LANGLEY, Wash. — I was just cutting into a juicy piece of steak that the chief executive of Uber, Dara Khosrowshahi, had grilled and plopped onto my plate, when one of his 8-year-old twin boys asked me: “Who was your worst interview and who was your best?”
I replied that Kevin Costner was one of my least favorite, because he was at the height of his fame and acting very sniffy. And Tom Ford and Elon Musk were two of the most fun, because I enjoy writing about operatic characters with out-of-this-world proclivities.
Mr. Khosrowshahi’s wife, Sydney Shapiro, looked across the kitchen table at her husband with a sultry Lauren Bacall smile. “You need to up your eccentricity,” she said teasingly.
He looked back at her, amused.
His 16-year-old son jumped in with an assist. “My dad’s a lizard person,’’ he said. The teenager said he had found a random post on the internet about a conspiracy theory contending that his father, Queen Elizabeth, George W. Bush and Bob Hope are all lizard people. “They’re reptilian aliens that can shape shift and control the world,” he explained. “Just know that if you pour water on him, he will melt. If he gets aggressive, don’t move. He can only see you if you’re moving.”
Actually Mr. Khosrowshahi, 52, is weirdly normal for Silicon Valley. He’s not growing a Neanderthal beard, living off salt juice or summering in outer space, but rather bucolic Whidbey Island, a brief ferry ride from Seattle.
In 2017, he left Expedia, where he had quintupled revenue in a dozen years, to take over Uber from Travis Kalanick, whose name became synonymous with overly aggressive business moves and the gnarly bro excesses of Silicon Valley.
“My dad’s advice was, ‘If a company that’s a verb offers you a job, say yes,’” he recalled.
Taking on one of the worst cleanup jobs in the history of American capitalism, at one of the most loathed companies, Mr. Khosrowshahi was like a dad who had to mop up after the frat party, put all the Solo cups away and get the vomit off the marble floor.
“He came into a nightmare,” said Barry Diller, who, juggling calls from his yacht, helped him nab the job after “the terrible board” deadlocked between Meg Whitman and Jeff Immelt.
Mr. Diller said his protégé has had “a miserable year or two,” slammed by Covid, but that “Dara is a great executive. And Uber is a great business — eventually.”
In his 2019 book, “Super Pumped: The Battle for Uber” (soon to be a Showtime drama by the “Billions” team), the New York Times reporter Mike Isaac wrote: “For some, there remains a lingering, persistent concern: Is Uber under Dara Khosrowshahi still going to swing for the fences? Or has Uber lost its appetite for moonshots and world domination — the alluring, Travis-like quests that attracted them to the company in the first place?”
Can this rational, charming chief without the edge, ego or cult following of wacky founders succeed in today’s insane economy? Does the incredible shrinking kingdom of Uber still dream big?
“Right now, I dream about pushing a button and getting a piano delivered to your home in an hour and a half,’’ Mr. Khosrowshahi said. “I think that’d be really cool.”
He continued: “We’ll keep working on go-and-get. Anywhere you want to go, anything you want to get, however you want to get it, we’ll be there for you.”
Is the era of mercurial jerk geniuses coming back?
“I don’t think that investors necessarily love them one way or the other,’’ he said, sipping a glass of California cabernet sauvignon, his Dutch shepherd, Loki, curled at his feet. “I think the press does and the Twitter-sphere does. But I think investors like returns.”
The toxic Travis culture is gone but no one seems sure of what the Dara culture is. Does he worry that this is not as sexy a company anymore as far as attracting investors and talent?
“My goal in life is not to build the most sexy company,” he said. “It is to build the best company.”
‘A Glimmer Moving Fast’
Mr. Kalanick undermined his successor at the start, according to Uber insiders, but Mr. Khosrowshahi finessed the founder slowly out of the business. The Kalanick crowd did not make it easy on “the math guy,” as some call him, with efforts to divide the company into Travis people and Dara people and whispers that the new boss was not on board with Travis’s mantra of BIGGER! FASTER!
