Uber CEO Dara Khosrowshahi easily ranks among America’s most obscenely paid CEOs. Khosrowshahi in 2025 was showered with $35.6 million in compensation, representing 360 times his employees’ median pay. The pay disparity is even more distorted because it excludes Uber’s drivers, whose blood, sweat, and vehicles generate much of the company’s revenues but aren’t regarded as employees. Khosrowshahi is hardly a man of the people.
Khosrowshahi’s chutzpah exceeds even his compensation. Uber these days is taking aim at Waymo, Google’s driverless taxi business that’s rapidly gaining traction and clearly has Khosrowshahi running scared. Hoping to derail Waymo’s momentum, Uber has been channeling its inner Zohran Mamdani in the San Francisco Bay Area and warning about a “two-tier transportation system,” claiming Waymo is concentrating on wealthy enclaves while avoiding lower income neighborhoods in Oakland.
Meanwhile, in Philadelphia, Uber is aggressively fighting the city’s attempts to impose a $1-per-ride fee to help fund the public school system. Uber claims the tax is “regressive” and will hurt the working class, conveniently ignoring that the money is intended to preserve the jobs of teachers educating children in the very kinds of neighborhoods the company professes to care so deeply about in the Bay Area.
Empty Suits and Visionaries
My bigger issue with Khosrowshahi, and why I regard him as an empty suit, is his lack of innovation. He was named Uber’s CEO in 2017, replacing co-founder Travis Kalanick, who in his day was widely regarded as a certifiable a-hole, although I’d argue Elon Musk, Mark Zuckerberg, and Sam Altman could give Kalanick a respectable run for his money.
In the nine years since Khosrowshahi took over Uber, the business hasn’t fundamentally changed all that much. Uber and Uber Eats, the company’s biggest revenue generators, were all Kalanick’s doing. While Khosrowshahi brought “operational efficiencies” to Uber and likely created a workplace where employees can belt out hearty renditions of Kumbaya with abandon, Uber largely stopped producing meaningful technological breakthroughs the moment Kalanick was pushed out the door.
What’s clearly panicking Khosrowshahi these days is Waymo’s breakthrough success and Elon Musk’s robotaxi ambitions, both of which threaten Uber’s long-term viability. Khosrowshahi has forged alliances with Waymo, Rivian, Lucid, and Amazon’s Zoox to offer autonomous ride-hailing services. Notably, his robotaxi partners are doing the heavy technological lifting. Uber simply wants to deliver their services through its app.
It is a strategy designed to extract toll booth revenue from other companies’ breakthroughs while positioning Uber as an indispensable gatekeeper. That’s hardly rocket science and, frankly, if Waymo had any marketing instincts, it would eventually choose to go it alone.
Uber is a tarnished brand, facing some 3,000 sexual assault and rape lawsuits involving its drivers, one of which a jury recently ruled was ultimately Uber’s responsibility.
Khosrowshahi claimed ignorance of rider safety data in a deposition connected to a lawsuit in which a jury ordered Uber to pay $8.5 million to a woman who alleged she was raped by an Uber driver. Khosrowshahi answered “I don’t know” or “I don’t remember” to at least 14 questions when asked whether he was aware that reported rapes during Uber rides increased 3% from 2022 to 2023, Courthouse News Service reported.
Passenger safety apparently is a critical component of the operational efficiencies Khosrowshahi focuses on.
Existential Threat
Underscoring that Kalanick was a real visionary, he recognized more than a decade ago that autonomous taxis were an existential threat to Uber’s business and took meaningful steps to protect it. Although Wall Street believed self-driving taxis were decades away, Kalanick argued the technology could be commercialized within years.
“The minute it was clear to us that our friends in Mountain View were going to be getting in the ride-sharing space, we needed to make sure there is an alternative [self-driving car],” Kalanick told Bloomberg in a 2016 interview. “Because if there is not, we’re not going to have any business.” Developing an autonomous vehicle, he said, “is basically existential for us.”
In early 2015, Kalanick launched Uber’s Advanced Technologies Group, or ATG, and forged a strategic partnership with Carnegie Mellon University, which had developed deep expertise in autonomous driving technology. Kalanick proceeded to poach dozens of the university’s top scientists, researchers, and engineers to establish ATG’s initial headquarters in Pittsburgh.
In 2016, Uber acquired self-driving truck startup Otto for $680 million, bringing founder Anthony Levandowski into the ATG fold. The acquisition triggered a trade secrets lawsuit from Alphabet, Waymo’s parent company, which claimed Levandowski had stolen thousands of confidential files from Google’s self-driving project before leaving the company. Levandowski denied wrongdoing.
Outsourcing Autonomy
The legal chaos surrounding Kalanick’s fast and loose construction of ATG eventually became a major factor in his corporate undoing, paving the way for Khosrowshahi to step in and essentially outsource Uber’s autonomous ambitions to another upstart autonomous driving company called Aurora Innovation.
