He talks about being a "pretty good" listener but, not catching the fact that people he respects and admires feel like he's constantly talking down to them.
It's an easy trap to fall into and I imagine a hard one to get out of (not because I'm not an asshole but, because I'm not rich enough to say that I'm in his position).
He just clearly doesn't understand himself. Startup culture looks at this thing called exiting as the very hard thing that very few people do sucessfully and then we look at the few that do it as some kind of oracle. We want answers to hard questions and automatically think that people that achieved success have found it.
Maybe he isn't this business savant and maverick. Maybe he just got lucky and the momentum of that took him over the line into success. I'm not saying it was easy but, maybe his success isn't because of the things he thinks it is.