Side Hustle School

Chris Guillebeau

Business EN 3536 episodes

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Episodes

Ep. 3479 - Q&A: “Is reselling gift cards a viable idea?” 11.07.2026

Today’s listener is thinking about buying and reselling unused gift cards. It sounds like an interesting idea, but is he missing something obvious? 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:&nbs...

Ep. 3478 - Failure Friday: “I tried to sell something no one wanted…” 10.07.2026

In this week’s Failure Friday segment, we hear from a seller of gift baskets for college alumni—or at least, that’s what she *tried* to sell. Unfortunately, buyer demand was non-existent. 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...

Ep. 3477 - TBT: “Hero’s Journal” Completes Epic Quest 09.07.2026

In this week’s “Throwback Thursday” segment, we undertake a valiant quest to hear from the co-founder of a legendary journal.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.comE...

Ep. 3476 - Q&A: “How to find markets for livestreaming events?” 08.07.2026

Today’s caller is working on providing livestreaming content creation services for small businesses and events. How can he find a niche or target market to focus on?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...

Ep. 3475 - Q&A: “How to best use a time of unemployment?” 07.07.2026

Today’s caller faces a big decision: during a time of unemployment, does she stretch her side hustle into a career, or go back to traditional 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...

Ep. 3474 - First $1,000: “I had no idea Hula Hoops were a seasonal business…” 06.07.2026

In this week’s First $1,000 segment, we hear from Holly the Hula Hoop Hustler. She’s now earning up to $2,000/month selling hula hoops on Amazon. But what about her first $1,000—how did she make that happen, and what did she learn? 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...

Ep. 3473 - STORY: Enjoy an Ice Cold Beverage in a Mug Made from Ice 05.07.2026

A visit to the outdoor sauna in the midst of a Minnesota winter inspires a mug made from ice that has sold over 4,000 units. 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...

Ep. 3472 - Q&A: “How should I promote my new app?” 04.07.2026

Today’s caller is wondering about where to go to promote a wellness app she’s made. Is promoting an app different from anything else? 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: SideHus...

Ep. 3471 - STORY: Tinder Matched Couple Swipes Right to Sell Cupcakes 03.07.2026

After meeting on Tinder, a couple takes a long walk through Central Park and decides to sell cupcakes for $20 each. Surprise: it works. 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: SideH...

Ep. 3470 - TBT: Comfy Pillow Provides Seatbelt Support for Cancer Patients 02.07.2026

In this week’s “Throwback Thursday” segment, we hear from the creator of the ParkPuff, a “go anywhere” seat belt pillow for cancer and surgery patients.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:...

Ep. 3469 - Q&A: “Where's the best place to hire contractors?” 01.07.2026

Today’s caller is starting a *second* side hustle and wants to know where to find the best virtual assistants and other contractors. 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...

Ep. 3468 - Q&A: “How do you determine a customer’s emotional needs?” 30.06.2026

Today’s listener is inspired to learn more about the “core emotional needs” of a potential customer, but isn’t sure how to do it or what to do with the info. Are these needs always the same, or do they vary? 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...

Ep. 3467 - First $1,000: “Clients don’t want Wordpress, they want a website…” 29.06.2026

In this week’s First $1,000 segment, we hear from the self-described “Wordpress Girl,” who starts a service helping female entrepreneurs get set up with a website.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....

Ep. 3466 - STORY: Music Graduate Makes Spare Change Filling Spare Rooms 28.06.2026

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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's...

Ep. 3465 - Q&A: “Help! I’m stuck trying to find my ‘ah-ha’ idea” 27.06.2026

Today’s listener has kept her eyes open looking for opportunities, but hasn’t spotted her “ah-ha” idea yet. How can she proceed when she really wants to move forward but isn’t sure how? 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...

Ep. 3464 - Failure Friday: “We accept your proposal… to resign” 26.06.2026

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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's...

Ep. 3463 - TBT: Beer Made from “Upcycled” Grain TBT: Blogger Explores Affiliate Marketing in India 25.06.2026

In this week’s “Throwback Thursday” segment, we hear from the co-founder of a business that turns upcycled grains from breweries into delicious snacks. 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...

Ep. 3462 - Q&A: “I stopped delivering for my Patreon…” 24.06.2026

An independent musician has a Patreon account funded by fans. Over the past few months, he’s stopped delivering updates and special features—but the fans keep paying. How should he handle this unusual problem?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 lesson...

Ep. 3461 - Q&A: “Should I pursue three ideas or just one?” 23.06.2026

Today’s caller has a dilemma: they have three independent ideas and aren’t sure whether they should eliminate any of them. How can they make the best decision?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...

Ep. 3460 - First $1,000: Indian Tutor Helps U.S. High School Students Learn Math 22.06.2026

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.Sh...

Ep. 3459 - STORY: Hawaiian Native Teaches Virtual Ukulele Lessons 21.06.2026

A Hawaiian goes all-in on the popular instrument of the islands, touring Europe and teaching virtual lessons by Skype. 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.comEm...

Ep. 3458 - Q&A: “How do you ethically source products made in overseas factories?” 20.06.2026

There are lots of advantages to sourcing a product from an overseas factory—but how do you know the working conditions are fair and environmentally responsible?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...

Ep. 3457 - STORY: Financial Blog Sprouts into $35,000/Month Money Tree 19.06.2026

A registered nurse and financial manager start a blog for millennials. After a rough beginning, they figure out their audience and go on to earn tens of thousands of 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 free guided lessons and listener Q&...

Ep. 3456 - TBT: Urban Hiker Leads Tours in San Francisco 18.06.2026

In this week’s “Throwback Thursday” segment, we hear from a woman with two successful hustles. Adapting to a changing world, she’s been able to thrive even in the midst of challenges.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...

Ep. 3455 - Q&A: “My ‘road trip kit’ for truck stops…” 17.06.2026

A listener has a cool idea: they want to sell a road trip kit. How can they put it together, and who is their ideal customer?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.comE...

About the podcast

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

Language

EN

Episodes

3536

Latest episode

11 lug 2026

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