Chris Guillebeau

Side Hustle School

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

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

Ep. 3356 - Q&A: “I’m a professional speed skater. How can I fundraise?” 10.03.2026

An athletic listener from Minnesota seeks advice on starting a fundraising campaign. Will he need to improve his social media for more people to notice? 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 note...

Ep. 3355 - First $1,000: Camping YouTuber Earns Affiliate Income 09.03.2026

In this week's First $1,000 segment, we hear from a frequent camper who begins making YouTube videos to show off gear and tips. This turns into a regular income stream as viewers make purchases. 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...

Ep. 3354 - STORY: “Productivity Nannies” Dig Co-Working Caves for Modern Workers 08.03.2026

Fall into a hole and don't come out until your work is complete! These three friends create daylong, distraction-free zones for the masses. 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: SideHustle...

Ep. 3353 - Q&A: “One-page business plan: what is the essential info?” 07.03.2026

I once published a one-page business plan that a lot of people have used and referred to over the years. Today, our caller wonders: what is essential about this plan? Can you really explain an entire business in a few paragraphs? 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 includ...

Ep. 3352 - Failure Friday: “Our first trade show was canceled with no refund…” 06.03.2026

In this week's Failure Friday segment, we hear from Chris Cavallari, who sells high-quality products with a Maine vibe. In March 2020, he prepared for his first wholesale trade show—and then the world closed down. 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. 3351 - TBT: The Tennessee Bachelorette Party Boom 05.03.2026

In this week's “Throwback Thursday” segment, we revisit a Nashville entrepreneur's journey in transforming the bachelorette party scene into a thriving 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 several days...

Ep. 3350 - Q&A: “What are the most profitable niches for teaching?” 04.03.2026

Some topics or niches are much more profitable than others. Today's caller is wondering if we can cut to the chase and just give him a list. Fair enough! Let's make that list. 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 da...

Ep. 3349 - Q&A: "I'm opening a new hair salon. How can I build my clientele?” 03.03.2026

A hair stylist is leaving her job to start her own salon. Awesome! What are some simple things she can do to kickstart her client list?  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...

Ep. 3348 - First $1,000: “I earn $3,000/month leading London walking tours…” 02.03.2026

In this week's First $1,000 segment, we hear from a walking tour guide in London. He leads tours only on weekends and brings in an extra £2,500 ($3,000) per 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 eac...

Ep. 3347 - STORY: Trader Joe’s Sign Artist Earns $43,200 Selling Tea-Stained Prints 01.03.2026

Discovering the art of tea-stained prints using publicly available (and free) art, a Trader Joe's employee begins earning $3,600 a month selling custom prints online. 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 w...

Ep. 3346 - Q&A: “I'm being headhunted... for my side hustle!” 28.02.2026

Our listener's side project was so successful that an outside company wants to hire him. That wasn't exactly the goal, though. 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 Em...

Ep. 3345 - STORY: Beard Oil Behemoth Expands to 35 Countries 27.02.2026

How one man grew his $46 idea into a six-figure monthly sales machine selling beard oil.   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...

Ep. 3344 - TBT: iPhone App Tracks Weight-Loss Progress 26.02.2026

In this week's “Throwback Thursday” segment, we hear from a developer in the U.K. who makes an app to help people with weight-loss goals.  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...

Ep. 3343 - Q&A: “How to break out of a sales slump?” 25.02.2026

Today's caller from California started her side hustle last year, and it was going well! Recently, however, business has taken a turn for the worse. How can she get out of the sales slump? 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&amp...

Ep. 3342 - Q&A: “What’s the best way to register domains?” 24.02.2026

There's no reason not to have your own domain now. But what's the best way to register one, and do you need to get every extension? 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.c...

Ep. 3341 - First $1,000: “Hyperfluent” Language Service Translates Into Profit 23.02.2026

In this week's First $1,000 segment, we hear from Eva Rosales, the founder of Hyperfluent. Her consultancy offers lots of different services, all focused around language acquisition and 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 an...

Ep. 3340 - STORY: Proud Mainer Brings Whoopie Pies to the World 22.02.2026

After her kids went off to college, this former stay-at-home-mom began baking whoopie pies in bulk. She now makes them by the tens of thousands, selling more than $25,000 in creamy inventory each 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...

Ep. 3339 - Q&A: “What kind of review platform would be best for online learning?” 21.02.2026

So many people are doing online learning of all kinds these days, but selecting the right platform can also be overwhelming. Today's listener wants to create a review site to help users compare options—how should she proceed? 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 incl...

3338 - Failure Friday: “They just weren’t interested in what we were selling…” 20.02.2026

In this week's Failure Friday segment, we hear from the co-owner of a business that livestreams weddings. When Covid struck, they thought they had the perfect opportunity to expand to a new market—but buyer interest fizzled.  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...

Ep. 3337 - TBT: The Mushroom Kingdom of North Carolina 19.02.2026

In this week's “Throwback Thursday” segment, we hear from the business manager of Phenomenal Fungi, which sells tinctures, cultures, and mushroom merch. It's been a busy year in the land of shrooms!  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...

Ep. 3336 - Q&A: “Is there a way to trade plane tickets for profit?” 18.02.2026

Today's listener has a creative idea, but also some sky-high problems to solve. Is it possible to trade unused plane tickets between passengers with different names? 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. 3335 - Q&A: “What separates small earners from big ones?” 17.02.2026

Every Side Hustle School story features someone who earns at least $500 a month apart from their day job. But some people earn a lot more, earning six or even seven figures from their side hustle. A listener wants to know: what separates small earners from big ones? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

Ep. 3334 - First $1,000: “I started by setting up a booth at the farmer's market…” 16.02.2026

In this week's First $1,000 segment, we hear from a woman who makes and sells essential oils. By customizing her product line and building relationships at a local farmers market, the business now provides half of her 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 f...

Ep. 3333 - STORY: Game of Cones: Two Women Make Architecturally-Inspired Ice Cream 15.02.2026

A nouveau-cream wave of ice cream debuts at Coachella, and everyone freaks out.  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...

Ep. 3332 - Q&A: “How to sell a reusable fork…” 14.02.2026

She's made a foldable tote bag attached to a set of eating utensils. How will she find her ideal customers?  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@sid...

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