re: #2, that's why god invented derivatives. contrary to popular belief, you CAN write derivatives on your private stock options - the derivatives will just al

re: #2, that's why god invented derivatives. contrary to popular belief, you CAN write derivatives on your private stock options - the derivatives will just also be worth nothing if the engineer leaves early / company folds / etc. and they will be a tax nightmare even if you take early exercise and handle everything correctly. i'd LOVE to see someone pull this off successfully though.