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

#2308 - TBT: “I transformed from work-from-home coach to corporate consultant…” 27.04.2023 6:47

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a work-from-home coach who started her side hustle at the beginning of the pandemic. After pivoting to focus on companies training their employees, she earns more than $4,000/month part-time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit...

#2307 - Q&A: “I want to do audio production for podcasts…” 26.04.2023 5:37

Today we hear from Michael in Delaware, who’s interested in starting a podcast production business as a side hustle. He’s got the experience with audio production, but isn’t sure where to begin with the business side of things. 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 include...

#2306 - Q&A: “I’m building a grocery-shopping app…” 25.04.2023 5:13

A listener is developing a mobile app to “revolutionize the way people shop for groceries.” How can they get it funded? 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...

#2305 - First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles 24.04.2023 5:34

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:...

#2304 - Q&A: “Sell more from my organic farm…” 23.04.2023 4:19

A listener is struggling to find new customers for her organic farm produce. Should she drop out of farmers’ school, or put her hand to the plow? 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: Side...

#2303 - Q&A: “I’m an accountant—how do I specialize?? 22.04.2023 4:21

As a solopreneur, this Canadian account is concerned that “choosing a niche” could mean losing his existing clients who don't meet that speciality. 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: Si...

#2302 - Failure Friday: Airbnb Is Harder Than It Looks 21.04.2023 6:51

In this week’s Failure Friday segment, we hear from a New York City resident who tries—and fails—to navigate the city’s tough rules on rentals. 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: SideHu...

#2301 - TBT: Camera Affiliate Earns $100,000 in Commissions 20.04.2023 7:59

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a camera gear affiliate who earns thousands of dollars a month from commissions. He’s earned more than $100k so far! 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 listen...

#2300 - Q&A: “When’s the right time to scale up?” 19.04.2023 5:07

A listener is in the exciting but uncertain phase of considering whether to transition his growing freelance web design side hustle into a full-time business. How can he make the wisest decision? 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 listene...

#2299 - Q&A: “3D-printed prosthetics for marine animals…” 18.04.2023 4:52

Here’s a new one: this caller wants to create customized 3D-printed prosthetics for marine animals like sea turtles and dolphins. Crazy or brilliant? Let’s investigate! 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...

#2298 - First $1,000: City Government Staffer Leads Virtual Events 17.04.2023 5:37

In this week’s First $1,000 segment, we hear from a virtual events planner. If you need a virtual wedding, networking event, or gender reveal party, she’s got it covered! 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 e...

#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....