This is gonna be pretty hard to figure out. I'd recommend you take it to someone knowledgable - a startup accountant or lawyer perhaps; they can give you compar

This is gonna be pretty hard to figure out. I'd recommend you take it to someone knowledgable - a startup accountant or lawyer perhaps; they can give you comparables. For the kind of money you're talking about you should definitely have a lawyer looking over the docs. I tried writing out some general advice, but there's so many possible scenarios: is the company hot, is growth flat, is it trying to sell to someone (PE firm or later stage investor), why are they even buying your stock? I agree with ralph84 that selling some smaller number keeps you in the game and also let's you cash out - founders and early employees regularly do this, and they are big believers in future upside. Also remember that even if the stock goes up in the future, you should price in the cost of having that money now (everything from the appreciation of a house you may buy, to factoring in expected value). Main advice: get a lawyer. If you're looking for someone to talk through the options informally, my email is in my profile.