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

#1659 - Q&A: Alternative banking for cannabis products? 17.07.2021

In many jurisdictions, sellers of medical and recreational marijuana have a huge problem: they can’t keep their money in a bank. If you don’t want to carry all your money around in duffel bags, what’s to be done?  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...

#1658 - Failure Friday: “They refused to listen to my big pitch…” 16.07.2021

In this week’s Failure Friday segment, we hear from the woman who invented the “peeLUX.” When she tries to pitch her product to the founder of Spanx, she runs afoul of the company’s lawyers. 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...

#1657 - TBT: Romance Novel Editor Goes All-In 15.07.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance romance novel editor who’s recently quit her job as a corporate recruiter to work on books full-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...

#1656 - Q&A: How to stay motivated when other people have the same business idea? 14.07.2021

Today’s listener has several business ideas related to her love of plants, and is looking for some direction. Let’s see if we can plant the right seeds! 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...

#1655 - Cheese Connoisseur Makes Legen-dairy Creations 13.07.2021

When a remote worker wants to show appreciation for healthcare staff, she stumbles upon an untapped market for charcuterie and cheese boards. 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: SideH...

#1654 - Q&A: This candle business is on fire! 12.07.2021

A listener in London wants to sell candles with inspirational quotes and artwork featuring Black women, and wonders if her idea is too specialized.  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. 1653 - Real Estate Agent Profits from Bulk Mail Biz 11.07.2021

Processing direct mail—as in, old-school snail mail—has freed this real estate agent from financial stress. 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 Email: team@sidehu...

#1652 - Q&A: “I’m running the numbers on a subscription service…” 10.07.2021

Today’s listener is trying to forecast profits for her subscription service, and wants to know what seems like a reasonable expectation. 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: SideHustle...

#1651 - Failure Friday: Failure Friday: “They promised the boat would be ready… but it wasn’t.” 09.07.2021

In this week’s Failure Friday segment, we hear from an Australian who leads small-ship Mediterranean tours. When he commissions a new ship from a local builder, it turns into a true disaster. This story is epic! 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 les...

#1650 - TBT: Hydroponic Indoor Plant System Branches Out 08.07.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of IG Works. The company specializes in indoor gardening kits that allow you to grow dozens of large plants in a small space. It’s truly un-be-leaf-able!  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...

#1649 - Q&A: How to profit from electric vehicle credits? 07.07.2021

The federal government offers a $7,500 tax credit for most electric vehicle (EV) purchases, and many states offer additional credits as well—but it’s a confusing process. Is there also a way for this enterprising EV fan to make money? 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 i...

#1648 - Digital Marketer’s Playlist Skills Pay Off 06.07.2021

A tech-savvy marketer in Charleston, South Carolina seeks to expand her side gig as a music bingo host. Did someone say ‘BINGO’? 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.c...

#1647 - Q&A: "I fell for a scam and want to help others..." 05.07.2021

After falling for a frustrating phone scam, our listener has an idea to turn the experience into a lesson for others. Is there a way he can get paid to make presentations to organizations? 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&amp...

#1646 - “Side Hustle Bread” Insta Account Sells $100,000 04.07.2021

As a joke, a baking hobbyist starts an Instagram account selling bread—but it quickly becomes a full-fledged business that brings in more than $100,000.  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...

#1645 - Q&A: Is there a market for online stand-up paddleboard lessons? 03.07.2021

Is there a limit to what can be done online? Today’s caller is testing it! Let’s consider if there’s a way she can teach stand-up paddleboarding from behind a screen.  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...

#1644 - Failure Friday: Antiracism Interest Grows, But What Do Clients Want? 02.07.2021

In this week’s Failure Friday segment, we hear from the founder of an agency that supports workplace inclusion and antiracism. Her business experienced major growth in the past year—but clients aren’t always sure what they really want.   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...

#1643 - TBT: Sexual Wellness Site Revs Up Reviews 01.07.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a sex-positive blogger who publishes a site that reviews toys and other products for sexual wellness. 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 seve...

#1642 - Q&A: Does it matter which email list software I choose? 30.06.2021

Today’s listener just got her website up (whoo hoo!) and now she’s wondering about the next step: which company to use for her email list.   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: SideHu...

#1641 - Social Studies Teacher Gains 1.5 Million TikTok Followers 29.06.2021

When a teacher looks for a way to connect with her students during lockdown, she starts her own TikTok account and goes to the head of the class with her viral videos.   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 eac...

BONUS: The Post-Pandemic Economy 28.06.2021

In this special episode, Chris Guillebeau talks with Tim Welsh, Vice Chair of Consumer and Business Banking at U.S. Bank. Tim tells us how small businesses are leading the way in the economy's recovery, as well as how banks can help address historic inequities and disparities. Spoiler: Tim does NOT recommend investing your entire savings portfolio in Dogecoin.  Side Hustle School features a new ep...

#1640 - Q&A: How does "yield farming" work? 28.06.2021

Did you know you can earn interest (sometimes at very high rates) for “staking” digital currencies? It’s a wild world full of risk, volatility, and—for some—potential.  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...

#1639: Graduate Uses Equestrian Art to Canter Out of Debt 27.06.2021

When a psychology graduate wants to pay off $65,000 in debt, she takes life by the reins and learns to scale her equestrian art 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 Q&A several days each week. 🎧 Show notes: SideHus...

#1638 - Q&A: How to sell a podcast as a paid subscription? 26.06.2021

Apple Podcasts, Spotify, and presumably some other networks are all jumping on the premium podcast train. If you want to start one—a podcast as a paid subscription–how do you do 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 se...

#1637 - Failure Friday: “It took me way too long to bounce back…” 25.06.2021

In this week’s Failure Friday segment, we hear from a personal finance blogger who gets zero response to a coaching program he’s excited about—and then takes two years to recover. Lots of good lessons here!   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...

#1636 - TBT: When the Pandemic Hit, This Product Went Up 70x 24.06.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-inventor of a device that allows public restroom users to open the door with their foot. Their business increased 70x at the start of the global pandemic!  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, th...

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