On 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 magazine—a 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.
“I wasn’t morally attached to this T-shirt line, but at the same time, I didn’t like the idea that a guy who’s an alleged satirist is going to sue me for making a T-shirt satirizing him. So I wrote this long post on it. It blew up,” he said. “It was like my micro-fame moment.” According to Mr. Sorgatz, daily readership went from 10,000 to 30,000.
Despite offers from First Amendment lawyers to take the case pro bono, Mr. Sorgatz opted to drop the cause. “It felt a bit weird that my First Amendment scenario was going to be fighting for the word ‘ho’ on a T-shirt,” he said, and chuckled to himself. “I didn’t want it to appear as though I was taking advantage of the situation for the sake of publicity. I really wanted them to back down. I really didn’t want to write the post.”
At his regular job, he produced MSNBC Web sites for the 2004 and 2006 Olympics. They liked his stuff, and he liked the sound of executive producer of a giant media company’s Web site on his business card. He sold MNSpeak.com, pocketed another few bucks, bought the domain for seattlespeak.com and headed west.
But Seattle didn’t agree with him. He was instrumental in msnbc.com’s purchase of newsvine.com, a user-generated news site known for covering the Virginia Tech massacre. But working for Microsoft dulled his senses.
Kerrrrplunk! Rex got here in a hurry on Thanksgiving weekend of ’07, and ran straight into a double-pane glass window separating his living room from ground zero. The broker had neglected to mention that the spacious one-bedroom apartment on the top floor of a Battery Park City high-rise overlooked the massive crater. Not only was the view “depressing,” he wrote in an email, “but it was a constant reminder that I’m not really a New Yorker—that I don’t yet have the experience or the clout.” Such mopey, wide-eyed vulnerability—whether real or an act—would prove to be catnip to New York women.
Mr. Sorgatz went home that Christmas for the first time in two years. He’d brought Nintendo Wii’s for his nephews. One night at 3 a.m., he was playing Guitar Hero in the garage, surrounded by his father’s two Harleys, Escalade, snowmobiles and gun rack. His father came in. “The door opens and I see him, and he goes to the fridge and I keep playing,” said Mr. Sorgatz. “He goes, ‘Hey, you want a beer?’ And I say, ‘O.K.’ This is more interaction than we’ve had in years. ‘What kind of beer would you like?’ So I say, ‘I’ll take a Bud.’ And he sets the Bud in front of me and says, ‘So you’re a Bud guy now?’ And I’m thinking, What? No. I mean, I don’t even know what that means? Does that make me gay? Like is that good or bad? So I say, ‘No, I don’t know. No.’ So he puts the Bud back in the fridge and says, ‘So what kind of beer would you like?’”
Back in New York, Mr. Sorgatz lined up a gig relaunching the Independent Film Channel’s Web site, which left him with too much time to work the bars. “The difference was that in Seattle there was no scene,” he said. “Once you met [sex columnist] Dan Savage that was it—there weren’t a lot of people that you wanted to know. Here, someone would say, ‘We’re meeting at the Magician,’ and you get there and you see a bunch of people you knew through the online blogging world.”
That world, his friend Mr. Steele explained, can include “everyone from your average ink-stained journalists, to legitimate bloggers, to Tumblr girls—who God knows what they do all day.” When he first began taking Mr. Sorgatz around, “He was like a kid in a candy store.”
“Certain factors help one’s—particularly a boy’s—sexual life,” Mr. Sorgatz told me. “The girl-to-male ratio here is so much greater than it is on the West Coast. And whenever you’re the new thing on the scene, you have an angle, a specialty—like just saying ‘I just moved here’ starts a series of interesting things to say to girls. And it was also mildly exciting that a lot of people I met knew my blog.” (Mr. Sorgatz has been updating www.fimoculous.com since 1998.)
“I remember the first couple months, just getting in a cab and feeling like I should scrub the PR off of me,” he said. “Everyone I met was telling me what this new thing was they were doing, and then I had to give back this thing that I am doing.”
Birthday parties became networking events in New York. He met his agent, Kate Lee at ICM, at one. Other nights, he’d tumble with yet another 20-something Tumblr girl.
Last summer, he said, “there was one morning when I realized that it was 9 o’clock in the morning and I had just left the Saturday Night Live after-after-party. And I was walking around Times Square still wearing my jacket, and still dressed up for the show—feeling lonely and looking for people to talk to and maybe a little enhanced mentally. And I remember walking up to a girl who was standing outside smoking a cigarette. She was a waitress at some tourist place in Times Square. I remember trying to talk her into leaving work, and spending the afternoon with me.” She said no.
A few weeks later he received an email from blogger Rachel Sklar; she was responding to his Twitter post that day, which had read, “Trying really fucking hard not to be part of the problem.” Ms. Sklar, who had met Mr. Sorgatz a few times, wrote that she liked the post. And, she liked his name was Rex.
They arranged to have dinner that night.
“We ended up talking the whole night. He was really interesting!” she told me. “But you know, he was very targeted. He knew what he wanted. He wasn’t aggressive—he was just aggressively great.”
The next weekend, Ms. Sklar accompanied Mr. Sorgatz to a beach house he’d rented in Montauk with Mr. Steele. In preparation for the trip, Mr. Sorgatz had made a “to bring” list on a Post-it note and stuck it to his computer: “Hamptons: Tent. Video Camera. Condoms.” Unfortunately, a Tumblr girl he was seeing happened to see the note Friday morning while he was in the shower. The girl, Leonora Epstein, wrote about the experience on a Web site, the Frisky, changing his name to “Phil.” She snooped in his medicine cabinet: accused him of having two bottles of foundation makeup in there. On Aug. 12, Gawker served up the whole sordid affair with some pictures of Ms. Sklar and Mr. Sorgatz frolicking on the beach. Word had also leaked out that he’d been writing an anonymous blog, titled Self-Loathing Nighttime Conversations.
“It made me feel like out of control. There was a message being created and I couldn’t manage it,” said Mr. Sorgatz. “I’m particularly averse to having people talking about me when I’m not around.”
Mr. Steele speculated that Mr. Sorgatz was merely constructing another one of his clever narratives and probably loved the attention. “He took this absurdly embarrassing situation,” he said, “and like spun it around where now it’s like a heroic tale of his sexual exploits!”
Mr. Sorgatz told me Ms. Sklar helped him through the situation. “She sort of helped me come out of that,” he said. “She’s my age. Similar career stuff going on. And she was sort of a solution to the problem of a lifestyle that really primarily revolved around 23-year-old Tumblr girls. She was like an exit strategy from that.”
Ms. Sklar said she wasn’t overly thrilled by her romp with Rex. “Had I known about his secret blog and his, you know, reputation for dalliances with the young literati of the city, I would not have played,” she told me. “I found out after and I wasn’t happy.”
“There was a moment when we were the hot new-media couple on the scene,” said Mr. Sorgatz. “Which she really liked. But I was really apprehensive about it. Towards the end, sort of the reverse happened, via the Internet. I think she felt sidelined at times; it’s rough when everywhere you go, somebody’s taking pictures and putting them on their Tumblr sites.”
Last month, someone started a Tumblr written from the perspective of Mr. Sorgatz’ scarf.
“Half of me thinks its fascinating to live life online,” said Mr Sorgatz. “And the other half wants to scream at the triviality of it all, like a good Midwestern person would do: ‘Why would we care about you people?!’”