These are intelligent people and the actions don't make sense when you look at the details, like your example of being in a fine position. That only leaves unaccounted for variables at play, and the best I've been able to tell is that its a cultural gap between the execs and the plebs that plays out even at small startups.

You see the same behavior in non tech companies when VPs find out what their senior software engineers are paid, and start getting upset at the similar salary level, even though that's the market price. Or in things like rules that only Execs get to fly first class. I had a an executive have HR look into me "breaking the rules" when he saw me in first class with him on the way to a company event after I paid to upgrade my own seat.