The Fall of the Cool CEO

CEOs used to be seen as cool. Now, not so much.

By: Peter Nomeland

"You're going to go through life thinking that girls don't like you because you're a nerd. That won't be true. It'll be because you're an asshole."

That's what Rooney Mara's character in "The Social Network" tells a fictional version of Mark Zuckerberg as she breaks up with him. I've thought about this line recently, especially after Tesla founder Elon Musk broke up with Grimes, ending one of the weirdest celebrity relationships in recent memory. The fact that we are so aware of who Zuckerberg and Musk are and their roles in our society is one of the more underrated and weirder developments in the boon of the digital age and the boon of Silicon Valley that caused it. Especially given that not all that long ago, tech CEOs were seen as mysterious and admired figures. They were cool. Now, it seems more like they are understood to be one, way too rich, and two, not cool in any way whatsoever.

Musk, who is in a back and forth with Jeff Bezos for the title of the richest man in the world, has emerged as one of the most polarizing figures in this discussion. Once known mostly as the guy who makes eclectic cars and wanted to go to space, Musk has become a controversial figure in recent years, from his politics to his labor practices at Tesla. He has a large internet presence, which has been the catalyst of some bizarre behavior in recent years, including when he strangely got into a Twitter fight with one of the Thai Cave rescue. Weirdo behavior

Zuckerberg, on the other hand, is much less confrontational than Musk, or even his portrayal in "The Social Network." Although he was the subject of that film and was the youngest TIME Magazine Person of the Year, he is mostly seen today as a weird, disconnected, and heavily memed figure who runs Facebook. In the years since "The Social Network," the company has come under fire for privacy concerns, misinformation, and your distant relative's weird oversharing. And as he's gotten older, the seemingly innocent baby-faced nerd persona of Zuckerberg faded, and Jesse Eisenberg's cold portrayal feels like real life by the day.

And there kind of lies the problem. All of these guys want to be Steve Jobs-like figures who, despite their flaws, are still admired by the masses, but the difference between then and now is we know so much more about these guys. Crucially, just because you have a ton of money and are a front-facing leader of an influential company does not mean you are seen as cool. 

As I write this, there are currently three shows that are about the rise and fall of CEOs that detail what happens when people try and replicate the "cool CEO" archetype, "Super Pumped," about Uber, "WeCrashed," about WeWork, and "The Dropout," about Elizabeth Holmes and Theranos. Theranos was a blood-testing company that proved to be a scam, and Holmes was recently convicted of several charges. She famously would wear black turtlenecks to look more like her childhood idol, Steve Jobs. In the show, she's shown to have a poster of him in her room. I guarantee you that no one has a Mark Zuckerburg poster.