His former roommates say that maniacal focus on Dropbox meant Houston never paid the rent on time. It took him 15 months to replace the driver's license he lost at Burning Man, forcing him to carry his passport as ID to get served in bars. He rarely shows up at his apartment except to shower and sleep, instead embedding himself in his Aeron chair at the Dropbox office.
That's the kind of obsessive-compulsive attention to detail that Houston and his team needed to pull off a technical tour de force: making Dropbox work on any device, with any operating system, on any browser and in any country. Dropbox engineers even hacked their way into Apple's file system to make the Dropbox icon appear on users' menu bars, a bold feat that blew away Apple's cloud team and caught the attention of none other than Jobs.
The Apple co-founder summoned Houston and his co-founder, Arash Ferdowsi, to Apple's Cupertino, Calif., headquarters in December 2009. They zipped down U.S. 101 in a rented Toyota Prius and nervously sat down in Jobs' conference room.
Jobs, in jeans and black turtleneck, cupped his tea. He warned them he was going after their market. And, in a jaw-dropping moment for Houston, Jobs made a pitch to buy Dropbox.
But Houston inherited his dad's cool-as-steel temperament and didn't fall under Jobs' spell (although he admits to having a sinking feeling in June when Jobs in his final keynote announced Apple's iCloud, which could eat Dropbox's lunch).
"I'm a Windows guy anyway," Houston said with a smile.
Reared in suburban Boston, Houston began playing with computers when he was 3. His dad taught him to program when he was 5. Even when Houston was solving math problems in high school, he would do it his own way. As a computer science major at the Massachusetts Institute of Technology, he hacked for fun, building an online poker bot that could automatically play and win multiple hands.
Houston had aspired to be an entrepreneur before he was old enough to shave. The kid who scored a perfect 1600 on his SATs dropped out of MIT for a year to start an online SAT prep company, but it wasn't the game-changer he was looking for.
Sitting in Boston's South Station in November 2006, Houston opened his laptop and realized that he had left his USB memory stick at home. So Houston said he did what any self-respecting engineer would do: He spent the four-hour bus ride to Manhattan writing code so that he would never find himself without his files again.
Houston teamed up with Ferdowsi, an MIT computer science student and the son of Iranian refugees from Kansas. They interviewed for and got a coveted spot in Silicon Valley incubator Y Combinator, the launch pad for many Silicon Valley companies. One day, they returned to their rental car to find the door ajar and their laptops stolen, but all of their work safe on Dropbox. They knew they were on the right track. Ferdowsi dropped out of MIT one semester before graduation.
With $15,000 from Y Combinator, they spent four months cranking out code 15 hours a day in a cramped apartment. In September 2007, they moved into a San Francisco apartment building filled with Y Combinator companies that Houston dubbed "Ellis Island for start-ups." They hired the smartest engineers they could find, mostly fellow MIT students, and started scaling the business.
Word of Dropbox reached the ears of Michael Moritz, the Silicon Valley venture capitalist famous for backing Apple and Google. His firm, Sequoia Capital, wrote Dropbox a big check and requested instructions for the wire transfer.
Houston and Ferdowsi just looked at each other. They walked over to the Bank of America branch near their apartment in North Beach and peered at the tellers standing on one side, the leather seats with account managers on the other. They slid into the leather seats and asked tentatively if there was a limit to how much a bank account could hold, and then watched goggle-eyed as their balance shot up from $60 to $1.2 million.
In March 2008, they posted a demo video to Digg and got 70,000 users overnight. Six months later when they launched, they had 100,000 users. Then came millions. And millions of dollars more from investors.
"Dropbox has an immediate 'aha' moment for everyone who uses it," said Forrester Research analyst Ted Schadler.
Dropbox is already profitable and making money (although Houston won't say how much). Every day thousands exhaust their free 2 gigabytes of storage on Dropbox and upgrade to 50 gigs for $10 a month or 100 gigs for $20 a month.
Next month, Dropbox is moving into an airy, 85,000-square-foot spread with views of the bay and its own cafe and gym. It will have enough room to grow from less than 100 to a few hundred staffers in the coming year. This is where Dropbox will make or break its future. It's little wonder that Houston's hair has begun to prematurely gray.
Houston says he stays grounded by hanging out with pals who are fellow entrepreneurs. Twelve of them rented apartments in the same downtown high-rise in San Francisco this year. And he still makes time for music. After all-hands meetings on "Whiskey Fridays," Houston gets out his dad's old acoustic guitar and jams with the other resident musicians at Dropbox.
Houston gets a wistful look as he thinks back to the early days of Dropbox when all he had to do was down an iced mocha and hunch over his keyboard all night long.
"You'd just sit down, do something, get it done, have it work and move onto the next thing," Houston said. "The joy is less immediate as things get bigger."