He has but from what I remember Rogan didn't really care to spend much time on the subject. Adam Curry is a subject matter expert on other issues so it makes sense. I also don't get the impression their friendship is very deep.
My feeling is that Rogan doesn't want to mislead his audience. I don't think we get bitcoiners on Rogan until someone orange-pills someone Rogan deeply trusts. The moment someone orange pills Jaime for instance, Rogan will have on a bitcoiner. I'd guess Jaime is a sneaker head nft-type though so he's currently probably hurting matters more than he's helping.
Of all the bitcoiners I can imagine, Saylor stands the best chance of getting on because he has high status otherwise. Rogan could be reasonably sure he's not getting scammed by a publicaly listed CEO. Saylor is also unlikely to get derailed with Rogan's endless "what-abouts."
I think you meant "When will Rogan have a Bitcoiner on and talk about Bitcoin?", because he's had several Bitcoiners on, but they talked about other stuff.