Why would any of their options be underwater? Going off of those estimates above, the pot split between shareholders after liquidation preference is 250million. Anyone who has shares is able to cash them out I imagine (how much profit dependent on how many shares someone is granted, which varies obviously but is still a positive net) — unless you’re implying the strike price is less than the share value?

Their last round valued the company at $600MM, so anyone with options at that strike isn't going to make any money.

Only if 409A valuation was at referred price which it almost certainly wasn’t

Not much, I'd imagine. It'd be like getting FB stock options upon joining and having it drop in price when the stock market tanked in March. That's the point of stock.

Presumably they were accelerated/repurchased out for $0? Replaced by ... what exactly? As a giphy employee what do you get out of the acquisiton beyond maybe some job security?

With "later on" in this case being the past four years.