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

Special Broadcast: The Money Tree Is Out! (+ New YouTube Series) 09.04.2020

Hey everyone, THE MONEY TREE is now available wherever books are sold—and I'm also starting a new, interactive YouTube show to talk about finding opportunities in the midst of uncertainty. Listen to this quick bonus episode to hear more. :) To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://pod...

#1195 - TBT: Show Me the Honey! Behind the Scenes of a Beekeeping Biz 09.04.2020

In this week’s “Throwback Thursday / Where are they now?” segment, we’ll hear from a professional beekeeper. Don’t buzz off until you’ve heard it!  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.   Share: #Side...

#1194 - Q&A: How to find target markets for livestreaming business events? 08.04.2020

Today’s caller is working on providing livestreaming content creation services for small businesses and events. How can he find a niche or target market to focus on? 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 we...

#1193 - Trinidad Burger Chef Sells Curry Creations on WhatsApp 07.04.2020

When a sales professional’s dreams of opening a restaurant are dashed, she comes up with a new way to market her gourmet burgers directly on social media. 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.   Share...

#1192 - CLASSROOM: The Power of Your Own Small Army 06.04.2020

Wondering how you’ll get your products and services to your ideal customers? Chances are, you already know some of the people who can help.  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.   Share: #SideHustleS...

#1191 - Software Tester Tunes Pianos for Harmonious Hustle 05.04.2020

A software tester and serial side hustler learns a new skill, “tuning” a profit in just over a week.  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.   Share: #SideHustleSchool Show notes: SideHustleSchool.com...

#1190 - Q&A: With the downturn in this economy, should I quit my job? 04.04.2020

Millions of people are experiencing massive disruption and wondering what to do. Here’s an example: How does the COVID-19 pandemic and everything associated with it impact a decision to quit your job and go full-time with your own project? 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 s...

#1189 - Q&A: What do you think about Shopify? 03.04.2020

Today’s caller has noticed a lot of people using Shopify to sell products. It looks easy to set up … but is it the best option? 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.   Share: #SideHustleSchool Show no...

#1188 - TBT: Southern Transplant Creates Watercolor Brand 02.04.2020

In this week’s “Throwback Thursday / Where are they now?” segment, we revisit a graphic designer who starts a watercolor brand that is sold in retailers throughout South Carolina and beyond.  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&...

#1187 - Q&A: What’s the best way to register domains? 01.04.2020

There’s no reason not to have your own domain now. But what’s the best way to register one, and do you need to get every extension? 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.   Share: #SideHustleSchool Sho...

#1186 - Mom Photographers Start Summer Camp for Kids 31.03.2020

When two photographers’ kids want to learn the trade themselves, the adults decide to see what develops with the idea of starting a summer camp. 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.   Share: #SideHus...

#1185 - CLASSROOM: Side Hustle Sprint! It’s Time to Break Out the Duct Tape 30.03.2020

What if you had to launch your moneymaking project in two weeks or less? What would you HAVE to do to get ready, and what are you putting off? 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.   Share: #SideHustl...

#1184 - Digital Marketer Makes Money Marketing Himself 29.03.2020

When a digital marketing specialist feels underpaid at his day job, he applies his skills to finding new clients of his own. 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.   Share: #SideHustleSchool Show notes...

#1183 - Q&A: Should I make a physical or digital book? 28.03.2020

If you want to publish a book, what is the best format—physical, digital, or something else? This listener wants to earn passive income from her “Grandma Creates” book, and is torn between the different options.  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 le...

#1182 - Q&A: Any tips for buying stuff at flea markets to resell? 27.03.2020

Reselling is the easiest way to get started making money outside your job. What are some tips to get started, and how can you find items to buy and sell? 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.   Share:...

#1181 - TBT: Best Guitar Lessons in the Universe 26.03.2020

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a university administrator who creates a sustainable full-time income from teaching guitar.  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...

#1180 - Q&A: Can I monetize my ideas without actually running the business? 25.03.2020

Can you focus entirely on idea generation and let someone else do all the work? Today’s caller wants to know if this is a “totally crazy” approach…  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.   Share: #Sid...

#1179 - Google Employee Becomes Career Coach for “Analytically-Minded People” 24.03.2020

While working at Google, a technical support employee gives unofficial career advice until her colleagues encourage her to start coaching more formally. 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.   Share:...

#1178 - CLASSROOM: Don’t Listen to This Boring Episode 23.03.2020

Business licenses, bank accounts, and record-keeping … it might be boring compared to product launches, but if you get a few easy things right in the beginning, it will be much less stressful moving forward.  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 lesson...

#1177 - Military Mom Makes Moola Managing Media 22.03.2020

When a military spouse looks for a way to make extra money, she stumbles upon a virtual job that provides assistance to both her clients and her family. 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.   Share:...

#1176 - Q&A: Should I distribute a new private label product myself? 21.03.2020

Today’s caller is wondering whether he should work with a fulfillment center for his first private label product, or do it all himself? There are pros and cons each way… what’s best for him? 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...

#1175 - Q&A: When should I become an LLC? 20.03.2020

Filing an LLC in this listener’s state is expensive … is it worth it? How should you make this decision for yourself?  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.   Share: #SideHustleSchool Show notes: Side...

#1174 - TBT: Designer Scales Personalized Wedding Products to $1M+ 19.03.2020

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a graphic designer who does custom illustrations for weddings and other events. It’s now a seven-figure 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 guided lessons and listener...

#1173 - Q&A: Where are my customers coming from? 18.03.2020

This listener sells a video tutorial series for students taking the MCAT—but she’s not sure where her customers are coming from. How can she acquire this valuable information? 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...

#1172 - Music Teacher Quits Job to Earn $100k on Fiverr 17.03.2020

This motivated music teaching student hits the perfect note by freelance writing on Fiverr. Later, she ends up leaving her job to go all-in.  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.   Share: #SideHustle...

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