy online marketing. Morgan shares details of a unique partnership with a DC nonprofit, fulfilling large bulk orders. A glimpse into the financial success reveals impressive profits without ad spend, all while balancing a full-time job. It's a story of helping others while thriving! 

Oct 29, 2025 • 8min
Ep. 3224 - STORY: Line Chef Makes Millions Cooking Up Apron Empire
 A chef transforms the humble apron into a multi-million-dollar empire while juggling restaurant shifts at night. Starting from her kitchen failures, she learns to design aprons without any sewing skills. Harsh feedback helps her refine her product, leading to a strong market presence through farmers markets and chef endorsements. Balancing two demanding careers, she grows her brand into a kitchen lifestyle phenomenon, emphasizing functionality and dignity. Her creative journey inspires others to pursue their side hustles! 

Oct 28, 2025 • 5min
Ep. 3223 - Q&A: “When does a logo actually matter?”
 A caller grapples with the dilemma of polishing branding versus finishing a product. The discussion reveals a two-checkpoint rule: prioritize validating the product before investing in visual identity. This approach encourages creativity without letting branding overshadow essential product development. Insights on balancing branding and functionality make the conversation both practical and engaging for aspiring entrepreneurs. 

Oct 27, 2025 • 6min
Ep. 3222 - First $1,000: “CRM Makeovers” for Real Estate Agents
 Discover how a HubSpot expert transforms messy CRMs for real estate agents in just three hours! By merging duplicates and streamlining follow-ups, they charge $500 for a quick and efficient cleanup. The discussion highlights the importance of tight scopes and fast results for successful side hustles. Learn valuable insights on pricing strategies and leveraging testimonials to attract bookings. This story showcases the power of a quick fix in a complex digital world, making it a must-listen for aspiring entrepreneurs! 

Oct 26, 2025 • 7min
Ep. 3221 - Weekend Workshop: The Premium Pricing Paradox
 Explore the intriguing Premium Pricing Paradox and how selling a $100 Alaska coupon book can lead to greater profits. Discover the origin story behind the Alaska Tour Saver and learn why charging premium prices attracted more engaged customers. Uncover effective sales strategies and the psychology behind pricing that builds momentum. Finally, find out how to apply these insights to your own side hustle, ensuring that delivering exceptional value makes higher prices feel like a steal! 

Oct 25, 2025 • 6min
Ep. 3220 - Q&A: “When is business coaching worth the cost?”
 Is business coaching worth the investment? Discover a metric to differentiate between a helpful mentor and a costly luxury. Chris discusses how travel sparked income ideas, like renting out an empty apartment on Airbnb. He tackles the dilemma of spending on a significant coaching fee for modest Etsy shop profits, while providing a checklist for assessing coaching programs. It's a blend of trusting data and intuition to make wise decisions on coaching expenses. 

Oct 24, 2025 • 6min
Ep. 3219 - Q&A: “Can I sell carbon-offset checks to small brands?”
 Explore the growing market for affordable carbon offset verification services as concerns about greenwashing rise. Learn how a simple quick-check audit can be designed for small brands that need reassurance without overwhelming effort. Discover strategies for validating demand and setting competitive pricing tiers while keeping the workload under two hours. This engaging discussion emphasizes the importance of testing ideas and adapting based on feedback, paving the way for sustainable side hustles. 

Oct 23, 2025 • 6min
Ep. 3218 - TBT: I Built a Supplement Guide People Actually Trust
 Discover how one TikTok video ignited a $40,000 affiliate business focused on supplements. Frustrated by misleading information, the creator developed a trusted guide that combines honesty and transparency. Learn about his journey from a simple comparison page to a thriving website, enhanced by a newsletter and savvy SEO tactics. Examine the challenges faced with AI traffic and the importance of maintaining control over an email list. This story highlights the power of evidence-based recommendations in the world of side hustles. 

Oct 22, 2025 • 7min
Ep. 3217 - STORY: Aussie Stretches Out with Online Store for Tall Women
 Tall women finally have a place to shop with a new online store dedicated to their unique sizing needs. Frustrated by the lack of options, one entrepreneur created a clothing line that fits women over 6 feet tall. Using Instagram for both customer feedback and design validation, she effectively shaped her brand, Height of Fashion. The founder scaled her business by outsourcing tasks while learning about every aspect of the supply chain. Each challenge has only strengthened her resolve to expand stylish options for tall women everywhere. 

Oct 21, 2025 • 5min
Ep. 3216 - Q&A: “How do I avoid a garage full of unsold kits?”
 Learn how to avoid ending up with unsold inventory by using a smart 'test-then-preorder' strategy. Instead of risking cash on inventory right away, create short demo videos to gauge interest. Capture leads by linking to a landing page for early-bird pricing, and set a clear threshold to decide if you should move forward. This approach minimizes risk and builds your email list. Discover effective ways to validate your product demand before diving into production! 


