Chris Guillebeau

Side Hustle School

Business EN ↓ 3654 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.

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

Author

Chris Guillebeau

Episodes

#2001 - Failure Friday: “Don’t let customers pay after services have been rendered…” 24.06.2022 7:40

In this week’s Failure Friday segment, we hear from the owner of a tutoring business. After getting paid for a successful session, she encounters the frustration of a credit card chargeback. 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...

#2000 - Side Hustle School Celebrates 2,000 Consecutive Episodes! 23.06.2022 7:50

It’s true, we’ve been making Side Hustle School every single day since January 1, 2017. Thanks for tuning in! The best is yet to come. 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: SideHustleScho...

#1999 - Q&A: “Can I offer a permanent price discount?” 22.06.2022 4:58

Our listener has seen furniture stores offer non-stop sales. Is there any reason they can’t have a sale that never ends in their 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: SideHustle...

#1998 - Hollywood Video Editor Shoots for the Stars 21.06.2022 7:25

An ambitious video editor (who also runs many side hustles!) uses a string of $5/month Craiglist ads to land thousands of dollars in 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: SideHustl...

#1997 - First $1,000: “No one in Boston could find a good pierogi…” 20.06.2022 7:32

In this week’s First $1,000 segment, we hear from the co-founder of Jaju Pierogi, a line of delicious Polish snacks now stocked in hundreds of New England grocery stores. 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...

#1996 - Q&A: “I'm being headhunted... for my side hustle!” 19.06.2022 4:58

Our listener’s side project was so successful that an outside company wants to hire him. That wasn’t exactly the goal, though. 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...

#1995 - Q&A: “I have 20 years of experience … how do I pick a niche?” 18.06.2022 5:07

Today’s caller draws on a lot of experience in production, branding, and more. She now wants to strike out on her own, but feels overwhelmed by all the options. Can we help her find the right focus? 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 lis...

#1994 - Failure Friday: “We tried to be everything to everyone…” 17.06.2022 6:04

In this week’s Failure Friday segment, we hear from the founder of Cleanlots, a parking lot cleanup service that’s been operating for decades. In its early years, Cleanlots expanded too quickly, learning a valuable lesson before pulling back to its core competency. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin...

#1993 - TBT: San Francisco Service Delivers Healthy Meals 16.06.2022 6:53

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a California meal prep company. His business continues to put food on the table! 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...

#1992 - Q&A: “How can I sell on a platform like NextDoor?” 15.06.2022 5:02

NextDoor is not primarily designed as a platform for you to go crazy and sell a bunch of stuff. If you want to sell there—what do you need to know? 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...

#1991 - Digital Illustrator Crafts Creative Designs 14.06.2022 5:47

An American expat living in France draws on her artistic ability and heritage to sell multiethnic graphic illustrations. 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:...

#1990 - First $1,000: “I wanted to be the guy with a laptop on the beach…” 13.06.2022 7:11

In this week’s First $1,000 segment, we hear from the founder of Maid This, a cleaning company that grows to millions of dollars in sales and allows the founder to work remotely. 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...

#1989 - Q&A: “I’m offering executive coaching at a high price…” 12.06.2022 4:40

Today’s caller is on their second attempt with a coaching service for busy executives. It’s a big-ticket item, but the first round didn’t go very well. What should they do differently for take two? 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...

#1988 - Q&A: “Can you make more from courses than anything else?” 11.06.2022 5:27

It’s a common path to go from being a Creator in a certain field to teaching people how to do something similar—so why not skip a step and go straight to making courses? 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...

#1987 - Failure Friday: “I acted like an inexperienced order-taker…” 10.06.2022 5:53

In this week’s Failure Friday segment, we hear from a writer who now earns a six-figure income from her freelance work. In the beginning, however, she had to learn to communicate better with potential 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 le...

#1986 - TBT: Luggage Storage Business Attracts Copycats 09.06.2022 9:25

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a luggage storage business for tourists. It was going so well that someone else decided to replicate the model for themselves, cutting into her customer base. How did she handle it? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without...

#1985 - Q&A: “Best way to get to market with nutrition bar…” 08.06.2022 5:10

A listener is launching an “all-in” protein bar. It’s a crowded market, but they’re, well, all-in. How can we help them get on the shelves of Whole Foods? 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 no...

#1984 - Data Scientist Profits from Viral Article 07.06.2022 6:49

After her Medium article gains attention, a data scientist creates an online community and series of courses, resulting in a new source of reliable 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. Sho...

#1983 - First $1,000: “I’ll never forget the moment I got paid…” 06.06.2022 8:21

In this week’s First $1,000 segment, we hear from Jennifer Sobel, a belly dancing coach (!) who takes her program online. It’s now a midsection-shaking success—but how did she get there? 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...

#1982 - Q&A: “Can I tell people where to find fake luxury goods?” 05.06.2022 3:54

A listener wants to sell a guide to replica luxury goods. She’s not going to sell the items themselves, just the information. Is this a good 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 notes: Si...

#1981 - Q&A: “How much time do people spend on these projects?” 04.06.2022 4:26

If you have at least one side hustle already, is it a couple hours a week, taking over your life, or somewhere in between? 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:...

#1980 - Failure Friday: “We locked ourselves in a room for six months to build it…” 03.06.2022 8:25

In this week’s Failure Friday segment, we hear from the co-founder of Sports Bookr, a service that helps sports facilities with online booking and scheduling. In starting up, the team learned that “validation” is not a one-time activity. 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...

#1979 - TBT: Voiceover Artist Grows Business With Gusto 02.06.2022 7:25

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a full-time voiceover artist. It started from a podcast about Downton Abbey! 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. Sho...

#1978 - Q&A: “How do I market and get my first customers?” 01.06.2022 5:11

Our caller today is like a lot of listeners: when the time comes to start a project, how do you market and attract your first customers? 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...

#1977 - This Balloon-Popping Tool Strikes Helium Gold 31.05.2022 7:27

A graphic designer flies high with an invention to bring balloons down to earth. 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...