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.
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.