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Travis Kalanick Plays the Mythic Role of the Rebel CEO Too Well

The Uber executive embodies everything Silicon Valley glorifies, and that’s exactly his problem

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

In 2005, Steve Jobs gave a commencement speech at Stanford University that detailed the virtues of rebelliousness, a characteristic that the late Apple CEO embraced in his path to becoming the most revered business leader in the tech industry. He told a story about dropping out of Reed College so he could instead sit in on the school’s famed calligraphy courses. It was that experience — discussions of sans serif fonts! spacing between letters! — that he said helped him design a consumer-friendly operating system for the Mac many years later. Jobs’s implication was clear: By doing something unconventional, he expanded his worldview and used it to his advantage. His parting words to the audience were “Stay hungry, stay foolish.”

A video of that speech has since been viewed more than 26.7 million times on YouTube, and is often passed around among startup founders as a kind of Silicon Valley gospel. Over the past two decades, the glorified agitator has become an almost mythic character among major tech companies. In Facebook’s early years, Menlo Park offices were plastered with signs that read “Move fast and break things.” Jeff Bezos once explained that Amazon was inventive because “we are willing to be misunderstood for long periods of time.” When John Legere was picked as the new CEO of T-Mobile, he underwent a jarring transformation from suit-wearing corporate cog to freewheeling “rebel CEO,” to rave reviews. Above all else, the tech industry has developed a powerful appreciation for outliers who are willing to skirt convention in the name of innovation.

But lately we’ve been forced to confront Uber CEO Travis Kalanick, a company figurehead who has interpreted his role as rebel to the extreme. At first glimpse, he fits the mold of your typical tech-industry maverick. He’s a UCLA dropout whose first peer-to-peer file-sharing startup crumbled after just barely dodging a copyright infringement lawsuit. He was undeterred enough to launch a second startup and rewarded handsomely for his grit with a cool $19 million sale in 2007. Along the way, he has earned a reputation for being — as one longtime friend put it in a 2015 Fast Company profile — “an incredibly aggressive person.”

In his role overseeing one of the most impactful startups of the century, he has embraced the tradition of Silicon Valley rule-breaking and taken it to some shady places. Some examples include but are not limited to: refusing to establish an effective human resources department, setting self-driving cars loose in San Francisco without the city’s permission, plotting to sabotage competitors, using Uber’s considerable influence to place pressure on local politicians, and creating a secret tool to circumvent law enforcement. When a revealing New York Times profile of Kalanick dropped Sunday, that list got a little longer. In order to prevent Chinese fraudsters from repeatedly taking advantage of new-driver promotions, the company reportedly wrote code that allowed it to track phones even after the Uber app had been deleted. Because this tracking method was forbidden in the App Store, Uber intentionally hid it from Apple’s engineers. It was only after Tim Cook threatened to kick Uber out of the App Store entirely that Kalanick chose to remove the feature. “A blindness to boundaries is not uncommon for Silicon Valley entrepreneurs,” the Times wrote. “But in Mr. Kalanick, that led to a pattern of repeatedly going too far.”

A Silicon Valley idealist might see that kind of company behavior as a positive thing — that Kalanick must do whatever he can to sidestep the bureaucracy of the world’s outdated systems and enlighten society to a more innovative transportation system. But given the “sheer expression of capitalistic force that the company represents,” as journalist and entrepreneur John Battelle once put it, there’s something much less innocent at play here. Kalanick isn’t tapping his inner rebel to find bold new solutions to tired problems. Nor is he not throwing out the tech-company playbook to follow his inner instincts. Kalanick is using clandestine methods and exploiting legal gray areas to operate his $60 billion company as if it’s immune to rules. There’s a big difference between disrupting a system and simply plowing over it.

And herein lies the problem with the rebel CEO trope in the first place: It’s quite often a story that companies tell to smooth over their abuses of power. The success of Uber has already had a massive infrastructural effect on our world, and the company is run by a man who does not hesitate to bypass the checks and balances meant to protect customers, competitors, cities, and employees, at whatever means possible. Kalanick may want you to believe that he’s only fulfilling the mythic role of the ruthless innovator, but let’s be real: That’s just a way to romanticize unregulated capitalism.