Uber's Wild Ride: NYT Reporter Digs Into Ride-Hail Giant's 'Whiplash' History

New York Times tech reporter Mike Isaac
September 4, 2019

Uber has seen its fair share of scandals, from raising prices on consumers in the middle of Hurricane Sandy to former CEO Travis Kalanick joking about a women-on-demand service called "Boob-er." Business Insider racked up a list of at least 49.

In his new book, Super Pumped: The Battle for Uber, New York Times reporter Mike Isaac charts the tribulations of the notorious ride-hail giant amid the world's reckoning with Silicon Valley and its promise to disrupt.

"I felt like Uber's a very dramatic story, with a lot of infighting and craziness," Isaac told Cheddar. "It felt like they really were the company that emblematized that the most. This is where you get obscene wealth and crazy power struggles and bro-culture all in one, very nice and tight-y package."

"I remember living in San Francisco in 2009 [to] 2010. I couldn't get a cab anywhere. Transportation [was] just not very great, all the time. The infrastructure was kind of crumbling," Isaac reminisces. "And this app comes along with the rise of the iPhone and makes it so that you can get a car almost immediately."

That convenience propelled Uber to become one of America's, and then the world's, most popular apps, but the company was frequently mired by reports of a reckless culture and inappropriate behavior by Kalanick. In 2017, he was forced to resign and Uber brought in former Expedia CEO Dara Khosrowshahi, who was tasked with pushing the company toward a public offering and reigning in costs.

But during the same period, tech was also forced to reckon with increasingly more aggressive ⁠— and critical ⁠— media coverage, Isaac explains.

"The past two years has really been this whiplash where everyone sort of realizes that tech is not just kids in hoodies doing fun things. It actually has very large effects on how we live our lives and go about things on a daily basis," he said.

When the company finally headed to the public market, it saw a less-than-stellar debut amid a slew of other 2019 tech IPOs, including its main competitor, Lyft.

Today, the tone around tech, Isaac said, has changed. He explains that we should expect more modesty, less Wolf-of-Wall-Street from Silicon Valley in the coming years. "I think it's going to be less about balling in the club and making it rain and more about keeping your head down and doing the right thing," he added.