Chris Guillebeau

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. Hosted on Acast. See acast.com/privacy for more information.

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

Ep. 3032 - Weekend Workshop: Launch Before You’re Ready 20.04.2025

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: publishing your offer! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the sho...

Ep. 3031 - Q&A: “How do I create and sell a premium online course?” 19.04.2025

In today's episode, we explore how to create a standout premium online course. Learn how to structure it, position it for a high price point, and stand out in a competitive market. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A sever...

Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?” 18.04.2025

What happens when a tech glitch disrupts your side hustle? In this episode, we tackle how to prepare for unexpected challenges without overcomplicating your operations. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each...

Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse 17.04.2025

In this week's Throwback Thursday segment, discover how this side hustler built a spring break site that soars to $8,000 during peak months by combining ad networks with carefully edited AI content. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and list...

Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle 16.04.2025

When this student found himself in thousands of dollars worth of debt, he made a simple $40 investment that would go on to transform his life and reach tens of thousands of people around the world. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and liste...

Ep. 3027 - Q&A: “How do side hustle ‘power laws’ work?” 15.04.2025

Why do a few things in your business drive most of your results? In this episode, we break down how power laws work and how to focus on what truly moves the needle. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each wee...

Ep. 3026 - First $1,000: From Text Messages to Digital Concierge 14.04.2025

In this week's First $1,000 segment, discover how one meticulous organizer built an online concierge service, offering tiered subscriptions for routine tasks and real-time support.  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A...

Ep. 3025 - Weekend Workshop: Making Time for What Matters 13.04.2025

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: how to spend 10% more time on your most important tasks. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit...

Ep. 3024 - Q&A: “What’s the ROI of renting out equipment or tools?” 12.04.2025

In this episode, we explore the ins and outs of running a tool rental business. Learn how to manage inventory, minimize risks, and maximize profits in this potentially lucrative side hustle. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&a...

Ep. 3023 - Q&A: “Could selling templates for AI tools be a business?” 11.04.2025

AI tools like ChatGPT are exploding in popularity, but can creating templates for these tools become a profitable side hustle? In this episode, we explore the opportunities, challenges, and potential pitfalls of this idea. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free...

Ep. 3022 - TBT: When Selling Prints Wasn’t Enough 10.04.2025

In this week's Throwback Thursday feature, discover how pivoting from digital art prints to creating mockups for Etsy and Shopify turned an underperforming side hustle into a high-demand service. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listene...

Ep. 3021 - STORY: Immigrant Couple Translates Heritage Into Children’s Flash Cards 09.04.2025

Two immigrants from Laos meet the needs of an underserved community, creating a series of dual-language flash cards and other resources.  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHus...

Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?” 08.04.2025

In this episode, we explore how service-based freelancers can manage last-minute client requests without sacrificing quality or burning out. Learn how to build buffer time into your schedule and set clear project boundaries. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes fr...

Ep. 3019 - First $1,000: Miami Divorce Planner Offers “Freedom Celebrations” 07.04.2025

In this week's First $1,000 segment, discover how a former wedding planner in Miami pivoted to organizing “freedom celebrations” for newly divorced clients, landing her first thousand dollars from two high-end events. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includ...

Ep. 3018 - Weekend Workshop: Design Your First Workflow 06.04.2025

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: creating clear, repeatable systems for running your business efficiently. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra m...

Ep. 3017 - Q&A: “How do I balance transparency with professionalism?” 05.04.2025

In this episode, we tackle the tricky balance of being transparent with your audience while maintaining professionalism. How can you build trust without oversharing or compromising your credibility? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and list...

Ep. 3016 - Q&A: “Is there still room to start a podcast in 2025?” 04.04.2025

Is it too late to start a podcast in 2025? In this episode, we tackle how to stand out in a crowded field and grow an audience for a niche topic. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: Side...

Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to Global Audiences 03.04.2025

In this week's Throwback Thursday segment, learn how a stationery-lover in Tokyo began shipping curated paper goods and writing supplies abroad—all while championing small artisan shops. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q...

Ep. 3014 - STORY: Accountant Earns $233,751 Reselling Items He Buys at Walmart 02.04.2025

A young accountant learns the art of reselling, purchasing textbooks, dental floss, and Cheerios from retail stores in bulk—then earns hundreds of thousands of dollars in profit by selling it online. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons a...

Ep. 3013 - Q&A: “How do I find my first clients without paid advertising?” 01.04.2025

In this episode, we help a new business owner attract their first paying clients without spending a dime on ads. Learn grassroots strategies for networking, social media, and building momentum from scratch. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons...

Ep. 3012 - First $1,000: Stay-at-Home Dad’s Virtual Garage Sale Venture 31.03.2025

In this week's First $1,000 segment, find out how a stay-at-home dad turned his neighbors' forgotten items into steady online income, taking a cut of each sale. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. S...

Ep. 3011 - Weekend Workshop: Make It Easy to Get Paid 30.03.2025

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: make it easy to get paid. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the...

Ep. 3010 - Q&A: “How to set better boundaries with clients?” 29.03.2025

In this episode, we explore how to manage client expectations when emotions get in the way. Learn how to set clear boundaries, navigate tough conversations, and keep your business running smoothly—even when clients slow down the process. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, t...

Ep. 3009 - Q&A: “How can I work fewer hours without losing income?” 28.03.2025

In this episode, we help a web developer reduce his work hours while keeping his income steady. Learn how to raise rates, outsource tasks, and restructure service packages to build a smarter, more sustainable business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free gui...

Ep. 3008 - TBT: Pet Furniture Maker Adds Digital Blueprints for DIYers 27.03.2025

In this week's Throwback Thursday segment, see how shifting from physical products to digital plans and online classes helped a woodworker reach more customers and streamline his business model. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener...

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