8 Insights Into Uber CEO Pick Dara Khosrowshahi From Peers and Rivals

From shining moments to times when he was a hard-ass, who is Dara Khosrowshahi, the current Expedia Inc. CEO and Uber's pick to take the helm at the ride-sharing company? What makes him tick business-wise? In 2016, we interviewed Khosrowshahi, and many of his peers and competitors for Skift's  Definitive Oral History of Online Travel. We bring you eight oral history anecdotes ranging from him modestly admitting his short-comings to pioneering moments and being a tough-as-nails business person. The anecdotes cover a lot of deals, and character-defining episodes, many of which have relevance for the tasks ahead at Uber. A philosophy of Being Unafraid to be Different Khosrowshahi has worked alongside Expedia-controlling shareholder Barry Diller since 1998, and they've been together through times when the online travel company has struggled and excelled. There have also been around a couple of dozen deals they've done together along the way. Khosrowshahi: "I think Barry [Diller] is always comfortable being a counter-programmer. One of the pieces of advice he gave me is that 90 percent of the time you're going to make the decision that everyone else is going to make because usually 90 percent of decisions are fairly obvious. But 10 percent of the time you're going to make a different decision and the key is what is that 10 percent. And he's always encouraged us – he's encouraged me – not to feel uncomfortable going against the flow. Because it's during those times when you go against the flow, when you actually make a difference. "If you're always going to go with the flow you're going to be a perfectly average company and that's certainly not necessarily something that I want to say after my career, that I was perfectly average. There's a comfort in that. There's a comfort in knowing, you know what, I'm not making the typical decision, I'm making a different decision. I know there's a risk. But I'm going to take that risk and I'm going to go for it. And Barry really encouraged us to go forward with that thinking. It's OK to be different. You want to be different as a company, you want edge, you want an angle that separates you from the crowd. Be careful what those choices are but you got to have an edge to be different." TripAdvisor Saved His Ass Khosrowshahi became a first-time CEO at Expedia when IAC spun off its travel holdings in 2005. [See my interview of the newbie CEO in September 2005.] He conceded in the oral history that he ha