

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

Jul 25, 2025 • 4min
Ep. 3128 - Q&A: “Both of my ideas are strong, but I can only do one…”
Stuck choosing between two great side hustle ideas? This discussion dives into effective decision-making strategies to prioritize your passions. One caller weighs the pros and cons of a food product versus a digital resource, aligning with long-term goals. Listeners will discover how side hustle paths can shift and evolve over time, offering insights into navigating these creative dilemmas. Tune in for helpful tips that turn uncertainty into opportunity!

16 snips
Jul 24, 2025 • 6min
Ep. 3127 - TBT: How Selling $2 Digital Products Earned $185,000
Discover the journey of a savvy entrepreneur who transformed a simple Etsy shop into a $185,000 success by selling $2 digital products. Learn how they nailed SEO strategies and adopted minimalist design to maximize profit without handling inventory. The discussion emphasizes the power of low-cost digital sales, highlighting the importance of consistency and creativity in crafting appealing offers. Join in to uncover the secrets behind turning small ideas into substantial earnings through smart sales tactics!

Jul 23, 2025 • 7min
Ep. 3126 - STORY: Nerdy Kickstarter Campaign Raises $1 Million
An Ohio man turns his passion for board games into a wildly successful Kickstarter campaign, raising over $1 million. His inspiring journey showcases how creativity and nostalgia can fuel innovative game designs. Listeners also get strategic tips on launching their own Kickstarter projects, emphasizing the importance of timing and marketing. This tale blends personal stories with practical advice, encouraging others to pursue their creative ideas.

Jul 22, 2025 • 5min
Ep. 3125 - Q&A: “How do I license my educational materials to a publisher?”
A listener seeks advice on licensing her educational materials to publishers for wider distribution. The discussion dives into strategies for presenting her content attractively and meeting publisher expectations. They also explore the perks of earning passive income through licensing and effective methods for managing order fulfillment. Insights into developing partnerships are shared, ensuring her valuable resources reach more educators.

Jul 21, 2025 • 6min
Ep. 3124 - First $1,000: Musician Creates Loop Packs for Video Editors
A freelance musician transforms his abandoned audio sketches into a successful product for video editors. With just twelve clean loops, he taps into the demand for royalty-free music and makes his first $1,000 in under a month. This fascinating journey highlights the power of creativity and recognizing market gaps, all with minimal marketing efforts. It's a perfect example of turning passion into profit!

Jul 20, 2025 • 8min
Ep. 3123 - Weekend Workshop: The Most Awesome Guitar Lessons in the Universe
Discover how a music teacher dramatically raised his rates from $50 to $120 per hour by transforming his positioning. He reframed his guitar lessons as unique experiences that prioritize emotional outcomes. By employing creative marketing strategies, he attracted committed students, leading to increased income and personal satisfaction. Join in for free guidance on starting your own side hustle in 2025 and listen to inspiring case studies of individuals earning extra money without leaving their day jobs.

Jul 19, 2025 • 5min
Ep. 3122 - “Can you sell ‘closure as a service??’”
Can you turn life's endings into a service? This discussion dives into the intriguing concept of graceful exits from jobs, relationships, and other ventures. It highlights the importance of supporting individuals through transitions while addressing the emotional challenges involved. The potential for a business centered on 'closure as a service' raises questions about market demand and effective communication strategies. Listen in for insights on how to navigate these endings and help others find their way forward!

5 snips
Jul 18, 2025 • 6min
Ep. 3121 - Q&A: “I want to build an app with ‘vibe coding…’”
Can you create an app just by describing your idea to AI? Delve into the concept of vibe coding, where natural language prompts help in app and website development. This method makes building applications accessible but comes with challenges in complexity and security. Discover how vibe coding can be a useful tool for side hustlers looking to test ideas and develop simple apps, all while setting realistic expectations for their projects.

Jul 17, 2025 • 6min
Ep. 3120 - TBT: No Snakes, Big Sales, and the Faux-Leather Hustle
Discover how a creative side hustler turned scraps into stylish faux snakeskin wallets using upcycled materials, all while promoting sustainable practices. Their unique story captivated ethically-minded consumers and boosted sales on Etsy. Plus, learn about the importance of targeting niche markets to create a loyal customer base. Tune in for insights on combining speed and quality in hiring as well!

Jul 16, 2025 • 7min
Ep. 3119 - STORY: Ex-Baseball Players Hit Home Run With Baseball Bat Subscriptions
Two former baseball players turned entrepreneurs launch a unique bat rental service that caters to thousands nationwide. They tackle financial hurdles for young athletes, making quality equipment more accessible. The story chronicles their transformation from pilot program to a thriving subscription model, sharing personal insights along the way. Their journey is a testament to the power of innovative thinking and community support in sports.


