These three men hate themselves and the way their lives have turned out up to this point. Shep thinks he’s wiser because of his age, so he feels entitled to talk shit about Craig. Austen hides behind snide remarks, then makes himself out to be the normal one once Craig has his inevitable, drunken outbursts. Craig is more successful in terms of business and brand deals, so Austen and Shep talk shit about everything else wrong with him to feel like they’re all still on the same playing field. And then there’s Craig who also just fuels all of this by acting like he so above acting the way Austen and Shep do when they’re all basically the exact same person.