I know that, but the question is if it can help? I don't think Wolfram is as significant as he thinks he is, but I think he's a lot more significant than a version without the obnoxious ego would be.
(1) You don't understand the distinction between having a big ego and being annoying. In this case I don't know what to say, except: thinking you're great doesn't necessitate telling everyone you're great.
(2) You do get the distinction, and you're really arguing that, big ego or small, immodesty is desirable. Again, there's not a lot to say here: it seems possible that Wolfram's success has a lot more to do with creating Mathematica than with telling people he's smarter than they are. If your position is really that being obnoxious (as opposed to merely having self-confidence) is useful, and that we should therefore be obnoxious, then so be it.