Yep, this is pretty normal. > It sounds like the company raised a round at too high of a valuation. Not necessarily. A company's valuation can shift up and do

Yep, this is pretty normal. > It sounds like the company raised a round at too high of a valuation. Not necessarily. A company's valuation can shift up and down due to many factors - but for whatever reason, they ended up underwater in the end. It's also common for executives that were able to get a company to acquisition to receive a "golden parachute" - e.g. a 7-figure bonus for a turnaround CEO getting the company acquired within X months of being hired. > The rules around options really suck here Some companies are moving to NSOs now too, which have much more flexibility in terms of post-termination exercise windows (up to 10 years, I think).