84 minutes with ... Dan Doctoroff

Surveying post-Bloomberg New York with the technocrat futurist behind Sidewalk Labs.

- Carl Swanson

DAN DOCTOROFF and I are standing on the 26th floor of the first tower to open in Hudson Yards, in the buzzy open-plan offices of a Google offshoot called Sidewalk Labs, for which he serves as CEO. Mostly young people, jacked up on free Joyride Coffee, are collaborating all around us, some putting Post-its on the floor-to-ceiling windows. Google’s parent company, Alphabet, calls its start-ups like Sidewalk “bets.” (Waymo, the self-driving-car company, is another one.) What Google is betting on is that its technologists can and should mediate our lives, for the good of all. In the case of Sidewalk, the goal is to make a better city, and the company is in search of a municipality to partner with on building a digitally optimized district from the ground up: an IRL beta-town. So far, Sidewalk has put those nine-foot-tall LinkNYC Wi-Fi kiosks on the sidewalks around New York. He also personally happens to be an investor in the company that runs Citi Bike, which I used to get over to the far West Side for the interview. (He lets me in on a secret: Sidewalk employees have their own private docking station.)

But we’re not here to talk about the city of the future; we’re discussing the city of today, the one built in the wake of 9/11. Doctoroff, then a partner in a private equity firm, was obsessed with the idea of bringing the Olympics to New York (the stadium was to be built where we’re standing now). He was recruited by Michael Bloomberg to be his deputy mayor for economic development and reconstruction. He was paid a dollar a year and resented by many career bureaucrats and political hacks for his lofty self-regard, something he admits he wasn’t always sensitive to. He’s written a book about those years—a combination manifesto- memoir—called Greater Than Ever: New York’s Big Comeback.