Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau 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.

Hosted on Acast. See acast.com/privacy for more information.

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Episodes

#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, 20236 minEp. 2201

#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, 20235 minEp. 2200

#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, 20235 minEp. 2199

#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, 20236 minEp. 2198

#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, 20235 minEp. 2197

#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, 20235 minEp. 2196

#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, 20235 minEp. 2195

#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, 20234 minEp. 2194

#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, 20236 minEp. 2193

#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, 20238 minEp. 2192

#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, 20225 minEp. 2191

#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, 20226 minEp. 2190

#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, 20225 minEp. 2189

#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, 20224 minEp. 2188

#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, 20225 minEp. 2187

#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, 20226 minEp. 2186

#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, 20224 minEp. 2185

#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 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@sidehustl...

Dec 24, 20225 minEp. 2184

#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 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 ...

Dec 23, 20226 minEp. 2183

#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 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@...

Dec 22, 20225 minEp. 2182

#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 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: SideHustle...

Dec 21, 20224 minEp. 2181

#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 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...

Dec 20, 20225 minEp. 2180

#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 learn? 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.c...

Dec 19, 20225 minEp. 2179

#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 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/question...

Dec 18, 20225 minEp. 2178

#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 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 not...

Dec 17, 20225 minEp. 2177

#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 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 sh...

Dec 16, 20225 minEp. 2176

#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 just three hours of coaching per 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 wee...

Dec 15, 20227 minEp. 2175

#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 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...

Dec 14, 20225 minEp. 2174

#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 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: SideHustleSch...

Dec 13, 20224 minEp. 2173

#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 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@sidehustl...

Dec 12, 20225 minEp. 2172
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