6 Famous Tech Gurus And Their Less-Known Crazy Habits

by Mark Anderson

Silicon Valley is known as a hub of innovation, where tech geniuses create the world of tomorrow. Every kid with some coding knowledge wants to wind up there, hoping to become the next Steve Jobs or Mark Zuckerberg. But though millions of the brightest virgins from all over the world worship these gurus like they’re easily winded Greek gods, they ignore that their success comes at a cost. And more often than not, that cost is that these billionaires become really, really, really weird. For example …


Mark Zuckerberg And Jack Dorsey Like To Take Their Workers On Surreal Field Trips

Typically, interactions with your boss’ boss tend to involve you getting run over by their driver on the way to the bus stop. But some CEOs are more interested in their underlings than others. Ironically, in the tech world, it’s the titans of social media who place a lot of importance on having some face-to-face time with all of their employees. And leave it to guys like Mark Zuckerberg and Jack Dorsey to find a way to tell someone “You and I are going on a little trip” and make the outcome somehow worse than being murdered in a motel bathtub.

For Facebook employees, Zuckerberg’s reign of awkward terror begins even before they get their first paycheck. Potential Facebook recruits are sent a weird email telling them they’re wanted by the company. After arriving at Facebook HQ, they’re quickly shuttled to a private room, forced to sign a bunch of NDAs, and then poof, Zuckerberg appears. He then takes these headhuntees on a walk up in the woods around Palo Alto, where tells them its history of tech and innovation before he stresses how badly he wants their talent all up in his company. One such recruit described it as “surreal,” and like he “was on a date” — two interviewing techniques that are a surefire way of giving your HR department stomach ulcers.

Justin Sullivan/Getty ImagesHey, did you see that movie about how big a creep I am? Anyway, lets go into the woods alone!

At least the CEO of Twitter and enabler of dangerously mouthy world leaders Jack Dorsey waits until you’re in the door to unleash weird expeditions on his workforce. In his other company, Square, Dorsey rounds up all the new employees every Friday and drives them like cattle down to the statue of Gandhi outside San Francisco’s Ferry Building. Then, like a low-rent Aristotle, he walks them through all of San Francisco’s most important districts while he explains his “Four Corners of Square” philosophy. Both he and Zuckerberg keep these practices hidden from anyone not working for them. If you’re only comfortable talking honestly to people who’ve signed an NDA, you might be a crazed tech billionaire.


Shigeru Miyamoto Is Really Into Measuring Stuff

For middle-aged men, hobbies are a great distraction from constantly recalling all the promotions they didn’t get. Popular ways to keep the murderous rage at bay include repairing vintage cars, crying in sheds, and woodworking. But for Nintendo CEO and manic pixie old man Shigeru Miyamoto, it’s measuring stuff.

What Miyamoto, a genius games developer, finds the most fun ever is predicting the lengths and weights of stuff, then measuring it to see how close he got. The man carries a tape measure everywhere. “For instance, I might guess that the table in front of us is about 1.2 metres long,” he told Nintendo.com. “Then I’d actually measure it with the measuring tape to check. If I got it right, I’d think: ‘I’m on form today!’ But if I missed the mark by a long way, I’d think: ‘I’ve been slipping a bit recently!'”

Kevork Djansezian/Getty ImagesYup, the guy who created Mario no longer lives in the same zip code as fun. That may be the most tragic thing weve ever heard.

He claims to have developed this habit when he first began building a house, which is interesting, as we’d figure him to be more of a brick-breaker than bricklayer. He’s so devoted to his measuring craft that Jimmy Fallon made an entire game out of it when he was on his show:


Peter Thiel Is A Straight Up Doomsday Vampire

Peter Thiel is known for many things. He co-founded PayPal. He owns a big share of Facebook. He was the first (openly) gay man to get on stage at the Republican National Convention. He bankrupted a major internet publication because they were mean to him. He’s a powerful, clever, driven man.

More importantly, he’s just. The. Freaking. Weirdest.

Let’s start off with the least crazy shit this maniac is known for: seasteading, aka making the plot of Waterworld actually happen. Thiel, an avid Trump supporter, has this weird little notion that freedom and democracy aren’t really compatible. As a result of this mindset, Thiel is investing heavily in creating floating islands where he can cast off the confines of this failed experiment we call America and impose a bunch of wonderfully oppressive regimes. To achieve his goal, Thiel dropped $500,000 on founding the Seasteading Institute, which is exactly as ridiculous as it sounds.

The Seasteading InstituteAt least it looks like itll devolve into a scenic Bioshock-esque nightmare.

Nevertheless, he still managed to drum up support for it in Silicon Valley — enough that earlier this year, they convinced the French Polynesian government to start letting them build their own floating city out there. Because it isn’t a proper libertarian utopia unless you include some third-world country weak enough to bully with your money.

But tax evasions aren’t the only laws Thiel wants to get rid of. He also wants to undo the laws of nature and time themselves. Thiel is a big fan of eternal life — his own, more specifically. His current goal is to live to be at least 120 years old, and to achieve that, he’s been putting a lot of crazy stuff in himself. Thiel has openly admitted that he’s experimenting with small doses of Human Growth Hormone, which you probably know best as that substance banned by Major League Baseball and that thing that got Lance Armstrong in trouble. But bulking up on weird hormones is nothing compared to his other life hack: parabiosis, a process which entails Thiel injecting himself with the blood of a much younger person. Drinking blood, defying nature, building his own nation free from the laws of man … has anyone ever seen Thiel walk into a church without catching fire?


