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.
