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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

3,527 episodesEN

Show overview

Side Hustle School has been publishing since 2016, and across the 10 years since has built a catalogue of 3,527 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 185 episodes already out so far this year. Published by Chris Guillebeau.

Episodes
3,527
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. 3466 - STORY: Music Graduate Makes Spare Change Filling Spare Rooms

Jun 28, 20268 min

Ep. 3465 - Q&A: “Help! I’m stuck trying to find my ‘ah-ha’ idea”

Jun 27, 20265 min

Ep. 3464 - Failure Friday: “We accept your proposal… to resign”

Jun 26, 20266 min

Ep. 3463 - TBT: Beer Made from “Upcycled” Grain TBT: Blogger Explores Affiliate Marketing in India

Jun 25, 20267 min

Ep. 3462 - Q&A: “I stopped delivering for my Patreon…”

Jun 24, 20265 min

Ep. 3461 - Q&A: “Should I pursue three ideas or just one?”

Jun 23, 20263 min

Ep. 3460 - First $1,000: Indian Tutor Helps U.S. High School Students Learn Math

Jun 22, 20265 min

Ep. 3459 - STORY: Hawaiian Native Teaches Virtual Ukulele Lessons

Jun 21, 20266 min

Ep. 3458 - Q&A: “How do you ethically source products made in overseas factories?”

Jun 20, 20265 min

Ep. 3457 - STORY: Financial Blog Sprouts into $35,000/Month Money Tree

Jun 19, 20267 min

Ep. 3456 - TBT: Urban Hiker Leads Tours in San Francisco

Jun 18, 20267 min

Ep. 3455 - Q&A: “My ‘road trip kit’ for truck stops…”

Jun 17, 20264 min

Ep. 3454 - Q&A: “Which is better: direct or indirect income?

Jun 16, 20265 min

Ep. 3453 - First $1,000: “My music was played on a Romanian TV show…”

Jun 15, 20266 min

Ep. 3452 - STORY: A Mental Health Counselor By Day, A Headband Artist by Night

Jun 14, 20266 min

Ep. 3451 - Q&A: “’Spaced repetition' practice with outsourced tutors from overseas?”

Jun 13, 20265 min

Ep. 3450 - Failure Friday: “I decided to give money to Meta…”

Jun 12, 20266 min

Ep. 3449 - TBT: These “Sweatpant Overalls” Produce Joy and Extra Pockets

Jun 11, 20267 min

Ep. 3448 - Q&A: “How to grow a YouTube channel with 121,000 subscribers?”

Jun 10, 20265 min

Ep. 3447 - Q&A: “How can I sell flash cards to pharmacy students?”

Jun 9, 20265 min
2026 Chris Guillebeau / Onward Project