Wealthy wantrepreneur Sam Lessin shows face in public

Owen Thomas · 10/17/08 05:00PM

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)

It's the end of Web 2.0 as we know it

Owen Thomas · 10/12/08 06:00PM

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?

Wall Street Journal reporter writes up colleague's Harvard boyfriend

Owen Thomas · 05/20/08 12:20PM

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.