Box's Aaron Levie Is Business Software's Outlandish Old Soul

Aaron Levie, the chief executive officer of Box, has this insane mound of unruly hair. It’s his thing. He tugs at it when talking, as if pulling words and ideas right out of his brain. He makes fun of it when speaking on stage. So do other people. At 28, this hair abomination should be as dark as it is thick, but it’s not. It’s gray, or at least graying rapidly on the sides and pretty quickly up front and on top.

The joke could easily be that Levie’s hair is gray because he works too much. That’s not quite it. Levie, by all accounts, does work an intense brand of odd hours—something like 10 a.m. to 3 a.m. The gray thing, though, comes from his most unusual place as the preternaturally old soul of business software.