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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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#block-80ebf5da h2 { width: 401px; } What It’s About When the pandemic causes everyone to go into lockdown, this craftsman straps in and pivots. Notes from Chris Episode 1798 I believe we can learn as much from failure as we can from success, if not more. It’s with this principle in mind that I offer you a weekly segment called Failure Friday: a co…
 
In this week’s Failure Friday segment, we hear from Chris Cavallari, who sells high-quality products with a Maine vibe. In March 2020, he prepared for his first wholesale trade show—and then the world closed down. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @ch…
 
#block-9210bc23 h2 { width: 401px; } What It’s About A champignon update from this fungi growing team. Notes from Chris Episode 1797 Welcome to Throwback Thursday / “Where are they now?” where we take an in-depth look at someone who’s story has evolved considerably since we first featured them. Last week, we heard from a former attorney and White H…
 
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…
 
#block-bcaf0da0 h2 { width: 401px; } What It’s About Today’s caller is in search of the perfect reselling product. Notes from Chris Episode 1796 Reselling is a simple business, and it’s easy enough to find something to sell once. Anyone can do it today. But for a real moneymaker, you need a source of products you can go to over and over. Today’s li…
 
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…
 
#block-3bc8444f h2 { width: 401px; } What It’s About It’s coming up Roses for these two sisters. Words of Wisdom Rachel shares an important reminder, “Don’t get stuck in analysis paralysis. If you spend too much time thinking about anything, you can talk yourself out of it.” Fun Fact Schitt’s Creek showrunner/actor Dan Levy was watching Keeping up …
 
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…
 
#block-bb511841 h2 { width: 401px; } What It’s About Today’s listener wants to publish a paid newsletter. Notes from Chris Episode 1794 Welcome to a new week! Paid newsletters have really taken off. I mentioned one recently that earns more than $300,000 a year. And guess what? It’s not the only one. One of the topics that is most lucrative probably…
 
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…
 
#block-83606d0a h2 { width: 401px; } What It’s About An expat living in South Africa teaches a global audience on how to master their finances. [podcast_details] Words of Wisdom Morgan shares some important advice about taking risks, “Magic happens outside of your comfort zone. Every time I feel nervous or scared about doing something, I get excite…
 
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…
 
#block-051e5d50 h2 { width: 401px; } What It’s About Today’s listener wants to know the pros and cons of selling content as a bundle. Notes from Chris Episode 1792 Today’s caller is making a podcast, video series, and maybe something else. All of it will be for sale, but they aren’t sure how to package it. Should it be a single “bundle” or sold sep…
 
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…
 
#block-3f42c667 h2 { width: 401px; } What It’s About A perfect SAT score doesn’t always mean a yes. Notes from Chris Episode 1791 I believe we can learn as much from failure as we can from success, if not more. It’s with this principle in mind that I offer you a weekly segment called Failure Friday: a collection of short stories all about mistakes,…
 
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…
 
#block-3240c309 h2 { width: 401px; } What It’s About An update from a former White House aide who now serves podcasters worldwide. Notes from Chris Episode 1790 Happy Thanksgiving! Welcome to Throwback Thursday / “Where are they now?” where we take an in-depth look at someone who’s story has evolved considerably since we first featured them. Last w…
 
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…
 
#block-92f129b6 h2 { width: 401px; } What It’s About Today’s listener seeks a prescription for the best (and most ethical!) way to market to health professionals. Notes from Chris Episode 1789 Happy Thanksgiving! Of course, in Canada Thanksgiving is old news—they get it a couple of weeks before us. Today’s caller is a Canadian listener launching a …
 
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…
 
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