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

#2008 - Failure Friday: “The experience of hearing rejection was important…” 01.07.2022 8:00

In this week’s Failure Friday segment, we hear from the founder of KindRoot, “hard candy gone good,” plant-powered lozenges for mind and body wellness. In her early days, she experienced rejection from multiple manufacturers and had to learn to trust herself. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

#2007 - TBT: Brooklyn Clothing Boutique Scales Up 30.06.2022 8:22

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of two businesses in New York City: a clothing line *and* a fashion boutique that features 25+ BIPOC-owned brands. 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 a...

#2006 - Q&A: “How many ‘wine-of-the-month’ clubs are there??” 29.06.2022 4:16

Today’s caller has seen many “of-the-month” clubs, ranging from wine, plants, and even all the way to pickles. With so many of them out there, does that mean the market is saturated? 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 sev...

#2005 - Bam! Pow! Crash! The Comic Book Reselling Hustle 28.06.2022 6:24

Drawing on a childhood affection for comic books, this mechanical engineer smashes his student loan debt with an online collectibles 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: Side...

#2004 - First $1,000: “My music was played on a Romanian TV show…” 27.06.2022 6:19

In this week’s First $1,000 segment, we hear from a musician who licenses songs for placement in TV shows worldwide. When he gets a check in the mail for a TV show he’s never heard of, he starts taking it more seriously. 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...

#2003 - Q&A: “Jumping into Twitch streaming…” 26.06.2022 5:46

A caller is getting into Twitch, the popular live streaming platform. How can she bring over her large Instagram audience? 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...

#2002 - Q&A: "I tried donation-only yoga, but no one donated..." 25.06.2022 4:50

Today we hear from a yoga teacher who offers a class at a nearby community center. It went well, except for one problem: her donation-only model didn’t produce much in the way of donations. 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...

#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...