You can stay in your seat too long

Most founders will tell you the hardest decision is when to hire, when to raise, when to cut. It isn't. The hardest one is about the chair you're sitting in.

The seat that got a company to $5M is not always the seat that takes it to $30M. The person is the same. The job isn't. And one of the quietest ways a business stalls is a founder running the next stage on the instincts that won the last one.

The clock you can't hear

Here's the part nobody tells you. When a company takes on capital and then gets stuck at a number, a clock starts. You can't hear it. It's running anyway.

Getting stuck is rarely loud. The revenue reaches a decent number and just sits there. Doesn't grow. And the people around you can't tell you what's wrong, because they haven't been where you are either. They're staring at the same dashboard you are, nodding at the same numbers.

The thing that's actually wrong is almost always findable. It's just sitting somewhere nobody's looking, because it looks normal, because it's always looked that way. Often it's a question underneath the business nobody ever settled. Who it's for. What it's supposed to be. Who should be running it now.

I left a seat once. I've watched others get removed from theirs.

A few years ago I was VP of Engineering at GrowthLoop. At some point the honest read was that the seat needed something other than what I was there to give, and I stepped back from it. That is not a comfortable call. You build the thing, and leaving the chair feels like leaving the company.

The alternative is worse, and I've watched it happen more than once. A founder stays in the seat past the point it fits. The number stops moving. And eventually someone who wrote a check decides the seat needs a different person in it. By then it isn't your decision. The capital makes it for you.

That's the real trap. Capital doesn't take your company. Getting stuck does. The capital just shows up to collect.

The move

Stepping back doesn't have to mean walking out. Most of the time it means changing what you own, not who owns the company. But somebody has to ask the question honestly, and you are the worst-positioned person to ask it about yourself, because you're the one in the chair.

So ask it before the market asks it for you: is the seat I'm in the seat this company needs next? If you can't answer that cleanly, that's the finding.

I still think about the ones who couldn't ask it in time. More than I let on.