This Month I’ve Been a VC Exactly as Long as I Was an Operator

This month I hit a strange milestone. I’ve now been a VC for exactly as long as I was an operator. Thirteen years each.

I thought the symmetry would feel clarifying. It mostly just feels strange. Maybe I’m officially a VC now. Or maybe I’m just no longer an operator. 🤷

Those first 13 years were three startups and something like 30 lifetimes. Launching a product and watching the first customer sign up. Unexpected churn. The hire that changed everything, the layoff I didn’t want to do. An issued patent with my name on it (see below)! And eventually selling our company to 3M.

Each of those moments hit immediately. And I didn’t go through them alone – building is a team sport. I bled with the same people every day, and I carried all of it home every night, whether I wanted to or not.

VC is different. The feedback loops stretch 7-10+ years. You can be confidently wrong or right for a decade before you find out. And when you are wrong, you don’t bleed. It’s more transactional, more solitary. I carry it home less. That’s a relief and a loss at the same time.

I fear my story is starting to feel dated. The numbers seem small, almost cute now. Our series A today would be a seed today. There was no a16z at this scale, no YC, little start-up content when I was building.

Am I a washed-up player telling stories about the good old days?

Would I go back? HonestIy I don’t think so. And I’m not entirely at peace with that. I kind of relish those days, but for now I’m a proud VC.

The question I wonder is what’s the half-life of operating experience? And when is it too late to ever go back to operating?