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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

3,479 episodesEN

Show overview

Side Hustle School has been publishing since 2016, and across the 10 years since has built a catalogue of 3,479 episodes, alongside 1 trailer or bonus episode. That works out to roughly 400 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 137 episodes already out so far this year. Published by Chris Guillebeau.

Episodes
3,479
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. 3420 - Q&A: “Have I found a way to accept PayPal payments with no fees?”

May 13, 20264 min

Ep. 3419 - Q&A: “How to grow a facepainting business?”

May 12, 20265 min

Ep. 3418 - First $1,000: “No one in Boston could find a good pierogi…”

May 11, 20266 min

Ep. 3417 - STORY: Store Manager Makes Micro Gainz For Macro Profits

May 10, 20267 min

Ep. 3416 - Q&A: “Is it still a good idea to sell Merch by Amazon?”

May 9, 20265 min

Ep. 3415 - STORY: Rustic Wall Hangings Rack Up Worthwhile Profits

May 8, 20266 min

Ep. 3414 - TBT: Personal Trainer Pumps Up Protein Pancakes

May 7, 20266 min

Ep. 3413 - Q&A: “How can I sell my own crossword puzzles?”

May 7, 20264 min

Ep. 3412 - Q&A: “How to share men's lifestyle advice that isn’t toxic…”

May 5, 20265 min

Ep. 3411 - First $1,000: Software Engineer Crafts Balloon Sculptures

May 4, 20265 min

Ep. 3410 - STORY: Athletes Create “Chewable Energy” Gum

May 3, 20267 min

Ep. 3409 - Q&A: “I bought and sold 75 Peloton bikes…”

May 2, 20264 min

Ep. 3408 - Failure Friday: “My Facebook page was taken over by hackers…”

May 1, 20266 min

EP. 3407 - TBT: Kindle Books Produce Passive Income for Aussie Novelist

Apr 30, 20266 min

Ep. 3406 - Q&A: “I want to make an asexual dating app…”

Apr 29, 20264 min

Ep. 3405 - Q&A: “The alarm clock that costs money if you oversleep…”

Apr 28, 20264 min

Ep. 3404 - First $1,000: Digital Art Reaches Physical Homes Worldwide

Apr 27, 20265 min

Ep. 3404 - First $1,000: Digital Art Reaches Physical Homes Worldwide

Apr 27, 20265 min

Ep. 3403 - STORY: Shoe Designer Runs After $1 Million Challenge

Apr 26, 20268 min

Ep. 3403 - STORY: Shoe Designer Runs After $1 Million Challenge

Apr 26, 20268 min
2026 Chris Guillebeau / Onward Project