"Taking away from Bob (who has done the work) to give to Billy (who only does what he has to) if fundamentally wrong."
This is where your analogy fails, being a rich person doesn't mean you have worked harder than people poorer than you. Furthermore, yes there is a lot of inequality in our world, does that mean we should just accept it? Shouldn't we strive to correct injustices? Being an american and indeed a reasonable human being i assume you believe in liberty and justice for all.
As for the self made people, their reward is their wealth, which if they truely have come from a disadvantaged background then surely they would be more than happy to help the people in their situation. Having climbed the dangerous mountain to success, surely they want to make the path a little less steep for the people that follow them. I do not subscribe to the doctrine that because i struggled to get where i am, he should too. Thats ludicrous and totally anti-progressive.
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