Stock options expiry: One important point that was not mentioned by OP is the typical contract clause most startups use that changes the expiry of your vested o

Stock options expiry: One important point that was not mentioned by OP is the typical contract clause most startups use that changes the expiry of your vested options from something like 10 years while you're employed to 30 days if you leave the startup. You took a below-market salary in exchange for equity options and if you leave your job you can't keep those options because you have to exercise them, otherwise they'll expire worthless. Basically, once you leave the company, you have to pay the company to buy its stock, otherwise your options expire and you get nothing in exchange for your sacrifice! See http://gigaom.com/2011/06/05/5-mistakes-you-cant-afford-to-make-with-stock-options/ http://gigaom.com/2011/06/05/5-mistakes-you-cant-afford-to-m...