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

#2482 - Q&A: “Is there a market for cool driftwood art?” 18.10.2023 5:46

An artist makes local driftwood into unique pieces of art. How can she cash in this treasure? 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@sidehustleschool.com Be...

#2481 - Q&A: “I’m seeing slow growth after three months of side hustling…” 17.10.2023 4:49

A Boston-area listener started a consulting service, but it’s not taking off in the way she hoped. How should she proceed? 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:...

#2480 - First $1,000: “Virtual Study Buddy” Offers Motivational Tutoring 16.10.2023 5:59

In this week’s First $1,000 segment, we hear from an educational psychologist who combined traditional tutoring with motivational coaching. Learn how targeted pricing, grassroots marketing, and client retention helped her offer a unique service 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,...

#2479 - Q&A: “An app to help consumers find class-action lawsuits…” 15.10.2023 4:56

Today’s caller is combining a background in law with tech skills to create something potentially groundbreaking—an app that connects people to class action lawsuits they could join. 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 seve...

#2478 - Q&A: “How do I develop my side hustle skill set?” 14.10.2023 5:43

This caller is a modern-day Renaissance man with skills ranging from programming to music production and even cooking. But with so many talents, he's feeling stuck, unsure which path to follow for his side hustle. 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...

#2477 - Failure Friday: Running a PR Agency Is Harder Than It Looks 13.10.2023 6:45

In this week’s Failure Friday segment, we hear from a communications graduate who planned to open a PR agency. Unfortunately, her first attempt didn’t work out as well as she’d hoped. 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...

#2476 - TBT: The Evolution of an Edible Insect Business 12.10.2023 5:26

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the visionary behind a cricket farm that specializes in edible insect snacks. He shares insights into how market shifts, supply chain challenges, and an organic grocery chain have shaped his unique business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mo...

#2475 - Q&A: “Failure Friday feels discouraging…” 11.10.2023 6:01

Our Failure Friday segment is a popular one—but a few listeners have pointed out that it can feel discouraging to hear about ideas that don’t work. Let’s look at this concern in some detail! 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...

#2474 - Q&A: “Best platforms for selling information products?” 10.10.2023 4:54

A digital marketer prepares to launch her first info product. What are some of the best platforms to use? 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@sidehustles...

#2473 - First $1,000: The Pacific Northwest Tiny Home Designer 09.10.2023 5:43

In this week’s First $1,000 segment, we hear from a side hustler in Olympia, Washington. He designs tiny homes—how did he get started with that? 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: SideH...

#2472 - Q&A: “What works best for a sprint-and-stop schedule?” 08.10.2023 5:46

A caller has a job that cycles between intense work and downtime, and he's looking for a side hustle to fit that rhythm. 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: t...

#2471 - Q&A: “My partner resents my side hustle…” 07.10.2023 5:31

A caller grapples with how to manage her side hustle while keeping her relationship happy. We talk about setting boundaries, the importance of communication, and ways to include your partner—or not! 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 list...

#2470 - Failure Friday: Turns Out Ideas Don’t Magically Happen 06.10.2023 6:25

In this week’s Failure Friday segment, we hear from a longtime listener who’s had a lot of side hustle ideas—but hasn’t taken action on them. Fortunately, he’s made a plan for moving forward more positively. 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...

#2469 - TBT: Action Figure Fan Sells GI Joe & Transformers 05.10.2023 5:53

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an action figure seller who actively buys and sells hundreds of GI Joe, Transformers, and other classic brands every 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...

#2468 - Q&A: “How much time do I need to spend?” 04.10.2023 5:42

In this episode, we help a listener figure out how much time she realistically needs to invest in a side hustle while managing her retail job and family life. 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. Sho...

#2467 - Q&A: “Should I quit my dropship hustle?” 03.10.2023 5:07

When is a side hustle just not viable? In this episode, we look at a few red flags that could indicate it's time to change your business or walk away. 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:...

#2466 - First $1,000: Sorority “Personal Brand Advisor” for Rush Week 02.10.2023 6:10

In this week’s First $1,000 segment, we hear from a junior at the University of Alabama who advises potential sorority sisters on how to improve their personal brands. Yes, this is a thing! 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&am...

#2465 - Q&A: “Can I earn money on Twitch without streaming all day?” 01.10.2023 4:40

In this episode, we tackle a question about monetizing a love for gaming and Twitch streaming without making it a full-time gig. Can you get paid for streaming and still have a life? 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...

#2464 - Q&A: “What’s the best way to monetize a small news site?” 30.09.2023 4:58

An independent journalist in New Mexico seeks to revitalize the local news, starting with his own independent website—but needs help with monetization. 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 note...

#2463 - Failure Friday: Halloween Festival Gets Rained Out 29.09.2023 6:01

In this week’s Failure Friday segment, we hear from a grade-school teacher who moonlights as the host of a fall festival. The big downpour that arrived on the big day turned out to be the least of her problems. 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 les...

#2462 - TBT: Parking Lot Striper Lines Up Repeat Business 28.09.2023 6:48

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a parking lot striper who’s built a seasonal, recurring business keeping parking lines looking spiffy. For less than five hours a week on average, he earns an extra $2,500/month Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job...

#2461 - Q&A: “I’m a Parisian architect building 3D models…” 27.09.2023 5:09

With over a decade of experience, this European architect is planning to venture into the realm of 3D visualization. How can he stack the building blocks in his favor? 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...

#2460 - Q&A: “A course to help parents learn sign language…” 26.09.2023 5:03

A listener wants to teach American Sign Language (ASL) to parents of newborns. How could she create the best possible online course? 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...

#2459 - First $1,000: Camping YouTuber Earns Affiliate Income 25.09.2023 5:40

In this week’s First $1,000 segment, we hear from a frequent camper who begins making YouTube videos to show off gear and tips. This turns into a regular income stream as viewers make purchases. 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...

#2458 - Q&A: “Is it better to sell low or high-priced courses?” 24.09.2023 5:29

It’s not a trick question: sometimes a low-priced course is much better than a high-priced one. 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@sidehustleschool.com...