The Harlem skin clinic on Frederick Douglass Boulevard in New York City is not the first place you'd expect to run into Jack Dorsey. But on a snowy December afternoon, the 37-year-old CEO of Square and chairman of Twitter appears to be in his element far from San Francisco, where the two companies he co-founded are headquartered on adjacent city blocks. The clinic's owner, Seven Brown, manages her business from her iPad, using Square's Register app and Reader credit-card swiper. When she talks about them, she keeps using the same word: fantastic.
Dorsey dropped in on Brown because she was going to be participating in a panel that he was moderating at Harlem's Apollo Theater that evening. Square organized the event and others like it across the country to discuss the pleasures and pitfalls of running a small business. "Our responsibility is not just to build a tool or a service," explains Dorsey. "It's also to provide a venue for conversation." That sounds a bit like Twitter, the social network that remains Dorsey's highest-profile venture. Thanks to its successful IPO in November, it's also the source of his biggest payday: his 4.3% stake is valued at about $1.5 billion.