advertisement CEO Aaron Levie On His Love-Hate Affair With Microsoft

Is there anything you like about Microsoft? “That’s a completely unrealistic question!” jokes Aaron Levie, founder of The fast-growing, enterprise cloud startup just scored another $81 million in venture funding…



Aaron Levie, the 26-year-old founder of enterprise cloud startup, always has something to say. He’s as witty as he is garrulous, rarely hesitating before catapulting into an answer. He ties his sentences together with an endless string of semicolons, seemingly, with a millisecond pause here or there to cram in reflexive discourse particles–so-yeah-so! or no-but-wait!–as if he speaks with a stutter but without impediment. But when it came to the question “What do you like about Microsoft,” the college dropout was speechless.

“Wait, wait, could you rephrase that?” Levie said after a long pause, chuckling. “That’s a completely unrealistic question!”

For Levie, Microsoft is both a competitor and an inspiration, the business equivalent of a mortal enemy’s picture tacked to a dartboard. Microsoft is the dominant player in the enterprise cloud space–it’s why Levie has a large banner (see above) hung in Box’s offices challenging his employees to create a simpler alternative to Microsoft’s SharePoint service. Every David needs a Goliath, in other words. Microsoft is his.

The startup is gaining on its competitor, though, growing Box’s user base to 7 million, and winning 100,000 business clients, among them such big names as Dell, T-Mobile, and P&G. Today, Box closed its latest funding round of $81 million, bringing its total capital raised to $162 million, with investors that include and Andreessen-Horowitz.

Of the new funding, Levie said, in character, “It’s an $80 million round–wait, really? It’s an $81 million round? Can we just give back $1 million or something? Yeah, so it’s $80 million, and then we accidentally added another million.”

The massive amount of capital will help scale; Levie wants his products and services to be accessible from any Internet-connected device, whether that’s via Mac or PC, Apple or Android tablet, or BlackBerry smartphone. It’s how hopes to stay ahead of the competition, even with a much smaller market share when compared to Microsoft.


But back to the question at hand: Is there anything he likes about Microsoft?

“You mean like today? Or in the past? I want to give you a thoughtful answer,” Levie jokes, quickly shifting into a more serious answer. “Well they’ve single-handedly slowed down the cloud more than any other company I can think of,” he says. “They’ve basically stunted innovation for like a decade. Wait, okay, okay, wait, I’ll think of something [I like about them]. Obviously we have immense respect for what they’ve done…We wouldn’t exist if Microsoft didn’t exist. We are solving problems that they created–so we’re actually happy about that!”

Levie is speaking here in slight jest, just as he would any other competitor. Regarding Oracle, for example, Levie says, “We are definitely trying to build a very enterprise-oriented company, and I think wearing a jacket is a part of doing that, particularly if you look at Larry Ellison. Though I’m not going wear the–god, what color was that?–manilla jacket he was wearing [last week].”

But the point here is clear: Box needs Microsoft as much as it wants to get rid of Microsoft, just as Instagram might target Flickr or Square might target VeriFone, and so forth. On the opposite end, startups certainly act as valuable inspiration for larger competitors. Microsoft needs competition from Box, Dropbox, and Salesforce to keep it from growing stagnant.

So it’s no surprise that when we reached out to Microsoft for comment, with the mere mention of a story that “concerns a Microsoft competitor,” a press rep asked, “Would this be a story?”

About the author

Austin Carr writes about design and technology for Fast Company magazine.