

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

Nov 6, 2025 • 6min
Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital
A fitness enthusiast turned a passion for gym equipment into a thriving media business. Discover how he transformed scavenged gear into quick flips, making impressive profits. Faced with burnout, he pivoted to sharing his expertise through a practical guide for home gym setups. Utilizing social media for marketing, he launched a successful newsletter that generated recurring affiliate income. Hear how his work not only boosted his finances but also helped others build their ideal home gyms.

Nov 5, 2025 • 8min
Ep. 3231 - STORY: The Coffee Grinder That Made $300,000
A petroleum engineer stumbles upon a lucrative side hustle reselling coffee grinders on Amazon. He starts small but quickly scales his venture to over $300,000 in revenue. The journey includes tackling a product disaster with a 90% return spike, which he resolves through stellar customer service. By redesigning the grinder and emphasizing loyalty, he transforms early customers into devoted fans. Ultimately, he leaves his corporate job to expand his brand even further, showcasing the power of research, creativity, and customer care.

Nov 4, 2025 • 5min
Ep. 3230 - Q&A: “How do I test Facebook vs. free traffic?”
Free traffic methods may feel safe, but paid ads could boost your hustle faster—if the numbers align. Discover how to set up a two-week ad experiment on a budget of $200, focusing on clear metrics to measure success. Learn to create different ad variants and assess lead quality through email engagement. Chris emphasizes the importance of knowing when to stop spending on ineffective ads and provides actionable tips to help you navigate the world of traffic generation.

6 snips
Nov 3, 2025 • 7min
Ep. 3229 - First $1,000: Shopify Library Becomes Paid Subscription
A developer found a clever way to address common Shopify theme frustrations by bundling quick fixes into a subscription service. With over 170 store owners signing up, he generated $2,500 monthly in recurring revenue. The launch strategy relied on straightforward marketing tactics and community engagement. Retention strategies, including regular updates and engaging content, kept churn rates low. This innovative approach transformed his freelance work, allowing him to focus on developing high-value snippets instead of repetitive tasks.

Nov 2, 2025 • 7min
Ep. 3228 - Weekend Workshop: When Getting Fired Becomes Your Best Break
Explore how losing a job can spark unexpected opportunities. Hear Michael's journey from layoff to launching a mattress business from an empty car showroom. Discover how innovative marketing strategies, like bicycle delivery, helped him stand out. Learn why embracing change and continuous education can lead to long-term success. Michael's story emphasizes viewing setbacks as stepping stones to freedom and new ventures. Tune in for actionable insights on starting your own side hustle!

Nov 1, 2025 • 5min
Ep. 3227 - Q&A: “Why won’t TikTok followers join my newsletter?”
Navigating the TikTok-to-email conversion challenge is today's hot topic. Discover why followers resist leaving the app and the typical opt-in rates for short-form content. Chris shares smart strategies to boost your newsletter sign-ups, like offering enticing incentives. Even a small email list can pay off over time, turning those who opt-in into warm leads. It’s all about understanding follower behavior and optimizing your approach!

Oct 31, 2025 • 5min
Ep. 3226 - Q&A: “Can I legally profit from salvaging barn wood?”
Explore the ins and outs of turning salvaged barn wood into a profitable side hustle. Understand the critical legalities like permits and liability. Learn practical tips on treating this venture like a demolition business. Discover the importance of securing a written salvage agreement and checking local regulations. Get insights on affordable insurance and running profit calculations before diving in. Plus, find out why selling locally through platforms like Facebook Marketplace is key to success!

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.


