I hadn't thought about Roberts position in this way but I do agree. But my thing is....is he wrong? I think he's come to understand, because he's uttered on several occasions how "STUPID" people are and i agree to an extent but he say's it with such conviction that it can get annoying, that you can't change people for the better, people are going to do what they want and you can either use that to your advantage or not. He's a CAPITALIST at heart which means he's only concerned with CAPITALIZING off of opportunities.
Have you read "How to win friends and influence people"?

Well in reading that I constantly contemplated the idea of what it means to persuade someone to do something and at the end of the day Persuasion is a form of Manipulation. Most people DESPISE criticism but LOVE to be praised, well how can an individual become a better person if they are already so great that they don't need criticism? You can't, and for this reason many people will always be pawns because they hate people who actually tell them the truth cuz its hard to face but love those who constantly lie to them long as they say something nice.

Now if one understands this, you are faced with two questions: Be noble and become hated, ostracized and poor or give the people what they want (not what they need) and you'll enjoy the luxuries this world as to offer. He doesn't hide the fact that he's a pure capitalist but he probably understands very well, as you stated, how labels can be dangerous so why shouldn't he play the game in the way that would best serve him?

I believe the underlying question or idea that is being contemplated is of Morality but the thing about morality is...there is no supreme being who decide what's moral and what's not, nor is there any punishment for not being moral. Social Darwinism is a very much real aspect of our society that won't being changing anytime soon, so Robert can spend his one life trying to do what's morally right and die a martyr or be "immoral" and enjoy the only life he has.
I myself don't want to be limited to one school of thought, I see myself as at Stoic Libertarian.