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When Humor Makes You Rich – Aaron Levie And Box

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Aaron Levie, the funniest CEO in America (and possibly the world), just became one of the richest comics never to appear on Saturday Night Live. His company, Box, went public last week and I couldn’t be happier for him (and them). In the Silicon Valley world of self importance and taking the absurd seriously, Levie built a serious business while having a constant laugh and becoming the funniest tech guy on Twitter.

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And the funniest part may be that his company, Box, has a very “square” name and business model…being the most secure cloud file sharing/storage company around. His jokes may be funny to the masses, but his focus has been on the companies most serious about moving to cloud safely. The contradiction of his sarcastic humor and serious focus are maybe the charm–his wit hasn’t hurt him in setting Box apart from the pack. That matters because cloud may be just getting started but it has quickly become a crowded space of newcomers like DropBox and traditional plays like Microsoft.

Humor At The Cutting Edge Of Tech

I’ve been incredibly lucky to watch a couple of significant tech moves in my lifetime. The first was the world’s move to PC’s when I was very young (my parents bought an Atari 400) but still old enough to know it was something brand new. The second great tech revolution happened when the world discovered cloud computing and realized that the PC, with all of its quality and obsolescence issues, didn’t need to dominate our world.

The leading edge of sweeping change is usually (wait, always) button-down, geeky and certainly not funny. But the world needs more humor and I am a big fan of anyone who can be sarcastic when everyone else is being way too serious. If Levie’s success encourages more in the tech industry to take themselves a little less seriously and have a little more fun, I’m all for it.

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