Two selections of his incessant prattling caught my attention.
I would almost sympathize with Bob here, but I know that it would be a waste. This emptiness might be from the fact that he knows that on some visceral level that his "work" give him no joy or fulfillment. Why would it? Does anyone remember Shakespeare's critics four centuries after the Bard shuffled off this mortal coil? Of course not! No respectable university or college course is going put his videos, blog posts, or his shitty book down as required reading on the syllabus.
As for the emotional need: could it be validation? Bob appears to be seeking affirmation from all the wrong source. Any "friendship" he seeks to have with Zoe Quinn, Brianna Wu, etc. will be transactional and completely conditional. He was willing to throw his boss and friend under the bus for ideology's sake and Quinn/Wu/Whoever would do the same to him in a Boston minute. Additionally, he seeks emotional validation of the Elites or "Intellectuals" who will never recognize his so-called gift and I imagine that is a factor in why Bob lashes out at "the Wasteland." He has "worked" so "hard" to get where he is now, but it is will hanging by a thread because he could still get fired or lose his Patreon bucks.
Maybe he is feeling this harsh bout of imposter syndrome because that is what he is: an imposter. He claims that he is this insightful and witty renaissance man of refined tastes and sublime intellect, but he is just one of the rubes. His friendships are superficial; no studio is going to listen to his ideas; and his knowledge of pop culture is more feeble than he would care to admit.