The Playboys of Tech

Technology’s emerging stars aren’t code-crunching wallflowers. They’re serial daters and socialites as hungry for fame—and women—as they are for fortune.

In the lobby of the Tumblr offices in New York, a young blonde receptionist in flip-flops is at work behind an enormous Mac monitor. When David Karp walks in, he has to sidestep the Rock Band instruments that are set up right in the middle of the office.

He looks alarmingly young, even for a 21-year-old. He extends an octopus arm and oversize hand and, sounding like a very polite teenager, says, "Hi, I'm David. Thank you so much for coming."

Karp is the founder and CEO of Tumblr, a software platform for tumblelogging. If a blog post is like an essay and a tweet is like a haiku, then a tumblelog is like stream-of-consciousness poetry. Users—upwards of 350,000 since the site launched—post bite-size thoughts, short videos, and candid pictures in a free-flowing style that, according to Karp, lets followers "see through the author's eyes rather than parse their editorial." Karp didn't invent tumblelogging, but his clever design has made Tumblr the preferred brand name among the online-networking elite.

When he was 17, Karp moved by himself to Japan, where he worked remotely for an American Internet company that knew neither the age of its IT guy nor the fact that he was telecommuting from the other side of the world. In February 2007, back home in New York, Karp designed and built the software for Tumblr in two weeks.

In Karp's office, on a white couch behind the desk, is his friend Charles Forman, 28, the founder of the gaming website iminlikewithyou. Like Karp, Forman left home at an early age. When he was 18 he headed from suburban Chicago to Korea and then to Japan, where he worked various programming jobs until he figured out how to combine his love of video games with his desire to be a Web magnate. On iminlikewithyou, social networking takes place via three-minute video games played in real time with online friends. Asked how he and Karp met, Forman deadpans, "Internet dating."

When the Internet boom flatlined in 2000, nobody anticipated that it would spring back to life a few years later, defibrillated by a demand for ways to socialize and self-promote instead of places to work and shop. MySpace, Facebook, YouTube, Flickr, CollegeHumor, Digg,—these sites were built by and for people who want to construct online identities for themselves by sharing first-person accounts of their social lives and forming huge pools of acquaintances. And unlike the first time around, the power players weren't just geeks gone rich, they were geeks gone famous. Guys like Mark Zuckerberg of Facebook became bona fide celebrities. By mid 2006, Jakob Lodwick of CollegeHumor and Kevin Rose of Digg were kings of the new online social scene, their blogs and twitterings followed by thousands and their every move covered by online tabloids like Gawker and Valleywag. Karp and Forman, and their West Coast counterparts like Pete Cashmore, founder of the social-networking site Mashable, represent the newest iteration of the tech star—and possibly the saturation point of Internet fame. For them, aggressive online self-promotion is as natural as text-messaging—and as much a part of the business as software development.

Karp, in a lightweight hoodie, and Forman, in a tight button-down shirt with the sleeves rolled up, leave the Tumblr offices around six. The two actually met not through JDate but through John Borthwick, who runs a Web-investment company called Betaworks, out of which both Tumblr and iminlikewithyou grew. They're on their way to something called New York Tech Meetup, the brainchild of Scott Heiferman, founder and CEO of, a website that helps people form clubs and groups off-line.

Sitting in bumper-to-bumper traffic, Forman produces a steady stream of non sequiturs. "I like people in cute T-shirts who look really angry," he says. Just as he's launching into a description of founder fetishism—that is, when a woman goes only for men who have started high-tech companies, his phone rings. His girlfriend, Julia Allison, is on the line. "She has it," he mouths. Then he says into the phone, "Of course I miss you. I always miss you."

A blogger and sex columnist for Time Out New York, Allison, who gives her age as 26 on her MySpace profile, is a regular subject in Gawker and a Wired cover girl. Her relationship with Lodwick was the stuff of Internet legend. They blogged so much about themselves and were tracked so closely by the online media that followers learned about every fight, every make-up, in real time. She's also an original fameballer, a term coined in the summer of 2006 by Lodwick at the height of the couple's notoriety. The word refers to the way in which Internet celebrity snowballs with each Gawker item or salacious blog post. Karp and Forman are expert fameballers. They're known for taking mock-homoerotic pictures of themselves holding hands or cuddling in bed, and leaking those pictures to Gawker.

Outside the Meetup, a couple of guys are handing out promotional stickers for their companies. "Charles? Are you Charles?" one of them asks as Forman brushes past. Forman hands the kid one of his oversize, multicolored business cards, which says on the back that if you've been handed one it's probably because he doesn't feel like talking to you. (Followed, of course, by an LOL.)

For the next two hours, tech-world strivers give presentations and the audience bombards them with questions like "How do you plan to monetize that?" Karp's girlfriend, the wide-eyed CNET blogger Caroline McCarthy, has joined them in the back of the auditorium, and the three whisper, take pictures of their feet and each other, and make comments about the "retards" in the audience until the presentations end and it's time for the invite-only dinner at an Italian restaurant a couple of blocks away.

