There's a difference to being a good chatshow/podcast host and a journalist holding someone's feet to the fire!
Dwarkesh is excellent at what he does - lots of research beforehand (which is how he lands these great guests), but then lets the guest do most of the talking, and encourages them to expand on what they are saying.
It you are critisizing the guest or giving them too much push back, then they are going to clam up and you won't get the best out of them.
I decided to listen to a Dwarkesh episode as a result of this thread. I chose the Eliezer Yudkowsky episode. After 90 minutes, Dwarkesh is raising one of the same 3 objections for the n-teenth time, instead of leading the conversation in an interesting direction. If his other AI episodes are in the vein as other comments describe, then this does seem to be plain old positive AGI optimism bias rather than some special interview technique. In addition, he's very ill-prepared in that he doesn't seem to have attempted to understand the reasons some people have for believing AGI to be a threat.
On the other hand, Yudkowsky was a terrible guest, in terms of his public speaking skills. He came across as combative. His answers were terse and he spent little time on background information or otherwise making an effort to explain his reasoning in a way more digestible for a general audience.
I think with any talk show it mostly comes down to how interesting the guests are. I kind of agree with you that Dwarkesh's steering of the conversation isn't the best, but he seems to put his guests at ease and maybe they are more forthcoming as a result. He is also obviously smart, and it seems that encourages his guests to feel compelled to give deeper/more insightful/technical answers than if they had been, say, talking to some clueless journalist. This was notable in his interview with Ilya Sutskever, who otherwise seems to talk down to his interviewers.
The main strength of Dwarkesh is the caliber of guests he is able to attract, especially for being so new to the game. Apparently he'll research a potential guest for a couple of weeks before cold e-mailing them with some of his researched questions and asking if they'll come on his podcast, and gets a very high acceptance rate since the guests appreciate the questions and effort he has put into it (e.g. maybe Zuck enjoying being asked about Augustus, and not just about some typical FaceBook fare).
If you were inclined to give him another try, then I'd recommend the Richard Rhodes or Dario Amodei episodes, not because of any great Dwarkesh interviewing skills, but because of what the guests have to say. If you are a techie then the Sholto + Bricken one is also good - for same reason.
As far as AI optimism, I gather Dwarkesh has moved to SF, so that maybe goes with the territory (and some of his friends - like Sholto + Bricken - being in the AGI field). While arguably being a bit too deferential, he did at least give some pushback to Zuck on AI safety issues such as Meta's apparent lack of any "safe scaling" tests, and questioning how Zucks "increased AI safety via democratization" applied to bio threats (how is putting capability to build bio weapons in hands of a bad actor mitigated by others having AI too).
I haven't listened to Dwarkesh, but I take the complaint to mean that he doesn't probe his guests in interesting ways, not so much that he doesn't criticize his guests. If you aren't guiding the conversation into interesting corners then that seems like a problem.
He does a lot of research before his interviews, so comes with a lot of good questions, but then mostly let's the guests talk. He does have some impromptu follow-ups, but mostly tries to come back to his prepared questions.
Dwarkesh is excellent at what he does - lots of research beforehand (which is how he lands these great guests), but then lets the guest do most of the talking, and encourages them to expand on what they are saying.
It you are critisizing the guest or giving them too much push back, then they are going to clam up and you won't get the best out of them.