He's a certain type of person who talks about skateboarding in a certain type of way. People who are bugged by that way of talking about things in general will only see the schtick (which it partly is) and probably not like it. Pretty much just like Weckingball except instead of a "muscle bro" schtick it's an "intellectual socialite" schtick.
At the end of the day, both of them are just people making keener observations than most about skateboarding, based on deep knowledge and appreciation.
Both of them annoy me at times, usually when they're saying something I disagree with. The rest of the time, they are doing the job that everyone says they wish Crob was doing.
edit* gaseous, I didn't listen to that podcast, felt pretty sure I would hate it, so I'm not trying to disagree with your take on it.