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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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Side Hustle School
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#2222 - Q&A: “I want to make and sell a pickleball paddle…”
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Did you know that pickleball is the fastest-growing sport in the world? In this episode, a listener from Arizona wonders about making and selling his own paddle. 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 les…
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Side Hustle School
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#2221 - First $1,000: “I get paid to take stock photos for licensing…”
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6:59
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6:59
In this week’s First $1,000 segment, we hear from a photographer who learns to take photos for stock image sites, earning a royalty every time one is licensed. Pretty cool! 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…
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Side Hustle School
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#2220 - Q&A: “Can't find the time to grow my business!”
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7:35
We often identify a lack of time as the primary obstacle to starting or growing a side hustle. Often, however, there’s a deeper problem behind the time struggle. Where’s the real resistance? 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 …
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Side Hustle School
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#2219 - Q&A: “A subscription to manage other subscriptions…”
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7:27
How many paid subscriptions do you have right now? I’m embarrassed to say I don’t know the answer for myself. Today, a caller wants to develop a tool to help people save money on their recurring subscriptions. I love this idea! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money withou…
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#2218 - Failure Friday: “I held a sock puppet show while processing transactions…”
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7:11
In this week’s Failure Friday segment, we hear from a sock seller who eagerly sets up at a trade show, only to realize his credit card processing equipment isn’t working. Oh no! 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…
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#2217 - TBT: “I put in long hours and worked hard to deliver quality work…”
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6:22
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a web developer who goes from corporate to self-employed, hunting down clients on online job boards like Upwork. 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…
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#2216 - Q&A: "Ebay selling feels less personal now..."
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7:52
Longtime listeners know that I got my start in the world of entrepreneurship when I was 19 and learned to sell on eBay. Today, a caller wonders: “Has eBay changed? It feels less personal.” 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 sh…
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#2215 - Q&A: “How to create ‘transformational’ online courses?”
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6:25
What’s the latest in online education? That’s what one of our listeners who’s also a course creator wants to know. I’ll focus my answer on “transformation,” an increasingly important concept for anyone who wants to offer any type of online course to be aware of. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…
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#2214 - First $1,000: “I earn £2,500 per month leading London walking tours…”
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7:13
In this week’s First $1,000 segment, we hear from a walking tour guide in London. He leads tours only on weekends and brings in an extra £2,500 ($3,000) per 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 l…
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#2213 - Q&A: “Can I sell a calendar sometime other than January?”
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5:48
Some business ideas are better suited for certain seasons—as we heard recently from a caller who referenced an episode about letters from Santa. This leads to a challenge for today’s caller, who has a brilliant idea … at an inopportune time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extr…
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#2212 - Q&A: “Is there a summer camp for side hustlers?”
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6:15
Today’s caller has an idea for adult summer camp with a side hustle focus. One of the reasons we have this segment is to look at different business ideas and consider how feasible they might be. So—is this an awesome idea, a terrible one, or somewhere in between? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies o…
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#2211 - Failure Friday: “The client was shocked by the amount of taxes they owed…”
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6:25
In this week’s Failure Friday segment, we hear from a new bookkeeper who makes a big mistake: she overstates the income on a client’s return. Yikes! 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 list…
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#2210 - TBT: “Expanding my product line paid off in a big way…”
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7:01
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7:01
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a seller of planners and journals. After expanding her product line and listening to customers, the business is thriving. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This…
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#2209 - Q&A: “Can I deduct clothes and haircuts on my taxes?”
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5:46
If you have a side hustle or even if you’re starting one and it doesn’t have revenue yet, you might be able to save a lot of money on your tax deductions. Listen to this caller’s question! 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 sh…
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#2208 - Q&A: “Which online resources are worth paying for?”
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6:44
You could spend an unlimited amount of money on services and resources these days. What is essential—and what can you not 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. This year, the show includes free guided lessons and listener Q&A sever…
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#2207 - First $1,000: “I was over the moon with my first sale…”
6:20
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6:20
In this week’s First $1,000 segment, we hear from an Etsy shop who’s served more than 1,500 customers and counting. How did she first get started? 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 listen…
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#2206 - Q&A: “Can you sue telemarketers and get paid?”
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6:29
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6:29
A caller refers to a story of a guy who earned $7,000 from suing an annoying telemarketing company. What a great idea! The next time you get an annoying sales call, don’t hang up until you get the caller’s info. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their…
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#2205 - Q&A: “No one is seeing my Instagram posts…”
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6:37
Aristotle once posed the question that philosophers have been debating ever since: if you post a selfie on Instagram and no one likes it, does it make a sound? (Also: how can you get more people to see your posts? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting the…
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#2204 - Failure Friday: “I had to reel in my losses and start from scratch…”
6:27
6:27
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6:27
In this week’s Failure Friday segment, we hear from a New England fisherman who opens his own fishing shop. All goes well until a big sporting goods store comes to town. 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…
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#2203 - TBT: “Teaching pole dancing has been incredibly rewarding…”
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6:29
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Florida pole dance instructor. She’s hooked! 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 …
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#2202 - Q&A: “Can you really work two full-time jobs simultaneously?”
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6:55
Multiworking—where people work multiple, full-time jobs simultaneously without either employer being aware of it—is a product of the pandemic remote work lifestyle. What are some tips for doing it successfully? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their …
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#2201 - Q&A: “How can you buy and resell electric vehicles?”
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7:06
In a few short years, electric vehicles (EVs) have gone from something novel to something that you see everywhere. When there’s high demand and relatively low supply, that creates price pressure. Our caller wants to know if they can take advantage of this. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of peopl…
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#2200 - First $1,000: “I started by setting up a booth at the farmer's market…”
6:14
6:14
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6:14
In this week’s First $1,000 segment, we hear from a woman who makes and sells essential oils. By customizing her product line and building relationships at a local farmers market, the business now provides half of her income. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without …
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#2199 - Q&A: “How to make a killer sales page?”
6:11
6:11
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6:11
Today’s caller is looking to create a sales page that converts well. They want to overcome the objections of anyone who looks at it with interest yet skepticism—which is how most of us feel when we’re thinking of buying something. Let’s give them some tips! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of peop…
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#2198 - Q&A: “How to sell a ‘stop smoking in 30 days’ course?
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7:23
Today’s caller wants to offer a course on quitting smoking, based on techniques that worked for them during their own struggle. They’d like to know they can sell it more effectively, or at least position it better. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting th…
