
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

5 snips
Jun 12, 2025 • 7min
Ep. 3085 - TBT: Print-on-Demand Store Crushes It Without Ads
Discover how an enterprising individual built a lucrative print-on-demand business by focusing on unique niches like mugs for retired paramedics. Learn the secrets of harnessing organic traffic and effective niche marketing without the need for ads. Delve into the strategies that make it possible to thrive in the print-on-demand landscape, from leveraging SEO to authentic customer engagement. This success story showcases the power of simplicity in launching a business while appealing to specialized audiences.

12 snips
Jun 11, 2025 • 7min
Ep. 3084 - STORY: Kiwi Coder Makes Extra $50,000/Year from Digital Paintbrushes
A talented New Zealand software developer turns her passion for calligraphy into profit by creating digital paintbrushes for Procreate. She shares her inspiring journey of earning an extra $50,000 a year from her artistic side hustle. Strategies like product bundling and engaging with the community play a crucial role in her success, all achieved without any advertising costs. This episode is a testament to how creativity and innovation can flourish alongside a full-time job.

Jun 10, 2025 • 5min
Ep. 3083 - Q&A: “Is a high-ticket offer the right move for my business?”
Can a high-ticket offer elevate your business or scare off clients? The discussion reveals when and how to introduce premium packages without alienating your audience. Strategies for maintaining customer relationships while boosting revenue through high-ticket sales are explored. Tips include catering to diverse clients and focusing on transformative services. Learn the balance between appealing pricing and the value offered, ensuring your business thrives with new options!

Jun 9, 2025 • 6min
Ep. 3082 - First $1,000: Partners Turn Neglected Washers into Solid Profit
Two friends embark on a bold adventure by purchasing a failing laundromat on the verge of closure. Through smart cost management and creative grassroots marketing, they breathe new life into the business. Their journey showcases the power of teamwork and innovative thinking in overcoming challenges. Discover the practical strategies they used to engage customers and turn a neglected space into a thriving source of profit. Join the conversation about transforming setbacks into opportunities!

Jun 8, 2025 • 7min
Ep. 3081 - Weekend Workshop: Grow What Works, Let Go of What Doesn't
Discover how to streamline your business while juggling multiple responsibilities, just like a pro on a book tour! Learn the magic of automation with tools like ShipStation to ease your shipping woes. Dive into strategies for maximizing your side hustle by focusing on what truly works and letting go of what doesn’t. A compelling case study of a photographer highlights the power of retail partnerships and the necessity of regular business audits for lasting success. Tune in for practical tips and inspiration for your entrepreneurial journey!

Jun 7, 2025 • 5min
Ep. 3080 - Q&A: “Should you fight unfair refund requests or just move on?”
Navigating refund requests can be tricky, especially when they don't follow your policy. Discover strategies for balancing business protection with customer satisfaction. Should you stand your ground or let it go? Find out when it’s smarter to move on. These insights are valuable for anyone running an online business and wanting to maintain good relationships while managing difficult situations.

Jun 6, 2025 • 5min
Ep. 3079 - Q&A: “How do I get featured in holiday gift guides?”
Get ready for the holiday rush! Discover how to effectively pitch your products to snag a spot in coveted holiday gift guides. Timing is key, and understanding the media landscape can make all the difference. Learn to craft compelling pitches and highlight your unique selling proposition. Quality photography and strategic follow-ups are essential, as is targeting niche publications. This is your guide to boosting visibility and sales this festive season!

Jun 5, 2025 • 8min
Ep. 3078 - TBT: How ‘Pinspiration’ Became a Full-Time Hustle
Discover how a former lifestyle blogger transformed her passion into a profitable Pinterest affiliate marketing career. Learn about her effective strategies for keyword optimization and direct product linking that skyrocketed her income. The podcast also discusses the advantages of using Pinterest as a primary revenue generator and offers insights on managing business growth while tackling challenges like order fulfillment. Tune in for inspiration on how to turn a side hustle into a full-time success!

4 snips
Jun 4, 2025 • 7min
Ep. 3077 - STORY: Four Friends Create Conversations, Earn $400,000 in 8 Months
Four Dutch friends transformed their deep conversations into a thriving venture, raking in $400,000 in just eight months. They faced various challenges but turned them into valuable lessons while building a meaningful project. Additionally, the podcast highlights another inspiring tale of friends who created a card game, designed to promote genuine connections in our digital world. Discover the power of conversation and connection through these captivating stories!

Jun 3, 2025 • 5min
Ep. 3076 - Q&A: “Should I add a live chat feature to my website?”
Is live chat a game changer or just more hassle for your business? Discover the pros and cons of adding this feature to your website. Explore how it can enhance customer engagement and potentially boost sales. Learn from a real-life case of a specialty coffee equipment store contemplating this addition. The discussion also highlights AI's role in chat systems and offers insights on whether live chat is a necessity for various business models.