Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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.

Author

Chris Guillebeau

Episodes

#1833 - Failure Friday: “My complacency set in over time…” 07.01.2022 8:01

In this week’s Failure Friday segment, we hear from Brock McGroff, founder of TheModestMan.com. While he was focused on other things, his website plateaued in traffic and then began a gradual decline. 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 li...

#1832 - TBT: Rocket Scientist Tutoring Reaches Zero Gravity 06.01.2022 5:55

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Thais Lage, the young founder of a Florida tutoring business that now has 25 staff tutors. She does this while working full time as an aerospace engineer! 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...

#1831 - Q&A: “I’d like to sell an Apple Watch guide…” 05.01.2022 4:52

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: SideHus...

#1830 - Self-Published Kindle Books Produce Full-Time Income 04.01.2022 7:49

A government administrator builds an offramp to his day job by self-publishing books using Kindle Direct Publishing. 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: te...

#1829 - First $1,000: “Don’t give up—your future self will thank you!” 03.01.2022 9:10

In the first version of a brand-new segment for 2022, we hear from Deya Aliaga Kuhnle, the founder of DBM Bootcamp. She now runs a six-figure agency—but how did she make her first $1,000? 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&...

#1828 - Q&A: How to monetize a year of 40 side hustles? 02.01.2022 5:58

Today’s listener wants to start 40 side hustles in 2022! Let’s see how we can support his ambitious project. 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@sidehu...

#1827 - New Year, New Season! Here’s What’s Coming Up 01.01.2022 7:04

We’re back with an all-new season! Here’s how year six (!) of Side Hustle School will work. Among other highlights: a new weekly segment, more stories + Q&A, and a $1,000 giveaway to one special listener. 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 lesso...

#1826 - Failure Friday: Self-Guided London Food Tours Fail to Excite 31.12.2021 7:50

Happy New Year’s Eve! In this week’s Failure Friday segment, we hear from Jennifer Earle, founder of Chocolate Ecstasy Tours. With her guided tour business in full swing, she decides to start a self-guided version called Taste Tripper. Unfortunately, this expansion proves to be unsustainable. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/qu...

#1825 - TBT: “Radical Tea Towels” Promote Historical Progress 30.12.2021 9:07

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Radical Tea Towels, a British family business that promotes historical progress and modern messages of change. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit...

#1824 - Q&A: Can you import contact lenses for resale? 29.12.2021 4:23

A listener thinks he’s found the ultimate arbitrage market—right before his eyes! Can he import contact lenses from outside the U.S. (where the price is much lower) and resell them at home? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site...

#1823 - New App Designer Jumps Into No-Code Development 28.12.2021 8:09

A nomadic designer launches an app development career in Switzerland, creating more than ten apps in a single year. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along!...

#1822 - Q&A: What's the best platform for my idea? 27.12.2021 4:31

Do you start with your idea, or start with the ideal platform for your idea? Today’s caller wants to remain “platform agnostic.” How should he proceed? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoy...

#1821 - Marketing Analyst Serves Up Gluten-Free Profit 26.12.2021 6:28

A home chef draws on her food limitations to whip up a popular blog that earns $5,000/month from ad revenue. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's fre...

#1820 - SPECIAL Q&A: Overnight delivery impacted by supply chain crisis 25.12.2021 4:11

A very special listener question came in overnight—all the way from the North Pole! Let’s see if we can help this caller with an urgent supply chain problem. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're...

#1819 - Failure Friday: “I had to take a hard look at my business model…” 24.12.2021 7:16

In this week’s Failure Friday segment, we hear from Allen Chiang, the owner of Retro Radio Farm. At first, he has too much business to handle—but when Facebook advertising becomes less profitable, he has too little. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193count...

#1818 - TBT: Home Haircut Tool Brushes Into Walmart 23.12.2021 7:21

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of The Cut Buddy, a tool for home haircuts. With everyone staying home last year, his business took off! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's mai...

#1817 - Q&A: How much money can you make per subscriber? 22.12.2021 4:53

When you’re building an email list and maintaining long-term relationships with subscribers, you want to know how much money those subscribers are producing. The metric known as customer lifetime value (CLV) can tell you! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193c...

#1816 - ‘Jack n ginger’ Admin Designs Island-Life Jewelry 21.12.2021 6:52

Drawing on inspiration from the islands of Hawaii, this office manager earns up to $4,000/month part-time with her island-style jewelry creations. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the...

#1815 - Q&A: How is side hustling dependent on the broader economy? 20.12.2021 4:30

If you have an existing side hustle—or plan to start one—do you need to pay attention to what’s happening in the economy? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it al...

#1814 - Freelance Writer Publishes Sixty Articles Each Month 19.12.2021 7:14

A freelancer finds her niche in the financial world, bringing in over six figures a year writing part-time. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's fre...

#1813 - Q&A: Video game developer wants to 'build in public' 18.12.2021 4:54

Our listener has an idea to design and code a mobile game in public, using a platform like Twitch. How can she attract followers? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pa...

#1812 - Failure Friday: “We went all-in on applying for a $2 million grant…” 17.12.2021 7:42

In this week’s Failure Friday segment, we hear from Suzanne Tucker, founder of Generation Mindful. Last year, her team decided to go all-in on applying for a big NIH grant—and the initial outcome was disappointing. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countr...

#1811 - TBT: Soap Springs Eternal for Non-Profit Employee 16.12.2021 6:13

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a soap-making adventuress who goes all-in on a squeaky clean side hustle. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjo...

#1810 - Should I start a new site for my food business? 15.12.2021 5:28

This listener has an older food blog that she hasn’t updated in a while, and now she wants to convert it to an ecommerce site. Is that the best approach, or should she start all over? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: Chri...

#1809 - Writing About Reality TV Becomes Rite of Passion 14.12.2021 7:21

A journalism teacher’s love of reality TV brings success from The Real World to the real world. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has b...