The many tech CEO fails of 2019

The end of the year is often presented as the perfect opportunity to take stock of one’s life. After all, what better time to embrace a loved one or to raise a glass and toast to friends? 

In 2019, one completely reasonable way to participate in this annual tradition is to acknowledge all the ways you didn’t fuck up the lives of those around you — unlike the many, fabulously wealthy technology CEOs that graced this year’s headlines.

With that in mind, let’s take a stroll down the pothole-ridden memory lane that is our modern era. On your left, marvel at the C-suite executives busily chipping away at the support structures of our barely taped-together society. On your right, observe the mess of labor violations, environmental catastrophes, and surveillance-state nightmares born of their efforts. 

Thankfully, our metaphorical crumbling street has plenty of schadenfreude to spare. Please, go ahead and help yourself. 

The Facebook CEO (and definitely real human) has had quite the year. While his wealth remained stratospheric, his reputation took a slightly less soaring path. The downward spiral was kicked off in part by a series of scandals and missteps that will, if we’re all still paying attention, haunt Zuckerberg for quite some time. 

Most recently, the CEO was grilled by Congress on his platform’s abysmal civil rights record. But that, most certainly, was not all. There was also the $5 billion fine from the FTC, the “clear history” tool that didn’t really clear anything, and that time Zuckerberg implied Facebook could have prevented the Iraq war. 

We should also decidedly not overlook the time Facebook co-founder Chris Hughes called for the company’s breakup, or when Zuckerberg’s cryptocurrency project repeatedly ate shit. 

Oh, and because why the hell not, Zuckerberg had a secret dinner with Donald Trump to help his trash year go down even further in flames.

You’d think someone carefree enough to crush liters of beer next to inflated lady bugs would have had a pretty relaxed year. And, well, usually you’d be correct. Unfortunately for Apple CEO Tim Cook, he seems to be the exception to that otherwise tried and true rule.

Let’s start with a topic ostensibly near and dear to Cook’s heart: privacy. While the CEO has repeatedly spoken about the importance of customer privacy, Apple’s flagship product, the iPhone, had a notorious privacy-violating blunder earlier this year. 

Remember the FaceTime bug? A simple trick gave bad actors (or teenagers) the ability to remotely turn on an iPhone’s microphone and, in some cases, camera. It was bad. It was really, really bad. 

Some other notable fails include Cook’s inability to stand up to Donald Trump, a seeming capitulation to the Chinese government, and, on a lighter note, the moment when he got lectured by Trump on iPhone design. 

Bottoms up, Tim! Next year is sure to improve. 

When you’ve mastered a potential sexting scandal, there’s nothing quite like screwing over middle America to really get the blood flowing. 

Amazon CEO and not-style-icon, Jeff Bezos, may be secure in his worldly riches, but even Scrooge McDuck-level wealth can’t make up for his more personal failings. 

His company’s efforts to sell facial-recognition technology to the government earned him widespread condemnation from human rights groups. That, combined with Amazon’s zero-fucks approach toward customer privacy represent substantial moral failings, if nothing else. 

One company alone is insufficient to contain the many fails of Elon Musk. 

The CEO of (among other things) Tesla, was recently forced to face the limits of engineering in the high-profile Cybertruck window-shattering incident pictured above. We’ll give him a pass on that, however, and instead call to mind Musk’s fantastic ability to continually dig himself deeper — a skill exemplified by the “pedo guy” defamation trail. 

Remember that? When Musk called a rescue diver a “pedo guy” on Twitter only to get sued by said diver? Yeah, that trial happened. 

And, while perhaps less of a legal headache, Musk’s spring release of an “RIP Harambe” rap is its own brand of train wreck. This, notably, came before the CEO temporarily deleted his Twitter account in June. It was also before Virginia transit officials mocked his Boring Company’s efforts to build futuristic car tunnels.

But, hey, as each succeeding year of the last decade has taught us, it could have been worse. It can always be worse. 

Which is something to keep in mind as we all silently pray for the repeated champagne toasts to wash away the last memories of 2019.