Drew Houston graduated from the Massachusetts Institute of Technology just seven years ago. But on Friday Houston was back on MIT’s campus as the school’s 147th commencement speaker, sharing stories about how he built Dropbox — and a whole lot more. It turned out to be an inspired choice.
Houston’s speech isn’t a brag fest about his success as a Silicon Valley entrepreneur. You’ll have to look elsewhere if you want to learn about how Dropbox’s cloud-based storage system has attracted more than 100 million users, creating a company that investors value at $4 billion or higher.
Instead, the 30-year-old Houston pulled back the curtain on his stumbling moments soon after graduation, when he wasn’t sure how to start the next chapter of his life. He recollections were funny, earthy — and instructive. They also matched the hopes and anxieties of his audience.
– The real world is different. As a student, you are “jumping through one hoop after another: get these test scores, get into this college. … All of that ends today.” Going forward, it’s probably impossible to have a grand plan.
– The happiest and most successful people “remind me of a dog chasing a tennis ball: their eyes go a little crazy, the leash snaps and they go bounding off.” Figure out what projects seize your attention in a way that you can’t resist. “It might take a while, but until you find it, keep listening for that voice.”
– Jealous of other people’s success? Good. That can be a very powerful motivator to get your own life in gear. Houston tells the story, soon after college of working alongside another MIT-er whose startup took off first. It was shocking to see “my faithful beer pong partner” building a company when Houston’s efforts were still sputtering. The upshot: that buddy “had given me just the kick I needed. It was time for a change.”
– Move to the right place. You want to surround yourself with inspiring people, Houston argues, and that’s a lot easier to do if you’re living in the global hub for your field. “There’s only one MIT. And there’s only one Hollywood and only one Silicon Valley. . . . You should go there. Don’t settle for anywhere else.”
– No one has a perfect grade-point average in real life. “When you’re in school, every little mistake is a permanent crack in your windshield. But in the real world, if you’re not swerving around and hitting the guard rails every now and then, you’re not going fast enough. Your biggest risk isn’t failing; it’s getting too comfortable.”
– You won’t ever be totally ready. So charge ahead anyway. “Instead of trying to make your life perfect, give yourself the freedom to make it an adventure.”
Picking Houston to be the commencement speaker was probably a bit of an adventure in its own right for MIT. During the past 20 years, the school has tended to go the safer route of picking world-renowned alumni who are much farther along in life. Examples include Fed chairman Ben Bernanke in 2006, Qualcomm founder Irwin Jacobs in 2005, and Xerox CEO Ursula Burns in 2011.
All the same, Houston’s remarks seem to have clicked with his audience. Attendee Ashin Modak, the 23-year-old recipient of a master’s degree in mechanical engineering, told the Boston Globe that listening to Houston made him realize how much more there is to do. “You’ve accomplished something, Modak told the Globe, “but there’s so much more to accomplish.”