Chris Guillebeau

Side Hustle School

Business EN ↓ 3645 episodi

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.

Visita il sito del podcast e sostieni chi lo crea: sidehustleschool.com

Autore

Chris Guillebeau

Categoria

Business

Sito del podcast

sidehustleschool.com

Ultimo episodio

28 ott 2026

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Episodi

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...

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 lesso...

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. Sh...

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....

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.co...

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. S...

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&amp...

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 se...

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.c...

Ep. 3454 - Q&A: “Which is better: direct or indirect income? 16.06.2026

A listener has a clear business idea, but isn’t clear about the revenue model. They can get paid through affiliate and advertising revenue (indirect), *or* through selling to consumers themselves (direct). Which might be better?  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...

Ep. 3453 - First $1,000: “My music was played on a Romanian TV show…” 15.06.2026

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 g...

Ep. 3452 - STORY: A Mental Health Counselor By Day, A Headband Artist by Night 14.06.2026

A mental health counselor gets a head start with a side hustle that brings in $3,000 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&A several days each week. Show notes:  SideHustleSchool.com Email: team@sidehustleschool....

Ep. 3451 - Q&A: “’Spaced repetition' practice with outsourced tutors from overseas?” 13.06.2026

Today’s listener has an intriguing idea: to aid in memory retention using spaced repetition but with outsourced tutors from other countries. Think of it like “Upwork meets Udemy.” Will it 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...

Ep. 3450 - Failure Friday: “I decided to give money to Meta…” 12.06.2026

In this week’s Failure Friday segment, we hear from the creator of a writing program. She wanted to reach more people, so she decided to give Facebook her money. What could go wrong?  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&amp...

Ep. 3449 - TBT: These “Sweatpant Overalls” Produce Joy and Extra Pockets 11.06.2026

In this week’s “Throwback Thursday” segment, we hear from the man who brought sweatpant overalls for men (really!) to America.  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...

Ep. 3448 - Q&A: “How to grow a YouTube channel with 121,000 subscribers?” 10.06.2026

This Australian listener already has a very popular home cooking YouTube channel with more than 100,000 subscribers. He’s now looking to expand his reach further. What comes next?? 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 sever...

Ep. 3447 - Q&A: “How can I sell flash cards to pharmacy students?” 09.06.2026

This listener has made a set of flash cards to help pharmacy students memorize generic drug names, but is having a hard time finding her market. What should she try? 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 we...

Ep. 3446 - First $1,000: Selling Vintage Clothes on Poshmark 08.06.2026

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 seve...

Ep. 3445 - STORY: Divorce Leads Banker To Boudoir Photography Empire 07.06.2026

Inspired by her own session after a divorce, a corporate banker finds her calling in boudoir photography. The business now earns multiple six figures a year! 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. 3444 - Q&A: “How do I choose a revenue model for my coaching business?” 06.06.2026

Most successful coaches have more than one source of income—but if you’re starting out and need to pick only one, which should you pursue? 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. 3443 - STORY: Tote-ally Functional Bags for Women on the Go 05.06.2026

Keep calm and carry on! After struggling with her bags on the subway one too many times, this New Yorker takes the problem into her own hands and makes over $100,000.   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...

Ep. 3442 - TBT: Bestselling Author Publishes Novels, Online Courses, and More 04.06.2026

In this week’s “Throwback Thursday” segment, we hear from an incredibly productive author who writes novels in the morning and makes online courses in the afternoon. Lots of lessons here!  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...

Ep. 3441 - Q&A: “Can I file a small claims suit against a big business?” 03.06.2026

Today’s caller is having a frustrating experience: they aren’t getting paid for work they’ve completed! Can they take their client to small claims court? 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 not...

Ep. 3440 - Q&A: “What's the best platform for my idea?” 02.06.2026

Do you start with your idea, or start with the ideal platform for your idea? Today’s caller wants to remain “platform agnostic.” How should he proceed?  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. 3439 - First $1,000: Florida Woman Becomes Pet Party Planner 01.06.2026

In this week’s First $1,000 segment, we hear from the go-to pet party planner of St. Petersburg, Florida. She plans doggie bashes and cat-a-versary parties. 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...

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