Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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.

Author

Chris Guillebeau

Episodes

#2208 - Q&A: “Which online resources are worth paying for?” 17.01.2023 5:14

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: SideHustleSchoo...

#2207 - First $1,000: “I was over the moon with my first sale…” 16.01.2023 4:50

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: Sid...

#2206 - Q&A: “Can you sue telemarketers and get paid?” 15.01.2023 4:59

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 les...

#2205 - Q&A: “No one is seeing my Instagram posts…” 14.01.2023 5:07

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 l...

#2204 - Failure Friday: “I had to reel in my losses and start from scratch…” 13.01.2023 4:57

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 eac...

#2203 - TBT: “Teaching pole dancing has been incredibly rewarding…” 12.01.2023 4:59

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 E...

#2202 - Q&A: “Can you really work two full-time jobs simultaneously?” 11.01.2023 5:25

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 less...

#2201 - Q&A: “How can you buy and resell electric vehicles?” 10.01.2023 5:36

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...

#2200 - First $1,000: “I started by setting up a booth at the farmer's market…” 09.01.2023 4:44

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 f...

#2199 - Q&A: “How to make a killer sales page?” 08.01.2023 4:41

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...

#2198 - Q&A: “How to sell a ‘stop smoking in 30 days’ course? 07.01.2023 5:53

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...

#2197 - Failure Friday: “On the day of the wedding, a huge storm rolled in…” 06.01.2023 5:28

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 f...

#2196 - TBT: “The monthly retainer was a huge confidence-booster…” 05.01.2023 4:58

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...

#2195 - Q&A: “My revenue has plateaued at $180,000/year…” 04.01.2023 4:55

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 li...

#2194 - Q&A: "How do you choose what to focus on?" 03.01.2023 4:15

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....

#2193 - First $1,000: “I make an extra $100/day fixing broken phone screens…” 02.01.2023 5:55

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 ea...

#2192 - Side Hustle School Season 7 Starts TODAY 01.01.2023 7:48

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 B...

#2191 - Q&A: “Driving an RV across the country—can I get sponsored?” 31.12.2022 4:43

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 inclu...

#2190 - Failure Friday: “I think I had some unrealistic expectations…” 30.12.2022 6:14

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 listene...

#2189 - TBT: “I was just a girl with a passion for plants…” 29.12.2022 4:38

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: SideHustle...

#2188 - Q&A: “What's the best way to sell a simple digital download?” 28.12.2022 3:46

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.c...

#2187 - Q&A: “How to share men's lifestyle advice that isn’t toxic…” 27.12.2022 5:05

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&am...

#2186 - First $1,000: “I went door-to-door selling home alarms…” 26.12.2022 5:49

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...

#2185 - Q&A: “I have a hard time asking for money…” 25.12.2022 4:05

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...

#2184 - Q&A: “Can I buy an existing small business?” 24.12.2022 4:32

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...