Trump and Kalanick: Twin Chief Executives Face Similar Problems


In the rinse-repeat rhythm of Uber’s PR crises, it’s easy to miss that this particular cycle has been a long one. Uber’s latest wave of negative press began in January with a backlash against CEO Travis Kalanick’s role on President Donald Trump’s White House business advisory panel. There’s some irony here, because Trump and Kalanick have so much in common.

Both men built success on a ruthless disregard for both convention and opposition; both have seen their rule-breaking instincts turn rapidly from assets into liabilities. Breaking through walls doesn’t necessarily work when you’re leading a large organization and working with powerful stakeholders.

Kalanick has been struggling to adapt since at least 2014, when he joked with GQ about Uber’s internal nickname, “boob-er,” for its ability to increase its own chief executive’s sex appeal. More than two years later, Uber apparently hasn’t been able to root out the culture of sexual harassment described by female engineer Susan Fowler.

In what looks like a related case of organizational failure, Uber failed to adequately vet a top executive, missing accusations of sexual misconduct at his previous job. Recode’s Kara Swisher did not fail to uncover those allegations.

Uber may have also failed at due diligence in a crucial acquisition—the self-driving car technology company, Otto. Waymo, a sister company to Google that is also developing self-driving cars, is now suing Uber. The suit alleges Otto’s founder, an ex-Waymo employee, based his company’s technology on stolen trade secrets.

Trump found himself in a somewhat similar situation, when his national security adviser, Michael Flynn, resigned. Flynn had apparently misled administration officials about the extent of his contact with the Russians leading up to Inauguration Day.

Meanwhile, media leaks are running rampant in Trump’s organization. Both Uber and the White House seem to be extraordinarily poor at some of the details of running a large organization. And both have shown a talent for pissing off powerful stakeholders who could be powerful allies.

For Trump, that may be changing: He got plaudits after his first address to Congress, not so much for the content of what he said, but for the cooperative tone he used in saying it. In the early days of the Trump White House, this stands out as remarkable.

Can Kalanick also change course? The pressure is on. Like Netflix in 2011, Uber knows that if it doesn’t kill its legacy business connecting drivers to riders, someone else will. If and when autonomous vehicles are common on our roads, this business will no longer be viable.

Maybe that’s why Kalanick can’t let his company slack, as he said in a dashcam video captured by an Uber driver and published by Bloomberg on Tuesday. Maybe that’s why he then turned to berating the driver for complaining about Uber’s fare cuts. Uber has been the company that helped more than a million make a living with their cars; it’s now trying to become the company that takes that opportunity away. That’s an awkward position that could make anybody want to lash out.

To be effective, both men will have to learn to control their tongues. More than that, they’ll need to find new ways to control large organizations that have apparently formed some bad cultural habits.

For Uber, now eight years old with some 7,000 employees, this will be difficult. Travis Kalanick is no longer on the panel that’s giving the White House business advice—but perhaps Donald Trump can learn from him just by watching his mistakes.

Travis Kalanick and Donald Trump. Photos by Dan Taylor/Heisenberg (left) and Gage Skidmore (right), CC BY-SA 2.0

Galen Moore is an editor, consultant and journalist. Most recently he was editor in chief at Streetwise Media, which publishes tech and venture capital news and analysis in four cities. Follow @galenmoore

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