Diller has a knack for identifying promising start-ups. While leading IAC and Expedia, the business mogul added the apps Tinder and HowAboutWe to his online-dating portfolio, which includes Match.com and OkCupid. But digital romance isn’t the only category catching Diller’s attention. Last summer, IAC acquired the Princeton Review as part of its expansion of Tutor.com. Though Diller has been involved in past relationships with both men and women, he has been married to fashion designer Diane von Furstenburg since 2001.