Shane Parrish's Knowledge Project podcast did a long interview with AngelList founder Naval Ravikant, covering a wide range of topics, and quite a bit of light philosophy.
It was a bit of a struggle for me -- he's such an unusual person, so different from me, and I found myself disagreeing deeply with some things he said about life and philosophy, and even more just with his tone of certainty. It's a reaction I have to Tyler Cowen as well.
That said, I do recommend listening. In particular, I found his point around 52:00 about not cherry picking from others' lives very profound.
For example, re: Naval's "I don't believe in macroeconomics", I propose that he found a country whose currency goes on and off the gold standard randomly and at different rates each time, and which suddenly floods the streets with bills unexpectedly, and other times orders all currency burned. No way of knowing if that would work better or worse than our system, right?
That's what feels so alternating to me... while he's clearly thought deeply and intelligently about a million things, and is smarter than me in a dozen ways, it also seems like he avoids settling his views in mutual appreciation of multiple opposing forces. He has to pick an absolute position. (Contra his claim that he doesn't do absolutes!)
Maybe that's connected to how he gets so much done: he seems to truly embody that dictum of "Hell yes, or not at all".