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Side Hustle School

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Rating
★★★★★
4.7
from
3177 reviews
This podcast has
2000 episodes
Language
English
Date created
2016/12/20
Latest episode
2026/02/03
Average duration
7 min.
Release period
1 days

Description

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/  

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Ep. 3321 - Q&A: “Should I start a new business or expand my current one?”
2026/02/03
This listener grew a side hustle to a full-time business—so naturally, now she wants to start another hustle! Is it completely new or an expansion of what she’s already been doing? 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3320 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer
2026/02/02
In this week’s First $1,000 segment, we hear from Elaine in Wayne County, Michigan. She’s an accountant for her day job and works as an engagement photographer for her side hustle. 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3319 - STORY: Physician Designs Plush Toys to Teach Anatomy
2026/02/01
A physician designs and manufactures plush toys in the shape of human organs. They are used to teach kids about the human body, and as “get well soon” gifts for hospital patients.  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3318 - Q&A: “How can I sell on a platform like NextDoor?”
2026/01/31
NextDoor is not primarily designed as a platform for you to go crazy and sell a bunch of stuff. So if you DO want to sell there—what do you need to know?  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3317 - STORY: Jiu-Jitsu Instructor Pins Down Mobile Workout Tool
2026/01/30
An unconventional workout tool becomes a hit on Kickstarter, then goes on to earn $20,000 a month for its creator.  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3316 - TBT: Designer Scales Personalized Wedding Products to $1M+
2026/01/29
In this week’s “Throwback Thursday” segment, we hear from a graphic designer who does custom illustrations for weddings and other events. It’s now a seven-figure 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3315 - Q&A: “How do I transition from Etsy to Shopify?”
2026/01/28
A listener has been selling on Etsy and wants to make the switch to Shopify. What’s the best way to do this? 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3314 - Q&A: “What's the best software to write a non-fiction book?”
2026/01/27
Today’s caller wants to know about the easiest and most helpful tools to write a non-fiction book. Unfortunately, books do not write themselves, but we’ll give him three resources that might make it easier.   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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3313 - First $1,000: “I still remember the day I hit the goal…”
2026/01/26
In this week’s First $1,000 segment, we hear from Jodi Carlson, who sells resources and materials for Girl Scout troop leaders.  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3312 - STORY: The Clothes Dryer That Changed a Family Forever
2026/01/25
When this government employee is let go from his job, he stumbles upon a reselling opportunity that would end up helping his family ride the coming recession—and eventually earn six figures in a single year.  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3311 - Q&A: “Get paid to help brands with their Terms & Conditions?”
2026/01/24
Today’s caller wants to help brands improve their Terms & Conditions, also known as T&C. Can she design and license a template that companies will pay for? 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3310 - Failure Friday: “We were incredibly disappointed…”
2026/01/23
In this week’s Failure Friday segment, we hear from the founder of Kettlebell Kings, an ecommerce shop. When a big early order from a supplier went terribly wrong, he had to regroup and learn resilience.  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3309 - TBT: “MomBox” Expands to Popular Subscription Box Service
2026/01/22
In this week’s “Throwback Thursday” segment, we hear from Kate Westervelt, the founder of MomBox. She’s gone from frustrated new mom to CEO of a growing startup! 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3308 - Q&A: “What are the ethics of paid referrals to therapists?”
2026/01/21
A listener with a YouTube channel about quitting smoking wants to earn commissions by referring viewers to therapists. What are the ethical and practical concerns 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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.
Ep. 3307 - Q&A: “Should I charge a flat fee or percentage?”
2026/01/20
A listener and her teenager have been getting off to a good start selling on Facebook Marketplace. They now have the chance to sell for others, and are wondering about some best practices.  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: [email protected] 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. 😎 🙏🏼  See omnystudio.com/listener for privacy information.

Podcast reviews

Read Side Hustle School podcast reviews


4.7 out of 5
3177 reviews
★★★★★
HeyTriciaC 2024/06/01
Motivating!
I love listening to this show. Every single time I find myself more motivated to keep up the pace! Thank you!
★★☆☆☆
SquareLover 2025/06/21
Good content, annoying ads
Great quick tips. But like 50% of the entire thing is ads. Super disappointing money grab :(
★★★★☆
54321AK 2025/06/12
Good stuff!
Thank you, it’s the little things we don’t think of!
★★★★★
Fitterthanyou 2023/11/24
Inspiration is good
Right after my morning meditation and coffee listening to side hustle school is the first thing I do. Each show inspires me every day. I'm gaining eno...
★★★★★
Cindi Kolf 2023/11/17
Love Side Hustle!
To the point with lots of good information! Thank you, Chris!
★★★★★
Berkeley knight 2023/09/15
Entrepreneurshipclass
Side hustle rocks
★☆☆☆☆
ib_cj 2023/09/29
If you like ads, this show is for you
On the outside, this podcast looked good; small segments of information on a specific subject. Well, I tried a few episodes and found that it’s just t...
★★★★★
Debbie (from Boston area) 2023/06/10
Awesome podcast!!
I have been listening to Side Hustle School since the 1st episode! I love hearing about everyone’s creative side hustles and how each one is different...
★☆☆☆☆
yUnoWorkSnapchat 2023/07/18
Episodes don’t hit the same. Now filled with ads. 😑
I used to be a huge fan. Side Hustle School podcast used to be a huge part of my everyday routine and workflow. Now, every episode’s littered with ads...
★★☆☆☆
Honest John 206 2023/06/12
No value
This podcast provides virtually no value. Seems like the creator’s focus is ad revenue. Way too many ads for a 6-7 minute podcast. The “guests” sound ...
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