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)