
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

Dec 27, 2024 • 7min
#2918 - Failure Friday: The Multi-Platform Freelance Overload
A freelance graphic designer shares her journey of moving from Upwork to Fiverr in search of more clients. While she initially found success, the shift resulted in dealing with lower quality projects and mismatched expectations. The discussion highlights the challenges of balancing multiple platforms and the necessity of prioritizing quality over quantity. Through her experience, valuable lessons about resilience and adaptability in freelancing emerge.

Dec 26, 2024 • 6min
#2917 - TBT: Analyst Turns Card Comparison Into Cash
Hear the inspiring story of a financial analyst who turned her expertise in card comparison into a profitable side hustle. She launched a platform that not only provides unbiased information but also engages users effectively. Discover the lucrative world of credit card referral programs, where commissions can range from $100 to $400 for successful referrals. This journey explores personal growth, education, and innovative income generation strategies in the competitive financial market.

Dec 25, 2024 • 5min
#2916 - Q&A: “What are the top 3 things I should do next?”
A listener grapples with the best next steps for their flourishing side hustle. The discussion emphasizes narrowing down to three key actions to maintain momentum. Practical advice is shared on how to streamline business growth, highlighting the importance of refining successful practices and creating efficient systems. Feedback from early customers is also crucial for continuous improvement. Packed with guidance, the conversation is perfect for anyone looking to boost their entrepreneurial efforts!

Dec 24, 2024 • 5min
#2915 - Q&A: “Best tools for managing a shared business inbox?”
Discover the best tools for co-managing a business email account among team members. Learn about options like HelpScout and HubSpot, which prioritize organization and communication. The discussion emphasizes how effective teamwork can enhance customer interactions. There’s also a focus on aligning strategies with business goals as the year wraps up, ensuring your team remains proactive in managing customer communications.

Dec 23, 2024 • 6min
#2914 - First $1,000: Data Analyst Codes Fantasy Sports Teams
Discover the journey of a data analyst who merges his love for sports with his knack for numbers to create winning fantasy sports algorithms. He shares his strategies for improving player lineups and how he turned that passion into a side hustle. By balancing his full-time job, he managed to earn over $3,500 in his first season. The discussion also emphasizes the significance of responsible betting and community engagement in building a successful business.

Dec 22, 2024 • 5min
#2913 - Q&A: “How do I understand ROI when buying a local business?”
Discover the secrets to calculating ROI when buying a local business. Learn how to estimate the payoff period and identify factors that influence profitability. Get tips on tools that simplify the analysis process. Explore practical strategies for making conservative profit projections and enhancing revenue. This insightful Q&A will equip you with the knowledge to make smart investment decisions.

Dec 21, 2024 • 5min
#2912 - Q&A: “I’ve been paying for subscriptions I don’t use!”
A listener grapples with the challenge of paying for multiple unused subscriptions. The discussion revolves around the importance of regular expense audits to identify unnecessary costs. Practical strategies for canceling services are shared, along with personal anecdotes. The conversation emphasizes how effective management of subscriptions can lead to significant savings, helping listeners regain control over their finances.

5 snips
Dec 20, 2024 • 7min
#2911 - Failure Friday: When My Side Hustle Took Over My Life
A tech professional shares the intense journey of turning a side hustle into a booming service, which soon spirals out of control. As stress mounts, balancing a full-time job and personal life becomes increasingly difficult. The discussion emphasizes essential lessons on setting boundaries and managing time to avoid burnout. Listeners are reminded of the common emotional challenges many face, especially during busy seasons, while inspiring a focus on renewal and resilience for the new year.

Dec 19, 2024 • 6min
#2910 - TBT: Graphic Artist Taps Into Planner Craze
Discover how a graphic artist transformed her love for bullet journaling into a flourishing Etsy venture while juggling a full-time job. The journey showcases her adaptability and creativity in navigating the side hustle terrain. Plus, learn about the benefits of AI design tools for quick website creation, perfect for bloggers and influencers. Tune in for inspiring stories, challenges, and insights that highlight the entrepreneurial spirit and the potential of turning passion projects into income streams.

Dec 18, 2024 • 4min
#2909 - Q&A: “How can I increase the average price per order for my online store?”
Explore innovative strategies to elevate the average order value in online retail! Discover the art of upselling and cross-selling with customer-friendly techniques. Learn about effective bundling discounts and enticing free shipping thresholds to encourage larger purchases. With practical examples and e-commerce tools, you can enhance your store's profitability while ensuring a delightful shopping experience for your customers!