

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

5 snips
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.

Jul 30, 2025 • 7min
Ep. 3133 - STORY: Metal Detectorist Gets Paid for Finding Lost Jewelry
A data developer and his kids transform their treasure-hunting hobby into a thriving side hustle. They dive into the world of metal detecting, unearthing lost jewelry worth over $100,000. Experience the thrill of discovery as they reunite cherished pieces with their owners. It’s an inspiring tale of family bonding and entrepreneurial spirit, proving that a passion project can lead to unexpected rewards.

Jul 29, 2025 • 4min
Ep. 3132 - Q&A: “How can I be persistent … without being pushy?”
A caller seeks guidance on how to be persistent in sales without crossing into pushy territory. The discussion navigates the delicate balance between persistence and aggression with effective communication strategies. Personal anecdotes illustrate the art of follow-up, emphasizing respect for potential clients while staying proactive. Techniques include proper contact limits and utilizing tools to maintain relationships without overwhelming prospects. It's a treasure trove of insights for anyone looking to excel in sales without sacrificing integrity!

17 snips
Jul 28, 2025 • 5min
Ep. 3131 - First $1,000: Sleep-Deprived Dad Creates Digital Baby Journal
A sleep-deprived dad harnesses the chaos of parenthood by creating a digital baby journal. Using Notion and sharing his creation with parenting groups, he transforms messy notes into an organized and profitable tool. In just a few months, he rakes in over $3,000 in sales without any ads or tech expertise. This story showcases the power of creativity and community in launching a side hustle while navigating the joys and challenges of new parenthood.

4 snips
Jul 27, 2025 • 7min
Ep. 3130 - Weekend Workshop: The Wordpress Revolution
This podcast dives into transitioning from a service provider to an educator, showcasing a journey from web design to creating a profitable online course on WordPress. It emphasizes the importance of understanding client needs and provides actionable steps for listeners. The episode also covers how to convert personal expertise into a teachable system, including testing course demand and shifting focus from service-based work to educational offerings. It's a practical guide for aspiring side hustlers.

Jul 26, 2025 • 6min
Ep. 3129 - Q&A: “Would people pay to disappear from the internet?”
Could a business help people vanish from the internet? This intriguing question opens up a discussion on the evolving market for digital privacy services. The podcast dives into the challenges of maintaining trust while offering solutions for online disappearance. It contrasts the desire for reduced visibility with the common trend of showcasing online profiles. Additionally, it highlights strategies for digital footprint cleanup, tapping into growing concerns over online privacy and the need for a trustworthy service.


