Unless the total price of the stock grant is financially negligible at the point of hire, the %5 tax difference isn't that great of an advantage compared to the

Unless the total price of the stock grant is financially negligible at the point of hire, the %5 tax difference isn't that great of an advantage compared to the risk since most startups fail. I think vested stock options not expiring a few months after leaving the company is far more valuable, but no one does that. It would allow you to put no money down and only exercise when the options are actually liquid without being forced to purchase the stock at some point due to circumstances not under your control.