>... you find out that the CEO sold the company at a bargain so liquidation preference kicked in and he just took a huge retention bonus instead. There's somet

>... you find out that the CEO sold the company at a bargain so liquidation preference kicked in and he just took a huge retention bonus instead. There's something potentially misaligned between the control of the founders and the final grant value on the other end. There are so many ways to distort this in the final exit deal and these are details that you probably won't learn about unless you happened to exercise stock before the exit happens. In general, the positive outcomes seem "capped" in that a founder is inclined to lock in their gains with an exit if the deal is reasonable for them. Maybe the option shouldn't be as a share of the company but a share of everything the CEO/founder makes from there on out. :) For really early stage, I generally assume that a founder is trying to at least 10x their net worth so any hand wavy exit estimate generally gets capped with that in mind.