While I agree that this is a very individual choice (at least one other has referred to it as a calculated bet), it's a bit appalling to generalize this and cod

While I agree that this is a very individual choice (at least one other has referred to it as a calculated bet), it's a bit appalling to generalize this and codify it into a checklist. The situations where you should go down this line of reasoning are very, very rare. This is not general purpose advice. General purpose advice: Learn to recognize a [sunk cost][1]. If you decide to be an early employee of a startup (especially one which is not yet profitable) build the expectation that there will be an uncertain future. Tell yourself that you're going to work fiercely hard, and be fiercely loyal as long as your employer can support you. Tell yourself that the experience gained will be worth the long hours and uncertain future. But please, please, don't tell yourself "I'll probably have to work without pay." Don't tell yourself in advance that you'll ride it out for the equity, or because it's just so interesting, or because these founders are geniuses/nice/cool/whatever. If they can't pay you, it's not time double down on what you're paying them; it's time to move on. [1]: http://en.wikipedia.org/wiki/Sunk_costs http://en.wikipedia.org/wiki/Sunk_costs