The two businesses also appear to have little in common. Like Uber, online travel giant Expedia is a data-driven marketplace that links sellers to consumers who are on the move -- but the connections pretty much stop there.
Yet Khosrowshahi, 48, has deep ties to Silicon Valley, many of them through his own family. Indeed, Khosrowshahi may have one of the most extensive family networks of anyone working in the technology industry today -- six of his relatives are highly successful Silicon Valley entrepreneurs or executives with strong ties to tech.
His brother Kaveh Khosrowshahi is managing director of Allen & Co., the influential boutique investment bank the runs the Sun Valley conference, a networking event frequented by tech elites like Facebook chief executive Mark Zuckerberg, entrepreneur Elon Musk, and Twitter chief executive Jack Dorsey.
His cousin Amir Khosrowshahi co-founded an artificial intelligence company, Nervana, that was acquired by Intel last year for $400 million (He is now an executive in Intel’s artificial intelligence unit).
His twin cousins, Ali and Hadi Partovi were early investors in many of the most successful tech companies produced by Silicon Valley over the last decade, including Airbnb, Dropbox, Uber, and Facebook. They also cofounded Code.org, an influential non-profit focused on improving computer science education across the United States.
Two other family members are Google executives. One cousin, Farzad Khosrowshahi, invented the software tool now known as Google spreadsheets, and is the executive that runs Google Docs. Another family member, Avid Larizadeh Duggan, is a general partner at Google Ventures, the search giant’s venture capital arm that invests in startups (Uber was an investment in the Google ventures portfolio) .
In an interview, Ali Partovi said that his cousin Dara was always someone he and his brother had looked up to. “My whole life, anytime I've faced a high-pressure decision, my model for mature behavior has been, 'What would Dara do'? He's one of the humblest and most even-keeled people I know.”
That trait in itself may serve the embattled Uber well, and will be a stark contrast to the leadership style of former chief executive Travis Kalanick. Kalanick is known to fly into fits of anger. (In one infamous episode that was caught on video earlier this year, Kalanick unloaded on an Uber driver who criticized the company’s wages.)
Many of the cousins went to the same high school, the Hackley School, a private prep school in Tarrytown, NY, Partovi said.
Over the years, they have helped one another, investing in each other’s companies and supporting one another’s ideas. The extended family moved to the United States between the late seventies and eighties, fleeing the Iranian revolution.
Their remarkable immigrant success story isn’t lost on them, which is why Khosrowshahi and his cousins became some of the most vocal opponents of President Trump’s immigration ban on Muslim Americans, including those from Iran. Shortly after the ban was issued, Khosrowshahi sent a memo to the entire Expedia workforce, according to Business Insider.
"I believe that with this executive order, our president has reverted to the short game,” he wrote. "The US may be ever so slightly less dangerous as a place to live, but it will certainly be seen as a smaller nation, one that is inward-looking versus forward thinking, reactionary versus visionary.” Khosrowshahi reiterated his concerns during a routine earnings call with investors.
While it’s not known who first tapped Khosrowshahi to come in to interview for the top job at Uber, conversations began in Seattle a few weeks ago, said people familiar with the discussions. At the time, the board was considering two other candidates with higher-profiles, GE chief executive Jeff Immelt and HPE chief Meg Whitman.
Negotiations lasted throughout the weekend, and the decision was a close call between Whitman and Khosrowshahi, people familiar with the discussions told the Post. Uber’s eight-member board debated until the very last minute on Sunday.
The talks were kept so secret that many of Khosrowshahi’s own family members were surprised when they heard the news, Ali Partovi said. “My phone has been blowing up with messages for my family for the last hour,” he said on Sunday evening.
As of Monday, Khosrowshahi was still pondering the job, according to an internal letter circulated among Expedia's staff by the company's chairman, Barry Diller. "Nothing has been yet finalized," Diller wrote, "but having extensively discussed this with Dara I believe it is his intention to accept."
Khosrowshahi won't be a cheap hire. He was named the highest paid chief executive in the U.S. by Equilar for his 2015 compensation, thanks largely to a long-term stock option package valued at $90.8 million he would gain access to over a period of several years.
As of Friday's close, that meant Khosrowshahi had unvested options worth about $97.5 million if he'd stayed on at Expedia, according to an analysis by independent compensation consultant Brian Foley. Yet he also has additional options that would be worth another $82.5 million if aggressive stock price performance targets were met, bringing the total to at least $180 million.
Foley said it is unlikely Khosrowshahi would give up pay to take the job at Uber -- and he could very well be paid more. "I suspect the real question is not how much he gives up but how much more did he get," said Foley. "He's in the catbird seat. They've now come to him -- it's got to be something that has some real sizzle to it."
Because Uber is a private company, the company will not be required to immediately release specifics on Khosrowshahi's pay, though it would become public if the company launches an IPO. But Foley expects the circumstances -- a high-profile, highly public search that included heavyweights like General Electric chairman Jeff Immelt and Hewlett Packard Enterprise CEO Meg Whitman -- would mean little will be left on the table.
"I have to figure they gave him new grants that would make him whole on whatever he would lose at Expedia and then threw a sweetener on top," Foley said, noting it would be unusual for a company losing its CEO to accelerate the vesting of his options. "They want to save that for the next guy."
Staff writer Jena McGregor contributed to this report.