Please, don't act like this is anything more than feigned humility poorly disguised as a tidbit of wisdom. Even calling it that is generous since he doesn't offer any real insight or solution.
The fact that you fail to understand why so many people agreed with that comment is equally mortifying. Is your blind sympathy for "rich guy problems" overpowering your ability to read between the lines?
So DHH is about to enter an extremely competitive race and he has good odds. I think it's fair to imagine that this has been the only thing on his mind for weeks. He then finishes second which is admirable by any standard and yet he is not happy. Frustrated with this, he analyses his own thinking and writes a blog post about it.
Do you really think that he thought "I'm going to brag, I just need an angle!"? Or, should he simply avoid writing because his situation is more privileged than most people?
The fact that you fail to understand why so many people agreed with that comment is equally mortifying. Is your blind sympathy for "rich guy problems" overpowering your ability to read between the lines?