>1) I have ~50k vested shares of stock (options?) but don't have any paperwork other than our original contract which says something about the next board meetin

>1) I have ~50k vested shares of stock (options?) but don't have any paperwork other than our original contract which says something about the next board meeting, it's all rather confusing. Nope, you have nothing. Zero. You got conned. Your offer letter probably says something like "This option grant is conditional on being approved at our next board meeting." If you never got a letter saying that the board approved your grant, you have nothing. Sucks to be you. Now you learned for next time. Did you ask your now-ex employer about exercising your options? What did they say? You can, if you want, talk to a lawyer, but he'll probably say the same thing I just said. Given that you are broke, you don't have the money to hire a lawyer and press this issue. Besides, there are two possibilities, both bad: 1. The startup is going to fail anyway. No point exercising your options. 2. The shares are worth more than the strike price. Now you have to come up with the money to exercise AND pay a huge tax bill. Plus, the shares probably aren't liquid. Plus, the startup can raise money at their next financing with a liquidation preference, and you can wind up with nothing even if the startup eventually sells for a decent amount. >2) Would it be wise to take advantage of a government run program like COBRA for insurance? I never used my insurance anyways, is it worth it to apply, and how are the chances that I will be accepted? Yes, this is worth it, because you might get sick. However, with health insurance exchanges, you might be able to get a cheaper bronze/silver plan. >3) My savings will not last long That's why you keep an emergency fund of 6-12 months' living expenses. Also, try to find a new job before quitting your last one.