I can tell you I couldn’t do it, no matter how hard I tried. I think it may be a combination of his background growing up around them and knowing the culture- the construction workers, the slum-lords his dad worked with, etc... he seems to have internalized and have an intuitive sense of the culture of his base. He may be a billionaire, but his roots and background is in that culture. He is an uneducated construction worker at heart himself- just one of the wealthiest ones. But he was never really ever accepted by the true intellectual and social elite of Manhattan, no matter how hard he tried. He was just way too unsophisticated, uneducated, too boorish, his manners and speech too boorish and coarse. Everywhere he went it was clear to all that he was just an unrefined, foul mouthed, uneducated construction worker, complete with the cussing, the cat whistles at every broad who walked by, the foul manners, etc... and didn’t matter how big his bank account, or how much he boasted and inflated it to try to fit in.
And what to make of his “Ivy League education” he keeps talking about? It was clearly just bought by his dad. He clearly has the vocabulary, rhetoric, and level of thinking of a middle schooler. It’s hard to imagine how he would be allowed to graduate high school with that, let alone go to some Ivy League school.
So this background has allowed him now to turn on those educated “elites” who spurned and rejected him for so long with a vengeance. If they refused to let him in, he would burn their house down.