Travis Kalanick is still the right man to lead Uber

The ride-hailing firm's CEO is a publicity nightmare, but would it still be Uber without him?

by Adam Gale
Last Updated: 24 Mar 2017
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A reasonable definition of a narcissist is someone who has a far higher opinion of themselves than others do. Now, I’m no psychiatrist. I’m not entirely sure a company can have a personality disorder. But if any of them has, it’s Uber.

The ride-sharing company says it uses ‘technology to give people what they want, when they want it’. For Uber drivers, it’s a ‘flexible way to earn money’, while for cities ‘we help strengthen local economies, improve access to transportation, and make streets safer’. It’s a glowing vision of the 21st century sharing economy. What’s not to like?

Well that depends who you ask. Taxi drivers the world over call Uber a cheat. Disgruntled Uber drivers call it a bully. Veteran investor Peter Thiel called it ‘the most ethically challenged company in Silicon Valley’.  

‘Airbnb has obviously done a much better job with its reputation than Uber has,’ says veteran Bloomberg journalist Brad Stone, whose book The Upstarts covers the rise of the two start-ups. ‘Uber has cared much less, and as a result has paid the price. Their brand seems to be the sum total of their missteps.’

As a rule, blaming the chief executive for bad PR is much too easy an excuse, and it’s true that in some respects Uber is the scapegoat for wider trends that it epitomises. It’s almost impossible, however, to separate Uber’s missteps from the mistakes and personality of its co-founder and CEO, Travis Kalanick.

A brilliant jerk?

It was Kalanick who shouted abuse at an Uber driver complaining about the company’s changing terms bankrupting him. It was Kalanick who joked about an imaginary ‘woman-on-demand’ app called ‘Boob-er’. It was Kalanick who more than any other Silicon Valley CEO stepped in it over Trump’s business advisory council.

He personifies the brash, brazen belligerence of Uber that rubs so many people up the wrong way, not least among them Jeff Jones, the company’s president, who resigned recently due to ‘differences over beliefs and approach to leadership’.

There are a lot of people, possibly including Uber’s investors, who might be wondering whether the wrong person left. Kalanick’s had a good run, but is it time for him to go?

Stone’s not convinced. ‘Without Travis, it’s hard to imagine what Uber is. He hit the accelerator at every junction, he conceived of it as this frictionless thing where you put an app in every car and own no assets. Even though he wasn’t the inventor of the product, he was the architect of the business model. Obviously he’s got to mature a bit, but the company’s very much tied to his identity.’

The same is true of Kalanick’s counterpart at Airbnb, Brian Chesky. They’re pugnacious, charismatic, extroverted, scrappy, the sort to be cracking jokes at a keg party (not to say anyone else would necessarily be laughing...) while the Bill Gates of this world were sitting at home with a nose bleed.

This is no coincidence, Stone argues. Both are by their nature controversial businesses, which means they were always going to get into fights.

‘Three months after Uber launches in 2010, it gets a cease and desist order from the city of San Francisco. That pretty much replicates all over the world. A Facebook or a Google could be inwardly focused, absorbed with the mechanics of their own business for a decade. Bill Gates probably went 20 years thinking he didn’t have to talk to a regulator. Uber and Airbnb had to start being lobbyists from very early on,’ says Stone.

At the same time, Kalanick and Chesky needed to be able to sell a concept that most investors and the general public initially found highly suspect. ‘We’re doing things our mothers told us never to do – get into a stranger’s car, walk into a stranger’s home,’ says Stone.

And when something goes wrong – horror stories of rapes and deaths are hardly unheard of – you need a fighter in your corner, not a wall flower. ‘The chapter of my book about the non-starters [early rivals to Uber and Airbnb that never made it] is there to demonstrate what it looks like when you’re not a jerk.’

Or a war CEO?

Kalanick was the perfect leader for Uber’s meteoric rise. Sidestepping outdated regulations, he attacked unprepared and often highly inadequate incumbents in cities across the world with superior technology. By the time the regulators got around to doing anything about it, Uber was too big – or at least, too popular – to fail, protected by an army of loyal users that Kalanick had mobilised.

But is that what’s required now? Entrenched across the world, Uber isn’t fighting for its life any more, in the way it once was. Stone sees parallels with Amazon, which in its early days sidestepped sales taxes (‘oh, we don’t have operations in that part of the world, sorry’) before coming to a negotiated settlement with authorities. But the fight, he says, is hardly over – and won’t be until regulators stop launching fresh assaults.

‘Uber’s here to stay, variants of it are legal everywhere, but the battle is now on supply. Can you take that frictionless process and say everyone’s got to take an English exam, and as a result 20% of your drivers will fall off the system? That’s not an existential threat but it could constrain growth.’

In ‘peacetime’, when (if?) Uber is an accepted part of the status quo, its investors may prefer a slick sweet-talker, but for the time being they need a war CEO.  That, above all, is why the board has defended Kalanick and will likely continue to do so.

No amount of bad publicity – or for that matter, leadership training, sober new COOs or diversity programmes – will change that, and nor will it change Kalanick. But as long as Uber’s bad publicity isn’t affecting its growth, perhaps it doesn’t need to.

The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World, by Brad Stone, is published by Bantam Press

Image credit: Heisenberg Media/Flickr


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