How many rounds of negotiating an offer do you think is reasonable? If you went back on base and got what you asked for, would be it be okay to go back and ask for more equity if you think there’s room (given the upside)? Or is it greedy at that point?

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I do salary first and other bonuses / benefits second. If I get what I want salary wise, I'll only negotiate other benefits that are truly important to me. If not, I'll use the 2nd conversation to try to bridge the gap.

So in your example if I got what I wanted salary wise, I likely would not further negotiate equity. But you do you. If you're going to come in upset about it and that will affect your outlook, then it's better to ask. But then D1's point is perfectly fair - why didn't you do your research to ask for a number you'd be happy with? Or ask higher to find a middle ground?

tl;dr - you can ask but you should also have a good reason as to why you didn't ask earlier, else it does not look good and sets a negative perception.

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