Dara Khosrowshahi, a family man taking the wheel at Uber

By Leslie Hook

His financial background will help him prepare the ride-sharing group for a public listing

Dara Khosrowshahi, the little-known Expedia boss who is about to become Uber’s chief executive, has a penchant for nice watches. When he met the Financial Times last year at Expedia headquarters, just outside Seattle, a Chopard peaked out from his cuff. Watches are “a man’s right to wear jewellery”, he said with a grin, adding that his wife gives him a timepiece every year.

It is a trait that will stick out in Silicon Valley, where the tech crowd eschews such displays, and Apple watches are more common than Swiss watches. But Mr Khosrowshahi, 48, is an outsider here in ways that go far beyond wristwear. When he takes up his post at Uber on Tuesday, he will step into one of the toughest jobs in tech and become the centre of a corporate drama that has at times threatened the future of Silicon Valley’s most valuable private company.

“I have to tell you that I am scared,” he wrote this week when he announced his move.

His outsider status could have advantages. The Uber saga has consumed the clubby world of San Francisco tech. But Mr Khosrowshahi will arrive from Seattle with relatively little baggage, a dark horse candidate not clearly favoured by one board faction or the other.

When he starts his new role on Tuesday, his background in banking and at Expedia means he will not be arriving entirely unprepared. The son of Iranian immigrants, Mr Khosrowshahi grew up outside New York and studied electrical engineering at Brown University. After graduating, he entered the world of finance and spent seven years working at Allen & Co., where Barry Diller, the chairman of IAC, was a client.

Mr Diller personally poached Mr Khosrowshahi after noticing the young analyst building the models around his hostile bid for Paramount Pictures. Their partnership has endured.

“I think he is first rate, obviously,” Mr Diller told the FT last year. “We kept giving him more and more responsibility and then — as has kind of been our playbook — without enormous experience, we put him into being responsible for Expedia,” Mr Diller said. “His own incubation is the reason he is such a first-rate CEO.”

At Expedia, Mr Khosrowshahi took the company public, with IAC remaining a big shareholder. He is no stranger to boardroom battles — experience that will be useful at Uber — as he had to navigate the dispute between John Malone and Mr Diller, both of whom sit on the Expedia board, at a time when Mr Malone’s Liberty Media was suing IAC.

In person, Mr Khosrowshahi comes across with a low-key friendliness — the word “calm” comes up a lot when other people describe him — and he dresses in a casual West Coast style, favouring colourful jeans. But after so many years in banking, he has never entirely shed the suit. He says he has tried though.

“I am kicking the banker out of me,” he said, with a laugh, in an interview with the FT last year, as he talked about the transition from working in banking to running a tech business. “I entered our business thinking finance first . . . figure out the finances first and everything else comes second,” he said.

Expedia disabused him of that notion. “For me, the biggest change has been that it is product and technology first now. If you get the product and technology right, then the rest usually falls into place.”

His background in finance will come in use at Uber, however, where he has a mandate to prepare the company for an initial public offering. He’ll also be negotiating a $10bn-15bn deal with SoftBank and other investors.

Many of Uber’s shareholders see Mr Khosrowshahi as the antidote for everything his predecessor Travis Kalanick was not — diplomatic, steady and a family man. (His office at Expedia was covered with pictures of his four children.)

Uber has been battered by crisis after crisis — including lawsuits, executives leaving in droves, investors ousting Mr Kalanick — and the company is trying to overhaul a toxic culture that was rife with sexism and harassment.

“He is super low-key, he is even-keeled, he is no bullshit,” said one shareholder, Mitchell Green of Lead Edge Capital, adding that the investors in his fund had been emailing him to say how delighted they were.

“He’s been a statesman travelling around the world,” says Hadi Partovi, Mr Khosrowshahi’s cousin who is also an investor in Uber, pointing out that this experience could help with the company’s regulatory issues.

“Dara has incredibly high integrity and he is a guy you can count on to do the right thing and to speak up,” said Mr Partovi, “but he does that with a humility and a smile that makes people at ease.”

Despite all this goodwill, Mr Khosrowshahi will not only face the challenge of dealing with Uber’s problems but also the difficulty of living up to such high expectations. After the company’s soul-searching over the past six months, its demoralised employees and disillusioned shareholders have become desperate for a saviour who will restore the company to its former glory.

Mr Diller said Mr Khosrowshahi succeeded at Expedia despite the fact that he was not the most experienced person for the job. The same might be said of his appointment to Uber, where he beat out two older and more experienced candidates. Uber’s problems have a more vicious nature and are on a different scale, something that even the talented Mr Khosrowshahi has not seen before.