Often when later stage companies start offering RSU there is a double trigger vesting. One is the normal vesting schedule where you earn the stock and the secon

Often when later stage companies start offering RSU there is a double trigger vesting. One is the normal vesting schedule where you earn the stock and the second is when the stock becomes liquid (acquisition, IPO). This way you wont get the tax hit until the stock is actually liquid. The downside is that you cannot get longterm capital gains tax treatment, instead it's taxed as ordinary income with your income tax bracket. Personally, I think all the tax optimizing on stock options doesn't seem worth it when most startup stock never see any returns. I wish IRS could find a way to fix this. It seems silly to pay taxes just because you own stock that is not liquid on any market and which you often can't even legally sell without company's permission.