Side Hustle School
One of my favorite early episodes is about an engineer who lost a pet chicken, then started selling tiny saddles for the surviving ones. Nearly $0 in startup costs. A real business. (Episode 10.)
Another favorite: a graphic designer who taught herself caricature drawing and went from $8/hour at her job to $250/hour on the side, and now makes over $100,000 working part-time. (Episode 15.) Or the two friends who couldn't get their distillery off the ground, so they sold homemade gin kits instead. 75,000 units later, it worked. (Episode 16.)
That's Side Hustle School. A new story every morning, seven minutes long, about real people earning real money on the side of whatever else they're already doing.
The thesis, in one sentence
Most of the people in this archive aren't famous, didn't go to business school, and didn't have a big idea. They had a small idea and stuck with it long enough for it to compound.
That's the whole show. The premise underneath all 3,400+ episodes is that you don't have to quit your job to build something real. Quit-your-job-and-bet-the-farm advice gets clicks. It also gets people broke. The people in this archive made it specifically because they didn't bet the house. A few hours a week, a small budget, patience.
Some of the businesses are now full-time. Others stayed deliberately small. A few quietly funded retirement.
What kinds of side hustles get featured
Every kind. The variety is the whole point. Across 3,400+ episodes you'll find:
- Services: freelance writing, custom illustration, dog hosting, voiceovers, wedding photography, virtual assistance.
- Physical products: homemade gin kits, astrology calendars, chicken saddles, custom dog bandanas, candy hearts, hand-bound notebooks.
- Digital products: Notion templates, lesson plans for teachers, ebooks, fonts, photo presets, niche apps.
- Content and audience: niche YouTube channels, paid newsletters, ad-supported blogs, monetized TikToks, hobby podcasts.
- Retail and resale: Amazon FBA, eBay flipping, vintage clothing, thrift-to-Poshmark, books-by-the-pound resale.
The episodes most people remember are the strange ones (chicken saddles, fish tank reviews, a single dad selling 75,000 gin kits). The episodes that change someone's life are usually the ordinary ones (the schoolteacher, the engineer, the nurse), because the listener thinks: that could be me.
Who Side Hustle School is for
You have a day job you don't hate. Maybe you even like it. But it's not the whole story you want to be telling with your time. And you're not interested in burning the boats to find out what comes next.
Or: you have a creative practice, a skill, or a hobby that earns nothing, even though you suspect it could. You don't need it to replace your salary. You'd just like it to be more than free.
Or: you're already running a small thing on the side, and you want to know what other people in your category have figured out: pricing, scaling, when to quit a hustle, when to double down.
If any of that lands: this show is for you.
Where to start
- Pick three episodes from this week in different categories: services, retail, digital. By the third one you'll know if this show is for you. (It probably is.)
- Browse the Side Hustle Finder by what you actually have: time you can spare, money you can spare, skills you've already built.
- Pick up the book: Side Hustle: From Idea to Income in 27 Days walks through a structured 27-day plan from idea to first dollar.
Why I started it
I started the show in 2017 because I kept hearing from readers of The $100 Startup who wanted more case studies. The book has 50 stories; readers wanted hundreds. So I built something that delivered a new one every day.
The format never changed. The host (me) never took a day off.