As a travel industry executive, Expedia CEO Dara Khosrowshahi has seen it all.

Khosrowshahi has been a stalwart figure in the travel industry for decades, beginning with his days working with Barry Diller as the online travel sector rose to prominence two decades ago. 

He got his start at Allen & Co., working in various roles at the investment bank from 1991 to 1998. Later at USA Networks (which became IAC) for Barry Diller, he helped acquire Hotel Reservations Network (Hotels.com, or 1-800-HOTELS) in 1999 and coordinated the explosive growth of the company as online travel began to hit the mainstream with U.S. consumers.

Immediately afterwards, Diller and Khosrowshahi worked to acquire Expedia from founder Rich Barton and his team, as detailed in Skift’s The Definitive Oral History of Online Travel.

The rest, so to speak, is history; the creation of the first online travel powerhouse, after Travelocity’s out-of-the-gate lead, that is, followed. There were growing pains and an unsuccessful battle to remain on top when a little Amsterdam-based startup that was acquired by the Priceline Group — namely Booking.com — passed Expedia and everyone else by.

He has served as Expedia’s CEO since 2005, guiding the company through a period of major growth followed by struggles against Booking.com.

Let’s look back on Khosrowshahi’s thoughts, in his own words, on the most important issues in travel and beyond.

Variety Matters

One crucial factor in Khosrowshahi’s move to Uber could be his experience developing multiple brands under one corporate umbrella. Uber has a huge valuation and plenty of money in the bank, but can’t seem to turn a profit, according to reports.

Could differentiated products help solve this problem for Uber? Uber’s strategy of global growth no matter the cost has seemed to fizzle out in recent years, compounded by the company’s organizational struggles.

Reflecting on his time at Expedia, Khosrowshahi told Skift in 2015 that having TripAdvisor as part of the Expedia Inc. portfolio during the mid-2000s was key to securing the company’s future when several other brands were stagnant.

As Uber moves to develop a wide-ranging mobility-as-a-service platform, a multi-pronged brand strategy could be extremely valuable.

“I guess I have [TripAdvisor CEO] Steve Kaufer to thank,” Khosrowshahi said. “Maybe he saved me my job. But having a portfolio, having different brands, allows you to invest in different parts of the business and TripAdvisor being a part of the family in those early years was a big part of where we are today.”

Dealing With Competition

“Speed takes care of a lot of mistakes,” Khosrowshahi said to Skift when reflecting on his time helming Expedia with TripAdvisor in the fold.

Perhaps the most important story in online travel in recent years has been the ascendance of Booking.com. The company has focused on hotels at a time when others like Expedia have had trouble growing in the marketplace while offering many different products.

Dealing with the company’s struggles as Expedia’s CEO has seemed to affect Khosrowshahi’s outlook on the industry as a whole.

“There are a lot of folks on this team who have been through the tough times and now I’d say times are better, and when you’ve walked through the fire together you get closer as a team and I think this team is closer than we ever have been,” Khosrowshahi said two years ago. “We’re very aligned but we’re not satisfied for a minute. We’re very energized and we think we can keep growing the company and I think we can keep moving at a really fast pace.”

Perhaps this experience is what attracted Uber to Khosrowshahi. Expedia’s acquisition of HomeAway in 2015 also shows his willingness to experiment outside the mainstream of online travel.

Looking Forward

Khosrowshahi has been a leader in online travel for a long time, and is no stranger to pushing innovative solutions to ease the pain points of consumers.

Last year at the Skift Global Forum, he doubled-down on the importance of voice search to the next wave of transformative change in the travel industry. As Uber moves to position itself as a travel super-brand, these sorts of technological advances will be crucial to how the company remains relevant to consumers while its competitors continue to grow.

No Fan of Trump

The Iranian-born Khosrowshahi had harsh words earlier this year for the Trump Administration following the chaos of the initial travel ban affecting visitors to the U.S. from predominately Muslim countries.

“The President’s order represents the worst of his proclivity toward rash action versus thoughtfulness,” wrote Khosrowshahi in a statement. “Ours is a nation of immigrants. These are our roots, this is our soul. All erased with the stroke of a pen.

“As Expedia Inc we will do everything we can to protect and help our employees and travelers. That’s our job. Hopefully our government can do its job, thoughtfully, and with just a bit of respect for our immigrant past.”

As the embattled Uber looks to reform its public image, the outspoken Khosrowshahi is not afraid to speak up for inclusive values.

Tags: expedia, uber
Photo Credit: Khosrowshahi speaks onstage at Skift Global Forum 2016 alongside Rich Barton (R), founder of Expedia; Jay Walker (far L), founder of Priceline Group; and Rich Barton, (L) CEO of Altimeter Capital. Skift