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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
 
After being asked by her friends and family to give them straightforward advice, a writer decides to see if she can get paid to make decisions for other people. 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 less…
 
A caller from the U.K. is wondering about how to use his degree in sport and exercise science in marketing a coaching service. 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 …
 
If you’re producing a safety-conscious event, how can you market it in a way that overcomes the fear many people have during the pandemic? 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 s…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a doctor who makes plush toys in the shape of human organs to teach kids about the body. 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 gui…
 
Today’s listener is wondering about Bitcoin, the world’s best known cryptocurrency—should he accept it as payment for his new app? 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 d…
 
After a partner in a marketing firm fulfills a lifelong dream of writing his own novel, he begins ghostwriting for others, penning children’s books and even poetry. 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 …
 
“Oh no, I got a complaint!” Every side hustler worries about it, but dealing with complaints doesn’t need to be overwhelming. These three strategies will help you make most customers happy, *and* to know when to stand your ground. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wit…
 
When a mechanical engineer and 4x4 fanatic tries to save money on his Jeep upgrades, he wrangles with local vendors for free parts—and winches himself to a new source of income. 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…
 
A listener from Singapore sells biodegradable party cups with cheerful designs. She’s selling them on Amazon, and wondering how to get noticed by more people. 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 lesson…
 
Our story of a woman in New Zealand who sells virtual paint brushes for iPad users was very popular, and a listener is wondering: are there any other “digital assets” that can be made 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,…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a wedding florist in Oklahoma who has a creative idea to offer DIY wedding flowers to brides across the country. 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, th…
 
A listener wants to build a fan site showcasing Black superheroes from DC and Marvel comics—how can he make money from 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…
 
After selling an unwanted collection of antiques, an insurance manager goes on a hunt for more inventory. 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. Share: #Si…
 
Today’s caller is hoping to improve her writing streak. How can we help her keep writing 1,000 words a day? 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. Share: #…
 
While staying up late one night, a mom and her daughter decide that they want to start a business together. 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. Share: #…
 
Today’s listener is starting to get paid for real estate photography. Should she offer a money-back guarantee in case a client is unsatisfied? 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…
 
They’ve been in the military for more than a decade, and they’re thinking ahead. What might be a good side hustle for a couple that moves frequently and might be deployed? 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 …
 
In this week’s “Throwback Thursday / Where are they now?” segment, we revisit a neighborhood coffee lover who follows a whim to a mobile roasting operation. 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 …
 
Aside from your website, your email list may be the most important tool in growing any new business. After you get it set up, 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…
 
When a professional development specialist can’t find “just the right” piece of jewelry, she makes it herself. Six years later, she’s mined a second income creating minimalist, Boho-chic jewelry. 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,…
 
How can you transition between projects (or a job and a side hustle) without constantly losing your flow—and how can you start a completely new project without just creating more “stuff” to worry about? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi…
 
A mom of two young daughters goes to look for used clothes, and ends up finding a new pastime of reselling items on Poshmark and other platforms. 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 listene…
 
When you upgrade your iPhone or Android smartphone, what do you do with the old one? Many of us trade them in, knowing that we aren’t getting a great deal but not wanting to hassle with an alternative. Today’s listener is hoping to profit from this problem—how should they proceed? Side Hustle School features a new episode EVERY DAY, featuring detai…
 
Today’s caller (from Egypt!) is teaching software development through an apprenticeship model, but most of his students aren’t paying. How can he convert some of these free students into customers? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This yea…
 
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an accountant who sells spreadsheet templates and other financial resources to creatives. 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 gu…
 
A listener is trying to decide how to price a new online service. Should she use the common SAAS (“software as a service”) model, or are there alternatives? 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 …
 
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