Aaron Levie seems quite ruthless:

There is none of that consumer Web “build what you love, and the masses will flock” sensibility here. Levie doesn’t care what he wants to build. He wants to build what they want. He wants to solve their problems, allay their fears, and fulfill their deepest, nerdiest IT desires. And he wants to build the next multi-billion enterprise software company doing it.

Okay, so IS he competing with Dropbox or not?

It sure does look like it:

Box is in the news today for something that at first seems entirely counter to what I describe above: It’s releasing a new $5 per user plan that’s aimed for small business, and doubling the amount of free storage it offers from 5 to 10 gigabytes. “We think doubling down on the freemium part of the business will bring us into companies of all sizes,” Levie says.

From hoodies to suits... but he still wears sneakers.

Both told him to spend way more time with customers, and he has. He slowly migrated from hoody to the jeans-and-a-blazer combo to now wearing suits everyday. (Even if they are still always topped off by his famous Day-Glo tennis shoes.)

Aaron Levie likes history and butt kissing:

In a Valley obsessed with what’s new, Levie is obsessed with history. The only unifying themes to the Box conference rooms are words and names that hearken back to the company and the Valley’s big moments. While a young Mark Zuckerberg once asked Marc Andreessen what Netscape did, Levie has a conference room named after the iconic Valley company. In a place where youth is prized because of what it doesn’t know, Levie sees his as a handicap he actively tries to overcome. [Andreessen, whose venture firm is an investor in Box, is an investor in PandoDaily as well.]

Aaron Levie doesn't prospect and he doesn't close:

One of the reason he has a good sales record is that he has a very professional, experienced sales team who knows exactly how to use him. He isn’t in charge of the process. He isn’t prospecting. He isn’t closing. He’s whooshing in once things look pretty good to give customers some comfort around where the company is headed. “By the time I’m having a conversation with a customer, it’s later in the process,” he says. In baseball terms, he’s more the middle-reliever bridging between the starter and the closer.