<![CDATA[Gawker: valleywag, sam lessin]]> http://tags.gawker.com/assets/base/img/thumbs140x140/gawker.com.png <![CDATA[Gawker: valleywag, sam lessin]]> http://gawker.com/tag/valleywag/samlessin http://gawker.com/tag/valleywag/samlessin <![CDATA[Blonde's Ambition Endangers Aspen Internet Dudefest]]> No one has been an Internet microcelebrity longer than Hilary Rowland, who began her Web career in 1995. But her hunger for attention could doom an April ski party for startup founders. Oh no!

The Summit Series, an event for Internet entrepreneurs under the age of 36, is gearing up for a third get-together, this time in Aspen.

Rowland, the founder of Hilary Magazine and New Faces, a modeling agency, was one of the few women who went to the last Summit Series, a phenomenally ill-timed November junket in Playa del Carmen, Mexico, for some 60 Internet-industry second-raters who partied and drank in the midst of an economic meltdown. (One attendee, Zappos CEO Tony Hsieh, came straight from laying off 8 percent of his workforce.)

The event was supposed to be off the record, with no names released, no photos posted, and no mention made of the event's existence. But Rowland, a very attractive blonde with a decidedly unattractive penchant for name-dropping, issued a press release and posted photos of the event for her vast number of Facebook friends. The summit's stated mission was the exchange of ideas and the promotion of charitable works. Perhaps that happened! But if so, Rowland's photographs did not document it:




Among the people Rowland exposed: Drop.io founder Sam Lessin, the son of a Wall Street banker who took 19 of his closest friends to his dad's vacation home in Cyprus, where they filmed a video of their frolics. The clip leaked and the event, promptly dubbed "Camp Cyprus," became an infamous example of the Web 2.0 set's irrational exuberance. In other words, Summit Series Mexico was only the second money-wasting event Lessin, whose startup is hardly setting the world on fire, got caught attending.

And that's the problem that the Summit Series' organizers are now facing. Rowland has proven that they can't keep the event private, and the likes of Lessin surely don't want to be caught out as wastrels a third time. Elliott Bisnow, the event's founder, is also trying to cajole invitees to the four-day Aspen event to pay $3,000; past events were free save for airfare. (Here's the full text of his emails, including an amusing followup to beg for ticket purchases.)

I suppose Bisnow could disinvite Rowland. But there will always be someone willing to barter privacy for a little taste of fame. Isn't that what the Internet was made for? With all her experience, Rowland should know that better than anyone.

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<![CDATA[Wealthy wantrepreneur Sam Lessin shows face in public]]> Drop.io founder Sam Lessin, the son of Croesus-rich Wall Street investment banker turned venture capitalist Bob Lessin, is obsessed with privacy, the chief selling point of his file-sharing startup. Which is why a video he and 19 of his closest friends filmed themselves cavorting at his father's vacation home in Cyprus ended up splashed all over the Internet. And why, after he'd successfully rendered himself infamous, he turned out at a journalist-infested birthday party thrown for CNET News reporter Caroline McCarthy and Scott Kidder, an employee at Valleywag publisher Gawker Media. Sure, Sam — keep telling everyone how important privacy is. And don't stop walking in front of cameras. He's shown here, at left, with a companion who's much more skilled at keeping his identity secret. (Photo by Random Night Out)

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<![CDATA[The vanity Facebook ad]]> Facebook's vaunted ad-targeting system, the buy-your-own ad tool meant to menace Google's $20 billion-a-year monster money machine, has become a joke. What only Internet-industry insiders seem to realize: It allows such minutely detailed targeting that people are now using it as a timewasting trick to amuse their friends — or total strangers. Underemployed rich kid Sam Lessin — yes, the one whose investment-banker dad provided the stage set for Camp Cyprus's Internet-destroying seaside froliccreated an ad meant to target his girlfriend, Wall Street Journal reporter Jessica Vascellaro. Gizmodo, a gadget website, has had an intern hopeful targeting a Facebook ad at employees of Gawker Media, the publisher of both Gizmodo and Valleywag, for months. And now some fellow has started promoting his son's Twitter feed.

The campaign isn't doing much for Johnny Nguyen of Crescent, Calif. Despite the ad, he only has eight followers on the microblogging site, which doesn't speak well for Facebook's efficacy as an advertising platform. But it does suggest a future for Facebook. Google is where people will go when they want to purchase customers. Facebook is where bored people will pay to entertain their friends, and lonely people will pay to feel like someone's listening to their Internet rants. Money can't buy you love, but it may get you a Facebook friend. Think of the money spent on 900 numbers by people who just want someone to talk to, and you can imagine the potential.

