On the other hand, I always had the sense that Benjamin regarded Gruber as a kneejerk Apple apologist, and this too could not have helped their relationship.
But their differences led to the show's magic. Their contrasting styles would turn the show into a focused, intimate meditation on Gruber's thoughts on industry (plus side interests of baseball, Kubrick, etc.), often serving as a preview of what written work would be to come on Daring Fireball. While it can come across as aloofness, Dan has the passive ability to subtly guide the conversation and give it some sense of structure, and he's great at knowing when to let the other person speak. There were also incredibly funny moments of East Coast camaraderie that would keep the side topics interesting and lively.
It seems that Gruber has taken all of this for granted in deciding his show is better without Benjamin. Quite sad.