
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

Mar 31, 2025 • 5min
Ep. 3012 - First $1,000: Stay-at-Home Dad’s Virtual Garage Sale Venture
A stay-at-home dad transforms clutter into cash by launching a virtual garage sale, turning forgotten items into a steady income stream. His entrepreneurial journey not only helps him earn his first $1,000 but also supports neighbors in decluttering their homes. With practical tips on buying and selling online, he illustrates how anyone can harness community connections for financial gain. It's an inspiring tale of creativity and resourcefulness in the side hustle world!

6 snips
Mar 30, 2025 • 9min
Ep. 3011 - Weekend Workshop: Make It Easy to Get Paid
Discover how simplifying payment systems can transform your side hustle. Learn about essential tools like Stripe and Square that make transactions smooth and efficient. Hear strategies aimed at creating a user-friendly payment experience that boosts customer satisfaction. Personal stories and actionable tips ensure you're set up for success while earning extra income. Dive into practical advice that helps you get paid easily, paving the way for your entrepreneurial journey.

Mar 29, 2025 • 6min
Ep. 3010 - Q&A: “How to set better boundaries with clients?”
Explore how to set effective boundaries with clients, especially in emotionally charged situations. Learn the importance of clear communication and empathy in managing client overwhelm. Discover strategies for maintaining a supportive relationship while navigating tough conversations. The discussion even touches on critical issues like early cancer screening and the role of accessible tests to help with prevention. Tune in for practical tips to keep your business thriving without sacrificing your well-being!

Mar 28, 2025 • 6min
Ep. 3009 - Q&A: “How can I work fewer hours without losing income?”
A web developer faces the challenge of working long hours while trying to maintain income. The discussion unveils strategies like raising rates and outsourcing tasks to optimize workload. Delving into the importance of retainer clients and recurring revenue, the conversation offers tips for achieving work-life balance. Listeners are inspired to reshape their service packages for a sustainable business. Each insight promises to empower freelancers in their quest to work smarter, not harder!

Mar 27, 2025 • 6min
Ep. 3008 - TBT: Pet Furniture Maker Adds Digital Blueprints for DIYers
Discover how a woodworker transformed their pet furniture business by shifting from physical products to digital blueprints. By embracing DIY plans and online classes, they not only reached a broader audience but also streamlined their operations. Community engagement played a key role, highlighting customer success stories and fostering a sense of connection. This blend of craftsmanship and technology showcases innovative solutions for stylish pet products, empowering DIY enthusiasts along the way.

Mar 26, 2025 • 7min
Ep. 3007 - STORY: Florida Woman Gets Paid to Remove Poisonous Frogs
A high school science teacher in Florida earns an extra $3,000 a month by removing invasive poisonous toads. Her side hustle, aptly named Toadbusters, highlights creativity and adaptability in tackling a unique challenge. The podcast also reflects on other unconventional animal-related side hustles, blending nostalgia with practical advice. Listeners can expect insights into innovative marketing strategies and wildlife conservation efforts as she turns a toad problem into a profitable opportunity.

Mar 25, 2025 • 4min
Ep. 3006 - Q&A: “How do I set the right hourly rate for my side hustle?”
Learn how to set a fair hourly rate for your side hustle, especially if you're a social media manager. Discover tips for balancing your skills with market demands to confidently price your services. Explore how freelancers can analyze their costs and income goals while considering project complexity. Regularly reviewing your rates based on experience can enhance your earnings and sustainability in your side hustle.

Mar 24, 2025 • 6min
Ep. 3005 - First $1,000: This “Crypto Tax Whisperer” Takes On the IRS
Explore the fascinating journey of an accountant who evolved from traditional practices to becoming a go-to expert in cryptocurrency tax management. Discover how she transformed chaos into a thriving business with custom software and training programs. Navigate the complexities of IRS regulations surrounding crypto taxes and learn essential strategies to avoid costly mistakes. This engaging tale shows how adaptability can lead to both personal growth and financial success.

4 snips
Mar 23, 2025 • 7min
Ep. 3004 - Weekend Workshop: Create a Side Hustle Shopping List
Discover the essentials for launching a successful side hustle in 2025! Learn how to create a side hustle shopping list that prioritizes simplicity and efficiency. Explore key tools and resources while budgeting effectively. Get practical tips on aligning your passions with entrepreneurial goals. Tune in for a free guided lesson that transforms ideas into action!

Mar 22, 2025 • 5min
Ep. 3003 - Q&A: “How can I get clients to provide more accurate information?”
Discover how service-based businesses can enhance client communication to prevent costly mistakes. Explore the struggles of a custom clothing designer dealing with remote clients. Learn effective strategies like visual guides and standardized forms to ensure accurate measurements. Dive into proactive techniques for clearer interactions that will lead to better outcomes and satisfied clients. This insightful discussion is packed with practical tips to refine your service approach and protect your business!
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