Uber CEO Dara Khosrowshahi Once Shared His Biggest Win—And Why He Fights Harder in Battles Now: 'It's My Fault. I Should Have…'
I'm LongbridgeAI, I can summarize articles.Uber CEO Dara Khosrowshahi reflected on his career, citing the failed acquisition of Priceline as his biggest regret due to lacking conviction as a first-time CEO. Conversely, he highlighted Expedia's acquisition of TripAdvisor as a major win, crediting swift action and strong leadership support. The article also notes his background fleeing Iran and Uber's current $147.42 billion market cap.
Uber Technologies Inc. CEO Dara Khosrowshahi once reflected on the defining victories and regrets of his career, revealing that one missed acquisition still stands out as the deal he wishes he had fought harder to secure.
Dara Khosrowshahi’s Biggest Career Regret: Letting Priceline Slip Away
Speaking during a 2025 episode of MD MEETS with Axel Springer CEO Mathias Döpfner, Khosrowshahi looked back on his tenure at Expedia and identified his biggest professional regret: failing to push harder for the acquisition of Priceline, the company that had acquired Booking.com.
Khosrowshahi said he believed the deal could have reshaped Expedia’s future but acknowledged that he pulled back after the company missed a quarterly target.
As a first-time CEO, he admitted he lacked the conviction he has today.
“It’s my fault. I should have fought harder,” Khosrowshahi said.
He also credited then-Expedia chairman Barry Diller with being willing to back bold decisions, adding that if he had pushed aggressively for the acquisition, Diller likely would have supported it.
Looking back, Khosrowshahi said he would have handled the situation differently if faced with the same decision years later.
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The Acquisition Khosrowshahi Counts Among His Biggest Wins
While discussing victories, Khosrowshahi pointed to Expedia’s acquisition of TripAdvisor as one of the most significant deals of his career.
Khosrowshahi said that Diller routinely challenged major acquisition proposals, requiring executives to defend their investment thesis.
He said he was deeply convinced of TripAdvisor’s potential and Diller trusted his judgment, allowing Expedia to move quickly on the transaction.
“I was quite convinced” about TripAdvisor, Khosrowshahi said, adding that the company’s ability to act swiftly helped make the acquisition a success.
From Fleeing Iran To Leading Uber
Khosrowshahi’s current net worth is estimated at $250 million, according to Celebrity Net Worth.
His family was forced to flee Tehran during the 1978 Iranian Revolution. After losing their possessions, the family relocated to southern France before eventually settling with relatives in Tarrytown, New York.
Today, the company he is leading, Uber, has grown into a transportation and delivery giant with a market capitalization of approximately $147.42 billion.
Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.
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