Dropbox: The Inside Story Of Tech's Hottest Startup

(This story appears on the Nov. 7, 2011 cover of Forbes.)

Here’s that rare Steve Jobs story, one that’s never been told, about the company that got away. Jobs had been tracking a young software developer named Drew Houston, who blasted his way onto Apple’s radar screen when he reverse-engineered Apple’s file system so that his startup’s logo, an unfolding box, appeared elegantly tucked inside. Not even an Apple SWAT team had been able to do that.

In December 2009 Jobs beckoned Houston (pronounced like the New York City street, not the Texas city) and his partner, Arash Ferdowsi, for a meeting at his Cupertino office. “I mean, Steve friggin’ Jobs,” remembers Houston, now 28. “How do you even prepare for that?” When Houston whipped out his laptop for a demo, Jobs, in his signature jeans and black turtleneck, coolly waved him away: “I know what you do.”

What Houston does is Dropbox, the digital storage service that has surged to 50 million users, with another joining every second. Jobs presciently saw this sapling as a strategic asset for Apple. Houston cut Jobs’ pitch short: He was determined to build a big company, he said, and wasn’t selling, no matter the status of the bidder (Houston considered Jobs his hero) or the prospects of a nine-digit price (he and Ferdowsi drove to the meeting in a Zipcar Prius).

Jobs smiled warmly as he told them he was going after their market. “He said we were a feature, not a product,” says Houston. Courteously, Jobs spent the next half hour waxing on over tea about his return to Apple, and why not to trust investors, as the duo—or more accurately, Houston, who plays Penn to Ferdowsi’s mute Teller—peppered him with questions.

When Jobs later followed up with a suggestion to meet at Dropbox’s San Francisco office, Houston proposed that they instead meet in Silicon Valley. “Why let the enemy get a taste?” he now shrugs cockily. Instead, Jobs went dark on the subject, resurfacing only this June, at his final keynote speech, where he unveiled iCloud, and specifically knocked Dropbox as a half-attempt to solve the Internet’s messiest dilemma: How do you get all your files, from all your devices, into one place?

Houston’s reaction was less cocky: “Oh, s–t.” The next day he shot a missive to his staff: “We have one of the fastest-growing companies in the world,” it began. Then it featured a list of one-time meteors that fell to Earth: MySpace, Netscape, Palm, Yahoo. 

Dropbox’s ascent has been just as stunning. The 50-million-user figure is up threefold from a year ago, and it has solved the “freemium” riddle, with revenue on track to hit $240 million in 2011 despite the fact that 96% of those users pay nothing. With only 70 staffers, mostly engineers, Dropbox grosses nearly three times more per employee than even the darling of business models, Google. Houston claims it’s already profitable but won’t reveal margins.

It’s only going to get better. That 96% of nonpaying customers is throwing their stuff into Dropbox at such a pace that thousands of people each day blow through the free 2 gigabytes of storage, and upgrade to 50 gigs for $10 a month or 100 gigs for $20. Even if Houston doesn’t sign up a single customer in 2012, his sales will double. As we go over this math Houston pauses to garnish this lovely inevitability: “But we will sign up many, many customers.”