Becoming the CEO of Uber in mid-2017 was just the latest milestone for the 49-year old Dara Khosrowshahi, who has lived an extraordinary life of both hardship and influence.
Khosrowshahi is now firmly in the spotlight at the head of the Valley's most valuable startup — which is going public on Friday, at an initial market cap of $75.5 billion — and one that's been under a microscope due to its meteoric growth and its well-chronicled troubles.
Here's the incredible story of Khosrowshahi's journey from refugee to tech mogul:
This is an update to a story originally published in August 2017.
Dara Khosrowshahi is 49. He was born in Iran, although he is now a US citizen. His last name is pronounced "Cause-Row-Sha-hee."
He was born into a prominent and wealthy family, founders of a major Iranian conglomerate involved in pharmaceuticals, chemicals, food, distribution. During the Iranian revolution, the company was seized and nationalized by the new government and his extended family fled the country.
Khosrowshahi arrived in the US when he was nine years old, an Iranian refugee. His family moved in with one of his uncles in Tarrytown, New York, a town with upscale roots on the eastern shore of the Hudson River, 25 miles north of Manhattan. Rockefeller had built a mansion there in 1906.
He and his cousins attended an Ivy league private prep school in Tarrytown called Hackley School. Previous students included George Hamilton and oil billionaire Fred Koch. He remembers those early years in the US fondly. "For the grown-ups, it was a difficult transition. The kids were able to party together, so it was fun.”
Another one of his uncles is the billionaire Hassan Khosrowshahi, who chose to go to Canada when the family fled from Iran. Hassan founded an electronics company called Future Shop (sold to Best Buy) and then created a conglomerate holding company that licenses pharmaceuticals and music.
All this means Khosrowshahi has a network of family members that are bigwigs in the business and tech worlds well beyond Expedia ...
For instance, his brother Kaveh Khosrowshahi is a managing director at Allen & Co., the investment bank best known for its ultra exclusive Sun Valley conference. A few cousins are Google execs. His cousin Amir Khosrowshahi is at Intel after Intel bought the AI company he co-founded, Nervana, last year for $400 million. His twin cousins Ali and Hadi Partovi sold their startup to MySpace back in 2009 for $20 million and went on to become power angels backing Airbnb, Dropbox, Uber, and Facebook and cofounding Code.org.
Not that life after Iran was all rosy. When Khosrowshahi was 13, his father went back to Iran to care for his own father, and the country would not let him leave for six years.
After earning an electrical engineering degree at Ivy league school Brown University, Khosrowshahi began his career in finance, working at Allen & Co through the 1990s. He still often attends the firm's famous Sun Valley conference.
He took an exec role at USA Networks and launched its early streaming efforts. “I was a complete failure," he said of the experience. "The cost of streaming content was higher than any advertising dollars you could earn. The better you did, the more you lost.”
Despite the humility of that statement, he wasn't considered a failure. He was actually the protégé of media industry icon Barry Diller. USA changed its name to InterActiveCorp (IAC) and on July 2001 Diller and Khosrowshahi crafted a deal to buy Expedia from Microsoft for about $1.3 billion.
Two months later, before the deal closed, 9/11 happened. In addition to the tragic loss of 3,000 lives, the incident also stymied the travel industry. It was a seminal moment for Khosrowshahi, "We had the opportunity to pull out. Barry said, ‘People are going to keep living and traveling, so we’re in," he said.
Khosrowshahi spent a few years as the chief finance/strategy guy at IAC until it spun Expedia out in 2005 with him as CEO and Diller as chairman.
He remained CEO until moving to Uber in 2017. In those 12 years, Expedia became the largest online US travel agency. Revenues grew from $2.1 billion in in 2005 to $8.7 billion in 2016. Like his mentor Diller, and like others in his family, Khosrowshahi is a deal maker equipped to run a conglomerate.
Expedia's stock did particularly well under Khosrowshahi's leadership, rising from $109 per share a year before his departure to well above the $140 level:
Expedia's board was so happy with Khosrowshahi's performance that, in 2015, it awarded him a massive $91 million stock grant, in addition to his nearly $4 million in salary and bonus, making him the highest paid exec on the S&P that year.
There was a catch. This stock was part of a long-term employment contract that vested over five years, and another huge chunk of stock would only be granted if he stayed with the company until 2020 and the stock price hit $170.
By some accounts, Khosrowshahi walked away from as much as $180 million by leaving Expedia before this huge stock grant vests.
Khosrowshahi is comfortable in the public eye. He's been an outspoken critic of President Donald Trump, speaking out against Trump's immigration ban and his statements on Charlottesville. Khosrowshahi tweeted "I keep waiting for the moment when our Prez will rise to the expectations of his office and he fails, repeatedly."
As a leader, he's the opposite of former Uber CEO Travis Kalanick. He's known as friendly, calm and drama free. His Expedia employees gave him a 94% approval rating on Glassdoor.
And beyond that, he's also a bona-fide geek, who loves "World of Warcraft," his Amazon Alexa, and believes technologies like voice search will change the future.
In 2012 he married Sydney Shapiro. The couple calls themselves "sci-fi geeks." The wedding was held in Las Vegas and she was wearing a T-shirt from heavy metal band Slayer. They have four kids.
Under Khosrowshahi, Uber has gotten into new businesses like electric bikes, even as it invests further in the popular UberEats food delivery business.
Still, his reign hasn't been totally free of controversy: In 2018, one of Uber's self-driving cars struck and killed a pedestrian. It paused self-driving car testing for nine months in the wake of the accident.
And now, in 2019, Uber is about to go public, at an initial market cap of $75.5 billion — but it could go much higher depending on how the market reacts to Uber's listing.
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