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
Podcast website
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 4:53
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 6:01
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 6:58
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 4:56
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 7:59
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 6:08
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 6:38
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 5:32
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 6:08
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 6:33
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 4:12
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 6:52
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 5:53
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 4:25
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&...
Ep. 3342 - Q&A: “What’s the best way to register domains?” 24.02.2026 4:04
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 7:22
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 8:10
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 5:17
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 7:19
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 7:54
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 4:45
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 5:23
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 4:59
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 7:19
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 4:50
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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