Dropbox's Next Chapter: Corporate Customers, IPO, Condi Rice, and Eddie Vedder

In November 2012, Drew Houston, co-founder and chief executive officer of Dropbox, the online storage service, dragged his employees to an offsite event at San Francisco’s Yerba Buena Center for the Arts. His purpose was to scare them. Tech CEOs are notorious for pretending to be humble and stirring motivate-the-troops paranoia, but Houston’s anxiety seemed real. On an overhead screen he displayed a black and white photo of a building out over a sea wall, threatening to topple onto the rocks below. “Are we this beautiful house sitting on top of a cliff?” he asked.

Dropbox was—and perhaps still is—the most celebrated startup in Silicon Valley. Two hundred and seventy five million people use it to manage their digital lives, storing personal documents, photographs, and videos across expanding collections of phones, tablets, and personal computers. The service is free up to 2 gigabytes of storage (rising if you refer friends, link an e-mail account, and so forth), after which a fee is imposed. Sensing that the company is centrally positioned in the dawning age of mobile computing, investors have piled in more than $600 million in venture capital. An initial public offering beckons sometime in the near future, and it will almost certainly make Houston a billionaire, with many of his 650 employees becoming worth millions.