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
Aug 29, 2025 • 6min
Ep. 3163 - Q&A: “Can MacBook arbitrage work as a side hustle?”
Can you profit from buying and selling Apple computers across borders? This discussion dives into the world of international tech arbitrage, unpacking both its allure and its practical hurdles. While opportunities exist, the challenges often prompt a rethink towards local strategies for reselling electronics. With real-life insights and expert advice, listeners learn about the complexities of turning a tech hobby into a lucrative side hustle.
Aug 28, 2025 • 5min
Ep. 3162 - TBT: Failed App Becomes Successful Consulting Business
Discover how a failed productivity app birthed a thriving consulting business. The host shares the transformative journey of turning setbacks into success, emphasizing resilience and personal growth. Learn the vital lessons of transparency and networking that helped overcome entrepreneurial hurdles. This engaging discussion showcases the power of pivoting and finding new paths, making it an inspiring listen for anyone tackling their own side hustle journey.
Aug 27, 2025 • 7min
Ep. 3161 - STORY: Curated Gift Boxes for Breakups and Baby Bumps
Two sisters unite their strengths to launch a unique business that creates curated gift boxes for milestone events like breakups and baby bumps. Their story highlights the emotional connection behind personalized gifts and the inspiration that comes from life’s challenges. With creativity and resilience, they navigate the competitive gifting market, making a mark that resonates with customers. Tune in to hear how they turned a moment of loss into a thriving venture!
Aug 26, 2025 • 5min
Ep. 3160 - Q&A: “Can Lyft drivers really make $2,000/week?”
Can Lyft drivers really pull in $2,000 a week? Dive into the intriguing world of rideshare earnings as the podcast breaks down what’s possible versus the reality of the gig economy. Discover how some drivers achieve high earnings with hard work and multiple gigs, but also learn that the average payout often falls short. Real stories and expert analysis shine a light on the true earning potential while offering valuable insights for those considering rideshare driving as a side hustle.
Aug 25, 2025 • 2min
BONUS: "Time Anxiety" Book and Free Quiz
The discussion dives into the concept of Time Anxiety and how it affects our daily lives. The speaker shares insights from their new book on managing time-related pressures. Listeners are encouraged to take a free quiz to assess their own experiences with time anxiety. There's a focus on how typical productivity tips can sometimes increase stress rather than alleviate it, inviting a fresh perspective on time management strategies.
Aug 25, 2025 • 6min
Ep. 3159 - First $1,000: YouTube Bonsai Channel Grows Into Online Store
Discover how a YouTube creator transformed a passion for bonsai into a booming online store. By selling tools and kits to their loyal audience, they achieved their first $1,000 and turned a niche hobby into a viable income. Tune in to hear inspiring tales of creative ventures thriving alongside traditional jobs, showcasing the impressive potential of a side hustle!
6 snips
Aug 24, 2025 • 7min
Ep. 3158 - Weekend Workshop: Template Biz Goes from Service to Scale
Discover how a college student transforms a simple résumé design service into a thriving template business. Learn key steps for launching a side hustle in 2025, including automation and smart marketing strategies. This journey not only showcases entrepreneurial creativity but also offers insights into generating passive income while juggling education and business. Get ready for practical tips and inspiring stories to kickstart your own side hustle!
6 snips
Aug 23, 2025 • 4min
Ep. 3157 - Q&A: “How can I make money from old YouTube videos?”
Learn how to breathe new life into your old YouTube videos and make money from them! Discover actionable strategies for revitalizing content to attract fresh audiences. Explore creative ways to repackage videos for platforms like TikTok and Instagram, turning past work into valuable assets. This insightful discussion emphasizes how you can unlock hidden income potential from content you already have!
Aug 22, 2025 • 5min
Ep. 3156 - Q&A: “Can you profit by reselling loyalty points or rewards?”
Can you profit from reselling loyalty points? This podcast dives into the intriguing world of flipping rewards and points for cash. It discusses the profitability and challenges involved, emphasizing the importance of research. Listeners learn about methods like credit card sign-ups and mileage brokerage, balancing the fun with potential risks. Insights from online communities like Reddit are also mentioned, encouraging an adventurous exploration in the side hustle realm.
Aug 21, 2025 • 6min
Ep. 3155 - TBT: From Abandoned Storage Finds to Museum Artifacts
Discover the journey of a side hustler who transitioned from flipping storage unit finds to providing rare historical artifacts for museums. This transformation emphasizes the importance of knowledge and meaningful sales, moving beyond volume. The episode highlights the preservation of history through entrepreneurship and the significance of finding the right talent for this unique mission, introducing tools like ZipRecruiter to streamline hiring.
