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

Ep. 3331 - STORY: Dog Stocking Hustle Earns Husky Payoff 13.02.2026 7:56

He never saw himself starting a side hustle, but when he noticed one of his marketing clients making bank on seasonal pet gifts, he just couldn't roll over anymore—he had to act. 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 s...

Ep. 3330 - TBT: The Accountant Who Sold Spreadsheets to Etsy Sellers 12.02.2026 8:25

In this week's “Throwback Thursday” segment, we hear from an accountant who sells spreadsheet templates and other financial resources to creatives. 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. Sh...

Ep. 3329 - Q&A: “Should I pay a publicist to book me as a podcast guest?” 11.02.2026 4:18

Today's caller is trying to build her brand as a lifestyle coach. Should she hire a publicist to book her as a guest on podcasts?  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...

Ep. 3328 - Q&A: “Why do online courses cost so much—or so little?” 10.02.2026 4:59

Online courses are everywhere! Some cost $20 and others cost $2,000 or more. Why is there no consistency in pricing—and how can you determine what *your* price should be?  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 sev...

Ep. 3327 - First $1,000: “I dropped off hundreds of orders at the post office…” 09.02.2026 4:43

In this week's First $1,000 segment, we hear from the creator of Dental Lace, the original zero-waste dental floss. It's now sold in retailers worldwide—but it all started with an idea that some people thought was crazy. 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...

Ep. 3326 - STORY: Inventor Unclogs Profits With Innovative Drain Solution 08.02.2026 7:44

A modern-day Edison creates a million-dollar product after constantly cleaning up loose hair in his household drains. 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...

Ep. 3325 - Q&A: “How can I become a personal finance influencer?” 07.02.2026 4:58

Today's caller wants to enter the world of personal finance experts and influencers. As she notes, she's not the only one! So if you want to break in—what do you do?  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...

Ep. 3324 - Failure Friday: “My virtual assistant was a fan of quiet quitting…” 06.02.2026 5:48

In this week's Failure Friday segment, we hear from the founder of an advisory service who hires his first assistant. The relationship starts well, but as the founder stops paying attention, things go downhill. 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...

Ep. 3323 - TBT: English Language Game Throws Down Amazon Gauntlet 05.02.2026 7:18

In this week's “Throwback Thursday” segment, we hear from an English teacher who turns his passion for verbs into online 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: SideHustl...

Ep. 3322 - Q&A: “Can I import rain barrels from the Netherlands?” 04.02.2026 4:20

A listener loves rain barrels (this is a thing) and she's found the perfect one in the Netherlands—but she lives in the U.S. Might she be able to partner with the company to become their national distributor?   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...

Ep. 3321 - Q&A: “Should I start a new business or expand my current one?” 03.02.2026 4:58

This listener grew a side hustle to a full-time business—so naturally, now she wants to start another hustle! Is it completely new or an expansion of what she's already been doing? 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...

Ep. 3320 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer 02.02.2026 5:32

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...

Ep. 3319 - STORY: Physician Designs Plush Toys to Teach Anatomy 01.02.2026 6:50

A physician designs and manufactures plush toys in the shape of human organs. They are used to teach kids about the human body, and as “get well soon” gifts for hospital patients.  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...

Ep. 3318 - Q&A: “How can I sell on a platform like NextDoor?” 31.01.2026 4:06

NextDoor is not primarily designed as a platform for you to go crazy and sell a bunch of stuff. So if you DO want to sell there—what do you need to know?  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...

Ep. 3317 - STORY: Jiu-Jitsu Instructor Pins Down Mobile Workout Tool 30.01.2026 7:03

An unconventional workout tool becomes a hit on Kickstarter, then goes on to earn $20,000 a month for its creator.  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: t...

Ep. 3316 - TBT: Designer Scales Personalized Wedding Products to $1M+ 29.01.2026 6:04

In this week's “Throwback Thursday” segment, we hear from a graphic designer who does custom illustrations for weddings and other events. It's now a seven-figure 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 includes free guided lessons and listener Q&A se...

Ep. 3315 - Q&A: “How do I transition from Etsy to Shopify?” 28.01.2026 4:43

A listener has been selling on Etsy and wants to make the switch to Shopify. What's the best way to do this? 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@sidehust...

Ep. 3314 - Q&A: “What's the best software to write a non-fiction book?” 27.01.2026 4:26

Today's caller wants to know about the easiest and most helpful tools to write a non-fiction book. Unfortunately, books do not write themselves, but we'll give him three resources that might make it easier.   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 gui...

Ep. 3313 - First $1,000: “I still remember the day I hit the goal…” 26.01.2026 7:39

In this week's First $1,000 segment, we hear from Jodi Carlson, who sells resources and materials for Girl Scout troop leaders.  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...

Ep. 3312 - STORY: The Clothes Dryer That Changed a Family Forever 25.01.2026 7:46

When this government employee is let go from his job, he stumbles upon a reselling opportunity that would end up helping his family ride the coming recession—and eventually earn six figures in a single 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 gu...

Ep. 3311 - Q&A: “Get paid to help brands with their Terms & Conditions?” 24.01.2026 4:32

Today's caller wants to help brands improve their Terms & Conditions, also known as T&C. Can she design and license a template that companies will pay for? 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...

Ep. 3310 - Failure Friday: “We were incredibly disappointed…” 23.01.2026 9:35

In this week's Failure Friday segment, we hear from the founder of Kettlebell Kings, an ecommerce shop. When a big early order from a supplier went terribly wrong, he had to regroup and learn resilience.  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 lesso...

Ep. 3309 - TBT: “MomBox” Expands to Popular Subscription Box Service 22.01.2026 7:05

In this week's “Throwback Thursday” segment, we hear from Kate Westervelt, the founder of MomBox. She's gone from frustrated new mom to CEO of a growing startup! 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...

Ep. 3308 - Q&A: “What are the ethics of paid referrals to therapists?” 21.01.2026 4:11

A listener with a YouTube channel about quitting smoking wants to earn commissions by referring viewers to therapists. What are the ethical and practical concerns of this idea? 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...

Ep. 3307 - Q&A: “Should I charge a flat fee or percentage?” 20.01.2026 4:38

A listener and her teenager have been getting off to a good start selling on Facebook Marketplace. They now have the chance to sell for others, and are wondering about some best practices.  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...