FWIW I don't ever recall having this reaction to Harry, though my memory is pretty bad and I think I'm easily manipulated by stories.
It may have something to do with being terse and blunt - this often makes the speaker seem as though they think they're "better" than their interlocutors. I had a Polish professor for one of my calculus classes in undergrad who, being a Pole speaking english, naturally sounded very blunt to our American ears. There were several students in that class who just though he was an arrogant asshole who talked down to his students. I'm mostly speculating here though.
I intended Leveling Up in Rationality to communicate this:
But some people seem to have read it and heard this instead:
This failure (on my part) fits into a larger pattern of the Singularity Institute seeming too arrogant and (perhaps) being too arrogant. As one friend recently told me:
So, I have a few questions: