What Uber Did

Do you remember your first Uber ride? Mine was New Year’s Eve 2012; one of my best friends booked an Escalade for 10 people. At that time, the two-year-old company was mostly just a fancy online way to rent a limo. When we all jumped out of the massive luxury SUV in downtown Philadelphia, it felt like an incredibly ostentatious performance, one that I remember thinking that I would only use for special occasions. There was no way this would become a normal way of getting around a city.

Just about two years later, in late 2014, Uber’s that opened up questions about a culture of discrimination and sexual harassment at Uber. Kalanick had already made sexist comments that primed people with an arrogant tech bro image, but there was also something systemic about it.

I think founders set the tone at the top. The main priority for them was just getting growth, and Travis had a real aversion to feeling like a “big company.” But at the same time, they didn’t have proper systems to spell out quite basic internal processes. With that came complete disregard for legitimate problems like sexual assault or sexual harassment, or drugs and partying. It was just kind of built into the system. And then when you have a bunch of super-aggressive personality types running around, you’re setting yourself up to fail.

One of the mantras Kalanick had about Uber is the idea of “transportation that is as reliable as running water.” That’s something local transportation departments have been trying to do forever on their own. How does Uber’s notion of doing this map onto the “grow or die” attitude?

Travis wanted to compete for most, if not all, of transportation. I don’t think that he would have been satisfied with saying “We’re just going to get so many people, but then just leave existing ridership on public transportation.” I think they wanted to go for it. That’s why they did those carpooling options and shuttles. That’s problematic in and of itself, because it creates a cycle in which [transit] ridership goes down, perhaps funding goes down, and some fundamental public services start to see problems.

Then there’s another part that’s still playing out: the privatization of gaps in transportation. At one point, Uber was marketing itself as a last-mile solution. They were saying, “We’re the one that serves you in these transportation deserts.” The scooter and bike stuff is very experimental and I’m curious about how they can actually make money on it. But it’s just hard. Clearly public transit hasn’t served every single need, but it might be getting harmed by this private company moving in.

At the same time, how are these private transportation services shaping the way the city operates? It may be having effects that were not even planned for. In San Francisco, where I live, traffic has dramatically increased just by the amount of Uber and Lyft drivers coming in from halfway across the state because the city is the best place to drive for profits. There are all these effects that I don’t think anyone at the company could have really foreseen or has been able to head off.

After a decade, it’s almost impossible for some people to imagine not having access to ride-hailing apps. But Uber is losing multiple billions of dollars every quarter. Is this ever going to be a sustainable business?

People ask me sometimes what the endgame is. I actually don’t know. The company isn’t profitable, and the ways of getting to profit are either increase fares for riders or decrease pay for drivers or some other magic profit center from one of their many initiatives that I haven’t really understood yet. I’m curious to think five years from now what that’s going to look like. It’s a great big question mark. After 10 years of existence, it does seem indispensable. But what is this going to look like in another 10 years?

You mention briefly how different the world could have been if Lyft had been bought by Uber. How much has Lyft influenced Uber as a company?

For a lot of Uber and Lyft’s lifespans, at least pre-2017, they were basically defined against each other. Lyft was the good-guy foil and Uber was the bad-guy dominant player. Lyft almost went out of business, and Uber brought it back from the brink through its own stumbles. They exist as the yin-yang in ride-sharing, even though they are largely the same service and similar people drive for both companies.

Now ride-sharing is a hard category to be in, and both company stocks are taking a hammering. They’re both going to be pressed to prove profitability. So we’ll probably see changes, whether that means higher fares or drivers get screwed. In the private company world, they were both defined against each other; now, in a public realm, they are both just in the same category of troubled company.

Uber is also spending so much to research driverless cars, especially with the legal trouble it created for Uber with Google and Waymo.

It really dawned on Travis that he let the fox in the henhouse when he let Google invest in his company. Google is working on this business that could totally take over Uber one day. Whether you believe or not that driverless cars are going to save everything—I’m not convinced—I think there are a host of other issues that come with moving into that besides the fact that technology is just not there. [Kalanick] believed that it was totally existential and they needed to pour billions into researching it. They still are, and it’s curious to me what the future of it is going to look like now, because it doesn’t seem super important to [current CEO Dara Khosrowshahi] externally and some of the enthusiasm is dampened. Killing a pedestrian in Arizona was a big deal, and that really hurt public sentiment.

It also just feeds right into the hubris that people see in Uber, with not caring about the consequence for other people.

It’s hard because people that work there do consider themselves harbingers of progress. I think the mentality for a lot of people that work on big systems that disrupt entrenched things is that there are going to be side effects; not all of them are going to be positive, but we’re moving toward something bigger and better. The point of this book, for me, is to be willing to take a closer look at the side effects and pay attention to them. With all “progress” you have to see what the costs are and how those play out and who they affect.

Something that I did not understand the scope of before reading your book was how much cybersecurity plays a role in these companies. These apps are able to see where all of their users and drivers are, and they can identify them in so many other ways. One data scientist at Uber compared their view into the world as being an “ant farm.” Are we not paying enough attention to the power that Uber and Lyft have over regulators, drivers, customers, and even journalists?

Oh my God, it’s unbelievable. Honestly, take it further than Uber and Lyft: Just imagine any company with the amount of information they have and what they can do.

Once you get to a big-enough size, you’re supposed to limit the ability of any employee to access information about an individual user, or at least have the system flag if someone gets into their accounts. These are just safeguards because companies are made up of people and people are flawed. Uber didn’t have any of those controls for a very long period of time. It was basically a free-for-all for anyone’s data internally, and they played with that and they have very little regard for how they treated it. It was disturbing. They tracked a journalist from her ride over to meet someone, and they displayed the entire driver map of people taking trips to a dinner party in Chicago. It’s real scary.

This is just a theme of Uber. It shows the extremes of how irresponsible people can become when you have no rules, unlimited money, and everyone on the sidelines—at least in the Valley—is cheering you on to go take over the world. I don’t think every tech company is like this. There are good people in tech trying to do the right thing. But a lot of the worst in the Valley came out in at least some of Uber’s employees.

The central figure of all of this is of course Travis Kalanick. Do you view him as a tragic figure?

It is kind of a tragedy. A lot of employees thought I was going to be totally one-sided, but that was not really what I was interested in. I just wanted to tell a more full picture of this guy. I think a lot of the things that drove him to success also took him out in the end. The best CEOs can grow and mature with a company as it grows and matures. Uber grew so fast, and I don’t know if Travis was able to change or grow with his company. Perhaps that’s the tragedy of it—he’s an Icarus-type figure where he just rose so quickly but then he fell.

Or he may come back again. He’s still a billionaire; he’s got this new company. So who knows what’s going to happen?

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