

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

Jan 3, 2026 • 6min
Ep. 3290 - Q&A: “What if you don't want to use social media?”
Ted, a creative from Charlotte, North Carolina, specializes in crafting motion videos and backgrounds for churches but has a strong aversion to social media. He raises the question of how to successfully market his business without it. The discussion pivots around matching marketing tactics to the target audience rather than forcing a social media approach. Chris suggests exploring traditional networking and direct outreach to engage church decision-makers, emphasizing that serving customers should remain the top priority.

11 snips
Jan 2, 2026 • 7min
Ep. 3289 - STORY: Rent the Chicken! An Egg-Cellent Idea Clucks Into Cash
A Pennsylvania couple has created a unique side hustle by renting out 2,000 chickens to urban homesteaders. This innovative idea allows city dwellers to try out chicken keeping without long-term commitment. The rental package includes everything from hens to delivery and costs around $350. With a $2,000 startup and franchising to expand nationally, they've turned a simple concept into a thriving business. Plus, customers enjoy fresh eggs and the fun of chicken care!

Jan 1, 2026 • 8min
Ep. 3288 - Side Hustle School Season 10 Starts TODAY
The new season kicks off with exciting updates and a fresh daily format! Listeners can expect a wealth of case studies showcasing real people earning extra money without leaving their jobs. There’s a focus on detailed analyses, including costs and outcomes. Recurring segments, like Failure Friday and listener Q&A, promise to keep things engaging. Plus, Chris introduces a Neurodiversion event in Austin for the neurodivergent community. It's all about empowering side hustlers with valuable insights and support!

Dec 31, 2025 • 9min
Ep. 3287 - STORY: Military-Themed Teddy Bears Help Kids Hibernate
A Marine dad turns bedtime struggles into success with military-themed teddy bears. His creation, a unique sleep system, leads to six-figure sales while bringing comfort to children. From sourcing materials on Alibaba to building a strong brand and navigating military exchanges, the journey is filled with challenges and triumphs. With a commitment to quality and hands-on fulfillment, this entrepreneurial tale showcases creativity and determination, all wrapped up in a cuddly package.

Dec 30, 2025 • 5min
Ep. 3286 - Q&A: “After nine years of daily episodes, what’s next?”
A longtime listener sparks a conversation about the future direction of the show. Exciting plans include revisiting archives and spotlighting past stories. Chris announces an engaging new event focused on neurodiversity in the workplace. There’s a commitment to continue daily episodes as the show enters its tenth year. Listeners are invited to participate with their questions and side hustles. Plus, upcoming resources on time anxiety promise to support those juggling multiple commitments. Stay tuned for a year filled with fresh insights!

Dec 29, 2025 • 5min
Ep. 3285 - First $1,000: A Discord Server That Pays the Rent
Discover the power of focused online communities as creators share feedback away from noisy public forums. Learn how Leonard built a thriving Discord server for sound design, emphasizing collaboration and a supportive atmosphere. His innovative monetization strategies, including a Patreon tier, allowed him to generate nearly $1,800 a month. With a small time commitment, Leonard found that fostering community connections led to real opportunities for members. Tune in to explore why human-run spaces are thriving in an age of AI.

Dec 28, 2025 • 6min
Ep. 3284 - Weekend Workshop: From Wedding Dresses to State Legislature
Explore the inspiring journey of a young entrepreneur who transitioned from designing wedding dresses to becoming a state legislator. Discover how she built her business through referrals and targeted marketing. Learn about her innovative approach to co-working spaces that accommodate creative schedules. Delve into her unique strategies, like 'strategic giving,' which enhance customer relationships. This tale underscores how entrepreneurial ventures foster leadership skills and pave the way for making a difference in the community.

Dec 27, 2025 • 5min
Ep. 3283 - Q&A: “How can I keep from negotiating against myself?”
A freelance photographer grapples with undercutting her own prices before clients even respond. The discussion dives into strategies for overcoming this self-sabotage, like publishing clear price packages to streamline negotiations. Listeners learn about using a concise pricing script to boost confidence and prompt client responses. The importance of reserving discounts for specific situations rather than offering them reflexively is emphasized. Overall, the conversation fosters confidence in valuing one's work and practicing effective selling techniques.

Dec 26, 2025 • 5min
Ep. 3282 - Q&A: “I’m ready to raise prices … but how?”
Struggling with raising prices? Discover why it feels daunting and learn to frame your value in a way that clients appreciate. Explore the strategic timing for price increases and how to gracefully phase in changes for existing clients. Get practical tips for crafting an effective email to announce new rates, ensuring your loyal customers remain happy. With market research insights, you'll be empowered to make data-informed decisions. Embrace the change and watch your side hustle thrive!

Dec 25, 2025 • 7min
Ep. 3281 - TBT: After 1,700 Years, I Outsourced Christmas
In this whimsical chat, Santa Claus, the legendary figure behind the North Pole toy enterprise, dives into his groundbreaking pivot after 1,700 years of in-house production. He reveals how he transitioned to a licensing model, allowing for passive income while keeping holiday magic alive. Santa discusses the shift due to changing demands and elf unionization, as well as the practicalities of his new business model, including the Santa-approved seal and partner dashboards. With innovations like Mrs. Claus’ shop and mentoring younger elves, Santa's sleigh is lighter than ever!


