To be honest I think most well adjusted people would understand that they themselves were annoying in as an undergraduate. I was an egotistical prick as an undergraduate, some of the things I did make me cringe looking back. But that's the nature of growing up.
Yes, but that general sense is not how the word is used there. If it were, it would be redundant. He's talking about a specific subgroup (budding Ivy League entrepreneurs?) that he finds annoying in a specific way. It's a class distinction.
