As a lot of people have noted, it's pretty weird that Mitt Romney was "shellshocked" by an electoral defeat that was widely predicted by public opinion surveys, betting markets, and The New York Times. That Romney fell prey to a certain amount of wishful thinking and thought he was going to win is very understandable. But surely some awareness that the consensus prediction of third party observers might come true should have penetrated into his inner-circle right? And isn't Romney supposed to be some kind of data-wizard genius investor businessman?
To speculate a bit, I think that people underestimate how problematic it can be to walk around life being a rich guy. The problem with being rich is that everyone stops telling you what they think and starts trying to get your money. You necessarily end up living your life in a fog of flattery and misinformation. And worse, because Americans genuinely admire rich people even people who aren't flattering you tend to give undue deference to your bad ideas. Live in that bubble for long enough—and Romney's been in it for a long time indeed—and you can end up pretty unmoored from reality.