

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

Aug 9, 2025 • 6min
Ep. 3143 - Q&A: “What are the best renewable markets for a side hustle?”
Discover the untapped potential of renewable markets for your side hustle! High school grads, new parents, and brides-to-be are prime customers waiting for your innovative ideas. Learn how to leverage pivotal life changes and seasonal demands to secure a steady flow of business. This insight is perfect for anyone looking to earn extra income creatively while keeping their day job.

Aug 8, 2025 • 6min
Ep. 3142 - Q&A: “What’s the business process for releasing an indie game?”
Thinking of launching your own indie game? Discover the ins and outs of releasing on Steam, from costs to marketing strategies. Solo developers face fierce competition and must find ways to stand out. Learn essential business processes and the importance of community engagement to boost visibility and drive sales. This episode is packed with actionable insights to help you turn your passion project into profit!

Aug 7, 2025 • 6min
Ep. 3141 - TBT: How My Print-on-Demand Shop Landed a Licensing Deal
Discover the inspiring journey of an independent artist who transformed her print-on-demand shop into a licensing success with a major retailer. Learn about the ups and downs of negotiation and how it impacted her creativity. The discussion emphasizes the thrill of entrepreneurship and the importance of customer trust and shipping solutions. It's a motivating reminder that anyone can turn their passion into a profitable side hustle!

Aug 6, 2025 • 8min
Ep. 3140 - STORY: Couple Goes From Crashed Drone To Soaring Side Hustle
A couple turns a drone crash into a lucrative coaching business, showcasing their innovative spirit. They share how they evolved from a struggling venture to a thriving educational platform by capitalizing on market needs. Their journey highlights resilience and the power of learning from setbacks, proving that inspiration can come from the most unexpected places.

Aug 5, 2025 • 5min
Ep. 3139 - Q&A: “Can I sell my ideas for inventions?”
Ever dreamed of cashing in on your inventive ideas without diving into full-blown business? Discover the ins and outs of licensing concepts as a savvy, low-risk alternative. Learn how execution trumps mere creativity and why creating prototypes and effective sell sheets can make all the difference. The discussion also emphasizes targeting the right companies to pitch your inventions, turning your creativity into a potential income stream.

Aug 4, 2025 • 5min
Ep. 3138 - First $1,000: Dungeon Master Markets Printable Game Maps
Discover how a veteran Dungeon Master monetized his passion for creating custom campaign maps. He transformed his hobby into a profitable venture by offering downloadable game maps to fellow players. Hear about his strategic marketing tactics that helped him earn over $1,000 soon after launching. This inspiring journey exemplifies how combining creativity with entrepreneurship can lead to success.

4 snips
Aug 3, 2025 • 8min
Ep. 3137 - Weekend Workshop: The Art of Professional Networking
Discover how to turn professional networking into a powerful tool for side hustle success. Learn from a construction entrepreneur's story on how to convert connections into income. Explore the journey of a project manager who bridges artists and developers, emphasizing the importance of communication and collaboration. Get practical tips on building relationships that matter and the structured steps to kickstart your side hustle in 2025. This engaging discussion is packed with real-world examples and actionable advice!

6 snips
Aug 2, 2025 • 5min
Ep. 3136 - Q&A: “How can I scale my coaching business?”
Discover innovative strategies to grow a coaching business even when your schedule is packed. Learn how to maintain personal connections while scaling up. Explore the benefits of digital products and group offerings to expand your reach. Adapt your business model and utilize technology to maximize effectiveness. This engaging discussion offers practical insights for aspiring coaches looking to balance growth with client intimacy.

Aug 1, 2025 • 5min
Ep. 3135 - Q&A: “Can you make money from a true crime podcast?”
Thinking of starting a true crime podcast? Discover effective strategies to stand out in a crowded market. Learn how to craft captivating content and attract an audience. Explore innovative monetization approaches to turn your passion into profit. Get valuable insights on building a foundation for long-term success while balancing a full-time job. This episode is packed with practical tips for aspiring podcasters!

Jul 31, 2025 • 6min
Ep. 3134 - TBT: How I Sold Curated Pop Culture Packs from Thrifted Merch
Discover the art of turning thrift store treasures into themed nostalgia bundles that resonate with pop culture fans. Learn how one entrepreneur transformed $10 finds into $60+ profit packs, highlighting the emotional connection these curated items create. Uncover strategies for delivering unique customer experiences while managing a bustling side hustle. This engaging conversation emphasizes the importance of effective marketing and streamlining operations in the world of resale.