Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•sidehustleschool.com

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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/

Episodes

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool...

Jan 23, 2023•6 min•Ep 2214•Transcript available on Metacast

#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 time. 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. Show notes: SideHust...

Jan 22, 2023•4 min•Ep 2213•Transcript available on Metacast

#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 idea, a terrible one, or somewhere in between? 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...

Jan 21, 2023•5 min•Ep 2212•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions ...

Jan 20, 2023•5 min•Ep 2211•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschoo...

Jan 19, 2023•6 min•Ep 2210•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on t...

Jan 18, 2023•4 min•Ep 2209•Transcript available on Metacast

#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 extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twi...

Jan 17, 2023•5 min•Ep 2208•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Co...

Jan 16, 2023•5 min•Ep 2207•Transcript available on Metacast

#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. 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. Show notes: SideHustleSchool.com Email: team@sideh...

Jan 15, 2023•5 min•Ep 2206•Transcript available on Metacast

#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? 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. Show notes: SideHustleSchool.com Email: team@sid...

Jan 14, 2023•5 min•Ep 2205•Transcript available on Metacast

#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, 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustle...

Jan 13, 2023•5 min•Ep 2204•Transcript available on Metacast

#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 without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @c...

Jan 12, 2023•5 min•Ep 2203•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehu...

Jan 11, 2023•5 min•Ep 2202•Transcript available on Metacast

#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 advantage of this. 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. Show ...

Jan 10, 2023•6 min•Ep 2201•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Ema...

Jan 09, 2023•5 min•Ep 2200•Transcript available on Metacast

#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. Let’s give them some tips! 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. Show...

Jan 08, 2023•5 min•Ep 2199•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@si...

Jan 07, 2023•6 min•Ep 2198•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Ema...

Jan 06, 2023•5 min•Ep 2197•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool...

Jan 05, 2023•5 min•Ep 2196•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool....

Jan 04, 2023•5 min•Ep 2195•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.co...

Jan 03, 2023•4 min•Ep 2194•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustle...

Jan 02, 2023•6 min•Ep 2193•Transcript available on Metacast

#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. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagr...

Jan 01, 2023•8 min•Ep 2192•Transcript available on Metacast

#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 sponsored for her own RV adventure.) 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. Show notes: SideHustleSchool.co...

Dec 31, 2022•5 min•Ep 2191•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com ...

Dec 30, 2022•6 min•Ep 2190•Transcript available on Metacast

#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 extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on...

Dec 29, 2022•5 min•Ep 2189•Transcript available on Metacast

#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 earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitte...

Dec 28, 2022•4 min•Ep 2188•Transcript available on Metacast

#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 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on t...

Dec 27, 2022•5 min•Ep 2187•Transcript available on Metacast

#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. Here’s the story of one guy who’s well on his way. 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...

Dec 26, 2022•6 min•Ep 2186•Transcript available on Metacast

#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 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. Show notes: SideHustleSch...

Dec 25, 2022•4 min•Ep 2185•Transcript available on Metacast