Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 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.

Author

Chris Guillebeau

Episodes

#2133 - TBT: “It’s scary but I trust that I made the leap for a reason...” 03.11.2022 7:16

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a multifaceted artist in Texas who makes ceramics, lettering projects, and even a weekly lunch series on YouTube. 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...

#2132 - Q&A: “I stopped delivering for my Patreon…” 02.11.2022 4:48

An independent musician has a Patreon account funded by fans. Over the past few months, he’s stopped delivering updates and special features—but the fans keep paying. How should he handle this unusual problem? 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 lesso...

#2131 - Q&A: “Should I pay to get verified on Instagram?” 01.11.2022 5:02

Today’s caller has a service that promises to get her Instagram account verified for the low, low price of $2,000. Is this an amazing deal or a terrible idea? 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. Sh...

#2130 - First $1,000: “I earn a thousand dollars a week selling MacBooks…” 31.10.2022 5:40

In this week’s First $1,000 segment, we hear from a college-aged reseller of MacBooks. He’s got it down to a science and is pulling in more than a thousand dollars a week part-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 seve...

#2129 - Q&A: “Where can I find my first employee?” 30.10.2022 5:17

Today a listener from Salt Lake City is ready to hire her first employee after growing her stationery brand slowly and steadily. What does she need to know? 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...

#2128 - Q&A: “Recovering after a failed partnership…” 29.10.2022 4:49

Today we’re going to hear from a caller who’s previous venture didn’t work out. That one was a partnership with a friend that ended amicably, and now our listener is ready to make another attempt of her 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 lesson...

#2127 - Failure Friday: “Apple rejected my game before it even launched…” 28.10.2022 6:35

In this week’s Failure Friday segment, we hear from a mobile game developer with an ambitious idea—so ambitious that it never got off the ground. 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: S...

#2126 - TBT: “Amazon booked a ‘Uke Night’ for virtual team-building…” 27.10.2022 7:02

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Honolua Ukuleles, based in Calgary, Alberta. 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. Side Hustle School fe...

#2125 - Q&A: “How can you resell video games if they’re digital?” 26.10.2022 5:48

Over the past decade, more and more video games are delivered digitally. There’s no packaging and no waiting … and also no resale market. Can anything be done? A young caller wants to know! 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...

#2124 - Q&A: “I want to be the Zoom Dog Trainer!” 25.10.2022 4:15

These days, we’re all used to Zoom and other videoconferencing for all sorts of things—but will it work for dog training?? 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...

#2123 - First $1,000: “I have 3 clients and $4,000/month in retainer fees…” 24.10.2022 6:00

In this week’s First $1,000 segment, we hear from a Social Media Manager from Toronto. She has a day job she enjoys but—naturally—also has a side hustle that’s bringing in $4,000 a month. 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...

#2122 - Q&A: “Where's the best place to hire contractors?” 23.10.2022 5:58

Today’s caller is starting a *second* side hustle and wants to know where to find the best virtual assistants and other contractors. 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....

#2121 - Q&A: "Help, my bank said I can't open a business account!" 22.10.2022 3:57

How do you keep your business and personal finances separate? Ideally with a different bank account—but this listener is having trouble opening one. 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: S...

#2120 - Failure Friday: “My anniversary sale was an epic fail…” 21.10.2022 4:40

In this week’s Failure Friday segment, we hear from the founder of a membership site that’s going very well—until the founder stops giving it the attention it deserves. 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 ea...

#2119 - TBT: “It’s like a gym you only pay for if you don’t go…” 20.10.2022 7:14

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Lazy Jar, an app that makes fitness pay—at least for the developer. 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....

#2118 - Q&A: “I want to make and sell firefighter merch…” 19.10.2022 5:10

Shoutout to all firefighters and other first responders out there! Today we’ll hear from one of them who wants to put his free time at the station to good use. 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. Sh...

#2117 - Q&A: “I want to sell AI-generated art from DALL-E…” 18.10.2022 4:56

AI art tools like Midjourney and DALL-E allow anyone to make all kinds of incredibly realistic, AI-generated images. Can you sell what you make? 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...

#2116 - First $1,000: “My sister and I made this game to honor our dad…” 17.10.2022 4:59

In this week’s First $1,000 segment, we hear from one-half of a sisterly team on a mission: inspired by their father, they’re making a combination board game and app that teaches people about the stars. 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...

#2115 - Q&A: “Like an airport lounge, just in a mall…” 16.10.2022 4:45

Today’s caller has just come from an airline lounge—one of the better ones, it sounds like. He has an idea to take the concept and introduce it in his local shopping mall. 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...

#2114 - Q&A: “My biggest problem is low self-confidence…” 15.10.2022 4:50

Today’s caller has a detailed technical problem … no, wait—they have imposter syndrome. Do you have it too? Let’s hear from them and consider what can 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 lessons and listener Q&A several days each week. S...

#2113 - Failure Friday: “I got sucked into hosting an MLM party…” 14.10.2022 5:35

In this week’s Failure Friday segment, we hear from someone who learns an awkward lesson: no one wants to come to your network marketing party. Don’t 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 several days each week. Sh...

#2112 - TBT: Typewriter Poetry for Weddings and Corporate Events 13.10.2022 8:04

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Rent Poet, offering typewriter poetry for events in West Hollywood 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&A several days...

#2111 - Q&A: “Which pages are most important on a website?” 12.10.2022 4:01

A consultant suggests that one of our listeners hire someone to create a bunch of specific pages organized around keywords. Is this a good idea? 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: Sid...

#2110 - Q&A: “I’m inventing underwater headphones for swimmers…” 11.10.2022 4:51

A listener is inventing underwater headphones—but he’s stuck in the manufacturing stage. Can we help him keep his head above water? 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....

#2109 - First $1,000: “I sell pots and other plant holders on Amazon…” 10.10.2022 5:11

In this week’s First $1,000 segment, we hear from a Fulfillment by Amazon seller. After detailed research, she found the perfect product for resale. 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:...