Why are the wealthy in America so insensitive to the problems of the poor?

I've seen this over and over--it especially amazes me with someone like John Boehner, who came from humble roots, worked hard, and was a self-made man. It seems like you reach a certain level of prosperity and you think everyone can just pull themselves up by their own bootstraps, including the sick, the elderly, and the unemployed. Not all poor people are welfare "bums"--I love the the opportunity and freedom in this country, but even with hard work, not everyone can be a millionaire. I don't understand how rich people are clueless on how hard the average American struggles to survive.