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!
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).