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

#1808 - Q&A: Am I better at working for others than myself? 13.12.2021 4:03

Today’s listener thinks she is better at working for others and is worried about whether she’s cut out for starting a side business. Is this just a matter of self-confidence? 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: ChrisGuillebea...

#1807 - Expat Teacher Draws Up Personalized Woodworks 12.12.2021 6:02

A teacher from New Zealand moves to Japan and creates custom wood art based on personalized memories. 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 h...

#1806 - Q&A: Can I become a paid Pokémon consultant?? 11.12.2021 5:12

Today’s caller wants to get paid to consult with obsessed Pokémon players. Millions of people worldwide play Pokémon Go (and a new game, Pikmin Bloom) every month. Is there a chance to strike it rich as a Poké-coach? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countr...

#1805 - Failure Friday: “All I had to do was hit the record button…” 10.12.2021 8:40

In this week’s Failure Friday segment, we hear from Side Hustle School team member Jedd Chang! When international travel slowed down, his online cooking club side hustle took off. It did so well that more than 200+ members tuned in for a big Zoom meeting—where Jedd forgot to hit the record button. What did he learn? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show...

#1804 - TBT: Mystery Trip Biz Doubles Down on Thrills 09.12.2021 7:07

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Dave Green, the founder of Mystery Trip. His in-person event planning service has adjusted well to a hybrid 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...

#1803 - Q&A: Can this social worker sell “personal care swag bags”? 08.12.2021 4:31

In today’s episode, a social worker hopes to sell swag bags as a personal care item for other social workers—but she’s struggling to get it off the ground. 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 en...

#1802 - CBD Oil Products Produce Big Profits 07.12.2021 6:25

After getting help for her own anxiety, a pharmacist creates natural health products that improve the bottom line, one drop at a 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, pl...

#1801 - Q&A: What if your drop-shipper drops out? 06.12.2021 4:55

Drop-shipping can be a great business model *sometimes*, but when you aren’t handling inventory, you’re at the mercy of the company that does. How can this listener protect herself from an unresponsive third party? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countrie...

#1800 - The Blog That Laid the Golden Egg 05.12.2021 6:43

A Wall Street accountant hatches a million-dollar business around raising chickens in her backyard. 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...

#1799 - Q&A: Why do so many apps push in-app payments? 04.12.2021 5:59

A listener is making her first app and wondering about the best way to structure payments. Also: a free idea for an app to help you unsubscribe from apps! 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 enj...

#1798 - Failure Friday: “Our first trade show was canceled with no refund…” 03.12.2021 6:10

In this week’s Failure Friday segment, we hear from Chris Cavallari, who sells high-quality products with a Maine vibe. In March 2020, he prepared for his first wholesale trade show—and then the world closed down. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countrie...

#1797 - TBT: The Mushroom Kingdom of North Carolina 02.12.2021 7:43

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the business manager of Phenomenal Fungi, which sells tinctures, cultures, and mushroom merch. It’s been a busy year in the land of shrooms! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193co...

#1796 - Q&A: Where can you find products to resell over and over? 01.12.2021 4:46

It’s easy enough to find something you can buy and sell once. But for a real moneymaker, you need a source of products you can go to over and over. Today’s listener wonders: where is it?? 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:...

#1795 - Unofficial Schitt’s Creek Cookbook Folds in the Cheese 30.11.2021 6:07

Two sisters fold it all in with a self-publishing venture that tastes like success. 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 published...

#1794 - Q&A: “I’d like to write a paid financial newsletter for women…” 29.11.2021 4:28

Paid newsletters have really taken off, with some earning multiple six-figures for their writers. This listener has an astute observation and an idea. How can we help her “get the bag”? 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: Ch...

#1793 - Accountant Trades Active Clients for Passive Course Sales 28.11.2021 5:14

An American accountant living in South Africa creates a financial wellbeing course for small business owners. The passive income she earns from the course allows her to drop many of her clients. 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...

#1792 - Q&A: How can I sell different kinds of content in a bundle? 27.11.2021 3:30

Today’s caller is making a podcast, video series, and maybe something else. All of it will be for sale, and they aren’t sure how to package it. Should it be a single “bundle” or sold separately? 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...

#1791 - Failure Friday: Test Prep Tutor Gets Rejected by 100 Publishers 26.11.2021 6:30

In this week’s Failure Friday segment, we hear from the founder of a standardized test prep service. Before he started his business, he earned a perfect score on the SAT—and then pitched a book that was rejected by more than 100 literary agents and publishers. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chris...

#1790 - TBT: “Recovering Attorney” Operates 7-Figure Podcast Service 25.11.2021 8:13

Happy Thanksgiving! In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a former attorney and White House aide who starts a service helping businesses with podcasts. It’s grown into a 7-figure operation! Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instag...

#1789 - Q&A: How to market consulting for health professionals? 24.11.2021 5:04

This Canadian listener is launching a learning platform for pediatric anesthesia. How can she reach her intended audience—and how can she serve professionals in this market from less-developed countries? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chr...

#1788 - Rustic Tiki Bars Turn Into Pallet-able Career 23.11.2021 5:50

Instead of heading to the elementary school classroom, this new teaching grad earns a good living making custom tiki bars for homeowners. Why not! 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 t...

#1787 - Q&A: How do people discover a new podcast? 22.11.2021 4:48

Podcasts have a “discoverability problem”: they don't rank in search terms or get links from other sites. If you have a new show, what can you do to make sure people will find it? 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: ChrisGu...

#1786 - Australian Shapes Crafty Shop During Lockdown 21.11.2021 7:26

After discovering the life changing magic of polymer clay, an Aussie uses her time in lockdown to create a one-stop shop for the maker community. 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...

#1785 - Q&A: How to market “lockdown art” project? 20.11.2021 5:01

A caller from New York City becomes well known for posting drawings and paintings to an Instagram account during pandemic lockdowns. Now he’s wondering: how can he monetize the attention he’s received? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chri...

#1784 - Failure Friday: “Weeks after launch, the website was totally dead…” 19.11.2021 5:15

In this week’s Failure Friday segment, we hear from Rupert Hunt, the founder of SpareRoom.com. It’s now the world’s largest roommate finder service—but in the early days, the team struggled to commit to it. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit...