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> works out in the event that the shares end up worthless

Then you're at parity with never exercising.




Yes, but you get the benefit of .7x exercising with the cost of never exercising.

Exercise, no successful IPO: lose $x exercise cost

Exercise, successful IPO: lose $x exercise cost, gain $y share sale benefit

No exercise, no successful IPO: gain/lose nothing

No exercise, successful IPO: gain/lose nothing

Service exercise, no successful IPO: lose nothing, maybe gain some AMT credits or capital loss carryovers

Service exercise, successful IPO: lose $x exercise cost plus interest, gain 0.7*$y share sale benefit

Your best best case is exercising yourself and getting the IPO, but you have to weigh that against the likelihood of it occurring and your personal risk tolerance for the $x cost to exercise.

I would never buy a lottery ticket, but I will always accept even .01% of a free lottery ticket.




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