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

#2432 - Q&A: “Planning to open a Virtual Reality arcade…” 29.08.2023

Today's caller hopes to combine his passion with the latest technology in Virtual Reality headsets. Are we ready for a “back to the future” VR arcade?  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...

#2431 - First $1,000: Virtual Assistant Specializes in Email 28.08.2023

In this week’s First $1,000 segment, we hear from a virtual assistant who does one thing only: manage the inboxes of busy startup founders. 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...

#2430 - Q&A: “I want to be a personal fitness influencer!” 27.08.2023

The world of “fitness influencers” is crowded and noisy, but there’s still a path to success for some. Can we help our listener make a credible plan to make money from her athletic expertise? 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&...

#2429 - Q&A: “Ready to go from small money to scaling a business…” 26.08.2023

We're shifting gears with our next caller. Instead of making a small amount of extra cash, he wants to “go big” and earn real money. Sounds good to me! Let’s explore the best way to make the leap to scaling your 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 gu...

#2428 - Failure Friday: Don’t Forget to Renew Your Domain Names! 25.08.2023

In this week’s Failure Friday segment, we hear from a personal finance blogger who failed to renew his domain name. It was then stolen by a company that provides content we don’t talk about on Side Hustle School. Don’t let this happen to 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, th...

BONUS: Gonzo Capitalism Is Now Out! 24.08.2023

After two years, my brand-new-book Gonzo Capitalism is now out in the world. You can find it at any bookstore or online retailer. Also! I'm visiting at least 16 cities:  chrisguillebeau.com/tour 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...

#2427 - TBT: Delaware Cinnamon Rolls Keep Rolling Out 24.08.2023

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Delaware baker who sells cinnamon rolls and more. Each month, she bakes up at least $1,500 in profit with little marketing. 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...

#2426 - Q&A: “How to offer UX/UI design consulting…” 23.08.2023

A British side hustler hopes to harness her new skills in UX/UI to venture into consulting. 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 o...

#2425 - Q&A: “Can I resell only Apple products?” 22.08.2023

Have you ever wondered if narrowing your focus in the buy-and-sell game could actually be a key to success? In today’s episode, we’ll hear from a reseller who wants to sell ONLY Apple products. 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...

#2424 - First $1,000: The Med School “Decision Doctor” 21.08.2023

In this week’s First $1,000 segment, we hear from a medical resident working in Chicago who has a side hustle as the med school “decision doctor,” helping students and interns navigate crucial decisions. 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...

#2423 - Q&A: “Do authors get paid for Kindle Unlimited books?” 20.08.2023

Authors who publish books in the Kindle Unlimited (KU) program earn royalties based on the number of page views you receive—but parts of the process remain a mystery. Let’s help an aspiring author decide if KU is the best fit for him. 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...

#2422 - Q&A: “How to help businesses transition to cloud services?” 19.08.2023

A caller in India has his sights set on the rapidly expanding field of cloud computing. What’s the best way to market a service targeted to small businesses? 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...

#2421 - Failure Friday: Bank Cancels TikTok Star’s Revenue Stream 18.08.2023

In this week’s Failure Friday segment, we hear from an aspiring travel blogger and TikTok streamer. After an initial run at making a good income, the banking partner she worked with dropped her from its affiliate program. 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...

#2420 - TBT: Life Coaching Didn’t Work; This Was Better 17.08.2023

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a coach who transformed from general life coaching (not a great business model!) to focusing more specifically on self-confidence. 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 less...

#2419 - Q&A: “How to set up a paid mastermind group?” 16.08.2023

A “mastermind” of peers in your industry can be a free, informal group—or it can be a profit center for the right person. How would you set up one that makes money? 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 wee...

#2418 - Q&A: “Do you know of a Business Bootcamp?” 15.08.2023

An engineer in Alberta wants to jumpstart his side hustle with a short “business bootcamp.” Does such a thing exist—and if not, might there be a market for 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. Sh...

#2417 - First $1,000: British Gaming Computer Navigates Brexit 14.08.2023

In this week’s First $1,000 segment, we hear from a British university student who builds custom computers, selling them to gamers looking for an edge in the form of faster performance. 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...

#2416 - Q&A: “Get paid to take photos with Snappr…” 13.08.2023

An amateur photographer signs up for Snappr, the service that describes itself as “Uber for photographers.” If you want to get paid to shoot portrait sessions, pay attention. 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 day...

#2415 - Q&A: “I HATE making sales calls…” 12.08.2023

A software consultant is getting off to a good start with his side business, but he has one problem: he *strongly* dislikes making sales calls. Let’s see if we can help out our fellow introvert! 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...

#2414 - Failure Friday: Couples’ Intimacy Coach Fails to Spark Passion 11.08.2023

In this week’s Failure Friday segment, we hear from an “up close and personal” intimacy coach for couples. Alas, her quest to become the Cupid of the digital age fizzled 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 day...

#2413 - TBT: Book Launch Manager Gets Paid to Pitch Authors 10.08.2023

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a book launch manager who gets paid to pitch authors. Specifically, she helps upcoming and newly released books to get more attention … by any means necessary! 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 s...

#2412 - Q&A: “I’m making $10k/month … but I feel overwhelmed.” 09.08.2023

This ecommerce business is taking off, but the owner isn’t sure what to do next. How do you handle an unexpected success? 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:...

#2411 - Q&A: “I’m ready to buy and sell sneakers!” 08.08.2023

An MBA student wants to get in on sneaker reselling. Does he have what it takes to put his best foot forward? 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@sidehus...

#2410 - First $1,000: Electric Vehicle “Sherpa” Offers Fast Delivery 07.08.2023

In this week’s First $1,000 segment, we hear from a guy operating an all-new side hustle: he helps electric vehicle buyers get their cars sooner! 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...

#2409 - Q&A: “Should I sell on eBay, Etsy, or Shopify?” 06.08.2023

Selling on multiple platforms can increase revenue, but also generates more headaches. For a busy side hustler who can only be in one place at a time, how should you choose? 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...

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