Super Pumped: The Battle for Uber

by Mike Isaac

Behind the scenes, Uber was hardly innocent. Recruiting ex-CIA, NSA, and FBI employees, the company had amassed a high-functioning corporate espionage force. Uber security personnel spied on government officials, looked deep into their digital lives, and at times followed them to their houses.

shopworn San Francisco adage that it’s better to sell shovels during a gold rush than to actually prospect for gold).

There’s a familiar line of thinking among the technorati: Good ideas are important, but venture capital is all about making the right bet on the right person at the right time. When sizing up a founder, a venture capitalist asks: Will this guy—and in the sexist tech industry, it was almost always a guy—be the one to take a startup from a handful of hard-working kids to a Fortune 500 company someday? Will this guy stick around when the shit hits the fan? Is this a guy I’m willing to bet millions of dollars on?

The app shot up in the App Store rankings, especially after it began receiving glowing initial reviews from the press. TechCrunch, now the company’s favorite industry blog, hailed UberCab’s model as innovative and disruptive, something akin to “Airbnb for cars.” Ironically, in just a few years startups would begin to describe themselves as the “Uber for x.”

Kalanick had proven himself to all his doubters. By 2014, Uber was a transportation behemoth, backed by the best of the best in venture capital and expanding globally. His company was growing so fast his rivals could barely compete. And yet every time he looked at his mentions on Twitter, he’d read at least two or three tweets from random people calling him a jerk. Two technology reporters in particular—Sarah Lacy and Paul Carr—seemed to be on jihad against Kalanick, blaming him for the “asshole culture” spreading throughout Silicon Valley. GQ had made him look like a caricature of a “bro,” a dirty word in techland. The opening sentence of a Vanity Fair profile—which he had hoped would be balanced—said he had a “face like a fist.” “What the fuck?” Kalanick wondered.

Kalanick knew he had made some unforced errors. In the midst of the GQ profile, he let it slip that his newfound tech celebrity, and the attendant riches, made attracting women much easier now than it was when, say, he was living with his parents while building Red Swoosh. On-demand women, he joked, wasn’t that far off. “We call that boob-er,” Kalanick told the reporter. Suddenly, Kalanick wasn’t just a grown man-child in readers’ eyes, he was a blatant misogynist. One particularly cringe-worthy paragraph in the GQ story had Kalanick quoting the infamous Charlie Sheen, describing Uber’s potential success as “hashtag winning.” He name-dropped boutique hotels in Miami like the Shore Club and SLS as places he’d rather be than hustling at Uber. He was trying to be honest—and perhaps a little bit cool—but to the public he sounded like an enormous douchebag.

More than most other tech companies, Uber prized the almighty Masters of Business Administration, a degree that signaled business acumen and, often, an alpha male mindset. Not every MBA grad was an asshole, by any means. It just seemed that many of the ones who were assholes tended to feel at home joining Uber.

“There are two schools of thought about Arianna,” Mort Janklow, a former agent to Huffington for her Picasso book, told Vanity Fair in 1994. “One is that it’s all deliberate and calculated and she’s ruthless. The other is that she really convinces herself beforehand. She sells herself first.”

For every woman in tech who had deflected sexual advances from a superior, or endured an inappropriate comment on Slack; for every female founder who saw men land funding for their subpar ideas over better, woman-led startups—the Fowler post perfectly articulated the harassment, the bias, and the abuse built into the “meritocratic” systems touted so arrogantly by tech utopianists.

Not only is Mike Isaac a great writer but also an astute observationist Makes me want to go through and read his old articles on NYT

My reporter trick is to play dumb and friendly; dumb and friendly is always more approachable than eager and prodding.

Then there was the dark horse candidate: Dara Khosrowshahi. A career executive and the current chief of the travel and logistics site Expedia.com, Khosrowshahi made plenty of sense on paper. He was a Brown undergraduate in bioelectric engineering who later turned investment banker at Allen & Company.

Interesting because the other top contender Immelt, was a Dartmouth engineering undergrad with an HBS MBA

Khosrowshahi worked hard in high school to gain entry into the Ivy League. “There’s this chip you have on your shoulder as an immigrant that drives you,” he later said of his childhood.