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The tax burden on the options would be well more than I can afford. And like you mentioned, my leaving would have a very negative impact on valuation.

My window is 2 years. So at least there is that. Although (not sure if I mentioned that), a bulk of my options came within the last year and I have a 1 year cliff with four years total vesting. So at best 30% of my total options are vested.

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How many more options would you get if you stayed the remainder of the year? Perhaps that could be worth it.

And perhaps another thing you could negotiate for is vesting acceleration.

Back of napkin math... staying an extra year would be slightly less than 50% more (the second 25% of my largest grant would hit and I'd have half of it).

This is part of what makes the decision so hard. And it's worth noting the valuation of the company is not terrible. If I had this valuation after 4 years I'd be ecstatic. Problem is it's been 7 and I have a lot of sunk cost.

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