Is This Really Boston’s Next Media Mogul?

Yes. His name is David Portnoy. And he’s building an empire – one blog post (and one babe) at a time.

LEDGE KITCHEN AND DRINKS is a three-minute walk from Portnoy’s office. There’s a crowd on this Thursday night, and it’s loud. Maybe it’s a jump-start to the upcoming Halloween weekend. Maybe it’s the warm weather. When I arrive, Portnoy is standing at the bar wearing what amounts to his version of formalwear: pressed white shirt, pastel plaid shorts, flip-flops.

I order a Sam Adams. He says he hates Sam Adams. We talk Halloween costumes: He’s going as Bodhi, the mystical surfer/badass bank robber portrayed by Patrick Swayze in the movie Point Break. “You’d never believe how hard it is to find a wetsuit in Boston,” he says.

In person, Portnoy is the antithesis of his online persona. He’s urbane, polite, and easygoing. He offers up a detailed description (at least for a dude) of his wedding in Newport a year ago, and of how he enjoys weekly dinner-and-a-movie dates with his wife, Renee. He talks about growing up on the North Shore, how he was an average athlete who played baseball at Swampscott High. And how, after getting an education degree from the University of Michigan (“They won a national title [in football] when I was there”) he moved back to Boston to work in sales.

He orders the steak tips. He wanted the burger, but decided against it because it’s too messy to eat in front of someone he “doesn’t really know.” On the flat-screen above, Bruins center Tyler Seguin scores against the Maple Leafs. “I haven’t been to a Bruins game in years,” he says. He doesn’t really go to too many Sox games, either. But on the occasion he does, he gets swarmed  by fans. “It takes me 45 minutes to walk down Lansdowne Street — so many people want to stop and take a picture with me.”

After ordering a Coors Light, Portnoy ruminates on one of Barstool Sports’s better-known contributions to American culture: “I invented the ‘Guess That Ass’ game,” he says, shaking his head. The daily trivia contest, a staple of the Barstool canon, is brilliant in its simplicity: El Prez crops a photo of a female celebrity so that only her backside is revealed. Readers then click on the photo to find out to whom said ass belongs. Tonight, his incredulity is directed at celebrity-gossip website TMZ, which  has taken to offering a “Guess the Badonkadonk!” feature on a semiregular basis.

“We’ve been doing it for years,” Portnoy says.

As we’re getting ready to leave, two twentysomething guys in baseball hats enter the room. Portnoy doesn’t know them, but as the two slide to the end of the bar, they chime in unison: “Hey, Prez.”