On June 1, 2026, Barry Diller's media conglomerate, People Inc., submitted an unsolicited bid, thrusting the veteran mogul back into the headlines. On Invest Like the Best, Uber CEO Dara Khosrowshahi reflected on his history with Diller, calling him "my business mentor and in many ways a personal mentor as well." Khosrowshahi recalled first meeting Diller while working as an analyst at Allen & Company on the Paramount LBO model.
Khosrowshahi spent thirteen years running Expedia under Diller before taking the helm at Uber. He detailed Diller's unique leadership style, explaining that while getting into an argument with him can be "unpleasant," the mogul is entirely devoid of corporate ego. If you argue with him and he realizes he is wrong, "he's delighted. He lights up because he just learned." According to Khosrowshahi, this relentless drive to find "the truth from the source material" is what sets Diller apart from defensive executives who rely purely on authority.
This unfiltered, combative approach to learning is exactly what has defined Diller's legendary career, from his early days at Paramount to his current maneuvers with People Inc. As Diller initiates yet another aggressive corporate play, the business world is watching to see if his classic, argument-driven style will once again yield a masterstroke.