Uber Technologies Inc. CEO Dara Khosrowshahi recently reflected on his career, identifying the acquisition of TripAdvisor as a major victory and the missed opportunity to acquire Priceline as his biggest regret. Speaking during a 2025 episode of MD MEETS with Axel Springer CEO Mathias Döpfner, Khosrowshahi discussed his tenure at Expedia and the lessons learned from high-stakes negotiations.

The Acquisition That Got Away

Khosrowshahi pointed to the failed acquisition of Priceline, the company that had acquired Booking.com, as his most significant professional regret. He explained that he believed the deal could have reshaped Expedia's future but pulled back after the company missed a quarterly target. As a first-time CEO, he admitted he lacked the conviction he possesses today.

"It's my fault. I should have fought harder," Khosrowshahi said. He noted that then-Expedia chairman Barry Diller was willing to back bold decisions and likely would have supported the acquisition if Khosrowshahi had pushed more aggressively.

A Defining Career Win

In contrast to the Priceline miss, Khosrowshahi cited Expedia's acquisition of TripAdvisor as one of his most significant wins. He described how Diller routinely challenged major acquisition proposals, requiring executives to defend their investment thesis. Khosrowshahi said he was deeply convinced of TripAdvisor's potential and that Diller trusted his judgment, allowing the company to move swiftly on the transaction.

From Expedia to Uber

Khosrowshahi's current net worth is estimated at $250 million. His family was forced to flee Tehran during the 1978 Iranian Revolution, relocating to southern France before settling in Tarrytown, New York. Today, Uber has grown into a transportation and delivery giant with a market capitalization of approximately $147.42 billion.

Uber Chief Executive Officer Dara Khosrowshahi has stepped down from the board of directors of Grab. The development was confirmed through a regulatory filing submitted to the United States Securities and Exchange Commission (SEC).

The filing, accessible via the SEC's EDGAR database, formalizes the departure of Khosrowshahi from the Southeast Asian ride-hailing giant's board. Grab operates across various sectors including delivery and financial services.

The document does not specify the reasons behind the resignation or provide details regarding an effective date for the change. Grab has not yet announced a replacement for the vacated board position.

This move marks a shift in the leadership dynamics between the two companies, which have historically maintained a complex relationship involving competition and past investments.