I find his questions to be anything but thoughtful. At times, he seems not to even know what to ask or even fails to understand what's being said.
Stephen Wolfram's episode has not many rather is pretty much almost all like that. Dr. Wolfram and Lex clearly seem to be on very very different planes throughout.
I found this again to be the case about with John Carmack's session.
Questions that I would have placed would have been what would be a 3D engine look like if Carmack is commissioned to build it today that must be cross platform? What technologies he thinks have future and if then in what direction.
Only explanation could be that maybe that's not the purpose of the podcast at all. The goal is to just have aimless, low caliber, ordinary conversation to keep it approachable for a wider audience.