The Silicon Valley Jerk Conundrum

Most people probably have no idea who Jeanette Symons was as a person, or even her name. Yet, she became one of Silicon Valley’s most famous entrepreneurs. She tragically died in the crash of her Lear Jet with her adopted son, some years ago. She is right up there with Steve Jobs in terms of her accomplishments, her intellect, and her utterly horrible personality. I worked for Jeanette.  This article from the San Francisco Chronicle is an excellent exploration of Silicon Valley entrepreneurs, and the “a**hole” conundrum of their eccentricities that can also make them highly successful. There has also been a recent major controversy about SV entrepreneurs arrogance and insensitivity to others. This is definitely NOT Canadian. My fear is that Canadians are not prepared for it. My students know that I have experienced this personally in my Silicon Valley career numerous times, most notably with the late Jeanette, founder of Ascend Communications, who was a notorious asshole like Steve Jobs. Not easy to reconcile it, other than to live with it. Human Resources people are an utter waste of time in situations like this. They have no idea what to do, can do nothing, and simply sit around waiting for Godot to arrive.  It all seems to work and few leave so long as the value of the stock options continue  to appreciate.

Why So Many Tech Founders Who Are Jerks Become Insanely

Rich And Successful

Alyson Shontell, provided by

Published 5:45 am, Saturday, January 18, 2014

“Startup DNA” is the idea that the world’s best entrepreneurs, like Steve Jobs and Jeff Bezos, have some inherent talent they were born with that made them successful.

The DNA is comprised of characteristics like “resilience” and “ability to accept risk.”

Another characteristic many top entrepreneurs share is arrogance. Or worse, just being a huge jerk. 

Recently, I met with a lot of people to discuss rising Silicon Valley star, Travis Kalanick.He’s the CEO of Uber, and his car-sharing service was recently valued at $3.4 billion. Friends have compared him to great entrepreneurs like Steve Jobs and Larry Ellison.

But Kalanick is a polarizing figure. He’s frequently described as both “awesome” and a jerk.

“Sometimes,” one acquaintance said of Kalanick, “–holes create great businesses.”

Another person noted how strange that concept was. How can people both both marvel atand dislike Kalanick?

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

Kalanick did not respond to a request for comment.

Outside of Silicon Valley, most people would agree. But inside, arrogance runs rampant and investors seem to reward ruthless behavior with piles of cash.

There are numerous examples of founders who have had moments of terrible behavior that later became infamous. The founders might not be jerks all the time, of course. Everyone has moments when they behave boorishly. But sometimes the stories are so unbelievable, it can leave a lasting negative impressive of the person — that whether criticism is deserved or not.

For instance, Mark Zuckerberg, who is now worth about $20 billion, famously ousted his friend Eduardo Saverin from Facebook. He also stole his business idea from the Winklevoss twins. “Yah, I’m going to f– them,” he told a friend over IM about the pair. “Probably in the ear.”

Snapchat CEO Evan Spiegel is in the middle of a lawsuit with his former Stanford friend, Reggie Brown. Spiegel lost his temper with Brown and locked him out of the app shortly after it launched. Once, Spiegel was so angry with his parents, he reportedly cut himself out of family photos.

Twitter’s co-founders back-stabbed each other repeatedly: Founder Noah Glass was booted out of the company. Ev Williams and Jack Dorsey were both given, and then stripped of, the CEO title. And Jeff Bezos, who runs Amazon, wreaks havoc in his organization by sending a single-character email: “?”

Even Steve Jobs, one of the world’s most-praised entrepreneurs, was said to have two sides. Jobs’ biographer, Walter Isaacson, portrayed the late Apple CEO as “Good Steve” and “Bad Steve.” An example: Jobs once stormed into a meeting and called everyone “f–ing dickless –holes.”

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

“Even people who worked with Jobs told me that they’d seen him make people cry many times, but that 80 percent 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 –hole.”

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