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
Podcast website
Latest episode
11 juil. 2026
Where to listen?
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Episodes
Ep. 3454 - Q&A: “Which is better: direct or indirect income? 16.06.2026 5:11
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 6:20
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 6:41
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 5:30
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 6:56
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&...
Ep. 3449 - TBT: These “Sweatpant Overalls” Produce Joy and Extra Pockets 11.06.2026 7:41
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 5:36
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 5:06
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 5:27
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 7:36
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 4:14
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 7:18
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 7:36
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 5:06
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 4:27
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 5:30
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...
Ep. 3438 - STORY: Dog Lover Fetches $250,000 in Canine Clothing 31.05.2026 5:46
A Minnesota woman turns her design hobby into trendy duds for the whole family, including furry companions. 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: te...
Ep. 3437 - Q&A: “How do I best prioritize next steps?” 30.05.2026 5:51
This listener has designed and printed a series of planners for new moms struggling with postpartum depression. How can she reach her target 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:...
Ep. 3436 - Failure Friday: “We went all-in on applying for a $2 million grant…” 29.05.2026 8:37
In this week’s Failure Friday segment, we hear from Suzanne Tucker, founder of Generation Mindful. Last year, her team decided to go all-in on applying for a big NIH grant—and the initial outcome was disappointing. 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. 3435 - TBT: 26,000 Handmade Hair Scrunchies 28.05.2026 5:27
In this week’s “Throwback Thursday” segment, we hear from a woman in Iowa who makes and sells a LOT of scrunchies. Long live the 90s! 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...
Ep. 3434 - Q&A: “Best way to get to market with nutrition bar…” 27.05.2026 4:28
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...
Ep. 3452 - STORY: Mental Health Counselor By Day, Headband Artist by Night 26.05.2026 6:41
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.c...
Ep. 3451 - Q&A: “’Spaced repetition’ practice with overseas tutors?” 26.05.2026 5:30
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. 3433 - Q&A: “Is the directory website model outdated?” 26.05.2026 4:21
A caller from Massachusetts has a small moving business and is thinking about adding a directory website that provides listings to movers from around the country. Is this business model outdated, or might it still have potential? 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 includ...
Ep. 3432 - First $1,000: “I wasn’t sure what to do, so I started selling sports cards…” 25.05.2026 7:26
In this week’s First $1,000 segment, we hear from a Los Angeles consultant who begins buying and reselling sports cards during the pandemic. He does it because it’s fun—but it also ends up being highly 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 gu...
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