[jackowayed]

> I don't think anyone would leave right before their stock was about vest, without a solid reason.

I wouldn't assume that there's some hidden reason for him leaving. First of all, leaving right before his stock is about to vest just means that he's leaving a little bit of stock on the table. As he said, the vast majority of his stock has already vested (as one would expect after 4 years), and he gets to keep that. It's the 5%, or whatever, of his stock that hasn't vested that he's losing.

I read this as "I've been working startup hours for way too long, and I'm tired of it, especially now that I have a kid I want to spend time with".

[guelo]

I've seen startups handle the "all my options are vested" motivation problem with what's called an evergreen program. An evergreen program keeps issuing options such that your monthly vesting rate remains constant after the initial 4 years.