Chris Guillebeau

Side Hustle School

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.

Be sure to visit the podcast's website and support the creator: sidehustleschool.com

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Nov 3, 2026

Where to listen?

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Episodes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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...

#2183 - Failure Friday: “The sleigh kept getting bogged down…” 23.12.2022

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&am...

#2182 - TBT: “I’m now charging $100/hour for personal training…” 22.12.2022

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 guid...

#2181 - Q&A: “How to plan for a big New Year's Sale?” 21.12.2022

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 s...

#2180 - Q&A: ”My customer tried to barter with me ... after the sale!” 20.12.2022

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...

#2179 - First $1,000: “I had no idea Hula Hoops were a seasonal business…” 19.12.2022

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 inc...

#2178 - Q&A: “An English-language anime club in Japan…” 18.12.2022

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:...

#2177 - Q&A: “Are pay-per-click ads cheaper on Pinterest?” 17.12.2022

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. T...

#2176 - Failure Friday: “No one wanted my idea, even for free…” 16.12.2022

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 se...

#2175 - TBT: “I’ve matched my previous salary with 15 hours a week…” 15.12.2022

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 th...

#2174 - Q&A: “Broker-liaison for overseas web developers…” 14.12.2022

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: SideHustleSchoo...

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