Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

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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#2219 - Q&A: “A subscripti...

01.28.2023

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 ...

Side Hustle School episodes:

01.28.2023 #2219 - Q&A: “A subscription to manage other subscriptions…” 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 ...
01.27.2023 #2218 - Failure Friday: “I held a sock puppet show while processing transactions…” 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 ...
01.26.2023 #2217 - TBT: “I put in long hours and worked hard to deliver quality work…” 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 ...
01.25.2023 #2216 - Q&A: "Ebay selling feels less personal now..." 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 ...
01.24.2023 #2215 - Q&A: “How to create ‘transformational’ online courses?” 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 ...
01.23.2023 #2214 - First $1,000: “I earn £2,500 per month leading London walking tours…” 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 ...
01.22.2023 #2213 - Q&A: “Can I sell a calendar sometime other than January?” 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 ...
01.21.2023 #2212 - Q&A: “Is there a summer camp for side hustlers?” 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 ...
01.20.2023 #2211 - Failure Friday: “The client was shocked by the amount of taxes they owed…” 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 ...
01.19.2023 #2210 - TBT: “Expanding my product line paid off in a big way…” 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 ...
01.18.2023 #2209 - Q&A: “Can I deduct clothes and haircuts on my taxes?” 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 ...
01.17.2023 #2208 - Q&A: “Which online resources are worth paying for?” 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 ...
01.16.2023 #2207 - First $1,000: “I was over the moon with my first sale…” 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 ...
01.15.2023 #2206 - Q&A: “Can you sue telemarketers and get paid?” 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. ...
01.14.2023 #2205 - Q&A: “No one is seeing my Instagram posts…” 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? ...
01.13.2023 #2204 - Failure Friday: “I had to reel in my losses and start from scratch…” 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, ...
01.12.2023 #2203 - TBT: “Teaching pole dancing has been incredibly rewarding…” 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 ...
01.11.2023 #2202 - Q&A: “Can you really work two full-time jobs simultaneously?” 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 ...
01.10.2023 #2201 - Q&A: “How can you buy and resell electric vehicles?” 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 ...
01.09.2023 #2200 - First $1,000: “I started by setting up a booth at the farmer's market…” 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 ...
01.08.2023 #2199 - Q&A: “How to make a killer sales page?” 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. ...
01.07.2023 #2198 - Q&A: “How to sell a ‘stop smoking in 30 days’ course? 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 ...
01.06.2023 #2197 - Failure Friday: “On the day of the wedding, a huge storm rolled in…” In this week’s Failure Friday segment, we hear from an event planner specializing in weddings. Everything goes perfectly at weddings, right? Okay, not so much … and in this particular wedding, everything goes perfectly WRONG. Side Hustle School features a ...
01.05.2023 #2196 - TBT: “The monthly retainer was a huge confidence-booster…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance commercial animator who works on TV shows and other projects worldwide. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
01.04.2023 #2195 - Q&A: “My revenue has plateaued at $180,000/year…” Today’s caller has built her side hustle to a thriving brand. They’re earning about $50,000 a year on $180,000 in sales. But even though that’s great, they have a problem: the business isn’t growing. Side Hustle School features a new ...
01.03.2023 #2194 - Q&A: "How do you choose what to focus on?" Today’s listener wants to start a retail business, but they aren’t sure whether it should be a clothing line or a home decor store. How can we help them decide? Side Hustle School features a new episode EVERY DAY, featuring ...
01.02.2023 #2193 - First $1,000: “I make an extra $100/day fixing broken phone screens…” In this week’s First $1,000 segment, we hear from a listener who’s earning a few thousand dollars a month with a very simple business model: fixing broken phone screens! Side Hustle School features a new episode EVERY DAY, featuring detailed ...
01.01.2023 #2192 - Side Hustle School Season 7 Starts TODAY We’re back with an all-new season! Here’s how year seven (!) of Side Hustle School will work. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
12.31.2022 #2191 - Q&A: “Driving an RV across the country—can I get sponsored?” Everyone, let’s pack all of our stuff up in an RV and hit the road. We just need a tripod for all those #vanlife photos we’re going to be taking! (Also, our caller wants to know how she can get ...
12.30.2022 #2190 - Failure Friday: “I think I had some unrealistic expectations…” In this week’s Failure Friday segment, we hear from a digital artist from the U.K. When he tried to launch an NFT project with 5,000 works of art, he sold only 10% before giving up and moving on. Side Hustle ...
12.29.2022 #2189 - TBT: “I was just a girl with a passion for plants…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an online plant seller who’s sold thousands of succulents. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
