
Side Hustle School
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/
Latest episodes

Feb 14, 2025 • 5min
Ep. 2967 - Q&A: “Is Valentine’s Day worth targeting if my product isn’t romantic?”
Discover how to creatively market your non-romantic products during Valentine's Day. Learn innovative strategies for holiday promotions that resonate authentically with customers. The conversation includes clever ways to theme your offerings, personalize marketing messages, and even utilize humor. It's all about finding unique connections and maintaining a positive outlook while engaging your audience.

Feb 13, 2025 • 6min
Ep. 2966 - TBT: How SEO Support Became a Reliable Monthly Payday
A freelance SEO auditor transformed their one-time reports into a successful monthly subscription service. This shift emphasizes adaptability and ongoing client engagement as key to building a sustainable business. The discussion also highlights the importance of celebrating SEO advancements with clients and explores the complexities of subscription models, balancing the benefits and potential pitfalls that come with them.

Feb 12, 2025 • 7min
Ep. 2965 - STORY: Coffee Lover Bets Beans On Workplace Coffee Subscriptions
An HR professional channels his coffee obsession into a thriving side hustle with workplace subscriptions. Discover his inspiring journey from corporate life to entrepreneurial success. The podcast highlights the booming coffee shop market, emphasizing the importance of recognizing unmet needs. It blends motivational stories with practical advice, proving that passion and problem-solving can lead to lucrative side ventures.

Feb 11, 2025 • 4min
Ep. 2964 - Q&A: “How can I build trust in a tax service for digital nomads?”
Discover how accountants can build trust with digital nomads while navigating the complexities of international tax services. Learn practical strategies for establishing credibility and leveraging community networks. The discussion also highlights the importance of showcasing expertise through educational content, enabling growth with confidence in a rapidly evolving market.

Feb 10, 2025 • 6min
Ep. 2963 - First $1,000: London Underground Photo Safaris
A London photographer combined sightseeing with photography lessons, creating unique urban photo safaris for tourists. Their innovative approach led to consistent bookings and rapid business growth. The discussion also touches on the balance between artistic integrity and social media pressure, using humor to highlight the importance of adapting strategies to meet market demands. It's an inspiring tale of turning passion into profit!

7 snips
Feb 9, 2025 • 7min
Ep. 2962 - Weekend Workshop: Become a Side Hustle Detective
Dive into the detective work of launching a side hustle! Discover the importance of researching existing businesses and market trends before diving in. Learn how to analyze competitors and identify gaps in your target market. This approach not only refines your strategy but also positions you for greater success in your entrepreneurial journey. Plus, enjoy free lessons and real-life case studies to inspire your side hustle dreams!

Feb 8, 2025 • 5min
Ep. 2961 - Q&A: “What’s the best way to pre-sell a product I haven’t made yet?”
Can you sell something that doesn’t exist yet? Discover how to navigate pre-sales effectively and test market demand before launching your product. Learn the importance of transparency and building customer trust. Dive into strategies like offering incentives for early supporters and choosing the right platforms. Get tips on managing expectations and refund policies to minimize risks. It's all about turning ideas into reality while connecting with potential customers!

Feb 7, 2025 • 6min
Ep. 2960 - Q&A: “How to price your services without undervaluing your expertise?”
A fitness trainer faces the challenge of pricing postpartum workout plans without undervaluing her expertise. Strategies for offering a range of options for different budgets are explored. The discussion emphasizes balancing affordability for clients with the need for sustainable income. Market research and tiered pricing models are highlighted as key factors in crafting effective pricing strategies. Insights into building a successful service-based business are shared, making this a valuable listen for aspiring entrepreneurs.

Feb 6, 2025 • 6min
Ep. 2959 - TBT: Personalized Travel Itineraries for Digital Nomads
Learn how a travel enthusiast turned a love for adventure into a successful business by crafting personalized itineraries for digital nomads in Lisbon. Discover the journey involved in offering free samples that blossomed into a thriving service across Europe. The stories highlight essential co-working spaces and cultural gems for remote workers. Explore the thoughtful approach to strategic upsells and the temporary yet significant nature of side hustles, especially from the perspective of an expat.

Feb 5, 2025 • 7min
Ep. 2958 - STORY: Florida Man Leads Scooter Tours After Watching Macklemore Video
A corporate refugee turns a passion for adventure into a profitable side hustle by leading scooter tours along sunny Florida beaches. Inspired by a Macklemore video, he creatively pivots from corporate life to entrepreneurship. Through innovative partnerships, he crafts engaging local experiences that resonate with growing tourist crowds. His journey showcases how adaptability, creativity, and determination can pave the way for a successful venture in the experience economy.