I listened to one of this guy's podcasts recently. The guest was impressive but Dwarkesh... Not so much. His questions were meandering and made it clear he didn't have much of a grasp on the subject matter. Does not surprise me that he is perplexed about the totalitarian regime's penchant for watching people.
For someone who interviews experts across a wide variety of disciplines (I've watched military professors, anthropologists, AI experts on his channel), I'd say Dwarkesh does a pretty damn good job. His interview with the Naval War college, he asked some mid questions, but the professor was able to use his questions as a launching platform to give informed insight, and it's one of my favorite interviews. I can't think of anyone else who interviews as well with such a balance of depth and breadth. It's clear he's a voracious learner and I'd bet he'll be even better than he is now in a few years. He's also really young, I'm not sure he's 30 yet.