Every successful tech company has made a few dumb decisions. (For example, Cracked wildly overestimated the demand for articles delivered via morse code.) But there are flubs, and then there are failures so embarrassing it's a wonder anyone survived the debacle. 

AOL Employed A "Digital Prophet" Who Didn't Predict Much of Anything

"Futurist" is one of the all-time great aspirational jobs. Invent an important technology or nail one big prediction, and you can spend the rest of your career cashing mid-six figure checks for telling Sundar Pichai that one day we'll all be robots. But, just like "programmer" became "code ninja" and "social media coordinator" became "internet rock star," even "futurist" wasn't enough for a company trying to paper over deep systemic issues with cool lingo. And so, from 2007 to 2019, AOL employed David "Shingy" Shing, a "digital prophet." 

4 Embarrassing Moments In The History Of Big Sites  David Shingy Shing

Jarle Naustvik/Wikimedia Commons

Who, in fairness, is EXACTLY what you think a digital prophet should look like.

E-Moses began his career in AOL's marketing department but, like all great speakers of truth, found a higher calling (that came with a higher salary). But what is a digital prophet, you ask? No one was ever sure. All sorts of companies pay people to try to predict future trends or, in Shingy's words, to watch "the future take shape across the vast online landscape," but Shingy apparently did little beyond spewing cacophonous buzzwords. The Washington Post called him "everything wrong with corporate America" New York Magazine dubbed him a symbol of AOL's "uncertainty and aimlessness," and the Independent dismissed one of his lectures as "insane gibberish." 

That's probably because he told listeners "embrace always logged in," "remix our budgets and embrace the fact that our brands are being utilised," and, most crucially of all, "I think sound in the future is very, very important." That clears up his job description, right? He was a William Gibson villain. 

But it's not fair to judge the man based on one speech. There was also the time he presented AOL's CMO with a cartoon bear and said it was "a thousand percent" a metaphor. And he decreed that the time people spend on their phones at home should be dubbed HoMo, for HomeMobile. We can't believe that didn't catch on! 

AOL once paid for an article that declared Shingy "a nexus of brand and individual, thinker and marketer, and analog and digital, making him the perfect choice to lead this conversation." While that sounds like Satan introducing one of his more ruthless minions, the conversation in question was about "brand love," which, as a millennial Doctor Moreau human-brand hybrid, Shingy was somehow supposed to promote. And truly, no brand is more beloved than AOL, a staggering zombie that will die off the moment the last of our grandparents leave this planet. 

After years as AOL's public face of shambolic ineptitude, Shingy's now working "autonomously with brands to help then achieve optimal presence in the marketplace." Which probably translates to "Have you tried using Instagram? That'll be $300,000, please."

Netflix Announced A Terrible Rebrand Without Even Checking To See If The Name Was Owned

There's a good chance you're skimming this article while Netflix plays in the background, but in 2011 Netflix was still figuring out how to make their "Next Episode" button single-handedly annihilate sex lives worldwide. Their DVD rental service was still an important complement to their nascent streaming empire and, in attempt to maximize profits from both, CEO Reed Hastings announced one of the greatest dumb business ideas: Qwikster. 

4 Embarrassing Moments In The History Of Big Sites Google  search terms for Netflix's Qwikster DVD rental service

Google

The fact that autofill immediately jumps to 'Debacle' should give a good idea of how well it went over.

The idea was to keep their streaming service under the Netflix label while rebranding disc rental as Qwikster, then charge two subscription fees. Somehow, having two accounts and a larger bill would be "convenient." Absolutely everyone hated it. Users denounced it as an arrogant cash grab. The name was mocked for sounding like a knockoff chocolate milk powder brand. SNL ripped into it. So did CNN. The @Qwikster Twitter handle was owned by a teenager with a stoner Elmo avatar, who wanted six figures to turn over his account. Netflix's stock price plunged, and there were serious concerns about the company's future. Tech journalists compared the debacle to New Coke. 

Qwikster lasted all of one month, and about the only positive was that Hastings was praised for acknowledging the colossal scale of his screw-up instead of doubling down. Between the dumb affair and Starz deciding to not renew their Netflix contract, The New Yorker even predicted that Netflix would be reduced to "an arthouse or cinephile operation" rather than the "industry-dominating standard for streaming, as it so recently seemed poised to become." So hey, there's a lesson about not letting your biggest mistake define you. 

One Of The Founders Of Vice Went On To Found The Proud Boys

Vice is the number one website for people who want to stay abreast of current affairs while reading passionate opinions on CBD oil. It was actually founded in 1994 as a print magazine called Voice of Montreal, becoming Vice in 1996 to sound less like a bad indie album. And one of its three founders, Gavin McInnes, would eventually launch noted fascist clownshow organization The Proud Boys. 

