"Oh the stories I could tell if only I could. But I feel that telling this positive story of the history of EY is the classy way to go out and I wish Engine Yard all the best in the world"
They wouldn't be normal people if there weren't a bit. It sounds like things went ok though, all things considered, and he's just ready for new things and a new place.
I don't think anyone would leave right before their stock was about vest, without a solid reason. :) But the key term is classy.
True story: in the early days of Merb, before it had really gotten a lot of attention, I once hit a show stopper - hopped on IRC, told him about my problem, he found the bug, fixed the bug, pushed a new release in something like 15 minutes IIRC, and stayed cool about it the entire time.
> 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".
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.
All businesses have their ups and downs. I was with a startup for 6 years and certainly have a good set of stories. It just isn't good karma to air dirty laundry.