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I would work out the difference between the salary at say Google vs what you took during your tenure at the startup then double it because of lack of upside.

Aside: If the co-founder is an HN reader, then they probably know the throwaway account is you. That is going to skew this negotiation.

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I believe this is a sunk cost fallacy. The present value of the shares not based on the OP's previous foregone financial opportunities.

Agree with this. What the OP could have made at Google is not his CEOs problem.

Might also be the other party testing the waters.

edit: of course, parent's comment regarding the other party is still sound and valid :).

lol, it is.

for the record, i'd probably do it if i was offered $500k.

Then ask for 500k.

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