To clarify, were you expecting a 20x payout on your stock, or was the payout was 20x less than what you were expecting? Either way, sounds like you got bamboozled when you signed the offer letter. I'd almost always take a higher salary at a startup. The vast majority of startups aren't anywhere near Facebook or Google.
I didn't expect anything with regard to stock value. I know that most startups are fly-by-night, and if the sale didn't happen when it happened, I was going to go somewhere else and leave behind my options.
The reason why I confronted her had less to do with the payout from the sale, and more to do with her general attitude towards compensation.
To put it bluntly, she continued to pay well below market rate, and if she didn't pay up, everyone was going to trickle out the door as we got market rate jobs elsewhere. No one works in an aqui-hire situation below market rate. Her views on compensation were so bad that she had me at the same starting salary that I had when I worked under the same parent company, 5 years prior.
Needless to say, shortly after my conversation with our CEO, she was fired by the parent company, and the new owners promptly fixed the compensation problem.
