I was so naive when I joined my first startup. When we were purchased, it came to light that the main guy never got around to signing my stock option agreement. He is a fucking mensch and signed it after the fact. Character buys a unique, abiding respect.
If it was not approved by the board at the correct time, that could be pretty illegal...
Also he negotiated a year off of our traditional 5-year vesting (at the time anyway) in the salt mine that is Microsoft, though he was never to take a position there himself.
I see no end to liquidity event horror stories. I'm so lucky.