12.28.2022 #2188 - Q&A: “What's the best way to sell a simple digital download?” Let’s say you have something to sell that is digitally delivered. What’s the best way to accept payment and get the item to buyers? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
12.27.2022 #2187 - Q&A: “How to share men's lifestyle advice that isn’t toxic…” I always love to hear from our community. You all are doing some interesting things! Let’s see if I can be somewhat helpful to Brody, who wants to share “non-toxic men’s lifestyle advice.” Side Hustle School features a new episode ...
12.26.2022 #2186 - First $1,000: “I went door-to-door selling home alarms…” In this week’s First $1,000 segment, we hear from a real-life door-to-door salesman. No really, this is a thing! Some door knockers can earn six figures a year or more, as long as they’re able to cope with repeated rejection. ...
12.25.2022 #2185 - Q&A: “I have a hard time asking for money…” Merry Christmas! Our listener today is a financial advisor who specializes in helping clients tackle their debts and get their finances in order. Just one problem: Julie doesn’t like charging for this important work. What should she do? Side Hustle ...
12.24.2022 #2184 - Q&A: “Can I buy an existing small business?” What if we could skip the whole startup phase of your side hustle and go straight to burgeoning retailer? None of that whole ideation thing, none of that trial and error—just operating a successful business? Side Hustle School features a ...
12.23.2022 #2183 - Failure Friday: “The sleigh kept getting bogged down…” In this week’s Failure Friday segment, we hear from a previous caller from the North Pole. Last year he was experiencing a supply chain crisis—this year, he tells a story of his early days. Side Hustle School features a new ...
12.22.2022 #2182 - TBT: “I’m now charging $100/hour for personal training…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a personal trainer who goes from clientless to fully booked. He’s raised his rates and has learned a lesson about burnout along the way. Side Hustle ...
12.21.2022 #2181 - Q&A: “How to plan for a big New Year's Sale?” January is a big month for the wellness industry, much more than the end-of-year holidays we’re in the midst of now. How can gym owners, trainers, nutritionists, and other wellness professionals prepare to capitalize on increased interest? Side Hustle School ...
12.20.2022 #2180 - Q&A: ”My customer tried to barter with me ... after the sale!” This really happened: after attending a paid workshop, a customer tries to barter by offering her energy healing services in lieu of payment. Uh … how should the event planner handle it? Side Hustle School features a new episode EVERY ...
12.19.2022 #2179 - First $1,000: “I had no idea Hula Hoops were a seasonal business…” In this week’s First $1,000 segment, we hear from Holly the Hula Hoop Hustler. She’s now earning up to $2,000/month selling hula hoops on Amazon. But what about her first $1,000—how did she make that happen, and what did she ...
12.18.2022 #2178 - Q&A: “An English-language anime club in Japan…” Today’s caller wants to start an English-speaking anime club in Japan. With the country recently re-opened for visitors, let’s get this party started! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
12.17.2022 #2177 - Q&A: “Are pay-per-click ads cheaper on Pinterest?” The two largest pay-per-click platforms are Facebook and Google—it’s how they make almost all of their money! But you can also run PPC ads on Reddit, YouTube, streaming platforms like Hulu, and even Pinterest—which is what our caller is wondering ...
12.16.2022 #2176 - Failure Friday: “No one wanted my idea, even for free…” In this week’s Failure Friday segment, we hear from a personal trainer who starts a virtual shoe-fitting service. Unfortunately, it stumbles out of the gate and never hits its stride. Side Hustle School features a new episode EVERY DAY, featuring ...
12.15.2022 #2175 - TBT: “I’ve matched my previous salary with 15 hours a week…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Los Angeles film editor who sets out to create a business serving other industry professionals. He now earns as much as his previous salary with ...
12.14.2022 #2174 - Q&A: “Broker-liaison for overseas web developers…” A caller has an idea to connect overseas web developers with clients in the U.S. How would this work, and how can they profit from it? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
12.13.2022 #2173 - Q&A: “Does anyone make money from cat videos??” Let’s talk about two of my favorite things in the world: cats and cat videos. A listener wonders if there’s any way to monetize them. How do all those cats get paid?? Side Hustle School features a new episode EVERY ...
12.12.2022 #2172 - First $1,000: “I help people get back their hacked accounts…” In this week’s First $1,000 segment, we hear from a coder with an unusual side hustle: he helps clients recover their hacked or lost Facebook accounts. In his first month, he’s already served fifteen people! Side Hustle School features a ...
12.11.2022 #2171 - Q&A: “Starting an instructional workshop…” A caller from Ireland wants to start his own instructional workshop. How are live events different from other services—and what are some tips for running one well? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
12.10.2022 #2170 - Q&A: “How do I focus on retaining clients?” Today we’re going to hear from a CPA in the midwest who wants to focus on retaining clients. This is more important than finding new ones! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...

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