Another one like that is Rubin. Especially since he was hanging with Peterson... But even before that. I have seen him gradually shift from flaming far-left liberal to a pretty hard core classic liberal, which is spittin distance to Conservatism.
I really enjoy the Intellectual Dark Web form - varied opinions siting down amicably for long discussions... In the end, those long discussions work more to Conservatives favor... You can't duck and dive like they do in the soundbite MSM.
My belief is that opinions typically regarded as "Conservative" come from, and withstand, in-depth critical contemplation. Guys like Rubin and Pool are living out that transition before our eyes; and yes, they are demonstrating the value of long-form, probing thought and discussion.
I regularly observe in my professional life the shortcomings of "education" as practiced in the United States (and perhaps more broadly in the West) - people are good at, and rewarded for, narrow and parochial specialist reactions to problems, but almost no one demonstrates that they actually know how to think. Perhaps the COVID-driven exodus of students from campuses (whether necessary or not) coupled with some Intellectual Dark Web free-thinkers, will drive toward an actual Renaissance of critical thought.