For most of my career I have fought on one side or the other in the eternal battle between unreasonable CEOs and reasonable CTOs. It’s always the same story: CEOs without a big tech background always coming up with ideas, CTOs trying to stem the flow, doing their best to manage expectations and deliver reasonably good products.
While helping bootstrap startups, for the last ten years I have been actively working to come up with a long series of design techniques to throw in the way of ambitious CEOs to slow them down. Yes, yes, good idea, but we need to go through a rigorous design phase, we need to user test, then we need to decide what impact it has, then we put it in an endless queue of kanban boards… you’re never gonna get it.
More recently, as the unreasonable CEO of a new small company, a bit by myself, a lot with a small and clever team of human and AI agents, I have been creating tons of stuff, both for my own company and for many of our clients. At an unprecedented speed. This is not a percentage increase, this is an order of magnitude.
And I have been happily dreaming with other CEOs of ideas, features, whole new products, without having any idea of how to get there but knowing that thanks to today’s magic (and counting on tomorrow’s improvements) we will get there, we will iterate, we will improve… we will figure this out.
It’s a bit like having a parachute that makes jumping off cliffs much safer. You have to believe it works, and I think it’s reasonable that many don’t. I’ve been jumping off these cliffs for a few years now, and yeah, sometimes you get a bruise. But it’s so much more fun.
Now I often find myself on the other side of CTOs. They want predictability. They want detailed plans. They want costs. They still have to deal with the rest of the company which is still moving at the glacial speed of 2025. I’m sure that eventually we’ll all get there, but while for a very long time I have fought on the side of CTOs, now I’m increasingly finding myself having much more fun playing with CEOs.
The most unreasonable, the better.