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
Podcast website
Latest episode
Jul 11, 2026
Where to listen?
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Episodes
#701 - Weekly Recap: Give the Gift of Podcasts 02.12.2018 13:26
In our forty-eighth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chr...
#700 - Dog Lover Fetches $250,000 in Canine Clothing 01.12.2018 6:19
A Minnesota woman turns her design hobby into trendy duds for the whole family, including furry companions. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisgui...
#699 - Carpe Libri! Budding Book Club Baron Brings in $6,400/Month 30.11.2018 8:17
A UK-based consultant builds a better reading habit by starting a book club that grows to 350 members. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebe...
#698 - Engineer Earns 7-Figures from “Crowd-Purchasing” Project 29.11.2018 7:51
A product development exec recognizes the need for a group buying platform for electronics and other items. After starting with $5,000, it now earns seven figures annually. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #S...
Special Feature: Squeaky Clean Side Hustle Becomes Full-Time Family Business 28.11.2018 5:40
A passion for plant-based, organic products scrubs up an unexpected family business. This special episode of Side Hustle School is brought to you by ShipStation. 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://podcastchoices.com/adchoices Side Hustle School features a new episode EVERY DAY,...
#697 - Magician Brothers Make Money Appear From Playing Cards 28.11.2018 6:45
Twin brothers turn their art of “cardistry” into a highly profitable business. It’s all fun and games as long as they don’t let their profits vanish…. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow no...
#696 - Proud Mainer Brings Whoopie Pies to the World 27.11.2018 7:40
After her kids go off to college, this former stay-at-home-mom begins baking whoopie pies in bulk. She now makes them by the thousands, selling more than $25,000 in creamy inventory each month. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the re...
#695 - Business Students Make $125,000 Selling Headphone Attachments 26.11.2018 9:19
Two friends always talked about starting a business. But it wasn’t until a run-in with some expensive headphones that they finally found the idea they’d been waiting for. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #Sid...
#694 - Weekly Recap: Ice Cream, Dog Stockings, and Luxury for Less 25.11.2018 11:24
In our forty-seventh recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @c...
#693 - Art School Model Starts Sexually Stimulating Side Hustle 24.11.2018 8:20
This biology student-turned-model had a penchant for writing about sexual wellness. She just had to find a way to make money with it—and she did. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes:...
#692 - “National Pie Championship” Judge Sells Off Inventory 23.11.2018 6:07
This lifelong baker was afraid of pies—but when she overcomes her hesitancy, she undertakes a baking adventure that leads to hundreds of satisfied customers. Get rich or pie tryin’! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. ...
#691 - Dog Stocking Hustle Earns Husky Payoff 22.11.2018 7:20
He never saw himself starting a side hustle, but when he noticed one of his marketing clients making bank on seasonal pet gifts, he just couldn’t roll over anymore. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustle...
Special Feature: Guitar Pedal Switches Shred Heavy Metal Profits 21.11.2018 5:21
When this musician can’t afford the latest guitar gear, he finds a way to build it himself, building a full-time income in the process. This special episode of Side Hustle School is brought to you by ShipStation. 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://podcastchoices.com/adchoices...
#690 - Luxury for Less! Best Friends Get Paid to Share Design Tips 21.11.2018 7:24
When two friends realize that their savvy shopping is a skill, they dive into the world of affiliate marketing. After investing a grand total of $46 startup costs, they earned $1,200 in month three. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what t...
#689 - Songwriter Makes Extra Money Giving Podcasts a Beat 20.11.2018 7:47
When a friend needs help writing music for his podcast, this full-time music producer tunes up his side hustle strings. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitte...
#688 - Game of Cones: Two Women Make Architecturally-Inspired Ice Cream 19.11.2018 8:32
A nouveau-cream wave of ice cream debuts at Coachella, and everyone freaks out. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau To learn more about...
#687 - Weekly Recap: Tater Tats, Car Seat Coats, and Comic Books 18.11.2018 10:13
In our forty-sixth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chr...
#686 - Business Analyst Creates Budding Side Hustle 17.11.2018 6:39
He puts the ‘can’ in cannabis products, finding a pot of gold at the end of a hazy rainbow. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau To learn...
#685 - Comic Book Curator Creates Custom Crate Subscription 16.11.2018 9:12
A Sacramento-based comic and collectibles owner sparks an interest in reading with a monthly comic book subscription box service. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool....
#684 - Dutch Engineer Sells TableTop Games for Second Income 15.11.2018 7:46
When a series of debilitating headaches makes it hard to work full-time, this Dutch A/V engineer diversifies his income to decrease his work hours. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes...
Special Feature: Texas Team Stitches & Ships 150,000 Socks Every Month 14.11.2018 3:57
Two friends create a “Sock of the Month” club that starts with $600 and grows to 23 employees. This special episode of Side Hustle School is brought to you by ShipStation. 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://podcastchoices.com/adchoices Side Hustle School features a new episode...
#683 - Aussie Couple Logs Six Figures Selling Wellness Diaries 14.11.2018 6:09
An account manager and her partner develop a self-care diary to help others prioritize health and well-being. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisg...
#682 - Working Mother Sells Coats to Buckle in Babies 13.11.2018 9:34
It’s unsafe for your child to be in a car seat with a puffy winter coat—but it’s a pain to dress and undress each time you enter the car. This working mother solves the problem. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Shar...
#681 - Farmer Makes “Tater Tats” for All Your Produce Tattoo Needs 12.11.2018 8:00
When a running joke doesn’t end up running its course, a side hustle seed takes root and begins to grow. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguille...
#680 - Weekly Recap: End of Civilization, Voter Postcards, and Nepalese Sherpas 11.11.2018 13:39
In our forty-fifth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @ch...
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