It's not that he's aging especially poorly and I don't think it's that he isn't taking care of himself (although he probably isn't). It's that he's been surgically altered to resemble a woman, none too skillfully, and he's beginning to approach middle age and so aging like a man. The more he tries to look like this hip, sassy, go-to-hell Woman in Tech, the more grotesque the final result is. A John who hadn't butchered himself or who at least was honest with who and what he was might be able to do something about how he looks. My ugly opinion notwithstanding, he ain't 25 years old anymore and he has to stop dressing like it, man, woman, or freakshow.
As for the interview itself, I was surprised by how softball it was. The one question that came across as fairly tough (why haven't you said anything about the new Wikileaks information, bein' a rootin' tootin' software engineer and all) is, of course, where he made his most laughable fuckups. "Oh the iOs is fine, it's nothing to worry about, I obviously know jack shit about the modern surveillance state, tee-hee."
The greatest moment is, of course, the very beginning. He drops the $250,000 loan (neglecting where it came from, natch), Gamergate, "I'm a software engineer," death threats, rape threats, the personal attention of the wicked Steve Bannon, Breitbart, and the alt-right ... in the first 50 seconds.
Never change, Congressthing.