SXSW: Dropping In on Dropbox’s Drew Houston

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Harry McCracken /

Dropbox founder and CEO Drew Houston

For a service that’s beloved by so many people, cloud-storage and syncing service Dropbox is surprisingly controversial. On one hand, venture capitalist (and Dropbox investor) Bill Gurley talks about the company someday being worth $40 billion. On the other, tech writer Farhad Manjoo, who loves the service, nevertheless thinks it’s not that big a deal: Online storage is a commodity, he says, and Dropbox doesn’t have the access to operating-system underpinnings that it really needs to do the job right.

Then there’s an opinionated observer who Manjoo cites and agrees with: Steve Jobs, who liked Dropbox enough that he offered to buy it for more than $100 million in 2009 — but maintained that it was a feature, not a service.

I use and like Dropbox and would be pleased to see it thrive forever, since it’s a scrappy, innovative startup that’s competing against the industry’s giants: Apple, Google and Microsoft. And here at the SXSW Interactive conference in Austin, Texas I got a chance to chat at a coffee shop with Drew Houston, the company’s 29-year-old founder and CEO.

At the moment, Dropbox’s big news is a revamped version of its browser-based version. Houston told me that one of of the goals of the facelift was to make the service feel a bit less like an old-fashioned file manager. Instead it focuses on letting you work with specific types of stuff — such as photos, which now get a special viewer of their own. That philosophy points the service in a similar direction to that of Apple’s iCloud, which is less about folders of files than it is about photos, videos and various types of documents, and the things you can do with them.

I asked Houston about critics like Manjoo, who say that the features that Dropbox provides are on their way to being commoditized into irrelevance. He said that seamless, reliable file management across multiple devices and platforms remains a major technical challenge, even for companies with formidable resources.

“We’re not the tenth company to try this, or the hundredth,” he noted, accurately. “If it were easy, some of these other smart people would have built it.”

Cloud storage, Houston argues, is like search engines. The fact that “anyone can make a text box return links to pages” doesn’t mean that any company can take on Google.

With both Google and Dropbox, Houston says, “the magic is in the engineering.”

He also told me that Apple’s iCloud and Google’s rumored storage service won’t render Dropbox obsolete, since Apple will focus on iOS and Google will concentrate on Android, leaving other platforms as “second-class citizens.” (Dropbox, by contrast, is available through its browser service plus clients for Windows, Mac, Linux, iOS, Android and BlackBerry.)

At the moment, more than 50 million people use Houston’s service. “Every couple of days, a billion files are stored on Dropbox,” he told me. “Wedding photos, tax returns, people’s most important stuff.” Users get only 2GB of space for free — a relatively parsimonious amount that competitors beat by factors of up to 25X — but Houston argues that the company’s paying customers are plunking down money because Dropbox offers peace of mind.

“What people love is not free space,” he said. “It’s that they could literally take their MacBook Air and throw it in the river and not lose anything…That’s been the promise for years. We brought it across the finish line.”

I know that Dropbox is regarded as indispensable by a high percentage of the hardcore nerds and nearly-nerdy people I run across. But I asked Houston if the service is for technically-sophisticated people or for everyone. He said that it’s already a breakout hit. At a recent conference, he met one person who had learned about Dropbox from his 80-year-old dad — and another who’d discovered it when his 8-year-old daughter recommended it.

“We’re like a Milton Bradley game,” he laughed — appropriate for all ages.