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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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show series
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the business manager of Phenomenal Fungi, which sells tinctures, cultures, and mushroom merch. It’s been a busy year in the land of shrooms! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitt…
 
It’s easy enough to find something you can buy and sell once. But for a real moneymaker, you need a source of products you can go to over and over. Today’s listener wonders: where is it?? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on I…
 
Two sisters fold it all in with a self-publishing venture that tastes like success. 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 enjoying the show, please…
 
Paid newsletters have really taken off, with some earning multiple six-figures for their writers. This listener has an astute observation and an idea. How can we help her “get the bag”? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Ins…
 
An American accountant living in South Africa creates a financial wellbeing course for small business owners. The passive income she earns from the course allows her to drop many of her clients. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Conne…
 
Today’s caller is making a podcast, video series, and maybe something else. All of it will be for sale, and they aren’t sure how to package it. Should it be a single “bundle” or sold separately? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Conne…
 
In this week’s Failure Friday segment, we hear from the founder of a standardized test prep service. Before he started his business, he earned a perfect score on the SAT—and then pitched a book that was rejected by more than 100 literary agents and publishers. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHus…
 
Happy Thanksgiving! In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a former attorney and White House aide who starts a service helping businesses with podcasts. It’s grown into a 7-figure operation! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Conne…
 
This Canadian listener is launching a learning platform for pediatric anesthesia. How can she reach her intended audience—and how can she serve professionals in this market from less-developed countries? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguilleb…
 
Instead of heading to the elementary school classroom, this new teaching grad earns a good living making custom tiki bars for homeowners. Why not! 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 mai…
 
Podcasts have a “discoverability problem”: they don't rank in search terms or get links from other sites. If you have a new show, what can you do to make sure people will find it? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram…
 
After discovering the life changing magic of polymer clay, an Aussie uses her time in lockdown to create a one-stop shop for the maker community. 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…
 
A caller from New York City becomes well known for posting drawings and paintings to an Instagram account during pandemic lockdowns. Now he’s wondering: how can he monetize the attention he’s received? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebea…
 
In this week’s Failure Friday segment, we hear from Rupert Hunt, the founder of SpareRoom.com. It’s now the world’s largest roommate finder service—but in the early days, the team struggled to commit to it. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguil…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Ella Cordial-Brockelsby, the owner of Cordial Greetings. She uses pyrography (!) to make and sell woodburned home decor, art, and drumsticks. This episode is on fire... Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.co…
 
Today’s caller started a blog with enthusiasm but then it fell into decline. What happens now? 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 enjoying the s…
 
Two friends team up to build “Airbnb for fishing,” a marketplace of fishing trips that connects guides and clients worldwide. 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: ChrisGuillebe…
 
Today’s caller wants to understand the business of app-making. What’s the average app designer income? What about the outliers? 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: ChrisGuille…
 
As her health improved, this Aussie of Lebanese heritage started converting meat-based recipes to vegan equivalents. She’s now sharing her recipes with the world. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries V…
 
A listener loves rain barrels (this is a thing) and she’s found the perfect one in the Netherlands—but she lives in the U.S. Might she be able to partner with the company to become their national distributor? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisgu…
 
In this week’s Failure Friday segment, we hear from the maker of “Big Bat Houses.” When demand for his product plummeted at the start of the pandemic, he was forced to regroup. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Bill Simpson, chief tap dancer of HowtoTapDance.com. From his homebase of Melbourne, Australia, he teaches the art of the tap to students all over the world. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions…
 
These days, there are many options to host your online course: Thinkific, Teachable, Kajabi, and others. Is there a clear winner? 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: ChrisGuil…
 
In need of extra money, an enterprising grad student starts selling his unused items online. He then branches out into consignment sales, with a twist: most of his inventory comes from friends and family. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguille…
 
Today’s listener made a website with something for sale, opened the cart for business, and no one bought anything. Womp, womp … what should he do next? 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'…
 
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