Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/

Episodes

#2154 - Give Thanks and Eat Pie: Special Thanksgiving Episode

In this special episode recorded in South Africa, Chris reflects on 5+ years of Side Hustle School and encourages listeners to eat more pie. 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 24, 2022•4 min•Ep 2154•Transcript available on Metacast

#2153 - Q&A: “How to profit from cover songs on Apple Music?”

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

Nov 23, 2022•5 min•Ep 2153•Transcript available on Metacast

#2152 - Q&A: “I want to make an asexual dating app…”

Today’s caller has an idea to start her own app for people who identify as asexual (where you don’t feel much sexual attraction to anyone). What’s the best path forward? 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: SideHustle...

Nov 22, 2022•5 min•Ep 2152•Transcript available on Metacast

#2151 - First $1,000: “I made a floor to ceiling chain of bananas…”

In this week’s First $1,000 segment, we hear from a Texas event planner who earns at least $2,000/month on the side. One early event featured a creative display of hundreds of bananas. 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 s...

Nov 21, 2022•6 min•Ep 2151•Transcript available on Metacast

#2150 - Q&A: “How can I make money with Zoom calls?”

Today’s listener wonders: how can the average person capitalize on the fact that so many people are much more comfortable with video calls these days? 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/question...

Nov 20, 2022•5 min•Ep 2150•Transcript available on Metacast

#2149 - Q&A: “I’m a professional speed skater … how can I fundraise?”

An athletic listener from Minnesota seeks advice on starting a fundraising campaign. Will he need to improve his social media for more people to notice? 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/questi...

Nov 19, 2022•6 min•Ep 2149•Transcript available on Metacast

#2148 - Failure Friday: “I invested in a franchise and now I feel stuck…”

In this week’s Failure Friday segment, we hear from an investor who buys into a national franchise—then realizes he’s essentially bought himself a job. 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/questio...

Nov 18, 2022•5 min•Ep 2148•Transcript available on Metacast

#2147 - TBT: “Amazon Merch” Seller Moves 7,000 T-Shirts (& more!)

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a livestreamer who uses Amazon Merch on Demand to sell t-shirts and other personalized items. She’s sold more than 7,000 so far! 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@sidehust...

Nov 17, 2022•8 min•Ep 2147•Transcript available on Metacast

#2146 - Q&A: “Are there any alternatives to Patreon?”

An independent musician is looking for “something like Patreon but different.” What are her options? 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: @chrisguillebeau Connect on ...

Nov 16, 2022•4 min•Ep 2146•Transcript available on Metacast

#2145 - Q&A: “How can I become a personal finance influencer?”

Today’s caller wants to enter the world of personal finance experts and influencers. As she notes, she’s not the only one! So if you want to break in—what do you do? 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: SideHustleScho...

Nov 15, 2022•6 min•Ep 2145•Transcript available on Metacast

#2144 - First $1,000: “Clients don’t want Wordpress, they want a website…”

In this week’s First $1,000 segment, we hear from the self-described “Wordpress Girl,” who starts a service helping female entrepreneurs get set up with a website. She’s currently in the midst of a rebranding, but still brings in at least $2,000/month on the side. 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 wee...

Nov 14, 2022•5 min•Ep 2144•Transcript available on Metacast

#2143 - Q&A: “I’d like to teach wilderness survival classes…”

An outdoorsman from Montana wants to teach survival skills, but isn’t sure how to start. Can we help him get out of the woods? 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: @c...

Nov 13, 2022•5 min•Ep 2143•Transcript available on Metacast

#2142 - Q&A: “Need to increase income as an adjunct professor…”

Today we hear from a professor of sociology who wants to make more money. Nothing wrong with that! Let’s see if we can help. 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: @chr...

Nov 12, 2022•5 min•Ep 2142•Transcript available on Metacast

#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, 2022•6 min•Ep 2141•Transcript available on Metacast

#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, 2022•7 min•Ep 2140•Transcript available on Metacast

#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, 2022•6 min•Ep 2139•Transcript available on Metacast

#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, 2022•5 min•Ep 2138•Transcript available on Metacast

#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, 2022•5 min•Ep 2137•Transcript available on Metacast

#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, 2022•4 min•Ep 2136•Transcript available on Metacast

#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, 2022•6 min•Ep 2135•Transcript available on Metacast

#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, 2022•6 min•Ep 2134•Transcript available on Metacast

#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, 2022•7 min•Ep 2133•Transcript available on Metacast

#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, 2022•5 min•Ep 2132•Transcript available on Metacast

#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, 2022•5 min•Ep 2131•Transcript available on Metacast

#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, 2022•6 min•Ep 2130•Transcript available on Metacast

#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, 2022•5 min•Ep 2129•Transcript available on Metacast

#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, 2022•5 min•Ep 2128•Transcript available on Metacast

#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, 2022•7 min•Ep 2127•Transcript available on Metacast

#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, 2022•7 min•Ep 2126•Transcript available on Metacast

#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, 2022•6 min•Ep 2125•Transcript available on Metacast