First, determine what leverage you have. How essential are you to the startup's success? (how much would it cost to "replace" you). This might be higher than y

First, determine what leverage you have. How essential are you to the startup's success? (how much would it cost to "replace" you). This might be higher than you think .. they may need a couple engineers physically in SV. What % of your equity is vested? With standard terms, I'm guessing 1/4th (so 0.25%), unless there is a cliff longer than a year (which I've never seen). How likely is the startup to exit in different scenarios: acquihire, bought for user base, bought for product, or IPO. How likely are each of these scenarios? Just remember, this is a pure business decision. Don't worry much about "loyalty", "promises", "reputation" etc. If you're seriously good, these things don't matter much. Simply calculate the likelihood and payout for the possible decisions and then pick. That's how good founders should make decisions and how good employees should make decisions. I wouldn't hire people who didn't think this way, or work for people who didn't.