Chris Guillebeau

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.

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

#1783 - TBT: Pyrographic Drumsticks Blaze Profitable Path 18.11.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Ella Cordial-Brockelsby, the owner of Cordial Greetings. She uses pyrography (!) to make and sell woodburned home decor, art, and drumsticks. This episode is on fire...   Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau...

#1782 - Q&A: “I stopped writing on my blog. Should I delete it or just leave it up?” 17.11.2021

Today’s caller started a blog with enthusiasm but then it fell into decline. What happens now?  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 been...

#1781 - Fishing Charter Marketplace Hooks Clients and Guides 16.11.2021

Two friends team up to build “Airbnb for fishing,” a marketplace of fishing trips that connects guides and clients worldwide.   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...

#1780 - Q&A: How much do app designers make? 15.11.2021

Today’s caller wants to understand the business of app-making. What’s the average app designer income? What about the outliers? 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...

#1779 - Plant-Based Lebanese Food Goes Online 14.11.2021

As her health improved, this Aussie of Lebanese heritage started converting meat-based recipes to vegan equivalents. She’s now sharing her recipes with the 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 y...

#1778 - Q&A: Can I import rain barrels from the Netherlands? 13.11.2021

A listener loves rain barrels (this is a thing) and she’s found the perfect one in the Netherlands—but she lives in the U.S. Might she be able to partner with the company to become their national distributor?    Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Vi...

#1777 - Failure Friday: “No one wanted a bat house during the pandemic…” 12.11.2021

In this week’s Failure Friday segment, we hear from the maker of “Big Bat Houses.” When demand for his product plummeted at the start of the pandemic, he was forced to regroup.   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: ChrisGuill...

#1776 - TBT: Tap Dance Teacher Offers Worldwide Lessons 11.11.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Bill Simpson, chief tap dancer of HowtoTapDance.com. From his homebase of Melbourne, Australia, he teaches the art of the tap to students all over the world.  Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on...

#1775 - Q&A: Best platform to host an online course? 10.11.2021

These days, there are many options to host your online course: Thinkific, Teachable, Kajabi, and others. Is there a clear winner?  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...

#1774 - Consignment Sale Secrets: Ask to Sell Your Grandma’s Stuff 09.11.2021

In need of extra money, an enterprising grad student starts selling his unused items online. He then branches out into consignment sales, with a twist: most of his inventory comes from friends and family.   Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit C...

#1773 - Q&A: I launched my site and nothing happened! 08.11.2021

Today’s listener made a website with something for sale, opened the cart for business, and no one bought anything. Womp, womp … what should he do next?   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...

#1772 - Toronto Songwriting School Harmonizes During Pandemic 07.11.2021

Two long-time friends work in harmony to maintain their songwriting school in the midst of pandemic disruptions.    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...

#1771 - Q&A: Idea for a “road trip kit” that sells at gift shops 06.11.2021

A listener has a cool idea: they want to sell a road trip kit. How can they put it together, and who is their ideal customer?  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 i...

#1770 - Failure Friday: “We hired a designer who said she could do everything…” 05.11.2021

In this week’s Failure Friday segment, we hear from the co-founder of TuckTats, which sells temporary tattoos to cover surgical scars. When they were just getting started, they found a designer who was a one-stop shop—or so they thought.   Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on...

#1769 - TBT: Southern Expat Redesigns Mississippi State Flag 04.11.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Micah Whitson, founder of a business that sells letterpress wall art for homes. Last year, he had the chance to redesign part of the Mississippi state flag!  Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on I...

#1768 - Q&A: Videographer hopes to provide remote filming services 03.11.2021

This videographer hopes to go fully virtual with his filming services. LinkedIn and other companies have done this recently—what does our listener need to know?   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...

#1767 - Solitaire Game App Earns $10,000/Month 02.11.2021

After a failed startup attempt, a developer revisits an old solitaire game he made as a side project. It now brings in a large amount of passive income every month. 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 y...

#1766 - Q&A: Which business models are evergreen? 01.11.2021

Opportunities come and go, but some business models stay around forever. Aside from reselling—which we cover from time to time—what are they?   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 sh...

#1765 - Nighttime Marathoner Has Bright Idea 31.10.2021

Tired of wearing bulky safety gear while running at night, this competitive runner invents a better solution.  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 fr...

#1764 - Q&A Halloween Special: How to market spooky savory pastries? 30.10.2021

Happy Halloween! In the spirit of the holiday, we have a listener in Canada who’s making a spooky treat for sale. What’s the best way she can reach a market of buyers?  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...

#1763 - Failure Friday: “We failed to account for the ingredients to success…” 29.10.2021

In this week’s Failure Friday segment, we hear from the co-founder of a business offering handmade goods from Nashville. The company’s early success leads him to believe he can replicate the model elsewhere. Spoiler: it doesn’t work!   Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Ins...

#1762 - TBT: Kindle Books Produce Passive Income for Aussie Novelist 28.10.2021

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Kyla Gardner in Melbourne, Australia. She’s created passive income from a series of self-published nonfiction books—and now she’s jumping into fiction.  Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instag...

#1761 - Q&A: Should I use an emergency savings fund for my side hustle? 27.10.2021

The headline says it all: should you use an emergency savings fund for a side hustle? Get ready for a personal finance cage fight! 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...

#1760 - Scented Santa Letters Become Sold-Out Seasonal Business 26.10.2021

A listener writes herself into a personalized letter business that earns $17,000 in three weeks.   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...

#1759 - Q&A: How to use Instagram to market my voiceover services? 25.10.2021

A listener wonders about using Instagram to market to companies that cast voiceover artists—and a real voiceover pro responds!   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...

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