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his return to Apple, and why not to trust investors, as the duo—or more accurately, Houston, who plays Penn to Ferdowsi’s mute Teller—peppered him with questions.
    When Jobs later followed up with a suggestion to meet at Dropbox’s San Francisco office, Houston proposed that they instead meet in Silicon Valley. “Why let the enemy get a taste?” he later shrugged cockily. Instead, Jobs went dark, resurfacing in June 2011, at his final keynote speech, where he unveiled iCloud, and specifically knocked Dropbox as a half-attempt to solve the Internet’s messiest dilemma: How do you get all your files, from all your devices, into one place?
    Houston’s reaction was less cocky: “Oh, shit.” The next day he shot a missive to his staff: “We have one of the fastest-growing companies in the world,” it began. Then it featured a list of onetime meteors that fell to Earth: MySpace, Netscape, Palm, Yahoo.
    Dropbox’s ascent has been just as stunning. The 50-million-user figure for 2011 was up threefold from a year earlier, and the company has solved the “freemium” riddle: 96 percent of those pay nothing, yet the company was able to hit $50 million in revenue that year—enough, Houston said, to make it profitable. With only seventy staffers, mostly engineers, Dropbox grossed nearly three times more per employee than even the darling of business models, Google.
    It got better. That 96 percent of nonpaying customers were throwing their stuff into Dropbox at such a pace that thousands of people each day blew through the free two gigabytes of storage, upgrading to fifty gigs for $10 a month or 100 gigs for $20. As we went over this math with Houston, pointing out that sales would double even if he didn’t sign up another customer (indeed, in 2013, Dropbox reached approximately $200 million in revenue), he paused to garnish this lovely inevitability: “But we will sign up many, many customers.” By mid-2014, Dropbox had 300 million users.
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    WHEN DROPBOX BECAME A verb (“Dropbox me”), Silicon Valley took keen notice. By 2008 Houston had raised $7.2 million—enough cash, given the company’s robust economic model, to get it into the black. In August 2011, Houston decided to go for the kill. He invited seven of the Valley’s elite venture firms to visit Dropbox’s San Francisco digs over a four-day stretch, and asked them for offers by the following Tuesday.
    Only one came back to him quickly. Just before midnight the eve offers were due, Dropbox’s head of business development—a former venture capitalist—suggested Houston either delay the round or even pull it. Houston’s reply: “We said Tuesday. It isn’t Tuesday.”
    Sure enough, every firm came back interested the next morning. Houston eventually made a deal, which closed in September 2011, that included Index Ventures as lead, plus Sequoia, Greylock, Benchmark, Accel, Goldman Sachs, and RIT Capital Partners. Many stretched their deal definitions to get in. It’s the stuff of instant Silicon Valley legend: While the soft market, and Houston’s insistence on dealing only with platinum-plated VCs, crimped his valuation a bit, five-year-old Dropbox still raised a whopping $250 million on a $4 billion valuation. “This is the hot company,” says one prominent investor who didn’t get in. “Everyone wanted to be a part of it.” Houston’s estimated 15 percent stake was worth, on paper, $600 million.
    Leaning back in an Aeron chair two weeks after the deal closed, across from a customized neon sign that reads “ITJUSTWORKS” with “just work” popping out in blue, Houston mused on what he would do with his new quarter-billion-dollar war chest. The single-room office on gritty Market Street would soon give way to an 8,500-square-foot spread with views of the Bay as the Dropbox staff swelled