Uber CEO Dara Khosrowshahi Would Rather Take the Train

“If I don’t exercise, my wife tells me I become Evil Dara," said Khosrowshahi, 54, who added that his runs and Peloton classes are like meditation for him. “I just beat the crap out of myself. If I’m thinking about my next gasp of breath, it makes me forget for a second about any worries that I have."

Since becoming the ride-hailing company’s chief executive in 2017, Khosrowshahi has taken Uber public and helped to introduce new safety features for riders and drivers. During an earnings release call earlier this month, the company announced its first-ever operating profit.

Born in Tehran, Khosrowshahi lives in San Francisco with his wife, Sydney Shapiro, and their two twin boys. He also has two children from his previous marriage. Before joining Uber, he was the CEO of Expedia Group. Here, he talks about the future of self-driving cars and shares the most important thing his mentor Barry Diller taught him.

What’s the first thing you do after waking up?

I sprint to the coffee machine to turn it on. I still haven’t figured out that timer thing, so I physically push the button to get as much coffee as quickly as possible. I have it with a ton of Cremora, which probably is not good for me but I don’t care, and Splenda, so my coffee is very sweet. It’s almost like a meal. I skip breakfast usually.

How do you get organized for the week ahead?

Wake up and check emails first and foremost. We’re a global company, so lots is happening constantly. I’ll check out how Europe is doing. Usually there’s a report on how the business did over the weekend. Then I’ll also read the news—the Journal, the New York Times and the FT—to get set on what’s going on around the world.

What do you look for in a new team member when you’re hiring?

What I look for above all is followership. I want to know who they’ve hired, who they’ve developed, because ultimately, you get exponential benefit, not just based on the individual, but everyone they’ve hired and developed.

Earlier this year, you spent time driving for Uber. What are you doing next to improve conditions for drivers?

I think it’s more employees using our products and getting in the shoes of a driver. Anyone who comes to Uber, they’ve used Uber, they’re passionate about the product, but as an eater or rider. I want that same passion and familiarity as a driver, as a courier, as a merchant, because ultimately we are a marketplace and we’re helping over five million people a year earn part-time or full-time. That’s an important responsibility, and we’ve got to take it seriously.

What was the most nightmare rider experience you had while driving?

It actually wasn’t a rider experience. It was when I was a courier. I was trying to deliver food and I couldn’t find where to drop it off. Trying to figure out the maze of apartment complexes was a challenge. The most fun was delivering food to a touch football game. I was like, “Where’s the building I’m supposed to be delivering to?" It was a field. There was a bunch of dudes.

What’s your preferred mode of transportation? If you’re going somewhere four hours away, would you rather drive, take the train, or fly?

Train, because it’s the most relaxing. You can look at the landscape, you don’t need to worry about anything. Flying’s still stressful with all the security and all that.

Uber piloted an autonomous vehicle service in Las Vegas at the end of last year and is testing autonomous delivery in other cities—what do you think the self-driving landscape will look like in one year? Five?

I think self-driving is a really promising technology, but the self-driving robots right now are student drivers. In a year, they’ll be in learning mode and experimentation mode. We’re working actively with players in trucking and delivery. I think in five years, you’re going to have small commercial applications happening and it will become more real. I think in 10 to 15 years, self-driving is going to have a much larger impact in our business, and we want to partner with every self-driving player out there. But we’ve got to make sure we build the business in a safe way.

What are the most important factors there?

Making sure that the self-driving car can handle all of the situations that are demanded of it. The advantage we have is, we can call on a human driver or a robot driver depending on the circumstances. If there’s a weather situation or certain time of night or certain destinations, it’s safer to hail a human driver. We can make that determination, and it requires close partnership with technology players.

How do you think about mentorship?

I’ve been mentored by incredible people. [Former Allen & Company president] Herbert Allen. Barry Diller has been a great mentor of mine. I wouldn’t have my job without them. One of the areas that I’m really focused on is mentoring young women and people of color to help them succeed in corporate life. Driving diversity at all levels at Uber is a big part of our talent strategy.

What’s the most important thing you’ve learned from Barry Diller?

Listening. He really values learning even though he’s an incredibly accomplished person. He listens, he’ll push back against you, and ultimately you both leave the meeting having learned something.

What was your biggest takeaway from running Uber during the pandemic?

For us to pivot fast. Eighty percent of our rides business disappeared almost overnight. Our delivery business exploded in a great way. We didn’t have time to consider what was next, we just had to move.

What do you do for self-care?

Dinner with my family. We put all the phones away, no distractions whatsoever. Having that time to talk about everyone’s day, laugh a little bit, make fun of each other—that time is really special to me. And cooking with my wife on the weekends. I’m an obsessive griller.

Do you have a signature dish?

Still working on the perfect grilled New York steak.

Do you have something you consider a vice or guilty pleasure?

I don’t think I’ve gone a day in four years without having a piece of chocolate.

What’s something you splurge on?

Remote-control cars and planes that I build and play with my kids—sometimes successfully, sometimes not.

What’s one piece of advice you’ve gotten that’s been important to you?

Bet on people. Herbert Allen very early on advised me to bet on people. I didn’t understand for 30 years but I do now.

This interview has been edited and condensed for clarity.

Write to Lane Florsheim at lane.florsheim@wsj.com