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.
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Auteur
Chris Guillebeau
Catégorie
Site du podcast
Dernier épisode
18 oct. 2026
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Épisodes
Ep. 3578 - Un-Tours Of Myanmar Offer Adventure and Unpredictability 18.10.2026 7:56
His friends kept asking him to lead tours of Myanmar, and he finally agreed. But he wasn’t going to stick to the usual sights—his ‘un-tours’ would be anything but typical. 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 e...
Ep. 3577 - Q&A: “Can I get paid to help iPhone owners switch to Android?” 17.10.2026 6:49
Today’s listener wants to serve the masses of people who buy Apple products but would shop for Android and PC devices if they knew what to buy. It’s an interesting market—how can he succeed? 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. 3576 - Failure Friday: “Amazon permanently banned my seller account…” 16.10.2026 7:17
In this week’s Failure Friday segment, we hear from Kelan from TheSavvyCouple.com. In his early days, he sold on eBay and Amazon. It was all going well, until a supplier problem led to him getting banned—permanently! 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 guide...
Ep. 3575 - TBT: The 7-Figure Dachshund Apparel Business 15.10.2026 7:45
In this week’s “Throwback Thursday” segment, we hear from the co-founder of Bean Goods, which sells dachshund-themed apparel for dogs and humans. 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: &nbs...
Ep. 3574 - Q&A: “Can I use another author's work in my book?” 14.10.2026 4:33
Today’s listener has a legal question that I can actually answer with some confidence: what are the rules about quoting or referencing someone else’s work in something you offer for 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&...
Ep. 3573 - Q&A: “How do I focus on retaining clients?” 13.10.2026 4:24
Today we’re going to hear from a CPA in the midwest who wants to focus on retaining clients. This is more important than finding new clients! 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: Si...
Ep. 3572 - First $1,000: “I succeeded by following contradictory advice…” 12.10.2026 7:41
In this week’s “First $1,000” segment, we hear from the seller of Pretty Old Books. What started as an idea to sell vintage book sets on Etsy turned into an entirely different 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 Q&...
Ep. 3571 - STORY: Guitar Player Chalks Up Success By Enjoying The Process 11.10.2026 7:39
A systems administrator and lifelong guitar player generates thousands per month writing about his musical hobby. 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 Ema...
Ep. 3570 - Q&A: “Can I offer a permanent price discount?” 10.10.2026 4:19
Our listener has seen furniture stores offer non-stop sales. Is there any reason they can’t have a sale that never ends in their 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:  ...
Ep. 3569 - STORY: Hand Lettering Artist Upgrades Photo Booth Props 09.10.2026 7:42
An illustrator gives boring wedding photo booth props a much-needed upgrade, creating an alternative to greeting cards at the same 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 each week. Show notes: SideHus...
Ep. 3568 - TBT: Physician Designs Plush Toys to Teach Anatomy 08.10.2026 7:25
In this week’s “Throwback Thursday” segment, we hear from a doctor who makes plush toys in the shape of human organs to teach kids about the body. 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 note...
Ep. 3567 - Q&A: “Can I resell items I get for free?" 07.10.2026 4:08
Today’s listener received some free display equipment at a trade show. Can he resell it without worrying, or does this create an ethical dilemma? 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. 3566 - Q&A: “An English-language anime club in Japan…” 06.10.2026 4:20
Today’s caller wants to start an English-speaking anime club in Japan. With the country recently re-opened for visitors, let’s get this party started! 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. 3565 - First $1,000: “I got paid to walk dogs while on work calls…” 05.10.2026 5:36
In this week’s First $1,000 segment, we hear from a Chicago native who starts “Day Job Dogwalking” during the pandemic. While juggling work calls with her employer, she gets paid (and eventually hires someone) to walk dogs in her neighborhood. 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. 3564 - STORY: Physical Therapist Sells 57,000 “Neck Hammocks” 04.10.2026 7:29
In trying to remedy his own workout injuries, this physical therapist invents a portable device to relieve pain. He then patents the device and sells 57,000 of them. 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. 3563 - Q&A: “What’s the 80/20 rule of side hustling?” 03.10.2026 4:23
Today’s listener is wondering about applying the Pareto principle to the world of side hustles. What can we learn—and what should we do differently as a result of this knowledge? 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. 3562 - Failure Friday: “My app kept crashing during the big pitch…” 02.10.2026 10:11
In this week’s Failure Friday segment, we hear from the founder of a project management tool. An early pitch to a major investor got off to a rough start. 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 no...
Ep. 3561 - TBT: “Graphic Designer for Dogs” Retrieves New Clients 01.10.2026 7:00
In this week’s “Throwback Thursday” segment, we hear from a graphic designer who started off by specializing in pet businesses. She’s now trying to go off-leash and retrieve clients in other industries … is she barking up the wrong tree? 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. 3560 - Q&A: “How can I rent out my spare bedroom on Airbnb?” 30.09.2026 4:46
An attorney who isn’t home much would like to earn passive income from renting out her spare bedroom. What does she need to know, and is there any way to make it easier? 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...
Ep. 3559 - Q&A: “How to sell a podcast as a paid subscription?” 29.09.2026 4:41
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&...
Ep. 3558 - First $1,000: “Beekeeping is forced zen: be present or get stung!” 28.09.2026 7:23
In this week’s “First $1,000” segment, we hear from Frank Mortimer, the self-described “Bee Man of New Jersey.” In his initial foray into selling honey at a farmers market, he learned several critical lessons. Among others: don’t forget the tasting spoons! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job....
Ep. 3557 - STORY: Amsterdam Bike Tours Become Passive Profit Center 27.09.2026 7:25
A traveler’s attempt to pay rent turns into one of Amsterdam’s premier touring companies. 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@sidehustleschool.com...
Ep. 3556 - Q&A: “How to profit from cover songs on Apple Music?” 26.09.2026 4:38
If you’re familiar with any of the major streaming platforms, you might be aware that there are cover versions of lots of popular songs. How does this work in the business sense? 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. 3555 - STORY: Continuing Education Directory Earns Six Figures 25.09.2026 8:06
An Australian woman leaves her marketing agency to launch a profitable business for architects in need of professional development credits. 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. 3554 - TBT: Satin Pillowcases Inspire Dreamy Profits 24.09.2026 9:22
In this week’s “Throwback Thursday” segment, we revisit a savvy idea to make silky, smooth, shiny pillowcases. 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@...
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