“I don’t know what Travis was doing,” Mr. Khosrowshahi said, in his deep, even voice. “Honestly, I didn’t spend a lot of time figuring it out. With me, he was generally helpful. Then he got out. He separated from the company, and I think that was a fine thing to do.
“We work with him at Uber Eats and that’s fine,” Mr. Khosrowshahi said. (Mr. Kalanick has a new start-up, CloudKitchens, which rents commercial space and turns it into shared kitchens for food delivery businesses.) “I’ll take Travis’s side for a minute, which is, I had to come in and be very clear that the company was no longer his. I had to be more forceful because of where we came from. I can completely imagine that hurting, because he’d built the company. I’m not necessarily defending him, but I understand how it would be tough for him. This was his life.”
Andrew Macdonald, the senior vice president of mobility for Uber, who has worked for both bosses, praised Mr. Khosrowshahi for changing “our culture values to do the right thing.”
“Are we as combative as we were seven, eight years ago? No,” Mr. Macdonald said. “Will Dara fight and push and take issues all the way for what he believes in? Yes. Travis was a really ferocious competitor. But the company definitely had blind spots as a result.”
Mr. Khosrowshahi had gotten through the Kalanick mop-up, the apology tour around the world, a shaky opening I.P.O. day and the scaling down, and the company was on its way to profitability. Then, the pandemic. He had to lay off 25 percent of his work force. Who wanted to get in a car with a stranger, even if there were anywhere to go?
“When coronavirus hit, we pulled back pretty aggressively,” he said. “We got out of some businesses. There are certain times where you should be conservative. And there are certain times where you go for it.”
He said he “didn’t have enough time to be depressed or to feel sorry.” As he was frantically trying to figure out if the company — already losing billions — could survive losing, in some places, 85 percent of its rides business, he discovered “a glimmer moving fast”: Uber Eats, an arm of the business he had been pouring money into for the previous two years, despite many investors being unhappy about it.
“When I joined, Eats was a $2.5 billion business,” he said. “We’re going to be over $50 billion now. Eats on a volume basis is going to be bigger than Rides chiefly because with Eats, we’re going to go to grocery and we’re going to the pharmacy and we’re going to every single local commerce category. It’s a bigger market.”
It hit him, he said, that all the businesses he had been shedding — scooters, electric bikes, autonomous cars, flying cars — “were a distraction to the mission. People are going to start moving again and this business — get anything and everything that you want in your house — was going to be bigger than any of us thought it was going to be.”
A few weeks ago, Mr. Khosrowshahi rode a bike, delivering for Uber Eats in San Francisco for two days.
“I was nervous at first,” he said, adding that some of it was fun and some of it was rough. “I nearly got killed delivering near the baseball park. The Giants game was starting, and traffic was nuts. My hypothesis is that someone knew that I’m a Mets fan.”
Around the time of Uber’s I.P.O. in 2019, Mr. Khosrowshahi suggested that the company could be the Amazon of transportation. Has that dream dimmed?
“I think we’re neighbors at this point and we’ll look over the fence and wave at them and maybe they’ll notice us waving, maybe they won’t,’’ he said. “But I think our house is going to get bigger.”
Now that parts of the world are back to calling for rides again, they’re suddenly way more expensive — 40 percent more, according to one estimate — and, thanks to Uber, there are far fewer taxis.
“It’s not where it needs to be right now,” Mr. Khosrowshahi conceded.
He said the company is “leaning in and investing super-aggressively to bringing drivers back. We told investors, we’re going to hurt our margins in the second quarter doing so.” He predicted that by September, prices will return “to nearly the good old days,” adjusted for inflation.
Some analysts note that Uber’s ride-sharing business seems to have an existential problem; wouldn’t its original business model only work if it used billions to subsidize the cost of rides until the transition to self-driving cars? But a driverless future is a long way off. Doesn’t Uber either have to charge a lot more for the rides or find some way to pay the drivers even less? Isn’t this fundamentally at odds with treating workers humanely?
