Side Hustle School
Chris Guillebeau / Onward Project
A daily show for everyone who works a regular job and wants to start an income-earning project on the side.
- 5 minutes 25 secondsEp. 3376 - First $1,000: “I went door-to-door selling home alarms…”
In this week’s First $1,000 segment, we hear from a real-life door-to-door salesman. Some “knockers” can earn six figures a year or more, as long as they can cope with repeated rejection. Here’s the story of one guy who’s well on his way.
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.
30 March 2026, 7:00 am - 6 minutes 25 secondsEp. 3375 - STORY: Firefighter Uses Chainsaw for Jumbo-Sized Woodworking
Taking advantage of some downtime, this Alberta firefighter picks up a chainsaw and begins carving out life-sized wooden bears. He sells his creations to universities, restaurants, and anyone who wants a unique (and large!) handcrafted item.
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.
29 March 2026, 7:00 am - 5 minutes 24 secondsEp. 3374 - Q&A: “Should I offer a pay-what-you-will price?”
This listener started a pen-to-paper initiative to connect people through snail mail. It’s starting well, but how can it scale—and is a Pay-What-You-Will pricing model the best option?
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.
28 March 2026, 7:00 am - 7 minutes 23 secondsEp. 3373 - STORY: Savvy Stationery Site Offers Cards for Divorce & Diwali
A director at a non-profit college of music creates an e-commerce site selling greeting cards with a twist.
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.
27 March 2026, 7:00 am - 6 minutes 37 secondsEp. 3372 - TBT: Frozen Yogurt Dog Treats Are No Barking Matter
In this week’s “Throwback Thursday” segment, we hear from the co-founder of a business that provides frozen treats for dogs.
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.
26 March 2026, 7:00 am - 5 minutes 35 secondsEp. 3371 - Q&A: “Any tips for buying stuff at flea markets to resell?”
Reselling is the easiest way to get started making money apart from your job. What are some tips to get started, and how can you find items to buy and sell?
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.
25 March 2026, 7:00 am - 4 minutes 23 secondsEp. 3370 - Q&A: “Can I tell people where to find fake luxury goods?”
A listener wants to sell a guide to replica luxury goods. She’s not going to sell the items themselves, just the information. Is this a good 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.
24 March 2026, 7:00 am - 6 minutes 29 secondsEp. 3369 - First $1,000: City Government Staffer Leads Virtual Events
In this week’s First $1,000 segment, we hear from a virtual events planner. If you need a virtual wedding, networking event, or gender reveal party, she’s got it covered!
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.
23 March 2026, 7:00 am - 7 minutes 36 secondsEp. 3368 - STORY: Veteran Turns Sweet Compulsion Into Obsessive Candy Hustle
After completing 30 years of service in the Air Force, a veteran who struggles with OCD creates a new income source by selling candy.
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.
22 March 2026, 7:00 am - 4 minutes 39 secondsEp. 3367 - Q&A: “I’m ready for more passive income—what should I do?”
Our listener is earning more than $50,000/year from three side projects. Whoo hoo! Still, he wants more of this income to be passive, because he’s doing a lot of work for it. How can he go to the next level?
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.
21 March 2026, 7:00 am - 7 minutes 39 secondsEp. 3366 - Failure Friday: “A $300 mistake cost me $100,000”
In this week’s new “Failure Friday” segment, we hear from the founder of a lifestyle and apparel brand who wakes up one day to find out he’s being sued.
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.
20 March 2026, 7:00 am - More Episodes? Get the App