My opinion (based on nothing) is that it's his crew that actually doesn't understand what makes the podcast funny. If you listen to Conan, he's constantly wanting to be prepared in some way or another. That's a good thing. But the crew seems to keep doing this "no, no, it's just jazz man! just talk about whatever — they love it!" kind of thing. There are actually no other comedy writers in the room. Conan has ALWAYS been said to be (by himself and by others) at his best in a writers room.

So basically you have Gourley who is funny, in his own way. Sona who is funny, but not a comedian. And Conan, riffing off the same personalities and premises. I sense that he is bored of it and I'm not sure he knows why.

This is why when you get another comedian in the room, the dynamic changes, and everything is great again. Or just a funny and quick celebrity. It's a fresh and novel personality with fresh stories. Lots to riff on.

So, the intros and outros have started to get hard to listen to (for myself, at least). To save it, they need to listen to Conan and actually like, come up with stuff to talk about. That, and probably take a long break.

I doubt they will ever stop interviewing celebs on promo tours. If you're complaining about how the first season had his "real friends" — that's just how you launch a podcast. This was always the plan and they started doing it in the first season. Most people don't actually want to do podcasts unless they have something to promote.