One thing I wondered is: is he a good candidate to learn philosophy or a bad one? He's smarter than most people (that's not saying much). He has lots of money and attention. He could have a ton of free time if he wanted to. He reads, he said he particularly likes biographies and mentioned reading about philosophers like Socrates. On the other hand, he's really busy with what he's doing, and he's already good at what he does. Most people could switch to philosophy without giving up anything very important.
I think the answer is: if he learned philosophy, he'd basically find himself in Gail Wynand's position. Rand covered this.
A couple days ago, an anonymous Fallible Ideas was especially impressed with Trump. I think he overestimates. Here's some of his flaws that Trump intentionally chose to share in a public book (he's hiding anything he considers a significant flaw! in fact he made a comment in the book about how people should hide their weaknesses in general.):
Trump at least somewhat believes in star signs. He's a Gemini and thinks that may help explain or determine his personality (like work ethic).
A visitor said Trump and his employees act like a family ... *having a fight*. Trump repeated that like it isn't terrible.
Trump didn't fire a bad employee for 2 years cuz he kept getting fooled by the guy's bullshit ("i'm about to get a deal done! almost there!")
Due to big mistakes, Trump used to have a net worth of more than 9 billion NEGATIVE dollars.
Trump thinks it's important to dress conventionally to please people. He talked about this a fair amount – he pays attention to it – and he said something like: don't give people extra reasons to reject you. (why would you want to deal with such bad people?)
Trump has conventional problems with diet and weight.
Trump was cowardly in the face of a friend making a huge mistake – didn't speak his mind. The disaster Trump saw coming then happened to his friend. (It was about a guy with 4 failed marriages getting a pre-nup this time. Trump is pro pre-nups in general. That was one of the many good points in the book.)
Trump doesn't like shaking hands (because germs) and wishes people would bow like in Japan instead. He shakes people's hands anyway out of fear that, if he doesn't appease them, they will dislike him. He said this clearly with an anecdote where he did it for that reason even though he had reason to be especially doubtful of the other guy's hand cleanliness at that moment. It wasn't even someone super important, just some kinda writer I think, maybe a journalist.
Trump's had significant book-mentionable issues with conventional ideas about revenge and payback. (He vaguely indicated improving somewhat and made some bland suggestions about focusing on more positive stuff when you can let problems go. He was very vague about when you can and can't just let a problem go. He told a story about spending more money on lawyers than was at stake in business to get back at people who screwed him. He didn't regret that, he presented that as a good thing. Maybe it's to teach people not to fuck him? But he didn't say that. He's not that great at explaining what he means. He tries to let examples speak for themselves way too much.)
Trump is into prestige. He likes to play golf with Bill Clinton and maintain lots of relationships with fancy people and brag about it. Trump doesn't seem to care that Clinton is a Democrat, and Trump is a Republican, and there's a big incompatibility there. No comment about that. Why would anyone want to be around Bill Clinton? What an awful guy. Fuck him. Trump with all his friends and stuff can't find anyone better than fucking Bill Clinton to play golf with? He's doing something wrong.
The book has a bunch of good stuff too (nothing GREAT or super notable though). It's a decent read, and quick. I think in general the lives of the rich and famous are really overestimated. This is just a sample of major flaws and problems Trump revealed about himself in one book containing only what he chose to reveal. This is what comes out when Trump does his best to present himself positively and seem great. That says a lot.