I (respectfully) disagree entirely with this conclusion. If you want to do analysis like this, you need to weight these numbers against the possibility of it h

I (respectfully) disagree entirely with this conclusion. If you want to do analysis like this, you need to weight these numbers against the possibility of it happening to get the expected value of each column. You have also simplified the smaller exit values to not include investor preferences (which means investors are first in line to get money, founders second, employees dead last). Additionally, most contracts do not allow for early exercise so lots of these ideas are moot. If you do not have early exercise in your contract and you leave the company it's usually a leading indicator of failure. Either the company laid you off to reduce burn (do not under any circumstances buy stock if you have been laid off), or you left the company for a moral/business/whatever reason. In the latter case, it seems unwise to put your money where your heart isn't. If you are optimizing your life for the best chance of striking it rich do not be a startup employee. Be a founder. Better yet, be an investor. There are lots of reasons to be a startup employee, but being in it for the options is not one of them. Treat them as worth $0 and negotiate for more cash or things you care about like vacation or part time hours.