Wealthy wantrepreneur Sam Lessin shows face in publicDrop.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)