Mark Zuckerberg's 13 Douchiest Moments

Image via Complex Original

Date: 2006

Zuckerberg’s outlandish pranks are well documented in David Kirkpatrick’s book, The Facebook Effect. Legend has it that he assembled a bogus slideshow based on a P2P side project called Wirehog to show investors at Sequoia Capital. The gag came about after board member Sean Parker convinced Zuckerberg the investment company would never invest in FB and blamed one of its power players, Michael Moritz, for his firing at Plaxo. Zuckerberg went into the meeting with a David Letterman-inspired presentation titled “The Top Ten Reasons You Should Not Invest In Wirehog,” citing absurd notions such as “Because Sean Parker is involved” and “We're only here because [a Sequoia partner] told us to come."

Date: Sept. 6, 2006 

Once Facebook introduced its News Feed, like all of its new features, millions of subscribers went ballistic and flooded the network with complaints. Zuckerberg’s response to everyone was a blog post titled "Calm down. Breathe. We hear you." Excuse us? The company’s PR savior Brandee Barker initiated some damage control by pressuring Zuckerberg to address users with a more subtle reply.

Date: Aug. 22, 2010

Blockzuck.com discovered the only person on Facebook that cannot be blocked is none other than the company’s capo. Anyone who tried to do so would be met with a "general block failed error" message. The site’s creator claims users were once able to block Zuckerberg. However, a Facebook rep went on to explain the ordeal: "This error isn't specific to any one account. It's generated when a person has been blocked a certain large number of times. In very rare instances, a viral campaign will develop instructing lots of people to all wrongly block the same person.” It's pretty obvious who made this call.

Date: January 2008

Since their first meeting in December 2007, Zuckerberg had his eyes on hiring the former Google executive. The two met up at a café in Atherton, CA and even in Sandberg’s home, but nothing transpired. Then came the World Economic Forum in Davos, where Zuckerberg managed to score a ride on Google’s private 767 with Sandberg and poached her throughout the entire trip right in front of Google executives. The rest is history. Larry Page should have duffed him for that one.

Date: 2005/2006

Zuckerberg's former ghostwriter Katherine Losse started at Facebook in 2005 and went on to expose the CEO's chauvinistic behavior in her new tell-all book: The Boy Kings. Losse recalls an incident where a male employee told a female worker at lunch "I want to put my teeth in you [sic] ass." The unnamed woman apparently brought the complaint to Zuckerberg, who addressed the remark at an all-employee meeting by saying, “What does that even mean?” Losse states she told Zuckerberg that sexual harrassment in the office was “unacceptable” and though she realized he listened to her every word...nothing registered.

Date: June 5, 2012 

In support of former partner and frenemy Sean Parker's new video chat startup, Airtime, Zuckerberg stepped into the ChatRoulette-esque environment and surprised a NY artist, Ronen V. Dude thanked him for creating Facebook and showed much enthusiasm throughout the convo, but told Betabeat.com that "after like 30 seconds he NEXTed me." On top of that, Zuckerberg didn't look all too thrilled to be on. So much for the favor.

Date: March 2008 

Former Facebook employee Katherine Losse recalls the moment when the team was introduced Sheryl Sandberg. According to her account, Zuckerberg held an all-hands meeting to get everyone acquainted with their new COO, but did it in the most inelegant fashion possible. His words: "Sheryl and I met at a party and we immediately hit it off…When I met Sheryl, the first thing I said was that she had really good skin…and she does." Classy.

Date: 2006

Back in the winter of 2006, Facebook executives, including Katherine Losse, rented a Tahoe house and got completely smashed. Losse recounts donning a bearskin, “complete with head,” that Zuckerberg found hilarious and had the company’s Facebook Photos creator snap a shot of her, which was then uploaded to an online album the following Monday. After seeing the pic, she noticed Zuckerberg “gesturing” at her arrogantly “like an emperor…commanding an employee, female, to submit.” Yep, that's exactly how it looks.

Date: Dec. 16, 2011 

Living true to his “I only eat what I kill” mantra, Zuckerberg played prankster by taking the head of a bison he slaughtered and hanging its head in Sheryl Sandberg’s conference room. Upon her return to headquarters, Sandberg was more than shocked to see the dead beast, which took up a good amount of space. Zuckerberg went so far as to nickname the bison Billy and drape it in a hoodie and Facebook fitted cap. 

Date: Jan. 4, 2012 

Months before taking the company public, Zuckerberg took then-girlfriend Priscilla Chan and several friends down to Uruguay’s southeastern coast for some R&R. But before heading out, he shot over a list of outrageous demands to the owner of the house he was renting. Not only did he demand all the furniture be removed and replaced, the house needed to be scrubbed down with “special chemicals” and each guest had to be given their own house servant. Guess when you’re balling like that you can be a dick with your demands.

Date: May 29, 2012

On his secret honeymoon in Rome, Zuckerberg and his wife grabbed lunch at a restaurant in Rome's "Jewish Ghetto" that tallied up to a measly 32 euros ($40) and left no tip behind. The owner, who goes by the name Umberto, claims the 28-year-old entrepreneur was extremely happy with his meal, but showed no gratuity when the bill came, leaving waiters shocked at his penny-pinching demeanor. Reports had him pulling the same stunt the night before at a historic trattoria in the heart of Rome called Pierluigi. 

Date: 2004 

“I have over 4,000 emails, pictures, addresses, SNS…People just submitted it. I don’t know why...Dumb fucks.” The infamous IMs shared by an anonymous college friend and then 19-year-old Mark Zuckerberg. Business Insider reports the exchange took place during the early launch days of The Facebook, with the CEO mocking users for their willingness to share personal data on the social network. He'll never live this one down.