The Win-Win Fallacy

Justin Rosenstein was largely unknown to the broader world, but he was a star in Silicon Valley. He had been instrumental in inventing several of its seminal technologies. A programming and product design phenom, he helped start Google Drive and was the co-inventor of Gmail chat. Then he moved to Facebook, where he was the co-inventor of Pages and the “like” button. More than a billion people were regularly using tools that Rosenstein crafted. He had been rewarded with stock said to be worth tens of millions of dollars. He wasn’t yet 30.

Rosenstein now faced a dilemma not uncommon among young entrepreneurs who have found early success: what to do with his money and his remaining decades on earth. He knew he wanted to improve the world, and he was guided by one of the reigning mantras of the age — that of the “win-win.” He decided that his method of bettering things would be to start a company, Asana, which sold work-collaboration software to companies like Uber, Airbnb, and Dropbox. He believed that Asana’s software could be his most forceful way of improving the human condition. “If we really could build a universal piece of software that could make everyone in the world who’s trying to do positive things 5 percent faster, right?—I guess we’ll also make terrorists 5