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Tech reporter Mike Isaac on whether you can build Uber without being a jerk

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The Vergecast interview

Illustration by Alex Castro / The Verge

On this week’s interview episode of The Vergecast, Verge editor-in-chief Nilay Patel sits down with New York Times reporter Mike Isaac to discuss Uber. Isaac has been reporting on the ride-sharing company for over five years, and he just released a book called Super Pumped: The Battle for Uber that lays out Uber’s rise and controversies.

The conversation covers how Uber got to where it is today, its interactions with companies like Apple and Google, and whether you have to be a “jerk” to start a company that changes the world. Below is a lightly edited excerpt of the conversation.

Nilay Patel: I think the big question raised throughout the book is: do you need to be that kind of founder to will this kind of company into existence?

Mike Isaac: Yeah, I put it less colorfully or more colorfully somewhere else. But it was just: do you have to be a jerk to build a world-changing company? And I don’t know if you have to be a jerk to build a world-changing company, but you might have had to be a jerk to build an Uber, you know? Just think of the barriers to entry in the taxi and transportation industries and how those differ from, say, a software business like Facebook. Mark Zuckerberg has made his fair share of enemies over the years, but he doesn’t have — or he didn’t, at least early on — like mob boss mafioso types ready to break his legs for entering their market or whatever.

So it definitely was a harder industry from the outset. And I think that took its toll on Travis [Kalanick]’s mind, along with the sense of distrust that he has for really anyone around him from being spurned by venture capitalists early on in his career.

As you’re writing the book, what’s the thing that you learned the most about these folks?

I think the question that I keep coming away from is: what does it take to build a great company? Do you have to be ruthless? Or is it like luck and timing, you know?

Travis has his strengths, and a lot of folks still wonder if they could have built Uber without Travis. But a lot of the stars really aligned to make Uber what it was during the time it was. There were lesser apps that kind of did the same thing that were around at the same time. But I think the ubiquity of the internet, the advent the iPhone, AWS becoming a thing... it just really took a lot of stars aligning to make this happen. And so I think part of it is luck, part of it is timing, and then part of it is: do you just have to be a ruthless jerk? Or can you be a nice company builder? I mean, I think about Steve Jobs. I think about, you know, what Larry and Sergey were like. I think about Zuckerberg and his sort of... Zuckerberg is a ruthless businessman. I know that firsthand.

And so I wonder if that’s just the laws of business. And maybe Uber had the unfortunate position of being the poster child of all the crappy things that one has to do or one can get caught doing on the way to building a huge company. But I would like to think that you can build something worthwhile and not be a jerk when you’re doing it.