[chatmasta]

What is your exercise window on the options? Are they ISO or RSU?

If you have ISO options with a 90 day exercise window, you'll need to pay the AMT tax on the difference between current valuation and strike price. If you joined as employee #3 and valuation of options is now $1m, that could be a substantial tax bill. If the company never exits you will have paid a bunch of tax money for shares you'll never be able to liquidate.

Also consider that if you feel you're so important to the company that leaving might cause it to fail, then your leaving will decrease the possibility of any exit and effectively devalue your options.

If you have a 90 day exercise window, perhaps you can negotiate it to 10 years, in exchange for reducing the back pay you are owed. That $60k is leverage you can use in any negotiation, whether for options terms, severance package, or non-compete agreement.

[throwawayAug16]

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.

[chatmasta]

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.

[throwawayAug16]

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.