In Retrospect, That Thing I Did With My Startup Was Dumb

How to fix what’s really wrong instead of what’s just easy

Joe Procopio
4 min readNov 3, 2022
image by cookiestudio

About six months ago, I did something really dumb with Teaching Startup, and it’s the kind of mistake I don’t want to make again. I’m not going to color the exact mistake here — this isn’t that kind of post.

What I do want to talk about is how recognizing the dumb things we do and learning from them is something that everyone says they do, but few actually do. And there’s a reason for that. And we’re going to address that reason together, so that we not only learn from our mistakes, but potentially fix the real problem.

I’d say I do a big dumb thing every couple months. And several smaller dumb things along the way during those months. And every few years, I do a thing so stupid that I wind up costing myself tens or even hundreds of thousands of dollars, personally, either in real cash or opportunity cost.

I do these dumb things by accident — well, accident in the sense that the outcome wasn’t what I intended. But I always pull the trigger. On purpose. Because I mean to do dumb things sometimes.

The trick is for every dumb thing that blows up in your face, you have to do two dumb things that work.

Why We Do Dumb Things



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at