Jack Ma Of Alibaba Uses His Conferences To Perform Musical Numbers

Alibaba has become an online retail juggernaut over the past few years, and it has famed entrepreneur Jack Ma to thank for that. Ma is the rare kind of CEO who’s both a savvy businessman and a natural-born showman. But sometimes his showmanship gets the better of him, suggesting that deep down, he never wanted to be a businessman. He wanted to be a star.

Ma has a tendency to derail his own company conferences with elaborate entrances. And when we say “elaborate,” we mean “headlining at Madison Square Garden” elaborate. Our favorite has to be when Ma, at his company’s 18th birthday party, arrived on stage performing a Michael Jackson tribute act — Ma-chael Jackson, if you’re nasty. During the performance, a masked Ma-chael rode out on a motorcycle, and as “Billie Jean” pumped out of the speakers, Ma-chael started to hip-thrust to no audible beat. If you can’t see the glorious video of his performance, imagine if that afternoon you spent trying to learn how to moonwalk had been directed and produced by Michael Bay.

Youku, via YouTubeWe saw 6 percent market penetration growth in the previous fiscal quarter. Shamona!

Eventually, after dancing like a shop teacher chaperoning junior prom, the MAsked MAn was revealed to be Ma, and some weird boxes popped out on stage to reveal a slew of Alibaba employees dressed like goth marionettes, who then started marching to the beat of “Black Or White.” It might not be a great message to send, having your employees literally dance to the tune of your madness while dressed as terrified puppets, but we’re pretty sure Ma gave more thought to that skit than anything else in the entire fiscal year.

Ma’s Michael Jackson tribute wasn’t the first of his community theater antics. In 2009, at a conference hosting more than 1,600 people, he busted a rendition of “Can You Feel The Love Tonight” while wearing a Mohawk, black lipstick, and a fake nose ring — something that really needs to be seen to be believed.

One attendee later recalled that “people outside of the company thought he was crazy. But those of us inside the company knew better.” They knew better than to call a billionaire who has thousands of unmarked shipping containers and a flair for the dramatic “crazy,” we assume.


Former Uber CEO Travis Kalanick Gave His Employees Unsolicited Sex Advice

Intimate conduct between co-workers has always been risky business, especially when one of the parties is signing the other’s checks. But while the fantasies of middle managers have birthed an entire porn genre about all of the creative ways a secretary can ask for a raise, in the real world, that kind of inappropriate behavior is finally getting shut down, with sexual harassment suits ousting many a powerful creep these days.

And speaking of sexual harassment; let’s talk about Uber.

Onfokus/iStockA topic they have some working knowledge of.

In 2017, Uber was hit by a torrent of claims of poor treatment of women, and that’s putting things lightly. Proving that trickle-down economics do work for bastard behavior, the accusations started up top with (now-former) CEO Travis Kalanick. Back in 2013, Uber was celebrating its launch in Miami, Florida — a city where it’s considered weird to not snort cocaine off of someone’s genitals on a Friday night. In order to keep things nice and PG, Kalanick reasoned that it might be a good idea to let his employees know that there would be some boundaries. He told them:

You better read this or I’ll kick your ass.

Strong start, threatening physical harm against your employees. Guess someone’s serious about sexual etiquette.

Do not have sex with another employee UNLESS a) you have asked that person for that privilege and they have responded with an emphatic ‘YES! I will have sex with you’

OK, so far so good, if you if ignore the whole “my Roman orgy, my rules” vibe. But Kalanick’s not finished.

AND b) the two (or more) of you do not work in the same chain of command. Yes, that means that Travis will be celibate on this trip. #CEOLife #FML.

There’s a lot to unpack there. How many company threesomes does Kalanick think are happening in Accounting? Is he referring to himself in the third person, like a sex-obsessed Elmo? And did he really describe his frustration about not getting to bang his own employees in hashtags? No wonder women don’t feel safe in his cars.


Bill Gates And Steve Ballmer Have A Weird Comedy Double Act

For as long as they’ve been around, Apple’s key marketing strategy has been that Windows PCs are awkward and nerdy, like your dad, while Macs are effortless cool kids, like Justin Long, somehow. And if you think Microsoft is run by just a bunch of lame dads who are into spreadsheets and updates … you’re mostly right, but there are a couple of exceptions.

For those who can’t watch, imagine Rick Flair in business casual.

That video features Microsoft CEO Steve Ballmer looking like he’s snorted about four lines of cocaine in order to get over some pretty crippling stage fright. Ballmer is a wild man on stage, notorious for his desperate energy and so so so much sweat. If you want your presentation to be hosted by someone who looks like he collects model train sets but acts like Gary Busey off his meds, Ballmer is your guy.

While a sound businessman behind boardroom doors, in public, Ballmer cultivated a reputation for playing the wacky sidekick to Bill Gates’ “so straight I can’t dance” straight guy. We can see why.

The pair also made a ton of silly company memos together, several of which have been “leaked” for the internet to enjoy — including bad SNL spoofs, sketches rejected from local middle school talent shows, and this always-fresh take on Austin Powers:

The downside of being the richest man on Earth is that no one feels comfortable slapping the bad ideas out of you anymore.

Isaac would happily sell his blood to Peter Thiel if it meant paying off his student loans faster. Follow him on Twitter.

Friendly reminder that Austin Powers was a whole beautiful trilogy you should watch now.

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