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Side Hustle School

Side Hustle School

Chris Guillebeau 3496 Episodes Jul 4, 2026

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 hear a different story of someone who's started a side hustle, including what went well, how they 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 and other books.

Episodes

Ep. 3472 - Q&A: “How should I promote my new app?” Jul 4, 2026 4:53 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 Jul 3, 2026 8:00 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 Jul 2, 2026 7:27 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?” Jul 1, 2026 5:32 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?” Jun 30, 2026 5:02 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…” Jun 29, 2026 4:32 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 Jun 28, 2026 8:53 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” Jun 27, 2026 5:05 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” Jun 26, 2026 6:25 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 Jun 25, 2026 7:04 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…” Jun 24, 2026 5:00 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?” Jun 23, 2026 3:56 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

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