Friday, as keynote speaker of their #StartupColumbia entrepreneurship festival, CORE hosted a conversation between Walt Mossberg (JRN ’70), editor of Re/Code and Dropbox founder Drew Houston. We sent Artur Renault, our reporter with his head in the clouds, to cover.
Houston, pronounced like the street downtown, not the city in Texas, could be a GS student in your introductory CompSci class from his informal demeanor and long-sleeve shirt; you’d never guessed that he created Dropbox, the world’s largest file-sharing platform. In fact, when Mossberg asked the room how many of us used Dropbox, you’d be hard-pressed to find an arm that wasn’t raised. “What, nobody uses Google Drive or OneDrive?,” he asked next. When a few hands went up, Houston shrugged—“Nobody’s perfect.”
Being that this was an entrepreneurship event, many people were interested in how Dropbox came to be, so Houston told us the story in detail. He was waiting for the Feng Wah Chinatown bus in Boston’s South Station and realized he had forgotten his thumb drive containing all his work. He also didn’t have any Family Guy episodes left to watch on his laptop, and he didn’t feel like the lady next to him, who may have been carrying a bag of crabs, would be interested in much conversation. Realizing that his four-hour trip had been doomed to boredom by the simple misstep of forgetting a thumb drive, Houston began coding what would become Dropbox on that very bus ride.
This wasn’t the only weird story about Dropbox’s origin. One of Dropbox’s first angel investors was a Persian rug salesman (one of the many that apparently exist in Palo Alto’s University Avenue). Nevertheless, Houston was surprised when he was invited to a meeting inside the actual rug store, where the investor had an actual meeting room. He was also surprised when that very investor was able to connect him to Sequoia capital, which eventually led to a meeting with Sequoia’s Mike Moritz. Houston told an amusing story about how he painstakingly calculated what drinks to have at home for Moritz, including many bottles of different kinds of Odwalla, only to have Moritz reply with “I’m good.”
Dropbox took off after Houston posted a video on Digg featuring many background jokes and memes. But his challenges didn’t stop there; he needed to define whether Dropbox would be an enterprise thing or a personal thing. He decided this distinction wasn’t one that needed to be labeled.
Houston was also very patient and attentive to Mossberg’s criticisms of Dropbox. These included the lack of a Microsoft Office/Google Docs-like productivity suite; Houston didn’t seem to think that was necessary. Mossberg was also quite angry at the fact that Dropbox suggests that you upload all your photos to Dropbox every time you turn on iPhoto or plug in your phone. “We’re just trying to help,” was his humorously pleading response. He made sure to advertise many of Dropbox’s new products, all aimed at “creating a space for all your stuff.” These include Mailbox for mail, and Carousel for photos. When tackled with questions about his competitors—some of whom offer cheaper storage—Houston retorted saying “It’s not about how many cents you pay per gigabyte; it’s about offering a better experience.”
But of course, as the audience was composed mostly of business school students trying to get their own startups off the ground, Houston was asked for multiple tips on how to be a good entrepreneur. He cited many of the classic ones, “improve yourself,” “hire the right people,” etc. But the main one was reading lots of books; Houston incessantly quoted many business books that he picked right off the top lists at Amazon, and have helped him immensely.
I don’t think many of the undergraduates at Columbia need help with reading, at this point. But all in all, Houston’s wisdom and experience is something everyone in that room stored in the cloud in their minds.