Imagine you had the money today (you'd already, automatically sold all the stock). How much would you buy? Once you've figured that out sell everything except

Imagine you had the money today (you'd already, automatically sold all the stock). How much would you buy? Once you've figured that out sell everything except the amount you would buy. This is the correct answer. When your publicly traded company pays you in stock, they're just giving you cash in an inconvenient form. If you wouldn't use this hypothetical cash to buy stock in your company, you should liquidate it all immediately. Note that so long as you have unvested stock and intend to stay at your company, you essentially already are invested in your company. And since you said your unvested stock is worth 10x your salary, you'll probably have more exposure to the stock than you ideally want even if you do sell all your shares. So keeping some probably doesn't make much sense.