I distinctly remember a specific Twitter comment, maybe 7ish years ago, that solidified my view on DHH as a person. It was a thread about remote work. Someone from South America commented trying to be nice to David, saying something like "you should work remotely from Chile, it has a great Ruby community" etc, to which his response was "I've no interest in living in a 3rd world country".
Notch-esque politics aside, that was mean-spirited, inconsiderate behavior which should not be applauded. From that day I strongly sensed that was who he truly was.