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

#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...

#2333 - First $1,000: Home Improvement Employee Moonlights as Renovation Aide 22.05.2023 5:59

In this week’s First $1,000 segment, we hear from someone who works at a home improvement store by day—and moonlights by advising homeowners on renovation projects. 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...

#2332 - Q&A: “I’m adding a subscription box for soaps…” 21.05.2023 4:17

A listener who sells handmade soap is considering adding a subscription box service, where customers receive a curated selection of products 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 listener Q&A several days each week. Show not...

#2331 - Q&A: “Cost-effective marketing strategies?” 20.05.2023 4:44

Today's caller is on a mission to find cost-effective marketing strategies for their side hustle. How do you get the word out without spending much money? 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...

#2330 - Failure Friday: Chicken Rental Service Fails to Egg-cite 19.05.2023 6:04

In this week’s Failure Friday segment, we hear from a Boise entrepreneur with the goal of bringing chickens to city dwellers. Alas, in the end the business is forced to flee the coop. 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...

#2329 - TBT: Handywoman Offers DIY Home Repair Workshops 18.05.2023 5:28

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Washington handywoman who operates a series of DIY Home Repair workshops. 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...

#2328 - Q&A: “Voiceover artist offers voiceover coaching…” 17.05.2023 4:42

A voiceover question from a voiceover artist on potential voiceover coaching for voiceover clients. Did you get that? Hint: it’s about voiceover. 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...

#2327 - Q&A: “Reaching the right audience with digital prints…” 16.05.2023 5:08

In today's episode, we have a question from a listener working on a side hustle creating and selling digital art prints online. How can he discover and reach the perfect audience? 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...

#2326 - First $1,000: Baltimore Photographer Starts Drone Instruction 15.05.2023 5:25

#2325 - Q&A: “I'm looking to leverage my existing skills…” 14.05.2023 5:09

In today’s episode, a talented graphic designer and marketer searches for a fulfilling side hustle that capitalizes on her existing skill set. How can you find one for yourself? 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...

#2324 - Q&A: “I want to offer home staging services…” 13.05.2023 5:15

A listener in Vancouver wants to start a home staging side hustle. How can she build a portfolio of clients and develop the right relationships? 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...

#2323 - Failure Friday: “Looking back on my picnic misadventures…” 12.05.2023 6:19

In this week’s Failure Friday segment, we hear from a Miami caterer who had a cute idea to sell customized picnic lunches. Unfortunately, things didn’t turn out the way she 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 severa...