> his motivations seem consistently petty and strange or just downright ludicrous. He's like an alien to me.
I think it could help to try to think of a historical figure that has done impressive things but which you don't have an overly negative view of. A lot of them seem really weird or alien. In democracies, political leaders are (sometimes!) more "normal" because they have to get elected. So think of a CEO/Founder you like (Jobs?) or earlier people (Napoleon? I dunno, pick yours)
Read a bio on them, they're pretty strange (I like Churchill, dude was wild).
It seems that to do extraordinary things you need some traits that make you ludicrous. I don't really know, but it's definitely a pattern