Allen came by his Wall Street credentials the old-fashioned way—he was born into them. His father, Herbert, founded Allen & Co. in 1922 with his brother Charles and the secretive siblings made a fortune in the 1950s and 60s investing in steel, shipbuilding, chemicals, drugs, and insurance. (Among their big winners: Syntex, the birth control pill maker.) In the early 1970s, the brothers turned over control over to Herbert Jr., who focused the firm on the entertainment industry, purchasing a controlling stake in Columbia Pictures. Allen & Co. sold its shares in the film company to Coca-Cola for $750 million in 1982 (and then helped the soft drink giant sell the business to Sony in 1989 for $3.4 billion, but Allen has since reigned as one of the most formidable advisers to media giants. To readers of the business pages, mind you, the longtime investment banker is as famous for his annual Sun Valley mogul retreat as for his actual banking business.
Over the past three decades, Allen has advised a long list of media big wigs including Barry Diller, Rupert Murdoch, Michael Eisner, Bob Iger, Gerry Laybourne, and Google founders Sergei Brin and Larry Page. But it isn't just Allen who is responsible for the firm's deep ties to the media/tech establishment. Allen's right hand, Stan Shuman, has advised Rupert Murdoch for years and spent more than a decade on News Corp.'s board of directors. And Allen & Co. rainmaker Nancy Peretsman is responsible for luring the likes of Oprah and Google to the firm—she's known Eric Schmidt since the two attended Princeton. And Steve Greenberg, the son of baseball Hall of Famer Hank Greenberg, tends to a growing list of sports clients like Major League Baseball.
The firm's heir apparent, though, is Allen's son, Herbert Allen III, who joined the company in 1992 and currently serves as president. (At the office, "Herbert" refers to the elder Allen; "Herb" refers to the son.) Today, father and son oversee a staff of about 250 at 711 Fifth in wood-paneled offices decorated with original Norman Rockwell paintings.
Forbes estimated Allen's net worth at $2.0 billion in 2008, earning him the No. 227 spot on the list of the 400 richest Americans.
Allen's annual Sun Valley confab, founded in 1983, is a who's who of the media-technology-private equity nexus. If you're not there, well, you're probably not important. Regular attendees include Bill Gates, Sumner Redstone, Rupert Murdoch, John Malone, Warren Buffett, Barry Diller, Dick Parsons, Jeff Bewkes, Jeffrey Katzenberg, Philippe Dauman, Edgar Bronfman Jr., Les Moonves, Howard Stringer, Mel Karmazin, Brian Roberts, Sergey Brin, and Larry Page. Lately, private equity hotshots (like Henry Kravis, Dan Och, and Wesley Edens) have become a main attraction at the shindig. At "Camp Allen," as the retreat has been called, it's long been a tradition for the assembled moguls to try to show they have a sense of humor. One year, ICM chief Jeff Berg inherited the "biggest prick in Hollywood" mantle from Mike Ovitz. They gave him a dildo.
Allen has married and divorced twice. His first wife, Laura Parrish, is the mother of his children: Leslie, Christie, Herbert and Charles. His second marriage was to Broadway dancer Ann Reinking. These days, he's often seen in the company of Gail Holmes, a Colorado horse breeder. (His second closest companion is Donnie, his black Labrador.) Allen lives in the Carlyle Hotel. (Other notables with apartments in the building include Barry Diller and Tom Ford.) He also has a house in Williamstown, Mass., near his alma mater, Williams College, a house in Southampton and a sprawling ranch in Cody, Wyo.