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

#1610 - Q&A: Will my web host design my website? 29.05.2021

A listener wants to know if their web host offers a “full service” option, or if it’s better to find another way to get the job done.   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: SideHustleS...

#1609 - Failure Friday: “My D.C. tour business was down 89%…” 28.05.2021

In this week’s Failure Friday segment, we hear from a Washington, DC tour guide who loses nearly all of his side income due to COVID-19.   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...

#1608 - TBT: Diabetic Travel Blogger Embraces #VanLife 27.05.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Irish travel blogger with type 1 diabetes. She’s recently moved to YouTube—and into a tiny home on wheels.  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...

#1607 - Q&A: How to best use a time of unemployment? 26.05.2021

A listener who experiences a layoff has a severance package that lasts two months. In addition to looking for full-time work, how can he build another form of financial security during this 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 liste...

#1606 - Sports Cards Trading Hobby Becomes Pandemic Payday 25.05.2021

When a perennial side hustler reconnects with his childhood hobby of sports trading cards, he brings in more than $20,000.  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 Em...

#1605 - Q&A: What’s the best way to market a guide to airline lounges? 24.05.2021

A listener wants to make an airline lounge access guide to help more people experience these magical places. What’s the best approach to creating and marketing 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...

#1604 - French Bulldog Blog Fetches Extra Bones 23.05.2021

After introducing a French bulldog into the family, a man finds a way to get paid blogging about 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@sidehustle...

#1603 - Q&A: How to become an affiliate manager for large launches? 22.05.2021

Some product launches have an “affiliate manager” who coordinates promotion efforts. How can our listener offer this service on a freelance basis?  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:...

BONUS: Planning for a New Tomorrow, Part III 21.05.2021

An asymmetrical opportunity is one where the risk is low but the possible reward is high. Starting a small business on a low budget is a perfect example: it might not work out, but if it does, there's no fixed limit to growth.  In this series of short episodes from our partner Dell, I'll share three examples of how ordinary people are exploiting asymmetrical opportunities to radically transform th...

#1602 - Failure Friday: “I thought I had the Midas touch...” 21.05.2021

In this week’s Failure Friday segment, we hear from a digital marketer who spends months creating a life-changing “killer app” that no one wants.   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:...

#1601 - TBT: Handbags for Active Women Goes Direct to Consumers 20.05.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Go Dash Dot, which sells handbags and other accessories for active women.  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...

#Ep. 1600 - Q&A: How to create a revenue stream not affected by Google? 19.05.2021

We made it to #1,600! A listener’s product review site is starting well, but every day they see how dependent it is on the whims of Google search results. Can anything be done?    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...

#1599 - Pastor Keeps the Faith with Clergy Subscription Boxes 18.05.2021

A Lutheran pastor creates breathing room in her budget with a popular subscription box for fellow ministers.  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...

#1598 - Q&A: Why do online courses cost so much … or so little? 17.05.2021

Online courses are everywhere! Some cost $20 and others cost $2,000 or more. Why is there no consistency in pricing—and how can you determine what *your* price should be?   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...

#1597 - “Bee Man of New Jersey” Buzzes Into Money Hive 16.05.2021

A beekeeper puts his bees to work, turning a hobby into a money-making hustle. Bee smart and listen to this episode!  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:...

#1596 - Q&A: Should I use Etsy's new platform or build my own website? 15.05.2021

A listener with an Etsy shop wants to open her own site as well. What’s the best way to branch 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@sidehustlesc...

BONUS: Planning for a New Tomorrow, Part II 14.05.2021

An asymmetrical opportunity is one where the risk is low but the possible reward is high. Starting a small business on a low budget is a perfect example: it might not work out, but if it does, there's no fixed limit to growth.  In this series of short episodes from our partner Dell, I'll share three examples of how ordinary people are exploiting asymmetrical opportunities to radically transform th...

#1595 - Failure Friday: “If it worked once, it should work twice… right?” 14.05.2021

In this week’s Failure Friday segment, we hear from a full-time blogger who migrates to YouTube. His first attempt is a big win, so he assumes he can do it again—but that turns out to be a big assumption. 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 an...

#1594 - TBT: The 7-Figure Dachshund Apparel Business 13.05.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Bean Goods, which sells dachshund-themed apparel for dogs and humans.   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...

#1593 - Q&A: “I want to bet on The Bachelor…” 12.05.2021

A listener wants to start an online marketplace where people bet on the outcome of The Bachelor. Millions of fans watch every week—is this a crazy idea?  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...

#1592 - A Doggie Bag With a Twist 11.05.2021

A Cleveland woman creates a dog walking accessory bag for active pet owners. Prototyping is ruff, but eventually she begins to paw-sper.  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...

#1591 - Q&A: Should I start a Substack newsletter? 10.05.2021

Substack and other services that offer writers the chance to publish paid newsletters are getting a lot of attention. What do you need to know if you’d like to jump in?   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...

#1590 - Social Worker Finds Calm, Makes Cash with Business Course 09.05.2021

A therapist and single mom earns extra income helping other therapists set up a private practice.  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@sidehustlescho...

#1589 - Q&A: Do I have to tell my customers where I'm based? 08.05.2021

A listener in Europe wants to sell online, primarily to Americans. Do his customers need to know he’s overseas?  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@s...

BONUS: Planning for a New Tomorrow, Part I 07.05.2021

An asymmetrical opportunity is one where the risk is low but the possible reward is high. Starting a small business on a low budget is a perfect example: it might not work out, but if it does, there's no fixed limit to growth.  In this series of short episodes from our partner Dell, I'll share three examples of how ordinary people are exploiting asymmetrical opportunities to radically transform th...

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