Chris Guillebeau

Side Hustle School

Business EN ↓ 3640 episodes

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.

Be sure to visit the podcast's website and support the creator: sidehustleschool.com

Author

Chris Guillebeau

Episodes

Ep. 3160 - Q&A: “Can Lyft drivers really make $2,000/week?” 26.08.2025 4:29

Can a Lyft driver really make $2,000 a week? In this episode, we break down rideshare earnings, what's possible, and what's rare. 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: SideHustleSchool.com...

BONUS: "Time Anxiety" Book and Free Quiz 25.08.2025 2:01

A short update on my new book, Time Anxiety, including a free quiz you can take and a discount on the ebook version for U.S. listeners.  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: SideHust...

Ep. 3159 - First $1,000: YouTube Bonsai Channel Grows Into Online Store 25.08.2025 5:50

In this week's First $1,000 segment, hear how a niche YouTube creator turned their passion videos into a Shopify store—selling products directly to their growing audience. 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...

Ep. 3158 - Weekend Workshop: Template Biz Goes from Service to Scale 24.08.2025 6:54

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 a budget résumé design service morphs into a template business that generates passive income. Side Hustle School features a new episode EVERY DAY, featuring detailed c...

Ep. 3157 - Q&A: “How can I make money from old YouTube videos?” 23.08.2025 4:17

Do you have any old videos that aren't getting views? In this episode, we look at creative ways to repackage, remix, and monetize your past content for new platforms or audiences. 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 severa...

Ep. 3156 - Q&A: “Can you profit by reselling loyalty points or rewards?” 22.08.2025 4:51

Can you really make money reselling loyalty rewards or points? In this episode, we break down the reality behind this internet hustle—and whether it's worth your time. 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...

Ep. 3155 - TBT: From Abandoned Storage Finds to Museum Artifacts 21.08.2025 5:44

In this week's Throwback Thursday segment, hear how a side hustler who once flipped storage unit items gradually specialized in rare historical items, and now supplies props and artifacts to small museums and exhibits. 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. 3154 - STORY: Civil Engineer Sells Hooded Baby Robes on Amazon 20.08.2025 8:15

After a civil engineer in Florida learns to sell hooded baby robes on Amazon, he moves to Bali with his wife, where he builds an app to help him find products. This app turns into a business that employs 80 people and serves 100,000 users.  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,...

Ep. 3153 - Q&A: “‘Love spells’ for sale on Etsy … is this real??” 19.08.2025 4:23

Truth is stranger than fiction, and some people really are selling “love spells” or magic charms online. In today's episode, we explore the weird world of digital spellwork. 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. 3152 - First $1,000: Book Summary Subscription Breaks Out 18.08.2025 5:58

In this week's First $1,000 segment, hear how one side hustler launched a paid weekly book summary subscription, combining AI tools with personal commentary to stand out in a crowded space. 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&am...

Ep. 3151 - Weekend Workshop: Emotional Products Command Premium Prices 17.08.2025 7:15

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: an industrial engineer creates nostalgia-themed handcrafted items. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wi...

Ep. 3150 - Q&A: “Do I need to worry about international taxes on digital products?” 16.08.2025 3:59

Selling digital products internationally? In this episode, we explain what small creators need to know about VAT, global taxes, and how to avoid expensive compliance mistakes. 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 da...

Ep. 3149 - Q&A: “Can you still make money flipping domain names?” 15.08.2025 4:56

Ep. 3148 - TBT: How I Knew It Was Time to Quit My Side Hustle 14.08.2025 5:05

In this week's Throwback Thursday segment, hear how a side hustler who ran a profitable online stationery business for five years made the difficult but deliberate choice to shut it down. 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. 3147 - STORY: Coffee Lovers Brew Quick Fix Into $1 Million Hustle 13.08.2025 8:21

While training for a 24-hour obstacle course challenge and working full-time, a GM employee turns cold brew into a moneymaking energizer.   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:...

Ep. 3146 - Q&A: “Can you buy or sell Instacart accounts as a side hustle?” 12.08.2025 4:44

Heard about people buying and selling Instacart accounts? In this episode, we explore whether it's a clever hustle—or a fast track to getting banned. 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 n...

Ep. 3145 - First $1,000: Ambient Train Noise Finds Global Audience 11.08.2025 6:28

In this week's First $1,000 segment, discover how a lifelong trainspotter turned ambient railway recordings into a digital product for sleep, study, and meditation. 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. 3144 - Weekend Workshop: When Your Side Project Replaces Your Career 10.08.2025 8:05

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: a failed grant application leads to a new business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

Ep. 3143 - Q&A: “What are the best renewable markets for a side hustle?” 09.08.2025 5:43

What do high school grads, new parents, and brides-to-be have in common? In this episode, we explore renewable markets—those endlessly refreshing customer pools—and why they're smart for side hustlers. 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 l...

Ep. 3142 - Q&A: “What’s the business process for releasing an indie game?” 08.08.2025 5:37

Thinking about launching your own video game? In today's episode, we explore how solo developers can publish on Steam—one of the biggest game distribution platforms—and what it really takes to turn a project into profit. 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 inc...

Ep. 3141 - TBT: How My Print-on-Demand Shop Landed a Licensing Deal 07.08.2025 5:43

In this week's Throwback Thursday segment, hear how an independent artist who launched a small print-on-demand store eventually landed a licensing deal with a major retail brand—and what the experience has been like so far. 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. 3140 - STORY: Couple Goes From Crashed Drone To Soaring Side Hustle 06.08.2025 8:00

A sky-high success story of a six-figure drone coaching business that begins after a man crashes a drone into a parked car in New York City. Look out!   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....

Ep. 3139 - Q&A: “Can I sell my ideas for inventions?” 05.08.2025 5:00

Have a bunch of invention ideas but don't want to start a business for each one? In this episode, we look at the reality of licensing product concepts—and why execution matters more than creativity. 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 an...

Ep. 3138 - First $1,000: Dungeon Master Markets Printable Game Maps 04.08.2025 5:19

In this week's First $1,000 segment, hear how a veteran Dungeon Master turned his custom campaign maps into a downloadable product for other players. 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:...

Ep. 3137 - Weekend Workshop: The Art of Professional Networking 03.08.2025 7:35

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: developing your skills as a “connector.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...