Side Hustle School

Chris Guillebeau

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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3,557 episodes
Updated Yesterday

Episodes3557

Newest first

Ep. 3500 - Q&A: “What's the best way to sell a digital download?”
Let’s say you have something to sell that is digitally delivered. What’s the best way to accept payment and get the item to buyers? 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.
Yesterday · 4 min
Ep. 3499 - STORY: Hedge Fund Manager Rocks On with Diamond Algorithm
“Have algorithm, will side hustle”: These financial traders applied their career know-how to a completely different industry. They’re now earning $5,000/month in affiliate commissions. 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.
Friday · 7 min
Ep. 3498 - TBT: Hydroponic Indoor Plant System Branches Out
In this week’s “Throwback Thursday” segment, we hear from the founder of IG Works, which specializes in indoor gardening kits that allow you to grow dozens of large plants in a small space. It’s truly un-be-leaf-able! 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.
Thursday · 6 min
Ep. 3497 - Q&A: “How much time do people spend on these projects?”
If you have at least one side hustle already, is it a couple hours a week, taking over your life, or somewhere in between? 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.
Wednesday · 4 min
Ep. 3496 - Q&A: “How to sell an online birth preparation course?”
A couple in the UK seeks advice on a birth preparation program course they’ve been revisiting in recent months. 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.
Tuesday · 5 min
Ep. 3495 - First $1,000: Vintage Luggage Upcycler Hits Ground Running
In this week's First $1,000 segment, an upcycler transforms forgotten vintage luggage into functional art pieces. 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.
Monday · 4 min
Ep. 3494 - STORY: The 50 Shades of Editing Romance Novels
A corporate recruiter pursues a steamy side business editing romance novels. 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.
July 26 · 8 min
Ep. 3493 - Q&A: "I sold more by raising my prices—is that wrong??”
Today’s listener has a moral dilemma: they made more money by raising their prices! (Wait, what’s wrong with that? Listen to their question to find out.) 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.
July 25 · 4 min
Ep. 3492 - STORY: Failure Friday: “My business partner was a convicted felon…”
In this week’s Failure Friday segment, we hear from Alan Perlman, the founder of a drone training company. His business now brings in seven figures a year, but it started with a rocky partnership. 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.
July 24 · 6 min
Ep. 3491 - TBT: “Kindness Kits” Spread Love and Draw Positive Returns
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from someone selling an unusual product that’s one-part social cause and one-part profitable business. What’s changed since we first featured him? 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.
July 23 · 6 min
Ep. 3490 - Q&A: “How can I make a product to help with applied learning?”
This listener wants to help people learn more actively. Sounds good, but how does it become a product or service? 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.
July 22 · 4 min
Ep. 3489 - Q&A: “I’d like to sell an Apple Watch guide…”
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.
July 21 · 4 min
Ep. 3488 - First $1,000: “I had literally zero intention of running a business…”
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.
July 20 · 7 min
Ep. 3487 - STORY: Chemical Engineer Zips Up Solution for Baggy Shirts
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.
July 19 · 7 min
Ep. 3486 - Q&A: “I’d like to sell a toolkit to sole proprietors…”
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.
July 18 · 4 min
Ep. 3485 - STORY: Atlanta Lawyer Walks Into Food Tour Biz
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.
July 17 · 7 min
Ep. 3484 - TBT: Multilingual Insurance Agent Creates Translation Course
In this week’s “Throwback Thursday” segment, we hear from a multilingual insurance agent who creates an online course on the art of translation. 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.
July 16 · 7 min
Ep. 3483 - Q&A: Are there any *good* MLM companies?
Today’s listener is at risk of falling prey to a shady network marketing (MLM) company. How do we know it’s shady? Because it’s a network marketing company! Listen and learn. 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.
July 15 · 4 min
Ep. 3482 - Q&A: “Recovering after a failed partnership…”
Today we’re going to hear from a caller who’s previous venture didn’t work out. That one was a partnership with a friend that ended amicably, and now our listener is ready to make another attempt of her own. 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.
July 14 · 4 min
Ep. 3481 - First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles
In this week’s First $1,000 segment, we hear from Priya in Bangalore. She has a side hustle helping men with their dating profiles—and she keeps busy! 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.
July 13 · 5 min

Side Hustle School

Ep. 3500 - Q&A: “What's the best way to sell a digital download?”

Ep. 3499 - STORY: Hedge Fund Manager Rocks On with Diamond Algorithm

Ep. 3498 - TBT: Hydroponic Indoor Plant System Branches Out

Ep. 3497 - Q&A: “How much time do people spend on these projects?”

Ep. 3496 - Q&A: “How to sell an online birth preparation course?”

Ep. 3495 - First $1,000: Vintage Luggage Upcycler Hits Ground Running

Ep. 3494 - STORY: The 50 Shades of Editing Romance Novels

Ep. 3493 - Q&A: "I sold more by raising my prices—is that wrong??”

Ep. 3492 - STORY: Failure Friday: “My business partner was a convicted felon…”

Ep. 3491 - TBT: “Kindness Kits” Spread Love and Draw Positive Returns

Ep. 3490 - Q&A: “How can I make a product to help with applied learning?”

Ep. 3489 - Q&A: “I’d like to sell an Apple Watch guide…”

Ep. 3488 - First $1,000: “I had literally zero intention of running a business…”

Ep. 3487 - STORY: Chemical Engineer Zips Up Solution for Baggy Shirts

Ep. 3486 - Q&A: “I’d like to sell a toolkit to sole proprietors…”

Ep. 3485 - STORY: Atlanta Lawyer Walks Into Food Tour Biz

Ep. 3484 - TBT: Multilingual Insurance Agent Creates Translation Course

Ep. 3483 - Q&A: Are there any *good* MLM companies?

Ep. 3482 - Q&A: “Recovering after a failed partnership…”

Ep. 3481 - First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles

Ep. 3483 - Q&A: Are there any good MLM companies?