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Side Hustle School

Side Hustle School

A daily show for everyone who works a regular job and wants to start an income-earning project on the side.

Chris Guillebeau / Onward Project · Chris Guillebeau

3,584 episodesEN

Show overview

Side Hustle School has been publishing since 2016, and across the 10 years since has built a catalogue of 3,584 episodes, alongside 1 trailer or bonus episode. That works out to roughly 410 hours of audio in total. Releases follow a near-daily cadence.

Episodes typically run under ten minutes — most land between 5 min and 8 min — though episode length varies meaningfully from one episode to the next. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-language Business show.

The show is actively publishing — the most recent episode landed yesterday, with 242 episodes already out so far this year. Published by Chris Guillebeau.

Episodes
3,584
Running
2016–2026 · 10y
Median length
7 min
Cadence
Near-daily

From the publisher

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. Sales and Distribution by Lemonada Media https://lemonadamedia.com/  

Ep. 3523 - First $1,000: “I wanted to explore AI-generated art…”

Aug 24, 20266 min

Ep. 3522 - STORY: Lather, Rinse, Recycle: Soapy Problem Leads to Clean Solution

Aug 23, 20267 min

Ep. 3521 - Q&A: “How do I find customers as a digital personal assistant?”

Aug 22, 20264 min

Ep. 3520 - Failure Friday: “After I was hit by a car, things got worse…”

Aug 21, 20266 min

Ep. 3519 - TBT: Bridesmaid-for-Hire Keeps Walking Down the Aisle

Aug 20, 20266 min

Ep. 3518 - Q&A: “Where do I begin if I want to make an app?”

Aug 19, 20264 min

Ep. 3517 - Q&A: “Should I start a new site for my food business?”

Aug 18, 20264 min

Ep. 3516 - First $1,000: “I built an Airbnb rental in my backyard…”

Aug 17, 20264 min

Ep. 3515 - STORY: Hair Braiding Workshops Help Trans-Racial Adoptive Families

Aug 16, 20266 min

Ep. 3514 - Q&A: “How to make a board game from start to finish?”

Aug 15, 20264 min

Ep. 3513 - STORY: Teacher Flips Sports Gear For $8,000/Month

Aug 14, 20267 min

Ep. 3512 - TBT: Southern Transplant Creates Watercolor Brand

Aug 13, 20267 min

Ep. 3511 - Q&A: “Do I have to sell as a SAAS?”

Aug 12, 20265 min

Ep. 3510 - Q&A: “How many tech tools do I need to master?”

Aug 11, 20265 min

Ep. 3509 - First $1,000: Paralegal Assists U.S. Immigrants to Canada

Aug 10, 20267 min

Ep. 3508 - STORY: “SwitchPod” Camera Tool Raises $415,748 on Kickstarter

Aug 9, 20266 min

Ep. 3507 - Q&A: “How to convert non-paying students into customers?”

Aug 8, 20264 min

Ep. 3506 - Failure Friday: “I had tears in my eyes reading the response…”

Aug 7, 20264 min

Ep. 3505 - TBT: Family Affirmation Cards Go Global

Aug 6, 20265 min

Ep. 3504 - Q&A: “How do you forecast earnings for a side hustle?”

Aug 5, 20264 min
2026 Chris Guillebeau / Onward Project