Chris Guillebeau

Side Hustle School

Business EN ↓ 3650 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.

Be sure to visit the podcast's website and support the creator: sidehustleschool.com

Author

Chris Guillebeau

Episodes

#2297 - Q&A: “How can I market my online yoga course?” 16.04.2023 5:25

In this episode, a yoga instructor looks to expand her business beyond the confines of her local studio. But how can she compete with so much free content? 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 n...

#2296 - Q&A: “Looking for low-risk, high-reward side hustles…” 15.04.2023 6:59

Our listener, Brenda, is a single mom with a full-time job, looking to supplement her income from the comfort of her home. Accordingly, we’ll be diving into the world of low-risk, high-reward side hustles! 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 a...

#2295 - Failure Friday: Flip Phone Reselling Fails to Cell Phones 14.04.2023 5:04

In this week’s Failure Friday segment, we hear from a serial side hustler with the brilliant idea to sell flip phones—because who doesn’t want a flip phone, amiright? In the end, he couldn’t “cell” a single phone. 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 l...

#2294 - TBT: eBay Consignment Seller Never Runs Out of Inventory 13.04.2023 6:34

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an eBay consignment seller who decided to focus on selling items for other people for a commission. How much commission? How does it work? Let’s 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...

#2293 - Q&A: “It’s hard to separate work from personal life…” 12.04.2023 5:05

In this episode, we're addressing a concern that many freelancers, remote workers, and side hustlers can relate to: striking the right work-life balance and staying motivated. 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 d...

#2292 - Q&A: “Makin’ a dog walkin’ app…” 11.04.2023 3:46

Woof! Today’s caller is a longtime listener with an idea for a mobile app that connects dog owners with local dog walkers. 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:...

#2291 - First $1,000: Sign Language Interpretation Pays for Europe Trip 10.04.2023 6:11

In this week’s First $1,000 segment, we hear from a school counselor with a side hustle in sign language interpretation. The extra income she earns goes to a college fund for her daughter, as well as a summer trip to Europe. 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...

#2290 - Q&A: “A social network to connect seniors with volunteers…” 09.04.2023 4:59

Our caller from Canada has an idea for a social network that connects senior citizens with volunteer "grandchildren" for companionship. How does it work, and will it be hard to compete with existing services like Facebook? 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...

#2289 - Q&A: “Bakin' cupcakes for fun and money…” 08.04.2023 5:06

Today’s caller likes cupcakes (who doesn’t??) and they want to turn their love of sweet treats into regular revenue. Live from the kitchen, let’s see what we can mix up! 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 eac...

#2288 - Failure Friday: “I tried wearing lettuce on my head to get attention…” 07.04.2023 5:50

In this week’s Failure Friday segment, we hear from an aspiring fashion blogger. After failing to catch the world’s attention with her belt-as-necklace feature, she tries wearing lettuce on her head. 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...

#2287 - TBT: Role-Playing Dungeon Master Earns $2,000/Month 06.04.2023 6:46

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Canadian dungeon master who hosts tabletop role-playing games. This side biz brings in an extra $2,000/month. 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&...

#2286 - Q&A: “Introducing the plant-based diet for pets…” 05.04.2023 4:56

Today’s caller is interested in starting a plant-based pet food delivery service. With the growing demand for healthier and more sustainable options for pets, she’s identified what she sees as a unique opportunity. 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...

#2285 - Q&A: “An outdoor adventure and survival training school…” 04.04.2023 4:35

Today we’ll hear from a caller with an idea for an outdoor adventure and survival training school for city-dwellers. You never know when this might come in handy… 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....

#2284 - First $1,000: “I watched home renovation shows and decided to try it…” 03.04.2023 5:05

In this week’s First $1,000 segment, we hear from a listener who flips houses when he’s not at his job in middle management. He learned from watching TLC shows! 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....

#2283 - Q&A: “Staying motivated when life gets hectic…” 02.04.2023 4:18

Life gets busy! How do you maintain motivation in the midst of it all? That’s what today’s listener is wondering about. I’ll give them—and you—three practical tips. 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 wee...

#2282 - Q&A: “An AI-powered personal shopping service…” 01.04.2023 5:37

Today's caller is looking to dive into the world of technology and fashion by starting an AI-powered personal shopping and styling service. She’s eager to get the ball rolling, but is also feeling overwhelmed by the prospect of starting a new business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi...

#2281 - Failure Friday: Minimalism Expert Becomes Disillusioned 31.03.2023 5:39

In this week’s Failure Friday segment, we hear from a woman who sets up to become a subject matter expert in the world of minimalism—before becoming uncomfortable with the commercial elements of the philosophy. 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 less...

#2280 - TBT: Corporate Exec Ditches Job for Side Hustle 30.03.2023 4:59

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance corporate auditor who leaves his corporate gig to strike out on his own, first as a side hustle and now full-time. 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...

#2279 - Q&A: “I’d like to offer Virtual Reality therapy…” 29.03.2023 4:56

Today's caller is exploring the intersection of psychology and technology and wants to bring virtual reality (VR) to the world of therapy. Is this possible?? 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...

#2278 - Q&A: “Tips for handling customer service and support?” 28.03.2023 4:50

You want to make sure you don’t end up in a situation where your limited side hustle time is spent only doing support—instead, you should be spending it on growing your business. But how do you do this, practically speaking? 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 f...

#2277 - First $1,000: Software Engineer Crafts Balloon Sculptures 27.03.2023 5:09

In this week’s First $1,000 segment, we hear from an engineer who takes out his daytime frustrations on a series of side hustle balloon sculptures. He’s a self-described balloon-atic! 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 se...

#2276 - Q&A: “I want to offer Creative Writing Workshops…” 26.03.2023 4:27

Today’s caller has a passion for creative writing and wants to turn it into a side hustle by offering workshops. How can they go from idea to income? 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:...

# 2275 - Q&A: “How can a designer stand out in a crowded market?” 25.03.2023 4:48

The market for web design is getting more crowded every day, and today's caller is looking for advice on how to make her business stand out from the competition. 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....

#2274 - Failure Friday: “My first client was a total nightmare…” 24.03.2023 5:13

In this week’s Failure Friday segment, we hear from a woman who had a goal of becoming a personal shopper, but was stymied by a difficult client. 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: Sid...

#2273 - TBT: Destination Wedding Officiant Travels Worldwide 23.03.2023 5:54

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a destination wedding officiant who helps couples say their vows in faraway locales. 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 we...