Vice's early tone was ... different. Recent headlines are "Neo-Nazi Terrorists Planned Fortified Compound in Michigan" and "Police Use Fire Engine and Tear Gas to Arrest Georgia Opposition Leader," while old print stories include "Bukkake On My Face: Welcome to the Ancient Tradition of the Japanese Facial" and "The VICE Guide to Shagging Muslims." It was horny and edgy, at least in the sense that a 14-year-old white kid saying the n-word thinks they're edgy. 

4 Embarrassing Moments In The History Of Big Sites cover of Vice magazine of a guy giving the middle finger

Vice

Pulitzer material, right here.

A 2007 issue about Iraq signaled a shift to more serious ambitions, and in 2008 McInnes left. Supposedly it was over "creative differences," although he was being called a white supremacist as early as 2003 and advertisers had apparently grown sick of his political outbursts. But McInnes' primary gig at Vice was a fashion column dedicated to mocking people's outfits, so he tried to parlay that into a career. His departure email included the cringeworthy line "There's a ton of other projects in the works ... and I'll announce them as they blossom into fruition like a hundred humid vaginas in the presence of God's boner," and then he spent a few years trying to live off of calling people gay for wearing the wrong t-shirt. 

McInnes wrote a couple of books and launched a rival publication, although Street Boners: 1,764 Hipster Fashion Jokes somehow failed to make waves and his new site, Street Carnage, was just a sad, subpar attempt to recreate Vice's dubious early years. Their logo was a cartoon of McInnes and his co-founder urinating, and "DO ALL BALLS SMELL THE SAME?" was a typical headline. There were 10,000 sites like this in 2009, and so McInnes' flopped. 

4 Embarrassing Moments In The History Of Big Sites screenshot of a Street Carnage essay

Streetcarnage.com

Though it did actually keep limping along until 2017 with only the classiest of hot takes.

It turns out that if your whole shtick is pretending to be an off-putting creep, you might actually just be an off-putting creep. McInnes' entire post-Vice career was a string of boring failures, and so naturally he founded an organization based on punching people who don't think he represents the pinnacle of human development. His rambling screeds about the evolutionary superiority of white people take on a different tone when you realize that his career fell apart precisely because he couldn't change with the times. 

None of this is to say that you should necessarily dislike Vice for the actions of a man who left them 13 years ago. It's just really funny that McInnes helped launch the exact kind of publication he now thinks is destroying western civilization. 

Facebook's Election Misinformation Problems Run Deep

If you had a pulse in 2020, you were aware that Facebook struggled with its role in America's election. An endless parade of pages called Eagle Flag Lover 1776 tried to convince the dumbest people you went to high school with that Joe Biden is a staunch Maoist, but America is far from the only country where Facebook is used to crank out moronic propaganda. A lengthy memo written by former Facebook data scientist Sophie Zhang highlights the worst offenders, and while we don't want to make it sound too bleak, Zhang wrote "I have blood on my hands by now." 

Lowlights include the ruling party of Azerbaijan employing troll farms to harass journalists and opposition leaders, fake accounts singing the praises of Honduran President Juan Orlando Hernandez (whose narrow re-election in 2017 was, to use the technical term, sketch, leading to the murder and torture of protestors), and the widespread amplification of COVID misinformation, among other problems Facebook did their best to ignore because they happened in countries Mark Zuckerberg can't find on a map. 

4 Embarrassing Moments In The History Of Big Sites Mark Zuckerberg staring off into space

Frederic Legrand-COMEO/Shutterstock

...Mark?  Crap, he's frozen again.  Could somebody reboot Zuckerberg? This part applies to him.

Many of these efforts weren't subtle, but Facebook's efforts to fight them lacked both manpower and willpower. Zhang, a midlevel employee, had to make triage decisions, essentially deciding which elections would have to put up with the most BS. She was told to prioritize North America and Western Europe, and so elections that devolved into chaos -- like Bolivia's in 2019 -- were allowed to run wild with "inauthentic activity." 

Sometimes Facebook meddled for the worse, like when they ordered employees to stop applying the company's own hate speech rules to anti-Muslim posts made by members of India's ruling party. India is Facebook's largest market, and so powerful people got to ramble about how mosques should be burned down and Muslim immigrants should all be shot. Imagine your weirdest uncle's rants getting an official stamp of approval.   

Zhang found that her concerns were largely ignored unless she skipped official channels and used Facebook's internal message board to rile up employees and demand action. But even then, Zhang was told to focus on spam and PR problems; essentially, widespread election interference was only an issue if it produced bad headlines about Facebook. A frustrated and burnt-out Zhang was eventually fired. So hey, maybe a data-harvesting empire run by people primarily concerned about their stock options shouldn't have massive political power. We're just spitballing here!

Mark is on Twitter and wrote a book.

Top image: Jarle Naustvik/Wikimedia Commons, Johnny Silvercloud/Shutterstock

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