Uber may be proof that ‘brilliant jerks’ are finally less welcome in Silicon Valley

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    20 Uber employees are being fired as the result of a 4 month investigation into the company’s toxic corporate culture. CEO Travis Kalanick is taking a leave of absence to “grow into the leader Uber deserves.” Kalanick has always been a polarizing figure, and many of the most successful tech CEOs have also been polarizing at times, from Steve Jobs to Mark Zuckerberg. What’s happening at Uber may be a sign that Silicon Valley’s historical tolerance for -and celebration of – “brilliant jerks” is changing.

After a four-month investigation into Uber’s corporate culture that resulted in the firing of 20 employees, cofounder and CEO Travis Kalanick is taking a leave of absence.

It could be a watershed moment for the tech industry and a sign that, finally, Silicon Valley will not tolerate “brilliant jerks” – effective leaders whose sometimes brash personalities can leave cultural issues in their wake.

This is a significant change from a few years ago – even months ago.

Historically, leaders who have been tough or controversial have built some of the most successful businesses, prompting the question of whether ruthless reputation actually helps you get ahead, especially in Silicon Valley.

‘Sometimes, assholes create great businesses’

A few years ago, I met with a lot of people to write an unauthorized profile of Travis Kalanick. Then, he was just a rising star with a startup worth $3.4 billion – a fraction of the nearly $70 billion investors think Uber is worth today.

Since then, I have spoken or met with Kalanick half a dozen times. In our interactions, I have never found him to be inappropriate or anything other than impressive. But since Uber’s inception, unflattering stories about him have circulated.

“Sometimes,” one acquaintance of Kalanick’s said to me during my reporting, “assholes create great businesses.”

Said another: “If Travis Kalanick is the Michael Jordan poster that young entrepreneurs have hanging on their walls, that’s sad. Being a jerk isn’t ‘awesome’ or ‘badass.’

Or is it?

Because everywhere you look, there are examples of billionaires who have behaved boorishly.

While Mark Zuckerberg is largely liked and respected now, it wasn’t always that way. He famously ousted his former friend, Eduardo Saverin, from Facebook after stealing his business idea from the Winklevoss twins. “Yah, I’m going to fuck them,” he told a friend over IM about the pair, as Business Insider first reported. “Probably in the ear.”

Twitter’s cofounders back-stabbed each other repeatedly: Founder Noah Glass was booted out of the company. Evan Williams and Jack Dorsey were both given, and then stripped of, the CEO title, which Dorsey has since reclaimed.

Snapchat CEO Evan Spiegel was sued by his former Stanford friend, Reggie Brown. Spiegel reportedly lost his temper with Brown and locked him out of the app shortly after it launched. College emails Spiegel wrote also show the 20-something founder used misogynistic language with fraternity brothers.

A Silicon Valley venture capital firm once told me proudly it declined to invest in Snapchat because of its founder’s behavior. A few years later, after Snap was worth billions, that same firm popped up on a term sheet.

The late Apple CEO Steve Jobs, one of the world’s most-praised entrepreneurs and Spiegel’s role model, was said to have two sides. Jobs’ biographer, Walter Isaacson, portrayed the late Apple CEO as “Good Steve” and “Bad Steve.”

Jobs, Isaacson wrote, once stormed into a meeting and called everyone “f—— d—less a–holes.”

Just because people have unflattering moments, it doesn’t mean they’re bad people. But they also haven’t been reprimanded very much for their behavior.

Until now.

Why bad behavior wins

Robert Sutton spent a lot of time conducting research for his book, “No Asshole Rule: Building a Civilized Workplace and Surviving One that Isn’t,” What he found was disappointing.

“Even people who worked with Steve Jobs told me that they’d seen him make people cry many times, but that 80% of the time he was right, ” Sutton said. “It is troubling that there’s this notion in our culture that if you’re a winner, it’s okay to be an asshole.”

It is troubling that there’s this notion in our culture that if you’re a winner, it’s okay to be an asshole.

The Atlantic’s Tom McNichol agrees. He wrote an article titled: “Be a Jerk: The Worst Business Lesson from the Steve Jobs biography.”

“Some aspects of personality have little or no bearing on whether a person performs well, and not a few people succeed in spite of their darker qualities,” he wrote.

So, is it possible to be nice and to be wildly successful in business? And in Silicon Valley, where people praise Steve Jobs’ bad habits, can you be financially rewarded if you’re nice?

“I want not to invest in jerks,” a London-based startup investor Eileen Burbidge told me a few years ago. “Personally I believe life is too short. [But] I have wondered if this is actually a bad philosophy as an investor. I’d like to think not but I’m supposed to back founders for the best ROI, not personality.”

I want not to invest in jerks …But I have wondered if this is actually a bad philosophy as an investor. I’m supposed to back founders for the best ROI

Mark Suster, a Los Angeles-based investor, also isn’t sure what to make of jerks in business. He listed “integrity” as a bonus characteristic when it comes to top entrepreneurs’ DNA.

“I believe that integrity and honesty are very important to most venture capital investors,” he wrote on his blog, Both Sides of the Table. ” Unfortunately, I don’t believe that they are required to make a lot of money.”

Many question whether Uber would have been successful at all if Kalanick wasn’t, as he calls it, “fire and brimstone.”

“As much as [Kalanick] is inspirational, he is controversial,” a former colleague of Kalanick’s said during my reporting. “If he were less brash, I don’t think he would get half as far as he did.”

Added another Kalanick acquaintance: “There is absolutely no way [Uber] would have gotten where it is without Travis and his arrogance. Not without him being like, ‘I’m going to take over the world.’ He has the Steve Jobs mentality that, ‘It’s my way or the highway.'”

Can nice guys finally finish first?

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Paul Graham has a “no asshole” policy for his startup accelerator, Y Combinator.
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Scobleizer via Flickr

Maybe now that Kalanick and his board are being forced to look in the mirror, things will finally change. Maybe Silicon Valley is finally ready for the nice guys to start winning, and for the rest to grow up.

One person who firmly believes you can be nice and succeed is Paul Graham. He created top startup accelerator Y Combinator and he made Sutton’s “no asshole” rule popular in tech.

“It’s certainly possible to build a multi-billion dollar startup without being a jerk,” Graham told me a few years ago, when I asked about the concept of brilliant jerks.

He added: “We’ve funded several, and the founders are all good people. In fact, based on what I’ve seen so far, the good people have the advantage over the jerks. Probably because to get really big, a company has to have a sense of mission, and the good people are more likely to have an authentic one, rather than just being motivated by money or power.”

Maybe Graham – like with many of his startup investments – was ahead of the curve.