Mr. Khosrowshahi demurred, saying that Proposition 22, a ballot measure in California that allows gig economy companies to keep treating drivers as independent contractors, never could have passed “in the bluest of blue states” unless a lot of drivers supported it. He said that about a year ago, he decided to focus not only on drivers’ independence but also on good pay.
Scott Galloway, a professor of marketing at New York University’s Stern School of Business, compares the Uber chief to Sheryl Sandberg, “the pretty face” that obscures the damage their firms are doing to society.
“That’s the first time I’ve been called a pretty face,” Mr. Khosrowshahi said wryly, before allowing: “Our system doesn’t work for a certain percentage of drivers who can’t figure it out, who can’t understand how to make it work. I do think that for that percentage — and it’s probably 10 percent of our drivers but when you’re talking about 10 percent of a million drivers on the road — that’s a lot of people who want to earn and our system isn’t working properly for. I do think that we have to build better safeguards for people who can’t make our system quite work the way that they want to work, or we’re willing to work with regulators to have certain safeguards like minimum earnings.”
‘It Ain’t Called Laborism’
In 1979, when Dara was 9, his Muslim family fled Iran to escape the revolution, leaving the fortune they had made from their large pharmaceutical and cosmetics company. They moved to an uncle’s mansion in Irvington, N.Y., for a couple of months before getting a condo in Tarrytown.
Once, his mother, Lili, had shopped in Paris at Dior, Saint Laurent and Celine. Now she had to go to work at the Madison Avenue Celine. Once, she had had a cook, two gardeners, a driver and a babysitter for each child; now the woman who had never set foot in a kitchen became her own cook.
She was laser focused on sending her sons to a good prep school, the Hackley School, in Tarrytown. Dara’s soccer and math skills made assimilation easy.
When his father returned to Iran to try to get his own father out, he was not allowed to leave the country for five years and missed Dara’s high school graduation. The businessman Herbert Allen Jr., whose sons were school friends with the Khosrowshahi boys, took the family under his wing.
“This man was an angel,” Lili said. “He took them on private planes, on the best trips ever, for summer vacations and skiing.”
Lili taught Dara to stay humble. He prefers giving his team credit to swanning. After George Floyd’s murder, he choked up in an all-hands meeting.
“My dad carries with him a bit of feminine energy that he learned from his mother,” said his daughter, Chloe, 20, a student at Brown University, her father’s alma mater. “He’s bold, but in his own way, a less obvious way. He allows other people’s voices to fill the room.”
Mr. Khosrowshahi said simply, “I just grew up in a circumstance where getting along was the way to survive.” (He is not religious but is fascinated by religious narratives.)
Tony West, the chief legal officer of Uber, said that Mr. Khosrowshahi is willing to take on legal risk to fix the Uber workplace. “We no longer have forced arbitration for claims of sexual harassment or sexual assault,” Mr. West said, adding that, in those cases, “We no longer use confidentiality agreements.”
Would Mr. Khosrowshahi want one of his own children to drive for Uber?
Yes, he said, but he would want them “to eventually have a full-time job, work in a technical field. I think actually some of the programs that we’re having now are to provide a bridge” to become a coder or salesperson at Uber or to get a free education. (The company has an arrangement with Arizona State University online to cover tuition for drivers.)
He is more laissez-faire about returning to the office than Jamie Dimon, who recently told The Wall Street Journal, “People don’t like commuting, but so what?”
Mr. Khosrowshahi said that because Uber is a combination of the virtual world and the real world — “the real world that punches you in the face all the time with its unpredictability” — his tech challenges are different than a site for ordering movies.
“The technology that needs to be built to have that hamburger show up in 30 minutes, guaranteed, is spectacular,” he said. “If there is a genius coder who is happier coding from Colorado and can come into the office once in a while to get to know his colleagues, it’s cool.”
