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

#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...

#2272 - Q&A: “How can customer feedback improve my marketing?” 22.03.2023 4:13

Gathering feedback from customers is an important tool for any small business owner, but it can be challenging to know how to use it effectively. Today, a caller seeks advice on how to incorporate feedback into a marketing plan. 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...

#2271 - Q&A: “How can I become a sustainability consultant?” 21.03.2023 4:21

With a background in environmental science and a passion for sustainability, today’s caller from Seattle is ready to launch a Sustainability Consultancy. But how can she reach her target audience and make her business a success? 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...

#2270 - First $1,000: Health & Wellness Writer Establishes Side Income 20.03.2023 4:26

In this week’s First $1,000 segment, we hear from a freelance writer who works in the health and wellness field. She now earns several thousand dollars a month part-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 and listener Q&A several days e...

#2269 - Q&A: “What are the most effective ways to promote my side hustle?” 19.03.2023 4:17

Sarah has a unique skill set—she’s a reiki practitioner—and is eager to put it to work in a side hustle. But how do you get the word out there in today's digital age? 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 w...

#2268 - Q&A: “How do I handle the transition from side hustle to full-time business?” 18.03.2023 4:52

Today’s caller is ready to go from side hustle to full-time business! It’s always exciting when this happens, but it also produces questions and concerns. 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...

#2267 - Failure Friday: The “American Ninja Warrior” Personal Trainer 17.03.2023 5:01

In this week’s Failure Friday segment, we hear from a personal trainer who wanted to specialize to succeed in a crowded field. The problem was, the specialization he chose may have been too specialized, or perhaps too intimidating. 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 inc...

#2266 - TBT: Successful Screenwriter Becomes Screenplay Consultant 16.03.2023 5:07

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance screenplay editor in Hollywood. In his new sideline, he consults on scripts from other aspiring screenplay wordsmiths. 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...

#2265 - Q&A: “Planning for a Haunted House in Dallas…” 15.03.2023 4:26

Today's caller has a spooky idea. She wants to create a haunted house attraction, but she needs some guidance in bringing it to life. Don’t be scared! Let’s help her 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 includes free guided lessons and listener Q&A several days ea...

#2264 - Q&A: “Indoor Vertical Farming has a lot of potential…” 14.03.2023 3:31

Today we’ll hear from a listener who’s passionate about sustainable agriculture and believes that indoor vertical farming is the way of the future, especially for those living in big cities. How can she turn this into a business? 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 includ...

#2263 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer 13.03.2023 5:06

In this week’s First $1,000 segment, we hear from Elaine in Wayne County, Michigan. She’s an accountant for her day job and works as an engagement photographer for her 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 lessons and listener Q&A sever...

#2262 - Q&A: “My dream is to own a Mobile Adventure Park…” 12.03.2023 4:22

Today's caller is taking a leap of faith with a new and unique idea for a mobile adventure park. How can she make her vision a reality on a low budget? 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...

#2261 - Q&A: “How do I choose a legal structure for my side hustle?” 11.03.2023 3:54

A new web developer wants to make sure they set up their business in a way that is efficient and effective, but they're not sure where to start. Let's see if we can help them find a solution. 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&...

#2260 - Failure Friday: The Influencer Who Quit Instagram 10.03.2023 6:42

In this week’s Failure Friday segment, we hear from an aspiring influencer on her unsuccessful attempt to become a professional Instagrammer … which ended with her quitting the platform altogether. 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 liste...

#2259 - TBT: “Car Parts Guy” Becomes Professional Reseller 09.03.2023 5:10

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Chicago car parts reseller. After his first couple of years scouring junkyards for deals, he now sources most of his goods online. 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 le...