This is very much how I feel. I don't have a lot of love for figures like Ralph, Nick, Baked Alaska, or Milo. I'm ambivalent on Ye. But I 100% sympathize with his trying to deal with Tim's line of argument and just deciding it isn't worth it. His questions were the exact opposite of polite or unchallenging.
He does this thing that all libertarians/'individualists'/classical liberals do under certain circumstances. They all have these little shibboleths that they have to bow down to, in order to prove that they're still 'good boys' and not outside the realm of polite political society. If you challenge any of these, they will then pretend that emergent phenomenon don't exist and will never allow the conversation to move an inch forward.
The only thing that you can do is point out how disingenuous, cowardly, and mind-shatteringly stupid what they're doing is, and then walk away, because at that stage they can't be convinced. They aren't reasoning out a position, they're refusing to be budged because they know that there will be social consequences if they put a toe over that line. Even if you impeccably argue your way around this, they will just keep repeating the same point like a broken record, because you can't reason someone out of a position that they didn't reason themselves into.
Kanye had already gone through this cycle once with Pool. He then delivered the necessary killshot to his flimsy argument: if individual actions cannot combine to create larger emergent, observable, and comprehensible phenomena, then why did Pool himself start out by saying that Kanye would be 'good for the black vote'? If we can dispense with talking only about individual black people and instead talk about the black vote as a larger, comprehensible thing brought about by the collective actions and interactions of myriad individual black people, why is it absolutely forbidden to perform the same process of abstraction when discussing Jewish power?
It was clear that, had the interview continues, every time that Kanye tried to talk about the elephant in the room and make his case, Pool would have talk over him and insist that they only ever talk about individual Jewish people like a bunch of autists. Imagine trying to talk to someone about the political history of black Americans in the 20th century, only for them to interrupt you anytime you tried to introduce a level of abstraction one step above the individual level. You simply wouldn't be able to communicate anything about the subject matter. Any reasonable people watching that interview will come away with the view that Pool was being a deliberately obtuse slimeball