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1. No, and I wouldn't believe them if they did.

2. Nonetheless, they have always delivered more than what was contractually obligated (in the form as a retention bonus at the new company or some other commitment).

In my case, both the startups were "sold" off to another larger holding. I personally, did not get anything worthwhile in a serious dollar amount so I chose not to exercise my options. Really, after the dilution your employee stock options are miniscule. And savvy startup CFOs will give employees small quantities of options not large.

EDIT: Yes, and these were not traditional Silicon Valley startups, they were NYC/Finance area startups. The original founders were not developers (your "bros"), they were finance guys!

Yes.