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Side Hustle School

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Side Hustle School

Chris Guillebeau / Onward Project

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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.
 
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When should you hire a designer and when should you “just get it done” on your own? In this listener’s case, she’s really not sure—let’s see if we can help her make the decision. 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 include…
 
Today’s caller has an idea to remix a historical event for a new generation. Forget about civil war reenactments—they want to create a reenactment of classic video game battles! 🍄 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 includ…
 
In this week’s Failure Friday segment, we hear from the co-founder of Master ABA, a site that helps families and professionals help children with autism. The two founders spent a great deal of time developing a membership that wasn’t compelling to their audience, before realizing their mistake and regrouping. Side Hustle School features a new episo…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Mike Lee, the co-founder of Soul CBD. After a successful boxing career, Mike hung up his gloves to enter the small business arena. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their …
 
This caller wants to start a print publication—nothing digital! What’s the business model of this potential business magazine? 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 …
 
A chance encounter at a funeral leads to a second act reselling vintage toy cars. 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 E…
 
In this week’s “First $1,000” segment, we hear from the creator of Metaphor Dice, the writing tool that plays like a game and helps you think more figuratively. How did he make his first $1,000, and what did he learn? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting…
 
After a friend had a negative experience working for a company that didn’t pay up, our caller wants to make sure this doesn’t happen to him. What can he do to be proactive about invoicing and collecting payment? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their…
 
When you have a particular business model in mind but people want to pay you for something else—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…
 
In this week’s Failure Friday segment, we hear from Brock McGroff, founder of TheModestMan.com. While he was focused on other things, his website plateaued in traffic and then began a gradual decline. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This …
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Thais Lage, the young founder of a Florida tutoring business that now has 25 staff tutors. She does this while working full time as an aerospace engineer! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money…
 
Today’s listener wants to make money helping people set up and get the best use out of their new smartwatch. What’s the best course of action? 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 government administrator builds an offramp to his day job by self-publishing books using Kindle Direct Publishing. 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.…
 
In the first version of a brand-new segment for 2022, we hear from Deya Aliaga Kuhnle, the founder of DBM Bootcamp. She now runs a six-figure agency—but how did she make her first $1,000? 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 sho…
 
Today’s listener wants to start 40 side hustles in 2022! Let’s see how we can support his ambitious project. 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 no…
 
We’re back with an all-new season! Here’s how year six (!) of Side Hustle School will work. Among other highlights: a new weekly segment, more stories + Q&A, and a $1,000 giveaway to one special listener. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. T…
 
Happy New Year’s Eve! In this week’s Failure Friday segment, we hear from Jennifer Earle, founder of Chocolate Ecstasy Tours. With her guided tour business in full swing, she decides to start a self-guided version called Taste Tripper. Unfortunately, this expansion proves to be unsustainable. Show notes: SideHustleSchool.com Email: team@sidehustles…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Radical Tea Towels, a British family business that promotes historical progress and modern messages of change. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisgu…
 
A listener thinks he’s found the ultimate arbitrage market—right before his eyes! Can he import contact lenses from outside the U.S. (where the price is much lower) and resell them at home? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on…
 
A nomadic designer launches an app development career in Switzerland, creating more than ten apps in a single year. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If …
 
Do you start with your idea, or start with the ideal platform for your idea? Today’s caller wants to remain “platform agnostic.” How should he proceed? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris'…
 
A home chef draws on her food limitations to whip up a popular blog that earns $5,000/month from ad revenue. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're …
 
A very special listener question came in overnight—all the way from the North Pole! Let’s see if we can help this caller with an urgent supply chain problem. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit …
 
In this week’s Failure Friday segment, we hear from Allen Chiang, the owner of Retro Radio Farm. At first, he has too much business to handle—but when Facebook advertising becomes less profitable, he has too little. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of The Cut Buddy, a tool for home haircuts. With everyone staying home last year, his business took off! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Con…
 
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