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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

3,630 episodesEN

Show overview

Side Hustle School has been publishing since 2016, and across the 10 years since has built a catalogue of 3,630 episodes, alongside 1 trailer or bonus episode. That works out to roughly 420 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 288 episodes already out so far this year. Published by Chris Guillebeau.

Episodes
3,630
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. 3569 - STORY: Hand Lettering Artist Upgrades Photo Booth Props

Oct 9, 20267 min

Ep. 3568 - TBT: Physician Designs Plush Toys to Teach Anatomy

Oct 8, 20267 min

Ep. 3567 - Q&A: “Can I resell items I get for free?"

Oct 7, 20264 min

Ep. 3566 - Q&A: “An English-language anime club in Japan…”

Oct 6, 20264 min

Ep. 3565 - First $1,000: “I got paid to walk dogs while on work calls…”

Oct 5, 20265 min

Ep. 3564 - STORY: Physical Therapist Sells 57,000 “Neck Hammocks”

Oct 4, 20267 min

Ep. 3563 - Q&A: “What’s the 80/20 rule of side hustling?”

Oct 3, 20264 min

Ep. 3562 - Failure Friday: “My app kept crashing during the big pitch…”

Oct 2, 202610 min

Ep. 3561 - TBT: “Graphic Designer for Dogs” Retrieves New Clients

Oct 1, 20267 min

Ep. 3560 - Q&A: “How can I rent out my spare bedroom on Airbnb?”

Sep 30, 20264 min

Ep. 3559 - Q&A: “How to sell a podcast as a paid subscription?”

Sep 29, 20264 min

Ep. 3558 - First $1,000: “Beekeeping is forced zen: be present or get stung!”

Sep 28, 20267 min

Ep. 3557 - STORY: Amsterdam Bike Tours Become Passive Profit Center

Sep 27, 20267 min

Ep. 3556 - Q&A: “How to profit from cover songs on Apple Music?”

Sep 26, 20264 min

Ep. 3555 - STORY: Continuing Education Directory Earns Six Figures

Sep 25, 20268 min

Ep. 3554 - TBT: Satin Pillowcases Inspire Dreamy Profits

Sep 24, 20269 min

Ep. 3553 - Q&A: “Would you join an introvert's networking club?”

Sep 23, 20264 min

Ep. 3552 - Q&A: “Can you really fly for free as an airline courier?”

Sep 22, 20264 min

Ep. 3551 - First $1,000: “My roommate threw a wad of hundred-dollar bills on the table…”

Sep 21, 20269 min

Ep. 3550 - STORY: It’s No Joke: Prank Musical Greeting Card Earns $36,000/Month

Sep 20, 20267 min
2026 Chris Guillebeau / Onward Project