Rex and the City

morgan 20 Rex and the CityOn Monday night, a dozen or so New York media types gathered at Rex Sorgatz’s top-floor apartment near ground zero to watch Gossip Girl on his enormous flat-screen TV. Among those in attendance at the weekly gathering in the long narrow living room were some dudes—Dodgeball.com founder Dennis Crowley; Lockhart Steele, of the Curbed sites; Gawker video editor Richard Blakeley. The rest of the room was dominated by attractive single women, including blogger Rachel Sklar, who had been Mr. Sorgatz’s girlfriend up until a few days before.

I cornered Mr. Sorgatz and put it to him straight: As a straight man, how can you justify hosting a Gossip Girl viewing party?

The 35-year-old, spikey-haired online consultant didn’t flinch. “It’s an awesome opportunity to invite girls over,” he said.

One comely 24-year-old lass in attendance, Caroline McCarthy of CNET.com, had reminded several of her friends to attend via the online service dodgeball. “@chuck bass’ penthouse,” she texted. (Chuck Bass is Gossip Girl’s bad-boy heartthrob; whether or not Mr. Sorgatz is a bad boy or a heartthrob, he seems to occupy that role for a certain segment of online ingénue.)

If the 14 months that Rex Sorgatz has spent learning to paddle in the intoxicating punch bowl that is Manhattan’s new new-media society were boiled down to a Twitter message, it might read: “Dotcom wonder boy attempts NYC media coup, scores twentysomething Tumblr girls and a blog written from the perspective of his scarf.”

In November 2007, Mr. Sorgatz chucked his comfy six-figure-salary perch as executive producer at msnbc.com in Seattle; packed up his three computers and massive book, CD and magazine collections; and moved to New York City. The idea was to start a small media company that would turn into something big, put him in line to be the next media big shot, like NBC Universal honcho Jeff Zucker. Not to mention the blogger scene in Seattle was as sterile as the Microsoft campus where his office had been for two years.

“What really sort of cracks me up about it is, he was really sort of pompous about why he wanted to move here,” said Mr. Steele, who was one of the few friends Mr. Sorgatz had in New York before he got here. “His reasoning was, and he said this to a lot of people, ‘I need to move to New York to fix New York.’”

Mr. Sorgatz says this was a gag he used in order to avoid discussing his slightly less ambitious plan to shake up online media. To Mr. Steele, it was simply “classic Rex.”

“That’s the great thing about Rex, he’s prone to outsized statements,” Mr. Steele said. “At times you get the feeling that this guy is just full of shit, that he’s going on about stuff that he has no idea about. And then like three days later, he’s like, ‘Oh yeah, I’m meeting with Lorne Michaels and redesigning Saturday Night Live’s Web site.’”

Mr. Sorgatz grew up in Napoleon, N.D., pop. 800. Two gas stations, five bars, nine churches and no movie theater. His grandfather and father owned a small bank. There were 27 students in his high-school class. One of them was Nancy Olson, who briefly dated Mr. Sorgatz senior year.

“He was always writing poetry and quirky short stories,” said Ms. Olson over the phone. “He was always carrying around books no one had ever heard of. I remember he had an anarchy symbol on his jacket.”

She added, “I don’t know that he was popular with all the girls, but he definitely knew how to go after the ones he liked. I think he had a girl in every other small town in the area. His dad used to call him ‘Love ’Em and Leave ’Em Sorgatz.’”

“Freshmen year of college, everything changed,” Mr. Sorgatz said of his time at the University of North Dakota. “This is the known part of my biography, I guess. My best friend was Chuck Klosterman.” Mr. Klosterman went on to become a music writer and memoirist, who in one book describes the would-be media executive as a hotdog-loving slob who spent his nights locked in his room writing a novel and his days asleep or glued to the first season of Real World.

After college, Mr. Sorgatz worked at The High Plains Reader, which was sold two years later. He took a job at the Grand Forks Herald. He’d been running their Web site for eight months when downtown Grand Folks caught fire; the Web site received an honorable mention when the paper was awarded a Pulitzer Prize for its coverage.

“I got asked to do not one, but two video reenactments of my harrowing escape of the fiery inferno,” he said.

Next stop: Minneapolis. With investors he started WebGuide magazinea TV Guide for the Internet. The magazine was a success; you could get it at Barnes & Noble. After two years he sold it for $750,000. He was 26. He bought a three-bedroom condo on the top floor of an old mansion that had been built by the Pillsbury family. He began throwing parties. “I was the dot-com kid who was doing well,” he said.

But then he had a bad idea: He tried to retool Fate magazine, the leading voice in paranormal literature, as a pop culture magazine. No go. He took a job running content development at Internet Broadcasting Systems, which produced and designed media Web sites for, among others, MSNBC. And he had a good idea: He started MNSpeak.com, a local news aggregator with user-generated content. “It became very popular and in many ways illustrated the shortcomings of daily newspapers,” he said. “It was this one-stop shop, where you could get all the links for all the news in the city.”

One of MNSpeak.com’s promotional ideas was to start a T-shirt line. “This was when it was still mildly cool to have a T-shirt company,” Mr. Sorgatz said. One of their shirts read, “Prairie Ho Companion.” Mr. Sorgatz received a cease-and-desist notice from Garrison Keillor’s lawyer;  Mr. Sorgatz recognized the letter for what it was: an all-expense-paid publicity campaign for his Web site.