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.

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

#2033 - Video Game Writing Class Is Real-Life Gamechanger 26.07.2022

An online teacher and mother-of-four creates a new learning experience that she calls “video game social clubs.” She’s currently earning $4,000/month working part-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...

#2032 - First $1,000: “Hyperfluent” Language Service Translates Into Profit 25.07.2022

In this week’s First $1,000 segment, we hear from Eva Rosales, the founder of Hyperfluent. Her consultancy offers lots of different services, all focused around language acquisition and translation. 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 list...

#2031 - Q&A: “What is Goblintown, and should I mint a free NFT??” 24.07.2022

A new trend in the wild world of NFTs comes from creators offering free assets (digital artwork) during an initial mint process. In some cases, the NFTs end up selling for thousands of dollars later—should you start trying to get them when they’re free?  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. T...

#2030 - Q&A: “I want to be the ‘posture guy,’ but how will I make money?” 23.07.2022

Today’s caller seeks to brand himself as The Posture Guy. Sounds catchy! How can he turn this memorable branding into a steady source of 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: Side...

#2029 - Failure Friday: Failure Friday: “We had no desire to help college students cheat…” 22.07.2022

In this week’s Failure Friday segment, we hear from the co-founder of Next Day Animations. Great business name! But before they found their ideal customer, the team tried a different name that didn’t work so well. 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...

#2028 - TBT: “Go Last Minute” Travel Site Goes Global 21.07.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Go Last Minute, a travel booking portal that now offers a whitelist option for licensing.  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...

#2027 - Q&A: “Too tired to hustle at the end of the day…” 20.07.2022

At the end of a long workday, how do you find the energy to work on your side hustle? Let’s give this listener (and you!) three quick tips to manage the overwhelm. 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...

#2026 - This Canadian Cleaning Service Earns $2 Million/Year 19.07.2022

A university lab technician cleans up with a local service business that grows to $2 million in revenue and 500 5-star reviews—all without quitting his job.     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. S...

#2025 - First $1,000: The Las Vegas Ghostwriting Service 18.07.2022

In this week’s First $1,000 segment, we hear from a Las Vegas ghostwriter. After writing a novel of his own, he branches out to write for casino bosses and other clients.  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 e...

#2024 - Q&A: "I'm opening a hair salon in a new area. How can I build my clientele?” 17.07.2022

A hair stylist is leaving her job to start her own salon. Whoo hoo! What are some simple things she (or any service provider) can do to kickstart the client list?  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...

#2023 - Q&A: “How can I land paid speaking gigs?” 16.07.2022

Our caller recently gave a talk at a women’s leadership event, and it went well. Now she wants to level-up and give more speeches—preferably paid ones. How can she break into this market?  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&amp...

#2022 - Failure Friday: “We opened the box and it was a totally different product…” 15.07.2022

In this week’s Failure Friday segment, we hear from the founder of Kettlebell Kings, an ecommerce shop. When a big early order from a supplier went terribly wrong, he had to regroup and learn resilience.    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...

#2021 - TBT: “Styles for Kidz” Goes Global with Video Classes 14.07.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Styles for Kidz, a Chicago organization that helps parents and kids with hair care.  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 severa...

#2020 - Q&A: “Does it really cost $100,000 to make an app??” 13.07.2022

How much does it cost to make an app? One of our listeners was quoted $100,000 from a local design studio, and they’re looking for a second opinion. 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: S...

#2019 - Adobe Expert Digitizes Millions of Family Photos 12.07.2022

A longtime Adobe employee creates the picture-perfect business by helping families store and digitize memories across generations.   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....

#2018 - First $1,000: “I quickly raised my price to $50 an hour…” 11.07.2022

In this week’s First $1,000 segment, we hear from a Returned Peace Corps Volunteer (RPCV) who starts a tutoring business on the side. After starting out at $20 an hour, he learns to specialize and raise his rates. 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...

#2017 - Q&A: “What is 'growth hacking’?” 10.07.2022

Is “growth hacking” just a fancy marketing term or is something anyone can apply? Hack into this episode to find out! 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...

#2016 - Q&A: “How do you profit from DeFi in a bear market?” 09.07.2022

Is decentralized finance the future … or the past? After a huge two years, many DeFi projects have fallen 90% or more. How can you profit during “crypto winter”? 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....

#2015 -Failure Friday: “Amazon permanently banned my seller account…” 08.07.2022

In this week’s Failure Friday segment, we hear from the co-founder of TheSavvyCouple.com. In his early days, he sold on eBay and Amazon.com. It was all going well, until a supplier problem led to him getting banned—permanently!  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 include...

#2014 - TBT: Cayenne Pepper Throat Lozenges Spice Up Flu Season 07.07.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the creator of an all-natural organic throat lozenge made with cayenne pepper. This cold remedy is on fire! 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&...

#2013 - Q&A: “I’m making an alarm clock that costs money if you oversleep…” 06.07.2022

That’s right, this alarm clock debits your bank account if you don’t get up in time. It’s sure to be a hit! The only problem: our caller isn’t sure how to make 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...

#2012 - Office Assistant Profits from Anime Imports 05.07.2022

After noticing a derth of anime items in the United States, this long-time lover of Japanese culture creates a thriving side hustle.   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...

#2011 - First $1,000: “I cold-pitched 10 brands and got my first 2 clients…” 04.07.2022

In this week’s First $1,000 segment, we hear from a freelance apparel designer who specializes in menswear. After having her first child, she set out to learn to work on her own.  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 severa...

#2010 - Q&A: “How can a travel website earn commissions?” 03.07.2022

Today’s listener wants to earn commissions on travel bookings by creating a website that funnels visitors to big agencies like Expedia. Is this a viable business model? 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...

#2009 - Q&A: “Should I pay $3,000 for my friend's mastermind??” 02.07.2022

A listener has a friend who’s part of a pricey “mastermind” group—and now our listener is experiencing FOMO. Are these groups worth the high price tag? 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...

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