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Side Hustle School

Side Hustle School

Chris Guillebeau 3496 Episodes Aug 23, 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. 3522 - STORY: Lather, Rinse, Recycle: Soapy Problem Leads to Clean Solution
Ep. 3522 - STORY: Lather, Rinse, Recycle: Soapy Problem Leads to Clean Solution Aug 23, 2026 7:00 An account manager solves the pondering question of “What happens to soap after it’s used in a hotel room?”—and turns it into a sustainable side 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 guided lessons and listener Q&A several days each week.Show
Ep. 3521 - Q&A: “How do I find customers as a digital personal assistant?”
Ep. 3521 - Q&A: “How do I find customers as a digital personal assistant?” Aug 22, 2026 4:49 Today’s listener is in search of his first customer! He wants to become a digital personal assistant to help people with tech support. 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 n
Ep. 3520 - Failure Friday: “After I was hit by a car, things got worse…”
Ep. 3520 - Failure Friday: “After I was hit by a car, things got worse…” Aug 21, 2026 6:16 In this week’s Failure Friday segment, we hear from an affiliate marketer who encountered an unusual problem: after he was hit by a car, the public knowledge of his business was used against 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 includes free guided lessons and li
Ep. 3519 - TBT: Bridesmaid-for-Hire Keeps Walking Down the Aisle
Ep. 3519 - TBT: Bridesmaid-for-Hire Keeps Walking Down the Aisle Aug 20, 2026 6:46 In this week’s “Throwback Thursday” segment, we hear from the woman behind “Bridesmaid-for-Hire,” one of our most popular episodes in year one. Her business has grown a lot since then, but she’s also learned some lessons in simplifying. 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
Ep. 3518 - Q&A: “Where do I begin if I want to make an app?”
Ep. 3518 - Q&A: “Where do I begin if I want to make an app?” Aug 19, 2026 4:17 This listener wants to make an app, but needs some help knowing where to start.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:
Ep. 3517 - Q&A: “Should I start a new site for my food business?”
Ep. 3517 - Q&A: “Should I start a new site for my food business?” Aug 18, 2026 4:26 This listener has an older food blog that she hasn’t updated in a while, and now she wants to convert it to an ecommerce site. Is that the best approach, or should she start all over?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. 3516 - First $1,000: “I built an Airbnb rental in my backyard…”
Ep. 3516 - First $1,000: “I built an Airbnb rental in my backyard…” Aug 17, 2026 4:51 In this week’s First $1,000 segment, we hear from a serial side hustler who builds an ADU in his backyard, allowing him to earn $1,500/month in passive rentals. He then uses the profits to buy another property.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. 3515 - STORY: Hair Braiding Workshops Help Trans-Racial Adoptive Families
Ep. 3515 - STORY: Hair Braiding Workshops Help Trans-Racial Adoptive Families Aug 16, 2026 6:41 A Chicago woman uses her side hustle to support her life, then adapts it to help more than 1,000 children in trans-racial adoptive families. 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. 3514 - Q&A: “How to make a board game from start to finish?”
Ep. 3514 - Q&A: “How to make a board game from start to finish?” Aug 15, 2026 4:24 Today’s listener wants to make a board game. There are many steps involved, and he’ll need to learn a lot along the way. But that shouldn’t stop him! Let’s see if we can help him 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&amp
Ep. 3513 - STORY: Teacher Flips Sports Gear For $8,000/Month
Ep. 3513 - STORY: Teacher Flips Sports Gear For $8,000/Month Aug 14, 2026 7:01 A teacher uses his love for sports memorabilia to bridge the financial gap between his teaching contracts—then goes on to create a highly profitable business.  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 eac
Ep. 3512 - TBT: Southern Transplant Creates Watercolor Brand
Ep. 3512 - TBT: Southern Transplant Creates Watercolor Brand Aug 13, 2026 7:21 In this week’s “Throwback Thursday” segment, we revisit a graphic designer who creates a watercolor brand that is sold in retailers throughout South Carolina and beyond. 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
Ep. 3511 - Q&A: “Do I have to sell as a SAAS?”
Ep. 3511 - Q&A: “Do I have to sell as a SAAS?” Aug 12, 2026 5:30 A listener is trying to decide how to price a new online service. Should she use the common SAAS (“software as a service”) model, or are there alternatives? 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

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