Obama famously stuck his foot in his mouth this week when he said that if you built a business, you didn't build it. Someone else did. And even though the left has been furiously covering for him, saying that what he said isn't really what he said, Obama meant what he said. He's the perfect example of someone who has never built anything in this life.
His private schooling as a child was because of his white grandparents. He did nothing to have these grandparents. It's most likely true that he got into Occidental College as a foreign student, thanks to his mom's second husband. He did nothing to have this stepfather. It's a sure bet that he got into Columbia and Harvard because of affirmative action due to the color of his skin. He did nothing to have Barack Obama, Sr., as his father.
Because the color of his skin got him into Harvard, he became president of the Harvard Law Review. Where, it should be noted, he did nothing. As stated before, he did nothing to get the color of his skin. He got book contracts because he was president of the Harvard Law Review because he got in Harvard because of the color of his skin.
He became an Illinois senator, a U.S. senator, and president solely because other people voted for him. He did not obtain these positions on his own.
It is easy to see, therefore, why Obama thinks like he does. After having never achieved anything on his own, he doesn't understand that some people actually work for what they have.