I know too many people who’ve had their stock zeroed out through dilution, preference vs common, partial buyouts where only some founders and investors get to sell, spurious “bad leaver” status for people who work for so-called competitors, forced resignations within particular timeframes that cause stock forfeiture, and on and on and on.
It would be an interesting addition to this guid to see these scenarios collected and enumerated with some tips around how to get caught out.