Barry Begins Again

MOST TECH BILLIONAIRES ARE PRECOCIOUS REVOLUTIONARIES.THEN THERE’S BARRY DILLER. THE FORMER HOLLYWOOD MOGUL HAS GROUND HIS WAY TO A $4.2 BILLION TECHNOLOGY FORTUNE, ONE UNSEXY SPIN OFF AT A TIME——AND AT 77 HE IS ABOUT TO START A FRESH.

- Antoine Gara

Resting on a curvy, arched sofa in his expansive office, the 77-year-old Diller has pleasantly meandered from chatting about the champagne flute-shaped floating island he’s building in the Hudson River to throwing barbs at Donald Trump to digressing into the French Revolution to describing IAC/InterActiveCorp, his evolving $20 billion internet assemblage. The pics in question documented a six-week summer yachting holiday in Europe on which Diller was accompanied by his fashion designer wife, Diane von Furstenberg, and a carousel of celebrity pals, from singer Katy Perry and actors Orlando Bloom and Bradley Cooper to Oprah and Jeff Bezos and his girlfriend, Lauren Sanchez.

It’s the Friday after Labor Day, and Diller is still bronzed from his floating adventures, which took him from Stockholm to Scotland, then to France, and on to Italy, the Greek islands and Croatia. He wears a black blazer and brown leather shoes without socks as if he’s just stepped off his beloved boat. The paparazzi picked up Diller’s trail on the island of Panarea in Italy and again in Venice, where Bezos cuddled with Sanchez. “It’s embarrassing to me,” says Diller of the publicity, so he changes the subject as raindrops pelt the patio of his corporate abode, designed by Frank Gehry in waves of shimmering white glass to resemble the sails of a Spanish galleon taking wind. “My wife says if I have an engine underneath me, I am happy,” Diller notes. “I just need to be on the water. . . . It’s such a great luxury to have a house that travels.”