Why do people always ask him the same questions? Is it the easiest way to get an interview with him these days, promising that you'll clone previous interviews?
Someone needs to sit him down and do nothing but ask about programming languages for an hour or two at some point.
On the other hand, the question about his homepage was neat.
Rogan and Fridman both ask very shallow questions. I want to see him get grilled by someone familiar with the subject matter. Anything less gets questions about the lowest common denominator.
I find him lacking intellectual curiosity, although I've only had limited exposure to him. Do you have something you'd recommend for a "deeper look" into him or his work?
Getting the exact same five answers from him repeatedly about what he thinks about startups and philosophy doesn't matter in any way, as you put it, and he's currently working on a programming language. Programming languages, it stands to reason, are what he should be asked about.
Someone needs to sit him down and do nothing but ask about programming languages for an hour or two at some point.
On the other hand, the question about his homepage was neat.