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

#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, 2022•4 min•Ep 2124•Transcript available on Metacast

#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, 2022•6 min•Ep 2123•Transcript available on Metacast

#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, 2022•6 min•Ep 2122•Transcript available on Metacast

#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, 2022•4 min•Ep 2121•Transcript available on Metacast

#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, 2022•5 min•Ep 2120•Transcript available on Metacast

#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, 2022•7 min•Ep 2119•Transcript available on Metacast

#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, 2022•5 min•Ep 2118•Transcript available on Metacast

#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, 2022•5 min•Ep 2117•Transcript available on Metacast

#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, 2022•5 min•Ep 2116•Transcript available on Metacast

#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, 2022•5 min•Ep 2115•Transcript available on Metacast

#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, 2022•5 min•Ep 2114•Transcript available on Metacast

#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, 2022•6 min•Ep 2113•Transcript available on Metacast

#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, 2022•8 min•Ep 2112•Transcript available on Metacast

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

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

Oct 12, 2022•4 min•Ep 2111•Transcript available on Metacast

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

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

Oct 11, 2022•5 min•Ep 2110•Transcript available on Metacast

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

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

Oct 10, 2022•5 min•Ep 2109•Transcript available on Metacast

#2108 - Q&A: ”Is there an app to evaluate business ideas?”

Today’s listener is looking for a specific resource: an app to help them evaluate and rank different business ideas. Does this exist? 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 Twit...

Oct 09, 2022•4 min•Ep 2108•Transcript available on Metacast

#2107 - Q&A: “Selling a user's guide to Shopify conversion…”

Today we’re going to hear from a listener with an idea to sell a guide on Shopify. You know Shopify—it used to be a little ecommerce plugin that competed with a bunch of others. Now it’s the gorilla in the room and a real competitor to Amazon. 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: SideHu...

Oct 08, 2022•5 min•Ep 2107•Transcript available on Metacast

#2106 - Failure Friday: “I tried to sell something no one wanted…”

In this week’s Failure Friday segment, we hear from a seller of gift baskets for college alumni—or at least, that’s what she *tried* to sell. Unfortunately, buyer demand was non-existent. 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 07, 2022•5 min•Ep 2106•Transcript available on Metacast

#2105 - TBT: “Mantra Medallions” Now Sold in 50+ Stores

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Mantra Medallions, offering inspirational keepsakes to carry in your pocket. Since we last featured him, he’s left social media and focused much more on retail relationships. 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...

Oct 06, 2022•8 min•Ep 2105•Transcript available on Metacast

#2104 - Q&A: "Help, my Amazon competitor is buying fake reviews!"

Today we’re going to hear from an Amazon seller with a problem that is (sadly) not unique: one of their competitors is buying up fake reviews, giving the competitor an advantage in acquiring more customers. Can anything 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 ...

Oct 05, 2022•5 min•Ep 2104•Transcript available on Metacast

#2103 - Q&A: “How can I start a Korean makeup channel on YouTube?”

Today’s caller from Korea wants to make a YouTube channel all about makeup. It’s a hot topic, with some creators earning a lot of money from large subscriber bases. 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: SideHustleSchoo...

Oct 04, 2022•5 min•Ep 2103•Transcript available on Metacast

#2102 - First $1,000: “I do watercolor paintings for corporate events…”

In this week’s First $1,000 segment, we hear from a Colorado artist who makes watercolor paintings at live events. He stumbled into this business idea and wasn’t sure what to charge at first, but then gained momentum. 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...

Oct 03, 2022•5 min•Ep 2102•Transcript available on Metacast

#2101 - Q&A: “Can I buy and resell plane tickets like concert tickets?”

Concert tickets are resellable—why not plane tickets? These days, most airfare is changeable or cancellable with minimal fees, so can you have a business buying early and selling 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 the s...

Oct 02, 2022•4 min•Ep 2101•Transcript available on Metacast

#2100 - Q&A: “I bought and sold 75 Peloton bikes…”

Today’s caller took advantage of the “pandemic Peloton” trend and resold dozens of them! He’s got a story for us, and he’s also wondering how to figure out what comes next. 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: SideHus...

Oct 01, 2022•5 min•Ep 2100•Transcript available on Metacast

#2099 - Failure Friday: “I had tears in my eyes reading the response…”

In this week’s Failure Friday segment, we hear from a jewelry seller who almost gets taken out of commission by a highly negative review. 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 ...

Sep 30, 2022•6 min•Ep 2099•Transcript available on Metacast

#2098 - TBT: “Thirty years a parking lot striper…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a longtime parking lot striper (not stripper!) who’s also written the definitive how-to guide on the topic. 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...

Sep 29, 2022•7 min•Ep 2098•Transcript available on Metacast

#2097 - Q&A: “I want to take my seminar on the road…”

A listener has been teaching a local seminar on speed-reading. She now wants to take her show on the road … and quickly! What does she need to do next? 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...

Sep 28, 2022•4 min•Ep 2097•Transcript available on Metacast

#2096 - Personal Finance Writer Monetizes Medium Posts

Hoping to pay off his debt, a policy analyst begins writing about personal finance. Before long, he was earning more than $5,000/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 the show: SideHustleSchool.com/questions Connect on Tw...

Sep 27, 2022•7 min•Ep 2096•Transcript available on Metacast

#2095 - First $1,000: “I left personal training to become a life coach…”

In this week’s First $1,000 segment, we hear from a personal trainer who makes a big change to become a life coach. Is she able to manifest her way to a full slate of 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: Side...

Sep 26, 2022•7 min•Ep 2095•Transcript available on Metacast