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
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.
4 snips
Jun 2, 2025 • 6min
Ep. 3075 - First $1,000: Marketing Pro Builds GPT Bots—No Code Needed
A marketer transitioned from consulting to creating custom GPT chatbots without any coding skills. Discover how they identified client needs, effectively engaged customers, and priced their services. Learn valuable insights about scaling a business in the tech space while keeping it simple. This story showcases the potential of side hustles, proving anyone can turn an idea into income with the right approach.
Jun 1, 2025 • 8min
Ep. 3074 - Weekend Workshop: Measure What Matters
Discover how to effectively measure what matters in your side hustle! Learn the importance of tracking key metrics for smarter business decisions. A practical example of a resume design business illustrates what numbers to focus on to adapt your strategy. Get ready to transform your side hustle in 2025 with actionable insights and free lessons that will guide you every step of the way!
May 31, 2025 • 6min
Ep. 3073 - Q&A: “What’s the purpose of more than one business bank account?”
Explore the benefits of having multiple business bank accounts in this discussion. Discover how separating personal and business finances can streamline cash flow and improve financial stability. Two key financial models are introduced to enhance your financial discipline. Managing your money better could mean paying yourself more effectively and setting a strong foundation for future growth!
May 30, 2025 • 5min
Ep. 3072 - Q&A: “Why do struggling businesses keep their doors open?”
How do some failing retail stores manage to keep their doors open? Discover the surprising factors that contribute to their longevity, including external funding and tax benefits. Explore the complexities of unprofitable businesses that persist due to loss leadership or personal passion. This discussion sheds light on the resilience required to navigate challenging environments while maintaining a business, revealing the intricate reasons behind keeping ventures alive despite financial struggles.
4 snips
May 29, 2025 • 6min
Ep. 3071 - TBT: From DIY Pet Tributes to Six-Figure Etsy Shop
A maker transformed grief into profit by turning a small Etsy shop for custom pet memorials into a six-figure success story. They expanded their product line to help grieving pet owners celebrate their companions. The journey highlights the importance of emotional connections with customers and efficient order fulfillment. Discover how strategic improvements and tools, like ShipStation, boosted their e-commerce management for enhanced satisfaction.
May 28, 2025 • 7min
Ep. 3070 - STORY: High School Student Earns $20,000 Making Wooden Bow Ties
A high school student transforms an unimpressive gift into a thriving business by crafting wooden bow ties. He capitalizes on his woodworking hobby, showcasing how passion can lead to profitability. Through challenges and successes, he learns about the importance of quality and standing out in the market. Remarkably, he earns $20,000 in just a year, proving that young entrepreneurs can make big waves with creativity and determination.
4 snips
May 27, 2025 • 6min
Ep. 3069 - Q&A: “I’m ready to sell my side hustle—how do I do it?”
Wondering how to sell your side hustle and not get shortchanged? Learn valuable tips on business valuation, finding the right buyer, and ensuring a smooth transition. The discussion includes real-life inquiries and expert strategies for a successful sale. Whether you're ready to cash in or just curious about the process, this insightful breakdown offers fresh perspectives and actionable advice.
