Arun Chaudhary is already a few sips into his Rams Head IPA when I arrive at the Pug on H Street in Washington, D.C. H Street is what passes for Brooklyn hipster in Washington these days, and Chaudhary appreciates that “it feels like a real bar, where people actually drink,” as opposed to bars where people network and preen. Chaudhary, who says he “made a business helping people project their authenticity,” craves it.

Chaudhary was the official White House videographer during Barack Obama’s first term. In other words, he was like …