I took the $300K
    [T]he bonus was a life raft against personal
    debts racked up while living in San Francisco
    at a below market salary

Never accept a below market salary unless you have serious skin in the game (i.e. founder-level equity). I probably sound like a broken record about this, but you have to assume that your equity in the company will never be worth anything, and—even if you are part of a 'successful' acquisition—you are liable to get an amount that brings you up to parity with the market...if you're willing to accept the golden handcuffs.Think of your options (or RSUs, or whatever) in a company as being a lottery ticket. Odds are, it won't pay out. If it does, it's likely to be a trivial amount. For the rare cases where things really work out well (early employee at Facebook/Google), please try to remember that you were really lucky.