At the meal, Karp, Forman, and McCarthy mostly keep to themselves. There's more photo-taking—Tumblr lets you "push" a picture from your phone right to your account, where it's posted instantly, allowing for real-time communication with your followers—and a lot of gossip. They talk about friends like Adam Rich of the Internet newsletter Thrillist and Mike Hudack of, both of them young company founders. Jacob Lodwick, who is not only a friend but an investor in Tumblr, comes over, as does Kevin Rose of Digg, the four-year-old site that lets readers give the news stories of the day a thumbs up or a thumbs down. Rose, a 31-year-old former TV host, is something of a role model; his company is valued at upwards of $300 million. Karp's and Forman's companies are comparatively embryonic, but in these halcyon days of Web 2.0, investors are happy to give promising ventures like theirs time to grow.

At around 11, Julia Allison arrives, dark hair swept up in a tightly sprayed coif, body squeezed into a tiny white dress.

"Hul-lo," she says, after greeting Forman, "hul-lo." She shakes the hand of each dinner guest until she's made her way around the table; the men look a little dazed. Then she sits down, legs crossed, cleavage heaving. Forman looks vacant. Karp and McCarthy are whispering to each other. Heiferman, his Meetup co-organizer Dawn Barber, and most of the middle-aged tech guys decide to call it a night. The fameballers close the joint.

The next evening Charles Forman shows up for dinner at a French bistro in Williamsburg wearing what appears to be the same tight-fitting blue shirt he wore the night before. He says he never made it home last night, explaining that the problem with dating Julia Allison is that she's "addicted" to fighting. That, combined with her standard 5 A.M. bedtime, means that Forman often doesn't get much sleep. And despite what Gawker readers might think, Forman is not a professional party boy. He actually has a company to run; he had to get up at 8 A.M. for a meeting. Forman got tinnitus when he was going through his last round of funding—he raised $1.5 million—and thought the money might fall through. He took to wearing headphones in public to drown out the noise.

Exhausted and slower than the night before, Forman is at the crux of the Web 2.0 star's dilemma. Sustaining fame by making sure accounts of your exploits with industry players and Internet starlets circulate in the right places is a full-time job. But so is getting a company off the ground. Karp and Forman consider the two pursuits inextricable. As fameballers, they stay busy fine-tuning and maintaining their personae. But a persona is not a person. A persona doesn't get work done. And a persona can't engage in a meaningful relationship. About a week later, Forman announces that he and Allison have split. He also says the tinnitus is gone. "I mean, it could just be a coincidence," he says.

On a Tuesday evening in San Francisco about a week later, Pete Cashmore is working the room at a stop on a promotional tour for Mashable. Cashmore, 22, is aggressively handsome. He's tall and slim as a reed, with a neatly shaved head and a superhero's square jaw. He started Mashable out of his bedroom in his parents' house in Aberdeen, Scotland, when he was 19. The site is a clearinghouse for social-networking news as well as a social-networking site itself. Cashmore says he used to stay awake for days on end, afraid he'd miss a breaking story. But now that Mashable gets 2 million visitors a month and has 13 employees, he's farmed out the blogging to other writers, heading up company "strategy" instead. Just this weekend he was hosting a party in Seattle; yesterday he was at Cisco overseeing some video that was being shot in conjunction with his site. "I haven't seen people in a while," he says, as his peers start to stream into the party. "But with the Internet, it's like you're never really gone. Communication today is so fluid that there's no real way of switching it off."

At the party, Cashmore high-fives his fans, throws himself into two-armed hugs, and drapes his arms around swooning women. There's a line of people waiting to be photographed with him against a backdrop that says MASHABLE U.S. SUMMER WORLD TOUR.

The party tonight was oversold—600 tickets purchased for a venue that holds 500—and by 9 P.M. it's packed. It's like a high-school mixer but populated by grown-ups, standing in little clusters, shaking hands, taking pictures of one another, networking as if their lives depended on it. There's a guy with a hand puppet, another in a YouTube sweatshirt. Cashmore's photographer, Mike, gets yelled at by a couple of girls because he didn't take their picture with Cashmore.

"I don't intentionally self-promote," Cashmore says in his soft Scottish accent. "I kind of just let it wash over me." He pauses. "I do worry that people will start thinking of me as some kind of 2-D character. I'm always written about in this sort of context," he says, gesturing at the party. "I mean, no one ever writes 'Pete spent the day working at home today.'" Another pause. "But there are competitive advantages to this kind of visibility, you know."

A block or two from Cashmore's party in the Portrero Hill neighborhood are the Digg offices, where the guy Karp and Forman call the "rock star of the industry" reigns supreme. Kevin Rose—"an old, old man," to quote Cashmore—never planned on going to the Mashable party. "I'm all partied out," he says. People magazine readers probably wouldn't know who Rose is, but among the Internet-savvy he's Brad Pitt. Rose, who dated Julia Allison a few years ago, is remarkably low-key compared with his younger counterparts. Drinking tea out of a mug covered with skulls and crossbones, he perks up when the talk turns to rock climbing (he's in a group called Geeks Love Climbing). He says he doesn't know what the term fameballer means. He also says he doesn't do things like wedge himself into nightclubs to have his picture taken with founder fetishists. "The scene is so small that there's no real need to schmooze," Rose says. "If you want to get something done, you just send out an e-mail and then, like, go for breakfast." Rose might even argue that the flashbulb-lit path that guys like Karp and Forman and Cashmore aim to take to stratospheric tech success doesn't necessarily lead there. But then, as Cashmore pointed out, Rose is very, very old.

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