"Is losing money really enjoyable?"
Funny
Very deep though.
To be honest, it is possible that very wealthy person could be gambling occasionally for fun. But am not sure if they do that with zero expectation of reward. Most fun things are quite addictive, that is why we are consume a lot of for stuff. So I wonder if a wealthy person who gambling for fun does that regularly or occasionally. The only reason he would gamble occasionally is if he has lots of other things that make him happy.