Context:

Barry Diller, a notable figure in Hollywood and media, has lived a life marked by both professional triumphs and personal struggles, finally speaking publicly about his bisexuality at the age of 83. Throughout his career, Diller has been a trailblazer in the entertainment industry, yet his private life remained largely hidden due to societal pressures and personal fear. His relationship with Diane von Furstenberg, which transitioned from a passionate romance to a lasting marriage, highlights his complex personal life. Despite his influential role in shaping modern media, Diller's memoir reveals his deep-seated fears and regrets about not being more open about his sexuality earlier. With a career spanning decades, Diller reflects on his life, acknowledging past mistakes and expressing a desire to have been a role model for others facing similar struggles.

Dive Deeper:

• Barry Diller has navigated a distinguished career in Hollywood, influencing the transition from traditional media to streaming, and has been instrumental in shaping the entertainment industry over the decades. Despite his professional success, he has only recently spoken openly about his private life, revealing a long-held secret about his bisexuality.

• Diller's relationship with Diane von Furstenberg began during the Studio 54 days and evolved from a passionate affair into a sexually liberated and enduring marriage. Their relationship is characterized by mutual understanding and acceptance, despite the challenges they faced, including von Furstenberg's brief affair with Richard Gere.

• His book, 'Who Knew,' offers a candid look into his life, discussing his troubled family background, struggles with identity, and the pressures of maintaining a public persona while hiding his true self. Diller's story also contrasts with the prevailing cultural narrative of masculinity, offering a more vulnerable perspective.

• Throughout his career, Diller has faced homophobia and societal expectations, which left him living a double life. He describes the era's constraints and his decision to remain private about his sexuality as a result of fear and societal pressure, despite his personal belief in honesty and authenticity.

• Diller's ventures into technology and digital content, including acquisitions like Expedia and Tinder, demonstrate his forward-thinking approach and adaptability in a rapidly changing industry. His investments have been pivotal in transforming the media landscape, even as he remains critical of some modern media practices.