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

#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...

#2358 - Failure Friday: Professional Line-Stander Sits Down 16.06.2023 5:40

In this week’s Failure Friday segment, we hear from a man with an idea to become a professional line-stander, waiting in line for concert tickets, new iPhones, and anything else that people wanted to pay him for. Unfortunately, this business idea fails to attract a crowd. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qui...

#2357 - TBT: Thyme Flies for These Scentsational Essential Oils 15.06.2023 5:37

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of Ebony’s Essential Oils. She’s built her side biz to more than $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&A several days each...

#2356 - Q&A: “How should I handle freelance contracts?” 14.06.2023 4:32

A freelance writer is using Chat-GPT to help draft his articles. So far, so good—but he needs help with figuring out client contracts. 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: SideHustleSchoo...

#2355 - Q&A: “I'm a seamstress with an interest in historical fashion…” 13.06.2023 5:10

A Chicago seamstress with a passion for historical fashion wants to create and rent out period costumes. How can we help her go back in 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 notes: SideHust...

#2354 - First $1,000: Personal Paparazzo Welcomes Los Angeles Visitors 12.06.2023 5:14

In this week’s First $1,000 segment, we hear from a “personal paparazzo” who does photo shoots for locals and visitors to the greater Los Angeles area. 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...

#2353 - Q&A: “Social ads for event planning…” 11.06.2023 4:32

A Boston side hustler is considering using social media ads as her marketing strategy. But like many first-time advertisers, she's unsure about how much to spend, where to start, and how to design her ads for maximum impact. 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...

#2352 - Q&A: “Promoting affiliate brands on my travel blog…” 10.06.2023 4:43

A travel enthusiast who’s been documenting her adventures on a blog is ready to monetize her platform. How can she do so authentically? 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: SideHustleSc...

#2351 - Failure Friday: Fortune Cookie Writer Fails to Foresee Profit 09.06.2023 6:03

In this week’s Failure Friday segment, we hear about a potential business of writing fortunes for fortune cookies. Sadly, this isn’t the story of the next Tesla or Amazon. 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...

#2350 - TBT: Biotech Recruiter Earns Commission for Job Placements 08.06.2023 5:40

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Indian-born woman who moves to the U.S. and starts a side hustle as a recruiter for biotech employees. After finishing grad school and building the business, she now does it full-time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

#2349 - Q&A: “How does a dog trainer start selling dog toys?” 07.06.2023 4:31

Being a dog trainer is so 2020. The real money is in dog toys! Let’s see if we can help this listener go from “woof” to “wow.” 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 E...

#2348 - Q&A: “I feel overwhelmed by Shopify…” 06.06.2023 5:11

A listener in Ottawa has recently opened a Shopify store, and finds the popular platform to be overwhelming. Can we simplify the process? 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: SideHustleSc...