I think I know what you're picking up on, but it's hard to describe without people interpreting me saying Dick is a "fake" or "phony." Let me put it to you this way, Asterios has commented how good Dick is at business and implied he has business not related to his internet show. One of the key skills of an entrepreneur going to have to learn or pick up on is salesmanship, because the core of any business is to convince people of your wares or services, and on top of that you have to convince all sorts of people your business is worth investing in. All salesmanship is at its core is effective communication to get someone to do something you wish them to do (buy something, give you a loan, work out a deal, ect). This can lead to someone coming off as well, off, because they are consciously aware of their communication in a way most people aren't. You ever notice how Dick's whole brand is being angry, yet he rarely gets into shouting matches with people? Closet I can think of is when the Killstream chat was calling him a cuck and he went on a rant about the Federal Reserve.
Personally I do like Dick, but I get bored of his own show by the half hour mark most of the time.
Oh please post it in this thread if it gets uploaded.