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<![CDATA[It's the end of Web 2.0 as we know it]]> The infamous Camp Cyprus 20 are trickling back home. And they feel fine. The twentysomethings of Camp Cyprus work at companies like Google, Facebook, and Blip.tv, all of which make a business of moving our lives online. They gathered at the Cyprus vacation home of Wall Street banker Bob Lessin, overlooking the wine-dark Mediterranean, at the invitation of his startup-founder son, Sam, for a vacation. And in this hyperconnected age, they must surely be aware that a lip-synching video they made of their trip was an Internet sensation, marking the end of an era. If they feel any shame for popping the Web 2.0 bubble, they are not blogging, Tumblring, Twittering, or FriendFeeding it. The only concession to embarrassment over the incident was making the video private — and of course, it promptly resurfaced on YouTube and elsewhere.

Sam Lessin, in public, is a privacy freak; privacy is the sales pitch for his staggeringly unpopular blogging and file-sharing startup, Drop.io. But he invited a bunch of known oversharers — Facebookers Dave Morin and Meagan Marks, Google Maps marketer Brittany Bohnet, and the like — to his dad's vacation home, permitted the filming of the video, and starred in it himself. I doubt he cared very much that it became an Internet sensation.

No, I suspect that this takedown had little to do with Web 2.0, and everything to do with Wall Street. Even before the mortgage bubble popped, launching the credit crisis, being showy with wealth just wasn't done in the circles Bob Lessin circulates in. Showing off your dad's sweet pad only seems like a good idea if you're a Harvard legacy in your early 20s.

So is this the end of Web 2.0? Depends on what you mean by "Web 2.0." No one can quite agree. User-generated content? It's cheaper than the professionally generated kind; in recessionary times, it seems like it's here to stay. Likewise the fad for creating programmable interfaces for websites; getting coders to volunteer their time to make your product better sure sounds better than hiring them.

No, the real test is whether this millennial generation will continue posting videos when they don't have splashy trips to celebrate. Will they continue updating friends with every change in their status, when the news isn't that they've gotten hired, launched a company, bought something expensive?

When their buddies can't find work, when their startups run out of money, when they start leaving town en masse, what will they do? Promise to stay Facebook friends?

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<![CDATA[On Sequoia's firing line]]> What plots are the members of "Camp Cyprus," a group of young webheads, cooking up? Perhaps we'll read about them in a Wall Street Journal front-page A-hed, since reporter Jessica Vascellaro was on the scene, along with Wall Street-scion boyfriend Sam Lessin, the CEO of Drop.io. Can you think of a better caption? Leave it in the comments; the best one will become the new headline of the post. Yesterday's winner: TheChris2.0, for "McCain and Whitman unveil Social Security plan." (Photo by Sam Lessin)

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<![CDATA[WSJ reporter parties in Cyprus with people she covers]]> You can never escape the media! Valleywag's favorite hot-tech-company couple, Facebooker Dave Morin and Googler Brittany Bohnet, weren't vacationing in Cyprus alone. A whole group, "Campcyprus," attended the get-together in the Mediterranean island's Turkish-controlled sector. And who was in the in crowd? Wall Street Journal reporter Jessica Vascellaro, who covers Facebook and Google, and her startup-founder boyfriend, Drop.io CEO Sam Lessin, the son of ultrawealthy investment banker Bob Lessin. Sam, who's normally obsessed with privacy, posted this photo of the couple. So cute!

And now I know why I got an out-of-office message from her when I complained about her nicking not one but two of my recent stories on Facebook for a Journal article! But I would have been more impressed with Vascellaro's honesty if she had said that she was going to Cyprus with "sources" rather than, as she Twittered, "buddies."

Catch Vascellaro's cameo in Bohnet's latest video:

Cyprus Lip Dub - Don't Stop Believing from Brittany Bohnet on Vimeo.

(Photo by Sam Lessin)

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<![CDATA[Wall Street Journal reporter writes up colleague's Harvard boyfriend]]> Vauhini Vara, who covers Facebook for the Wall Street Journal, is leaving the newspaper to go back to school. Why not write up a friend on the way out the door? In a profile of Harvard graduates inspired by — or jealous of — Mark Zuckerberg's startup success, she includes Sam Lessin, cofounder of Drop.io. A file-sharing startup which has raised only $3.9 million wouldn't normally rate a mention in the Journal, one would think. But Lessin is also the boyfriend of Jessica Vascellaro, the Journal reporter who's moving to Silicon Valley to cover Yahoo and Google.

Lucky Lessin. He's also the son of Bob Lessin, a former vice chairman of Smith Barney and Jefferies & Co. turned angel investor. Both are Harvard graduates, and the Lessins have given generously to Harvard.

There's absolutely no reason to believe Vascellaro influenced Vara to write about Lessin. Indeed, there's no reason for higher-ups at the Journal to look askance at the relationship, and shame on them if they do. But it's hard to imagine Lessin came to Vara's attention otherwise. Vascellaro, too, is a Harvard graduate. And gaining connections in influential places is what going to a school like Harvard is all about. Vara's article didn't mention that.

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