Disruption, once the mantra of Silicon Valley, has now become a dirty word. What are the ethical boundaries of disruption?
“I do think there’s power in a name,” he said. “Our system is called capitalism. It’s designed to optimize for long-term growth of capital. When people wonder, ‘Well, are capital owners advantaged over labor?,’ it ain’t called laborism.”
But he mused that sometimes the system “works too well”: “I think capitalism has its claws in our democratic societies in ways that has allowed it to overly optimize for its benefit.”
Washington is taking a decidedly darker view of Silicon Valley. President Biden named Lina Khan, a fan of ratcheting up regulations on tech giants, as the chairwoman of the Federal Trade Commission and signed an executive order zeroing in on anticompetitive practices.
Pete Buttigieg, who joined a protest outside Uber’s headquarters in 2019, now leads the Department of Transportation. Marty Walsh, who fought Uber as mayor of Boston, now leads the Department of Labor; in April, he talked about the need to reclassify some gig workers as employees.
While noting that “our regulatory sandbox is much more city and state than it is federal,” Mr. Khosrowshahi said that this tech-lash is inevitable.
“I think, just like Uber, some of them grew up too fast and some of them didn’t take responsibility for their power and I think now they’re being called to reckon, and I think it’ll ultimately result in a better, more balanced society going forward,” he said. “My hope is, it doesn’t destroy what we built.
“Sometimes the emotional takes over and I think that’s destructive but I think the age of ‘I built a platform, I’m not responsible,’ that time is over. And now the question is, what does the responsibility look like? Defining it and putting guard rails around it, I think that’s a healthy thing.”
Is he worried that ProPublica, which recently revealed that many top chief executives pay little or no taxes, has his tax records?
“I think that they will have less of a problem with my tax record,” he said. “I think there are real issues that are being raised there.” While he doesn’t blame other chief executives for following the law and trying to save money, he calls the tax system a “monster.”
“There are constantly these lawyers knocking on my door to build these crazy trusts and all that,” he said. “Sometimes I feel like an idiot not answering. I’m the dope who’s not doing all this stuff. But it’s just not what I want to be spending my time on.”
Do the captains of the cloud and industry making obscene gobs of dough deserve it?
“I think if you define fairness by ‘fair market value,’ then C.E.O.s are paid fairly,” he said. “I think if you define fairness by how you think society should value people, then I think C.E.O.s are paid too much. You could put me in that group. The system, the way it’s designed with these compensation consultants, creates a significantly inflationary environment. Every single comp committee wants to pay their C.E.O. at the 60th to 75th percentile, because no one ever wants an average C.E.O., God help us.”
What did he learn from the fallout after he downplayed the Khashoggi execution by Saudi leaders, who are major shareholders in Uber, as “a serious mistake?”
“I learned to not make excuses,” he said flatly.
Does he pay attention to politics in Iran, with that country still in the clutches of zealots?
“I think that it is a shame that Iran is so cut off from the United States,” he said. “I think there’s some unfortunate history there. The Iranian culture is more ancient than the Islamic religion. It’s a deep culture, and there is an innate love that Iranians have for American culture and Americans. I’m hoping that that connection can come back again.”
He jokes that he and his wife have found a solution for peace in the Middle East. She has his name tattooed in Farsi on her wrist, and he has her name tattooed in Hebrew on the back of his neck. He visits Twitter twice a day, and Instagram at night — to heart his wife’s posts.
I ask about their impromptu wedding in the Little White Chapel in Las Vegas.
“I had the bright idea,” he said. “I wanted to get married. I wanted it to last, because it was my second marriage and I’m madly in love with Syd. I said ‘Let’s get married on 12-12-12.’ It’s a lucky day. We went to Las Vegas to get married. It was us and about 10,000 Chinese people looking to get married because it’s a very, very lucky day there.”
