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

#2383 - Q&A: “Need help attracting first clients…” 11.07.2023 5:03

A sales coach for Etsy and Shopify sellers is looking to expand her initial client base of friends and family members. 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...

#2382 - First $1,000: Airbnb Marketer Increases Rental Rates 30% 10.07.2023 5:36

In this week’s First $1,000 segment, we hear from a guy who helps Airbnb property owners and managers grow their listings and revenue. 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: SideHustleScho...

#2381 - Q&A: “Should I build a website for my freelance coding hustle?” 09.07.2023 4:57

Does this freelance programmer need a website? If so, what’s the simplest and most effective way to make it? 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@sidehus...

#2380 - Q&A: “How do I pinpoint the right side hustle idea?” 08.07.2023 6:25

A recent college graduate needs help choosing a side hustle that aligns with her professional skills and personal passions. 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...

#2379 - Failure Friday: “SnoozeCubes” Hustle Experiences Sleepy Sales 07.07.2023 6:44

In this week’s Failure Friday segment, we hear from the founder of SnoozeCubes, sleeping pods for offices. If you haven’t heard of this business, it’s because it never got up to Super Bowl ad-level. 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...

#2378 - TBT: Copyeditor Proofreads Tech Reports & Marriage Proposals 06.07.2023 5:47

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a tech employee who moonlights as a freelance copyeditor and proofreader. 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 no...

#2377 - Q&A: “Can I create a fictional character for Cameo shoutouts?” 05.07.2023 5:43

Last month we talked about buying Cameo shoutouts to promote a business. This caller has a different idea: can they create a *fictional* character and offer shoutouts for sale? 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...

#2376 - Q&A: “OpenTable isn't good, how can we do better?” 04.07.2023 5:01

Today’s caller wants to make an alternative to restaurant reservations. He’s got ten years of experience in the industry, but will that be enough to create a platform at scale? 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...

#2375 - First $1,000: “Logo Lady” of Upwork Builds Design Speciality 03.07.2023 6:01

In this week’s First $1,000 segment, we hear from an HR specialist who’s also known as the “Logo Lady” of Upwork. She does only logos, which has been key to her success, and allows her to earn a good side income in a manageable number of hours. 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,...

#2374 - Q&A: “Can you grow a side hustle using Reddit?” 02.07.2023 5:36

Reddit is known as “the front page of the internet.” Can it also be a viable way to grow your business or 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 several days each week. Show notes: SideHustleSchool.com Email: tea...

#2373 - Q&A: “Should I feel bad about side hustling at work?” 01.07.2023 4:59

This caller is running her side hustle on company time. How do we feel about 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the sho...

#2372 - Failure Friday: “Hangover Helper” Business Sobers Up 30.06.2023 5:46

In this week’s Failure Friday segment, we hear from a San Francisco man with a dream to serve party goers who had partied a little too hard. Unfortunately, this idea soon encountered a sobering reality. 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...

#2371 - TBT: Coder By Day, Cockatiel Companion By Night 29.06.2023 5:55

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a remote programmer who pet-sits in different states for weeks at a 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 each week. Show not...

#2370 - Q&A: “What are some mediums besides blogs, podcasts, and YouTube?” 28.06.2023 5:11

You’ve heard about blogging, podcasting, and making videos for YouTube—but if none of those options sound appealing, are there others? 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: SideHustleScho...

#2369 - Q&A: “Separating business and personal expenses…” 27.06.2023 4:37

This personal trainer is struggling with separating his personal and business finances. Can we give him a boost so he can get back to focusing on push-ups? 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...

#2368 - First $1,000: Smartphone Photography Instructor Snaps Up Profit 26.06.2023 5:36

In this week’s First $1,000 segment, we hear from an Austinite who operated a side hustle teaching people to take better photos with their smartphones. He did this for two years before moving on to a new project. 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...

#2367 - Q&A: “Designing tiny homes for vacation rentals…” 25.06.2023 4:32

In today’s episode, a caller from Israel wants to create sustainable tiny homes for vacation rentals. How can we help them along? 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...

#2366 - Q&A: “Why don’t you self-publish your books?” 24.06.2023 5:50

These days, self-publishing is easy and affordable. In this episode, an aspiring author wonders about MY books: why do I still work with a traditional publisher?? 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....

#2365 - Failure Friday: On-Demand Haiku Poet Shows Restraint 23.06.2023 6:25

In this week’s Failure Friday segment, we hear from an aspiring poet who wants to get paid for on-demand haiku at public events. Unfortunately, the idea is a bust. 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...

#2364 - TBT: “CityScapes Art” Earns Passive Income Every Day 22.06.2023 6:04

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Shopify seller who earns passive income every day from sales of his city art prints. He’ll tell you how he did it, how he decided on pricing, and how he markets the business *without* using social media. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon...

#2363 - Q&A: “Should I hire celebrities on Cameo to shoutout my cookie hustle?” 21.06.2023 4:51

The owner of this home-based cookie business is thinking of paying for celebrity shoutouts from Cameo. Is it worth it? 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: tea...

#2362 - Q&A: “Pickleball tournament for fun and profit…” 20.06.2023 4:56

Let’s play pickleball—and maybe even get paid for it! A listener from Santa Monica hopes to monetize his passion for the fastest-growing sport. 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...

#2361 - First $1,000: London Plant Stylist Blossoms, Blooms 19.06.2023 5:20

In this week’s First $1,000 segment, we hear from an indoor plant stylist offering at-home consultations in London. Get ready to get leafy! 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: SideHustl...

#2360 - Q&A: “Daily Painting for a Year…” 18.06.2023 5:21

A watercolor artist from New Mexico hopes to monetize her project of painting every day for a year. 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....

#2359 - Q&A: “Using LinkedIn to grow a voiceover biz…” 17.06.2023 4:23

A listener seeks advice on how to optimize her LinkedIn profile to showcase her voiceover work to prospective clients. 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: tea...