Under the terms of the 2020 deal, Uber agreed to invest $400 million into Aurora in exchange for a 26% ownership stake. Khosrowshahi also joined Aurora’s board. The arrangement supposedly guaranteed that when Aurora eventually released self-driving vehicles, they would launch on Uber’s network.
“I’m looking forward to … bringing the Aurora Driver to the Uber network in the years ahead,” Khosrowshahi said when the deal was announced.
Aurora’s co-founders had deep roots in the autonomous driving industry. CEO Chris Urmson previously led Google’s self-driving team, which eventually became Waymo. Chief Product Officer Sterling Anderson directed Tesla’s Autopilot efforts. Chief Technology Officer Drew Bagnell, an associate professor at Carnegie Mellon University, was part of the 2015 academic exodus that formed Uber’s ATG team before leaving to become an Aurora co-founder.
Aurora eventually chose to focus on self-driving trucks, recognizing that the chaotic and unpredictable nature of urban passenger transportation remained further away from becoming a safe and truly profitable reality. Instead, Aurora pivoted toward the trillion-dollar American freight market.
Making History
The gamble has begun to pay off.
In May 2025, Aurora made history by officially launching the world’s first commercial driverless freight service operating entirely without a human safety driver behind the wheel. Utilizing its flagship “Aurora Driver” system, the company began hauling commercial cargo for paying customers along the heavily trafficked Interstate 45 corridor between Dallas and Houston.
Aurora recently signed a commercial contract with McLane Company, a Berkshire Hathaway subsidiary, to launch fully driverless hauls for the distributor’s restaurant supply chain, alongside an agreement with Hirschbach Motor Lines detailing plans to eventually scale its autonomous fleet to 500 trucks.
Although Aurora has yet to post a profit and its stock price trades below its initial public offering price, it is now valued at roughly $15 billion and has demonstrated that the near-term gold mine of autonomous technology may not lie in replacing a human Uber driver, but in revolutionizing the backbone of global logistics.
Destroying Cruise
While Aurora mastered autonomous long-haul freight, GM’s Mary Barra in 2024 opted to shutter the company’s Cruise autonomous driving subsidiary, which in 2022 was valued at $30 billion, equivalent to nearly half of GM’s current market capitalization. GM invested more than $10 billion in Cruise, which Barra deemed too costly despite GM earmarking roughly $23 billion for stock buybacks over the past three years.
Yet Barra last year lured Sterling Anderson away from Aurora with a compensation package reportedly valued at roughly $40 million, a striking sum for an executive whose expertise lies not in GM’s immensely profitable gas-powered trucks and SUVs, but in autonomy, robotics, and software.
Months later, Barra sold 40% of her GM holdings, according to securities filings, reducing her personal exposure even as the company continued repositioning itself around software and autonomous driving technology. Earlier this year, GM President Mark Reuss sold more than $38 million worth of company stock.
Cruise co-founder Kyle Vogt was immensely respected in autonomous driving circles and regarded as one of the industry’s premier AI and hardware engineers. Vogt arguably achieved more tangible milestones in consumer urban autonomy than Sterling Anderson and his former colleagues at Aurora.
Vogt and his team scaled a massive fleet, logged more than 5 million driverless city miles, conducted roughly 250,000 public passenger rides, and expanded operations into Austin and Phoenix. He successfully took passenger robotaxis out of the lab and turned them into a commercial reality for ordinary city residents.
Vogt didn’t have kind words for GM after Barra shuttered Cruise.
Tellingly, one of Anderson’s first major hires at GM was Rashed Haq as the company’s vice president of autonomous vehicles. Haq previously spent five years at Cruise as its head of AI and robotics, suggesting GM’s core problem may never have been a lack of autonomy talent so much as leadership judgment and strategic conviction.
Full Circle
With Anderson’s hiring, the autonomy saga effectively came full circle. Khosrowshahi inherited Kalanick’s ambitious self-driving operation only to hand much of it over to Aurora. Anderson helped transform Aurora into an autonomous freight leader. Barra then paid roughly $40 million to recruit Anderson to help rebuild expertise at a company that, through Cruise, once appeared to lead the industry.
Bob Lutz, GM’s legendary former vice chairman, foresaw years ago where autonomy could ultimately lead the automobile business. Lutz once observed that consumers bought Chrysler vehicles because Lee Iacocca, much like Elon Musk today, was perceived as a visionary leader people wanted to follow.
Lutz also warned that autonomy could eventually destroy the emotional bond between consumers and car companies.
“Once we have transport modules, you order off the phone and brands won’t matter anymore,” Lutz said in a 2016 interview with Car and Driver. “When brands don’t matter, the auto industry ends.”