How long do you expect the lockup to be? Depending on the company, there's a pretty good chance that you won't be able to cash in the options until after at le

How long do you expect the lockup to be? Depending on the company, there's a pretty good chance that you won't be able to cash in the options until after at least 1 quarter worth of earnings, and those have not been friendly, in the last few years. And of course you probably have the 1 year cliff to deal with, so maybe that's longer than the IPO plus earnings, and by then, are you confident that the company will continue with growth targets? Remember, IPO has a lot of growth built in, so the IPO price expects that the company continues to grow super quickly, and with no more capital. If the company doesn't do that, the stock options are worth nothing. And remember that you have to buy the options before you can sell them, so unless you do that as part of the sale, you risk being out the money plus the taxes. It's risky. My opinion, take the cash. Cash is king, and you're "guaranteed" that money regardless of stock performance. Invest it hoe you want, the other stock being lottery tickets. If the company IPOs you'll get stock as bonuses most likely anyways. This is all my opinion of course. I am negative on most companies' ability to stand up under Wall Street scrutiny.