Early in my career, I was working at Borland International. It was the first place I’d ever worked where I had stock options — and I was clinging to every single one of them like they were sacred objects.
One night in Hong Kong — jet-lagged, sticky-shirt tired — I’m at a bar with our VP of Sales. He mentioned, casually, like he was ordering another round, that he’d just sold every one of his vested shares. He smiled, like this was the most obvious thing in the world.
I must have looked like I’d been slapped, because he laughed and explained his logic: “If the stock keeps going up, I’ll do fine with what I’ve got left. If it goes down, I’ll be thrilled I sold when I could. And if I keep doing a good job, they’ll always give me more.”
That conversation changed the way I think about equity. Forever.