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In Pictures: The 12 biggest gaffes by high-tech execs

Tim Cook admires Macs running Windows. Mark Zuckerberg flop-sweats. Marissa Mayer fancies herself a graphic designer. The bigger the names, the bigger the embarrassment when things go awry.

  • The 'oops!' heard 'round the world Late last week, Apple CEO Tim Cook tweeted a photo of himself touring a Texas factory that produces Mac Pros. Nothing special, right? Until you looked behind him and spied a pair of iMacs running Windows. Oops. Now, Cook’s gaffe was minor and harmless, but it’s hardly the first time a tech exec has made a highly visible mistake. Let’s take a look at some of the more memorable ones, starting with a big promise that never paid out.

  • What's a few GHz, more or less? At 2003’s WWDC keynote, Steve Jobs stood onstage and announced the Power Mac G5. Powered by dual 2.0GHz PowerPC 970 processors, the top-of-the-line G5 was the fastest Mac that Apple had released to date, and according to Jobs, it would reach 3GHz within a year. Technical challenges hampered the PowerPC 970’s development, though, leaving Jobs in the uncomfortable position of having to explain why the Power Mac G5 was stuck at only 2.5GHz the following year. The moral? Always err on the side of caution when discussing future products.

  • Ballmer laughs off the iPhone If someone comes along and shows you the future, you probably shouldn’t laugh at it. Microsoft’s Steve Ballmer learned that the hard way when he laughed off the iPhone in a January 2007 interview. Ballmer pooh-poohed the iPhone as being too expensive and said its lack of a physical keyboard “makes it not a very good email machine.” Keyboard-less phones quickly took over the smartphone market. Microsoft’s Windows Mobile OS fell further and further behind iOS and Android. It wasn’t until Windows Phone 7’s release in 2010 that the company had a proper, modern, touchscreen-centric mobile OS.

  • Sad Larry Page is sad :’( The keynote at Google I/O 2013 was already a long, disorganized mess when Google CEO Larry Page took to the stage to discuss Google’s vision of the world. Over the course of an increasingly agonizing and awkward 45 minutes, Page expressed sadness at the state of the tech industry. The Internet did what the Internet does best and proceeded to make a mockery of Page’s seemingly earnest comments, complete with the obligatory parody Twitter account. If you’re a tech CEO, do not underestimate the Internet’s propensity for snark and sarcasm.

  • A Flash in the 'Pad It’s hard to believe now, but the lack of Flash on iOS was once a controversial topic. In January 2010, when introducing the iPad to the world, Steve Jobs demonstrated the new tablet’s web-browsing prowess by visiting a website...that required Flash. When the blue “missing plug-in” icon appeared in place of Flash content on the page, some members of the audience actually chuckled. With all the care Jobs, the master showman, put into his presentations, it was surprising that he failed to sidestep a perceived shortcoming of the product he was demonstrating.

  • Zuckerberg can’t stand the heat Mark Zuckerberg isn’t known for his stage presence. Or rather, he is known for it, but for all the wrong reasons. Case in point: His appearance at the 2010 D:All Things Digital conference. While onstage fielding questions about Facebook’s privacy practice, Zuck was seriously sweating it—figuratively and literally. He fumbled over questions and was sweating so profusely that Kara Swisher and Walt Mossberg actually stopped the interview to ask him if he’d like to take off his hoodie. “I never take off the hoodie,” Mark replied. Moments later, he succumbed to the heat and took off the hoodie. Good call, Mark.

  • Zuckerberg, meet Samberg (as Zuckerberg) At Facebook’s 2011 F8 conference, comedian Andy Samberg opened the keynote, dressed as Mark Zuckerberg. After a few minutes of Samberg’s impression of Zuck, The real Zuckerberg stepped out...and couldn’t keep a straight face. It's just as awkward as it sounds, but you’ve got to admire Zuckerberg’s sense of humor.

  • Eric Schmidt says creepy things While CEO of Google, Eric Schmidt had the tendency to say things that were sure to give just about anyone the creeps. Take, for instance, this list of unnerving quotes from Fast Company, and this one from Gizmodo. And then there’s this gem: “We know where you are. We know where you’ve been. We can more or less know what you’re thinking about.” Right. I think I’ll go hide in a cave now.

  • Carol Bartz tells Michael Arrington where to go Former Yahoo CEO Carol Bartz isn’t afraid to speak her mind, and vividly at that. At TechCrunch Disrupt 2010, Bartz took issue with a question from TechCrunch’s Michael Arrington, and in a testy response, told Arrington to “f**k off.” Onstage. In front of a live audience. Tell us how you really feel, Carol.

  • Leo Apotheker reverses course on WebOS In April 2010, under then-CEO Mark Hurd, HP announced it had bought Palm for $1.2 billion. Less than four months later, Hurd found himself out of a job, and Leo Apotheker became HP’s CEO in September. Apotheker initially made Palm’s WebOS a priority: HP announced the TouchPad tablet in early 2011, and stated that it would ship PCs with WebOS in the not-too-distant future. Through the spring and early summer, Apotheker affirmed HP’s commitment to WebOS, going so far as to reorganize HP’s PC business to ensure WebOS would make its way into as many HP products as possible, according to BusinessWeek. But by August, the dream was all but dead when HP unceremoniously killed off its WebOS-based phones and tablets. HP’s board of directors canned Apotheker a month later and hired former eBay CEO Meg Whitman to take his place.

  • Marissa Mayer designs things If you’re going to hype your new logo with a marketing gimmick, you'd better deliver. Too bad Marissa Mayer didn’t realize this in September 2013, when Yahoo introduced its new logo at the end of its “30 Days of Change” hype-fest. The new logo, which Mayer herself helped design, was not well received, and it quickly became the butt of Internet jokes.

  • App.net is profitable—because it has no employees This one sounds like something straight out of a Dilbert comic strip. In May, App.net CEO Dalton Caldwell announced that enough people had renewed their membership in the social network for it to be “profitable and self-sustaining on a forward basis.” Good news! Except he had this to say in the very next paragraph: “The bad news is that the renewal rate was not high enough for us to have sufficient budget for full-time employees” Oof. Maybe it would’ve been better to just come out and say that your company is in financial trouble.

  • Woz takes to the ballroom floor Say what you will about Apple co-founder Steve Wozniak, but the guy clearly does not shy away from trying new things. Case in point, in 2009, he was among the celebrity dancers on ABC’s Dancing With The Stars. Although his stint on the show had some memorable moments—like when he danced The Worm—Woz was booted from the show in Week 4.

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