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

#2408 - Q&A: “An at-home escape room kit…” 05.08.2023 5:39

Live from Ireland, this chemical engineer has a passion for puzzles and mind games—and she wants to sell an at-home escape room kit! How can we get this cool (yet constraining) idea unlocked? 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&...

#2407 - Failure Friday: “Once I knew I had ADHD, everything made more sense…” 04.08.2023 7:22

In this week’s Failure Friday segment, we hear from a self-employed programmer who struggled with motivation and procrastination. After many years of difficulty, he received an ADHD diagnosis that led to much improved habits. (I’ve been there! I have ADD, too.) Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

#2406 - TBT: Georgia Fruit Stand Seller Sees Juicy Returns 03.08.2023 5:37

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a fruit stand seller in Georgia. After three years of setting up shop, it now earns more than $50,000 a season. 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&...

#2405 - Q&A: “Career coaching, live from Tokyo…” 02.08.2023 4:57

A listener in Japan wants to leverage 15 years of cross-cultural experience into an online venture. 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...

#2404 - Q&A: “Help, I only have $100 to spend!” 01.08.2023 5:29

A single mom from Detroit is ready to start side hustling, but only has $100 to spare. Is there anything she can do? (Short version: YES.) 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...

#2403 - First $1,000: Freelance Animator Makes Snappy Commercial Videos 31.07.2023 6:01

In this week’s First $1,000 segment, we hear from a financial analyst with a secret side hustle making snappy short videos. 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...

#2402 - Q&A: “How does a gadget reviewer expand his platform?” 30.07.2023 5:21

A tech enthusiast hopes to go from unboxing on YouTube to reaching more people on different platforms. 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...

#2401 - Q&A: “Am I too late to the side hustle party?” 29.07.2023 5:07

Do you ever feel like you’re too late to something? That’s what this longtime school teacher is feeling. Good news: she’s *not* too late, and neither are you. 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...

#2400 - Failure Friday: The Dial-a-Poem Hotline 28.07.2023 6:46

In this week’s Failure Friday segment, we hear from a longtime poetry lover who offers a service called Dial-a-Poem: basically a personal poetry hotline. 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...

#2399 - TBT: Hand Lettered Wedding Invites Are Here to Stay 27.07.2023 5:39

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a retail associate who uses her calligraphy skill to start a side hustle offering hand-lettered wedding invitations. 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 listen...

#2398 - Q&A: “Starting out in real estate in San Francisco…” 26.07.2023 5:24

If you want to flip houses, is San Francisco really the best 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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleS...

#2397 - Q&A: “I’m ready to make an app! Uh, what should it be?” 25.07.2023 4:56

Calling in from Seattle, Amy is a software developer who's been mulling over the idea of creating her own mobile app—but what kind of app should she make?? 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 n...

#2396 - First $1,000: Selling Vintage Clothes on Poshmark 24.07.2023 6:31

In this week’s First $1,000 segment, we hear from a seller of vintage and modern clothes who uses the online marketplace Poshmark to sell thousands of dollars of clothes each month. 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...

#2395 - Q&A: “SEO consulting for small businesses…” 23.07.2023 4:30

A digital marketing professional wants to start side hustling. How can he position himself to serve local businesses with SEO? 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...

#2394 - Q&A: “Should I become a financial advisor for healthcare workers?” 22.07.2023 5:28

Today’s caller works as a data analyst in the health sector, but she's also got a keen interest in investing. Might there be a way to combine these talents for one side hustle to rule them all? 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...

#2393 - Failure Friday: Ghost Tours Fail to Scare Enough Clients 21.07.2023 5:55

In this week’s Failure Friday segment, we hear a spooky story: an attempt at offering a ghost tour of Denver fails to scare enough people into signing up. 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...

#2392 - TBT: Game Consoles, VCRs, and Typewriters for Sale 20.07.2023 6:01

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a reseller who specializes in retro electronics including vintage game consoles and typewriters. 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...

#2391 - Q&A: “How to sell a ‘Democracy in Action’ program?” 19.07.2023 6:07

A listener looking to inspire others to become more active in their local government wants to start a subscription service of some kind. 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...

#2390 - Q&A: “Can I tell someone else’s story on my podcast?” 18.07.2023 5:23

If you make a storytelling podcast, can you tell someone else’s story without their permission? 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...

#2389 - First $1,000: Indian Tutor Helps U.S. High School Students Learn Math 17.07.2023 6:15

In this week’s First $1,000 segment, we hear from an Indian listener. He’s built a bustling business as an online math tutor for high school students in the U.S. 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....

#2388 - Q&A: “What should I sell on Fiverr?” 16.07.2023 6:28

A digital nomad with a range of skills wants to offer services on Fiverr. How should he specialize to be most efficient and profitable? 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...

#2387 - Q&A: “It’s hard to compete with bigger firms!” 15.07.2023 4:57

A talented designer is facing competition with larger design firms in her area. How can she stand out and make her mark? 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: t...

#2386 - Failure Friday: Homemade Hummus Subscription Fails to Smash 14.07.2023 6:48

In this week’s Failure Friday segment, we hear from a listener with a tangy idea. Drawing on her Lebanese ancestry, she tries to create a “homemade hummus subscription box. Alas, those chickpeas failed to smash themselves into a hit. 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 i...

#2385 - TBT: Project Manager Side Hustles as Home Inspector 13.07.2023 6:05

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a project manager in the construction industry who has a side hustle as a home inspector. This second job earns several thousand dollars a month! 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...

#2384 - Q&A: “How to use the Pomodoro method in my side hustle?” 12.07.2023 5:38

The Pomodoro method is a classic productivity tool. How can this listener—or anyone—use it when building their 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: SideHustleSchool.com Email...