

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 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.

Jul 15, 2025 • 5min
Ep. 3118 - Q&A: “How can I launch a no-recipe cooking channel?”
Can a no-recipe cooking channel be a money-maker? The hosts dive into the art of kitchen improvisation, discussing its potential as a unique niche in the food industry. A listener from Tallahassee shares her aspirations, prompting a conversation about developing an engaging brand and connecting with audiences through intuitive cooking. Tips for aspiring creators on assessing their ideas for market success are also highlighted, sparking inspiration for those looking to blend creativity with culinary skills.

Jul 14, 2025 • 5min
Ep. 3117 - First $1,000: From Power Rangers to Profits in Two Weeks
Discover how a toy collector transformed a passion for vintage figures into a profitable side hustle. By leveraging estate sales and eBay, he created a low-stress resale system. Focusing on collectibles like Power Rangers and Star Wars, he shares practical tips for managing inventory and maximizing profits. Tune in for inspiration on earning extra income without quitting your day job!

Jul 13, 2025 • 8min
Ep. 3116 - Weekend Workshop: The $3,000/Month Cruise Ship Review Site
Learn how a wedding gift sparked a thriving side business focused on cruise travel. Discover the importance of niche markets as a couple transforms their experience into a valuable resource for first-time cruisers. This entertaining session dives into key steps and concepts for building side hustles in 2025, emphasizing the potential of turning personal experiences into profit. A valuable guide for anyone looking to earn extra income without leaving their job!

Jul 12, 2025 • 5min
Ep. 3115 - Q&A: “How much inventory should I keep on hand?”
Discover the art of inventory management in small businesses, especially when resources are tight. Learn how to strike the perfect balance between having too much and not enough stock. The discussion includes practical strategies for sales forecasting and managing limited product runs, particularly for perishable items. Entrepreneurs will pick up tips to navigate these crucial challenges while fostering growth and efficiency.

Jul 11, 2025 • 5min
Ep. 3114 - Q&A: “Is it okay to use a fake name for my business?”
Using a fake name in business can spark debates about ethics and privacy. This discussion looks into the pros and cons of staying anonymous while running a side hustle. It highlights the balance between creative marketing and ethical practices. Listeners gain insights into potential risks and legal considerations, ensuring a safe approach to entrepreneurship. Plus, it poses the question of whether privacy is a smart move or if it veers into shady territory.