Side Hustle School podcast | Listen online for free

3550 episodes

Ep. 3489 - Q&A: “I’d like to sell an Apple Watch guide…”
07/21/2026 | 4 mins.
Today’s listener wants to make money helping people set up and get the best use out of their new smartwatch. What’s the best course of action?

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.
Ep. 3488 - First $1,000: “I had literally zero intention of running a business…”
07/20/2026 | 7 mins.
In this week’s First $1,000 segment, we hear from Lindsay Gordon, who left a career at Google to become a “career coach for analytically-minded people.”

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.
Ep. 3487 - STORY: Chemical Engineer Zips Up Solution for Baggy Shirts
07/19/2026 | 7 mins.
When an engineer receives a ridiculously baggy work shirt, he grabs it by the collar and designs a DIY tailoring device. Four years later, he’s sold $150,000 of them.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.
Ep. 3486 - Q&A: “I’d like to sell a toolkit to sole proprietors…”
07/18/2026 | 4 mins.
Today’s listener has an idea to sell a toolkit to help sole proprietors become more efficient. What are the pros and cons of this idea?

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.
Ep. 3485 - STORY: Atlanta Lawyer Walks Into Food Tour Biz
07/17/2026 | 7 mins.
An Atlanta lawyer creates a thriving and unexpected walking tour business.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.

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About Side Hustle School

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. Hosted on Acast. See acast.com/privacy for more information.

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