Uber CEO Dara Khosrowshahi reveals his ‘nightmare’ moonlighting as an Uber driver

Chloe Taylor
Updated 4 min read
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If you ordered food through Uber Eats last year, there’s a chance you put the company’s multimillionaire boss in what he describes as a “nightmare” scenario.

CEO Dara Khosrowshahi shared his experiences as an Uber driver and courier in an interview with the Wall Street Journal published on Monday.

The initiative, called "Project Boomerang" internally, saw Khosrowshahi driving the streets of San Francisco on several occasions. When asked about his worst 'nightmare' experience, he revealed it wasn't actually involving any passenger he picked up in his car.

“It was when I was a courier,” Khosrowshahi told the WSJ. “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.”

He added, sarcastically, that “the most fun” order saw him delivering food to a touch football game.

“I was like, ‘Where’s the building I’m supposed to be delivering to?’” he explained. “It was a field. There was a bunch of dudes.”

Although Khosrowshahi said his biggest difficulty as a courier was finding his way to customers, it’s far from the only problem he faced during his various shifts.

Back in 2021, Khosrowshahi told the New York Times that he “nearly got killed” by traffic when the San Francisco Giants were playing.

On the bright side, Khosrowshahi said his work experience had taught him that Uber needs to do more to make its drivers passionate about what they do.

“Anyone who comes to Uber, they’ve used Uber, they’re passionate about the product, but as an eater or rider,” he said.

“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.”

Uber doesn’t exactly have the best relationship with all of its drivers.

The company successfully sued to block raises in New York City last year, while drivers in other parts of the country have accused the company of discriminatory account suspensions or deactivations.

Uber has also found itself in legal disputes with drivers over their employment status, both in the U.S. and overseas.

In a bid to show drivers he was learning from his work experience, Khosrowshahi took practical steps to make working for Uber a smoother experience, revamping the app after realizing first-hand how unnecessarily complex it was to sign up as a driver.

But despite attempting to improve his drivers’ lots, Khosrowshahi’s “Project Boomerang” still wasn’t met with complete enthusiasm.

After sharing details on how much he earned during his shifts, Khosrowshahi received some backlash from social media users relating to the rates of pay on offer for Uber Eats couriers.

“What a surprising conclusion that you, the CEO of Uber, had a great experience working this job,” one Twitter user said at the time. “Now try doing it as your only source of income.”

Khosrowshahi's total compensation package as Uber’s chief executive reached $24.3 million last year.

CEOs on the frontline

Khosrowshahi isn’t the only big-name CEO that has taken to working frontline shifts in a bid to connect with his workforce.

Incoming Starbucks CEO Laxman Narasimhan told his employees in March that he planned to work as a barista in one of the company’s stores every month.

Taco Bell’s chief executive Mark King also took to the frontlines after he joined the fast food giant in 2019, working a crew shift that he said taught him “what happens with the products, the way they’re displayed, the way consumers interact, [and] the way retailers interact with consumers.”

Meanwhile, Airbnb CEO Brian Chesky promised last year to “live on Airbnb,” explaining in a tweet that he planned to stay in a different listing every couple of weeks.

This story was originally featured on Fortune.com

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