It's basically the same mechanism that causes the tax liability though, I wasn't arguing for the size of the issue In the stock option case you only get a tax

It's basically the same mechanism that causes the tax liability though, I wasn't arguing for the size of the issue In the stock option case you only get a tax liability if you buy something that's worth more than you paid for it - if you have options, either buy them the day they are granted (and take the risk that you wont stay, or the company will die, etc) and lock in the lower long term capital gains tax, or wait until the day you sell the stock and do an exercise/sell transaction which will likely be taxed at source and end up on your W2, at your full marginal rate. The thing you should not do is the middle thing - buy your stock between these two dates then you'll pick up a tax liability on the capital gains to that point. Talk to someone who understands ISOs and taxes - when you are first granted your stocks and whenever you plan on changing their state