Q: By all accounts, Square runs more smoothly than Twitter? A: "It has to, though. Yeah, you’re dealing with people’s money. I mean, it’s extremely emotional. If you lose 140 characters, people are like, “Eh.” If you lose $140 or even $1.40, it’s important."
When Jack Dorsey co-founded Twitter in 2006, he had no idea he and his colleagues were creating what would become a universally accessible, global, seamless, 24/7 platform for tens of thousands of people to yell at him. In any case, back then, billionaire tech execs were still — at least in some circles — figures of admiration, rather than a locus of fear and suspicion for many on the left and right alike. Social media has succeeded all too well in its disruptive mission, reshaping societies in ways they’re still struggling to understand. That leaves the likes of Dorsey, who’s been the CEO of Twitter since 2015 (after an abortive initial run from 2006 to 2008), grappling, Sorcerer’s Apprentice-style, with an ever-growing slate of issues of daunting complexity.