10 Most Embarrassing Geek Photos

10 Most Embarrassing Geek Photos

NICK DOUGLAS — Underneath all that decorum and collared polyester, geeks have crazy personalities waiting to bust out. Normally they have to suppress those personalities to appease investors and look like Real Important Bosses. But when they find their time to shine, they pull poses that would make Star Wars Kid proud. Here are the top ten photos some geeks wish time forgot. (Warning: some shots are a touch NSFW.)

10 Most Embarrassing Geek Photos



He's so...what's a word that's almost but not exactly the opposite of dreamy? Actually, there's some hipster charm to that tousled-haired boy genius known as Bill Gates. What do you think is going through his mind as he gazes at the camera with bedroom eyes?

10 Most Embarrassing Geek Photos



I won't pretend that venture capitalist Steve Jurvetson, who invested in Hotmail, Skype and other companies after working at HP and Apple, is chagrined by a photo that he uploaded himself. Even if he looks like Star Trek ensign Wesley Crusher on summer vacation.

10 Most Embarrassing Geek Photos



Before Sergey Brin founded Google, apparently he was one of those sitcom characters who dresses in drag for an episode, leading to a wacky adventure in which some burly guy thinks he's a hot woman. As well as that dress fits, Sergey is no Bugs Bunny.

10 Most Embarrassing Geek Photos



Even exhibitionist tech pundit and former Tech TV star Chris Pirillo eventually got embarrassed over this shot of him baring it all in Alaska. At least he has the best ever argument for shrinkage.

10 Most Embarrassing Geek Photos



Philip Kaplan of FuckedCompany, however, has no such shame. That's why, if Marshall McLuhan is the patron saint of Wired, "Pud" is the patron saint of Valleywag. The man who danced around the ashes of the dot-com crash waltzed around with two girls in a live webcam stream. Try sticking that on YouTube.

10 Most Embarrassing Geek Photos



You can tell Michael Arrington is not sure what he's doing in this photo with marketer Tara Hunt, but even after he learned, the TechCrunch blog founder pulled the shocker back out months later.

10 Most Embarrassing Geek Photos



Why are 37signals founder Jason Fried and the founders of San Francisco web-dev house Adaptive Path so embarrassed by this bathtub shot by Maggie Mason? It reveals them for the sexy city slickers they are. Besides, in San Fran, just be thankful they were wearing their swim trunks (though for all we know, Jason could skinny-dip in the tub).

10 Most Embarrassing Geek Photos



Microsoft staff, 1978. Bill Gates is actually proud enough of this photo to keep it on his corporate biography page.

10 Most Embarrassing Geek Photos

10 Most Embarrassing Geek Photos



I can understand the topless photo of bloggers Robert Scoble and Shel Israel: they were pulling a stunt for their book Naked Conversations (back when Scoble spent more time getting naked and less time being a dick). But the naked-with-laptop shot? Dude, maybe it would have worked if you didn't flop your tits over the screen.

10 Most Embarrassing Geek Photos



I've always felt that RSS guru Dave Winer had some latent cause for all the aggression that makes him abuse so many people. What could that possibly be? He looks happy here in this sauna full of naked young men. Aha, obviously there's Dave's hidden passion: he's a closet lover of hot...sweaty...climates. That dirty Californian rainforest-botherer.