The two were fixed up by Sydney’s mother and the mother of one of Dara’s friend who were part of a “Jewish mothers’ dating network,” as he put it.
“She thought he was a C.E.O. egomaniac but that she’d get a free dinner,” Chloe, one of two children from Mr. Khosrowshahi’s first marriage, told me later.
Ms. Shapiro, 43, dressed in a black linen top and pants and absently braiding and unbraiding her long blond hair, said of her mother: “She was worried because I graduated college and then I wanted to go work on a farm in Costa Rica and then I went to Ozzfest as a photographer’s assistant and she was like, ‘You need to settle down.’ I couldn’t have imagined having anything in common with a C.E.O. No.”
Mr. Khosrowshahi laughed, noting, “Her mom still can’t say my name right.” (Say it like this: DAR-uh Koz-row-SHA-hee.)
After they had been dating awhile, Ms. Shapiro told him that he should go do the C.E.O. thing and date a flock of supermodels and then, when he wanted to settle down, come back.
“He had just gotten divorced,” she said. “He came back, though.” He calls her “Shapiro”; she calls him “dude.”
Chloe said that the man known as a “Dad” in Silicon Valley takes the role just as seriously at home.
When she was little, her father — a fan of Joseph Campbell, Greek myths, sci-fi and George R.R. Martin — would concoct children’s stories set in faraway kingdoms with magical wishing flowers and golden owls that could stop time.
When Chloe broke the news last year that she was, as she dryly put it, “an Iranian lesbian,” he gave her a fist bump and told her, “It’s the best time in the world to be gay.”
The family has a more formal home in Pacific Heights in San Francisco, the city where Uber’s headquarters are. But Whidbey is their “happy place.” And life on the little island seems pretty sweet (even if, or perhaps because, you can’t hail an Uber here). Their brown shingled house has the feel of a fairy tale cottage, nestled in an enchanted-looking woods. Mr. Khosrowshahi has a game room, where he plays board games and card games with his sons, and he installed a funicular that goes down to the rocky beach on the Puget Sound, which is usually too cold for swimming.
Asked how he maintained his preternatural steadiness in the face of the cascading woes of the last few years, he gestured toward his home and family.
“I’ll always have this,” he said. “I think Uber is icing on the cake. It’s a big cake and I want it to be really tasty.”
Confirm or Deny
Maureen Dowd: Travis Kalanick is crazier than Travis Bickle.
Dara Khosrowshahi: Who’s Travis Bickle?
Travis sends you emoji-laden texts.
You like the casting choices for Showtime’s forthcoming “Super Pumped” show about Uber.
Only if Daniel Day-Lewis plays me.
The Lyft co-founders are too nice.
I don’t think they’re nice at all.
You love “Death Cab for Cutie.”
In the right pensive moment, absolutely.
You would smoke a blunt on Joe Rogan’s podcast.
Depends on the hour.
You believe in aliens.
Not until I see evidence of them.
In college, you introduced yourself as “Darren Kay” because you worried that no one could pronounce your name, but then you stopped using it because you worried that it sounded like a porn name.
Confirm. Those were dark days.
Like many a cougar, you enjoy William White’s TikTok videos, in which the 21-year-old sings ’80s songs.
I know this makes me really uncool, but I have not gone into TikTok yet.
Uber plans on letting people pay for their rides with Bitcoin.
I just don’t see it. Deny.
Raistlin Majere is your favorite Dungeons & Dragons character.
I love Dungeons & Dragons, but I don’t know that character.
You wooed your wife over World of Warcraft.
She was a night elf, she played it once, and she still loved me afterwards. Which is a very strong statement.
Your wife wore a Slayer T-shirt to your Vegas wedding.
And she looked good.
You decided to leave Expedia once Barry Diller made Joey Levin the chief executive of IAC.
Had nothing to do with that.
When you got the Uber job, your daughter found out via a New York Times push notification.
Absolutely true. The Times beat me to the punch.
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