The brash, self-promotional wine entrepreneur turned social media star still has his share of critics—but he also has another success on his hands with digital agency VaynerMedia.

The judges of the 88th Miss America pageant, which was held last September in Atlantic City, were mostly names you know, people of considerable fame. They included former supermodel Kathy Ireland, NFL great and Dancing with the Stars winner Donald Driver, and Olympic gymnast Shawn Johnson.

And then there was Gary Vaynerchuk. When ABC’s host Chris Harrison (of Bachelor fame) introduced him—“an entrepreneur, author, and social media master”—Vaynerchuk held up his phone and mimed the act of taking a selfie.

It was a perfect (and perfectly predictable) joke at his own expense. Vaynerchuk has created two successful companies; he is a bestselling author; he can command six-figure fees for speaking engagements; and he has 1.1 million Twitter followers. But he is largely unknown to the American television-viewing public. Rather, he is Internet famous. That fame happened by design and by years of meticulous planning—and it has drawn vocal critics for a style that is loud, bombastic and blatantly self-promotional. (A sample exhortation from a video commanding people to subscribe to his YouTube channel: “Fucking follow me, right now.”)