Side Hustle School

Side Hustle School Podcast

Latest Episodes

#2344 - Failure Friday: “Fake Wedding Guest” Biz Fizzles Out

June 2, 2023 - 05:43
In this week’s Failure Friday segment, we hear from a side hustler who tries selling a service as a fake wedding guest who helps to fill...

#2343 - TBT: Vancouver Bike Tours Takes Scenic Route

June 1, 2023 - 05:15
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a cycling tour business that serves...

#2342 - Q&A: “How can I host a yoga and wellness retreat?”

May 31, 2023 - 04:11
Today’s caller is a yoga instructor with a vision to organize wellness retreats in serene locations. Let’s stretch our minds and see if...

About The Show

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.

More Episodes

#2344 - Failure Friday: “Fake Wedding Guest” Biz Fizzles Out

June 2, 2023 - 05:43
In this week’s Failure Friday segment, we hear from a side hustler who tries selling a service as a fake wedding guest who helps to fill...

#2343 - TBT: Vancouver Bike Tours Takes Scenic Route

June 1, 2023 - 05:15
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a cycling tour business that serves...

#2342 - Q&A: “How can I host a yoga and wellness retreat?”

May 31, 2023 - 04:11
Today’s caller is a yoga instructor with a vision to organize wellness retreats in serene locations. Let’s stretch our minds and see if...

#2341 - Q&A: “There’s no money in personal training…”

May 30, 2023 - 05:05
Most personal trainers that I’ve talked to agree on one thing: there’s not much money in just the personal training. This is true even...

#2340 - First $1,000: Baltimore Photographer Starts Drone Instruction

May 29, 2023 - 05:59
In this week’s First $1,000 segment, we hear from a Baltimore photographer who finds inspiration high in the sky. His new business...

#2339 - Q&A: “How to offer content strategy services…?”

May 28, 2023 - 04:44
As a successful freelance copywriter, today’s caller is looking to transition into content strategy. How can he rebrand himself and find...