Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau sidehustleschool.com
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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Episodes

#2141 - Failure Friday: “I wish I hadn’t told my friends about my hustle…”

In this week’s Failure Friday segment, we hear from a tech employee who starts an after-hours side hustle. This turns out to be … a mistake. 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 Be on the show: SideHustleSchool.com/questions Connect ...

Nov 11, 20226 minEp. 2141

#2140 - TBT: NYC Opera Singer Moonlights as Home Contractor

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a New York City opera singer, home contractor, and primary caregiver. Like many side hustlers, she stays busy! 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 Be on...

Nov 10, 20227 minEp. 2140

#2139 - Q&A: “What’s the best way to outline a business idea?”

Let’s say you have an idea. What do you do next? Learning to develop this skill can help you with a lot of things, not just business ideas. 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 Be on the show: SideHustleSchool.com/questions Connect o...

Nov 09, 20226 minEp. 2139

#2138 - Q&A: “Can I make and sell Notion templates?”

The productivity app Notion describes itself as a a project management and note-taking software platform. It comes with 100 templates, but you can make your own—and our caller wants to sell the ones they make. How can they do that? 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...

Nov 08, 20225 minEp. 2138

#2137 - First $1,000: “I make $3,000/month with Instagram DMs…”

In this week’s First $1,000 segment, we hear from a listener with a very creative strategy: she earns up to $4,000/month through Instagram Direct Messages (DMs), without having much of a following of her own. This is a good 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: SideHustleSchool.com ...

Nov 07, 20225 minEp. 2137

#2136 - Q&A: “When is it too late to change a business name?”

If you haven’t launched and realize your business needs a different name, it’s easy enough to change. But what about when you’re already up and running—is there a point where it’s too late? 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 Be on ...

Nov 06, 20224 minEp. 2136

#2135 - Q&A: “Millions of dollars for white noise tracks for Spotify ... this is crazy!”

A business recently made headlines for earning $9 million by streaming white noise tracks on Spotify. Is this still feasible for others—and if not, how can you find something like this in the first place? 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@sidehustlesc...

Nov 05, 20226 minEp. 2135

#2134 - Failure Friday: “My Facebook page with 40,000 fans was hacked…”

In this week’s Failure Friday segment, we hear from a coach who had been building her business on Facebook—until she made a mistake and clicked a password reset link from a hacker. 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 Be on the show:...

Nov 04, 20226 minEp. 2134

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

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 Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be...

Nov 03, 20227 minEp. 2133

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

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehus...

Nov 02, 20225 minEp. 2132

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/...

Nov 01, 20225 minEp. 2131

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show...

Oct 31, 20226 minEp. 2130

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

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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/qu...

Oct 30, 20225 minEp. 2129

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

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustl...

Oct 29, 20225 minEp. 2128

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Con...

Oct 28, 20227 minEp. 2127

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

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 features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money withou...

Oct 27, 20227 minEp. 2126

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

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on ...

Oct 26, 20226 minEp. 2125

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

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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chris...

Oct 25, 20224 minEp. 2124

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

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on th...

Oct 24, 20226 minEp. 2123

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

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.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitt...

Oct 23, 20226 minEp. 2122

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions ...

Oct 22, 20224 minEp. 2121

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

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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleS...

Oct 21, 20225 minEp. 2120

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool....

Oct 20, 20227 minEp. 2119

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com...

Oct 19, 20225 minEp. 2118

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Conn...

Oct 18, 20225 minEp. 2117

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustlescho...

Oct 17, 20225 minEp. 2116

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

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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHust...

Oct 16, 20225 minEp. 2115

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com...

Oct 15, 20225 minEp. 2114

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/qu...

Oct 14, 20226 minEp. 2113

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

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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHu...

Oct 13, 20228 minEp. 2112
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