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from 70 to 200, still an absurdly low number given the company’s size. And Houston would see whether he could realize the vow he made to Jobs about building a major company, or else fall prey to the MySpace-esque hazards Jobs predicted. “I have to learn how to be big,” he said.
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    IT WAS JUST BEFORE midnight on a Monday, and Houston turned his favorite late-night watering hole, the bar in San Francisco’s W Hotel, into a fraternity party—literally. The first to arrive was Adam Smith, who was a fellow Phi Delta Theta at MIT before dropping out to start an e-mail search company, Xobni. Then came Chris, Jason, and Joe (who has a Dropbox tattoo on his arm because he feels “Drew is changing the world”), more MIT brothers aiming to live a California dream they all imagined back in Cambridge as “billionaires, bottles, and babes.” With girlfriends in tow, Smith and Houston gulped glasses of Pinot and reminisced about the summer they spent coding in boxers because the A/C was down. “Those were the days,” smiled Houston with his arm around Smith. “Just me and my code. None of this hiring and firing business.”
    Houston clearly drew strength from this group—he even recreated the fraternity living experience in San Francisco, moving into the same downtown building as Smith and ten other entrepreneurs. If dropping out of college was a watershed moment for the likes of Bill Gates, Michael Dell, and Mark Zuckerberg, then staying in was equally transformative for Houston, particularly his fraternity experience.
    The just-me-and-my-code default, after all, is wired into his DNA. His father is a Harvard-trained electrical engineer; his mother, a high school librarian. Growing up in suburban Boston, he began tinkering at age five with an IBM PC Junior. His mother, correctly deducing that her son was becoming a code geek, made him learn French and hang out with the jocks, and refused to let him skip a grade. During summers in New Hampshire she took away his computer, even as he griped about being bored in the woods. “She was subtle about making me normal, I guess, and I can appreciate it now.”
    At fourteen, Houston signed up to beta test an online game, and began rooting out security flaws. They soon hired him as their networking programmer, in exchange for equity. That year, at a school assembly, one speaker asked the group: “Raise your hand if you know what you want to be when you grow up.” Houston was the only kid out of 250 with his hand up. “I wanted them to call on me, but it was rhetorical. I wanted to run a computer company.” He worked at startups throughout high school and college. Dropbox is his sixth.
    By freshman year at MIT it seemed his mom had failed. Most of his time was spent coding. He was finally convinced by Daniel Goleman’s book
Emotional Intelligence
that “smarts weren’t enough” if he wanted to run a company. So he spent the ensuing summer on the roof of his frat reading business books. “No one is born a CEO, but no one tells you that,” says Houston. “The magazine stories make it sound like Zuckerberg woke up one day and wanted to redefine how the world communicates with a billion-dollar company. He didn’t.” Then he signed up to be rush and social chair, “a crash course in project management and getting people to do stuff for you.” (His roommate, Joe, recalled otherwise: “No one else wanted to do it.”)
    When Adam Smith left the house in September 2006 to start Xobni in San Francisco, it gave Houston proper motivation. “If he could do it, I knew I could,” said Houston. “I wanted to live the dream and felt stuck eating Hot Pockets.” His MBA from Phi Delta Theta was complete.
    The idea for Dropbox was born three months later on a bus to New York. He had planned to work during the four-hour ride from Boston but forgot his