I took the $300K
<p><pre><code>    [T]he bonus was a life raft against personal
    debts racked up while living in San Francisco
    at a below market salary
</code></pre>
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.<p>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 <i>really</i> lucky.