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

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

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

There are two triggers on dumb things that every entrepreneur pulls.

The first trigger is on the initial dumb thing, which is more accurately described as the crazy thing. Our startup idea. We love pulling that trigger.

I have no problem with crazy startup ideas. I mean, it’s easy to talk about starting a normal, rational business. If you told me you were going to open a restaurant in a well-trafficked area of town, I’d ask some questions, and I’d listen. If you told me you were going to start a company that teaches mice to execute certain instructions like re-running wiring in a house, I’d ask even more questions, and I’d stop listening only when you stopped making sense.

But if you told me you were going to start a business that allowed anyone in the world to order a product online and have it shipped to their door two days later, regardless of how normal and reasonable that…