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

#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...

#2347 - First $1,000: Florida Woman Becomes Pet Party Planner 05.06.2023 4:59

In this week’s First $1,000 segment, we hear from the go-to pet party planner of St. Petersburg, Florida. She plans doggie bashes and cat-a-versary parties. 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...

#2346 - Q&A: “I have so many exciting ideas!” 04.06.2023 5:20

Today we've got Sam on the line from Massachusetts. He’s wrestling with a conundrum many of our listeners may find familiar: several exciting ideas for a side hustle, but trouble in deciding which one to pursue. 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...

#2345 - Q&A: “Navigating regulations for selling herbal remedies…” 03.06.2023 3:47

A Utah botanist wants to sell teas and tinctures, but also wants to make sure she follows local regulations. Let’s put our green thumbs to work and see if we can help. 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...

#2344 - Failure Friday: “Fake Wedding Guest” Biz Fizzles Out 02.06.2023 5:43

In this week’s Failure Friday segment, we hear from a side hustler who tries selling a service as a fake wedding guest who helps to fill seats for brides and grooms while getting the party started on the dance floor. 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 guide...

#2343 - TBT: Vancouver Bike Tours Takes Scenic Route 01.06.2023 5:15

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a cycling tour business that serves visitors and locals. 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:...

#2342 - Q&A: “How can I host a yoga and wellness retreat?” 31.05.2023 4:11

Today’s caller is a yoga instructor with a vision to organize wellness retreats in serene locations. Let’s stretch our minds and see if we can help. 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: S...

#2341 - Q&A: “There’s no money in personal training…” 30.05.2023 5:04

Most personal trainers that I’ve talked to agree on one thing: there’s not much money in just the personal training. This is true even when it’s expensive! Today’s caller wants to transition from in-person, individual sessions to online group classes. What’s the best strategy here? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money w...

#2340 - First $1,000: Baltimore Photographer Starts Drone Instruction 29.05.2023 5:59

In this week’s First $1,000 segment, we hear from a Baltimore photographer who finds inspiration high in the sky. His new business teaching drone photography is taking off! 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...

#2339 - Q&A: “How to offer content strategy services…?” 28.05.2023 4:43

As a successful freelance copywriter, today’s caller is looking to transition into content strategy. How can he rebrand himself and find clients in this new space? 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...

#2338 - Q&A: “Selling tote bags, but need to raise prices…” 27.05.2023 4:48

Does the world need more tote bags? Apparently the answer is… maybe! Let’s hear from a listener selling eco-friendly tote bags at local markets and online. They’re wondering about the right time to raise prices. 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...

#2337 - Failure Friday: Rent-a-Friend Fails to Launch in Tulsa 26.05.2023 6:11

In this week’s Failure Friday segment, we hear from a small-town side hustler who tries to follow a popular business model from Japan. Unfortunately, the idea is lost in translation. 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...

#2336 - TBT: Social Media Manager Earns $4,000/Month Part-Time 25.05.2023 5:45

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a social media manager who focuses on female fitness coaches and influencers. 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...

#2335 - Q&A: “I sell pet bandanas. How can I reach pet influencers on Instagram?” 24.05.2023 5:29

She sells handmade pet bandanas, and wants to take her business to the next level—but she’s struggling with pet influencers not getting back to her. 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: S...

#2334 - Q&A: “Going from weddings to corporate photography…” 23.05.2023 3:47

A semi-professional photographer has been specializing in wedding photography, and is now looking to expand his services into corporate events and product photography. How can he do this while maintaining his 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 guide...