Jack Dorsey was glum. It was 2009, and we were in Baghdad, among a group of Silicon Valley movers and shakers on a State Department junket to visit businesses, universities, and the eerily deserted Iraq National Museum. But back home, all the moving and shaking in the company he had invented—a short-form blog platform called Twitter—was happening without him. Twitter was taking off, but Dorsey had been bounced from his leadership role, and his cofounders, Evan Williams and Biz Stone, were taking public victory laps, appearing on talk shows and at conferences. Dorsey, a person whose emotions run deep, was in distress, as he confessed to me during a late-night discussion. The situation still stung when I met him a few months later, when he took me to his apartment to show me his new idea, a little acorn-shaped doodad that could make your phone into a credit card swiper.
Revenge, they say, is a dish best served cold, but in the next few years, Jack Dorsey was presented with a lavish feast, served not only piping hot but probably vegan as well. Or maybe keto. Not only did that weird app turn into Square—now valued at nearly $100 billion—but in 2011, Twitter’s CEO Dick Costolo, who had replaced Williams, tapped Dorsey to be the company’s part-time product guru. Four years later, Dorsey stepped in for Costolo to once again become Twitter's leader. The man who invented the service and changed the world by giving instant voice to anyone, for better or worse, was finally back in charge of his creation.
Can one person run two big public companies? Dorsey insisted he could. After all, didn’t his idol Steve Jobs run Apple and Pixar?
The key would be assembling a team that would take the company to glory with a part-time leader. With Square, Dorsey has clearly done this, but Twitter’s record has been mixed. It’s been a constant frustration that usership never reached the billions that marked the ceilings of other social networks. The fact that the company punched beyond its weight in terms of influence always raised the question: Why didn’t Twitter weigh more? The company ran through an endless stream of product Svengalis, official and otherwise.
In terms of policing Twitter’s content, Dorsey was the Hamlet of Silicon Valley, acknowledging the problems but hesitating to take the severe measures required to address them. Every woman who posts something even mildly controversial must expect a blizzard of horrid misogynistic responses. Only relatively recently has Twitter offered serious responses to its troll problem. And while Donald Trump is a problem that no one has figured out how to deal with, Dorsey allowed the misinformer-in-chief to use Twitter as his bullhorn for too long. (On the other hand, Dorsey’s call to permanently ban Trump after January 6 was gutsier than Facebook’s timid “suspension.”)
In other respects, Dorsey quite delightfully broke unspoken rules about the way a CEO is supposed to behave. Weirdness abounds in corporate suites, but seldom is it displayed so brazenly. There was his diet. His beard. His nose ring. And his obsessions: denim, perambulating, and, more recently, crypto.
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You could argue endlessly about whether someone else could have done better. But you can never dispute that, for the past six years, Twitter was run by someone who was its very soul. He exulted in its timeliness and verve, and embraced its messiness. He playfully taunted his critics, who kept pestering him for an edit function. There is no way—no way—that Jack Dorsey would rename his company after some dream of a metasphere.
For the past year and a half, Jack Dorsey almost certainly knew that his time was limited. “Activist shareholders,” notably at Elliott Management, decided Twitter would be ripe for giant gains once they got the finicky CEO out of the way and put someone in to boost financials in the short term. Let Dorsey concentrate on his other billion-dollar company! Dorsey managed to stave off the assault, but only by cutting a deal that put some of the invaders on his board, and agreeing to meet some difficult internal goals. It now appears that the clock has run out. Effective today, Twitter’s CTO Parag Agrawal, a 10-year veteran of the firm, will be a member of the board and the new CEO. There’s also a new chairman of the board: Bret Taylor, a board member who is also president and COO of Salesforce.
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Dorsey himself explained things differently. “This was my decision and I own it,” he wrote, naturally, on Twitter. The company needs change, he said, and the presence of a founder at the helm severely limits that possibility. (Some might argue that only a founder can make truly significant changes, but whatever.) He enthusiastically endorsed Agrawal, who began at Twitter as an engineer, and also praised Taylor. “Sometime next spring” he will relinquish his board membership entirely, to let the new team operate free of his influence.
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Twitter might be viewing Agrawal in the mode of Sundar Pichai of Google: a technically oriented, low-key leader who can guide producers and engineering while pleasing Wall Street. Taylor is one of Silicon Valley’s most respected leaders, a former Googler (he helped launch Maps) whose Salesforce role puts him in the center of the industry. Even with a full-time CEO and a powerful chair, Twitter still will face difficult challenges in moderation (the trolls still flock there), monetization, and product development. But some recent innovations, like a premium subscription service, show that some of the dust is already being swept.
One thing will never change. Dorsey said it himself, in a tweet mysteriously posted this weekend, which now makes perfect sense.
“I love Twitter,” he wrote.
Fittingly, many of the thousands of replies to that tweet voiced complaints about the service. Dorsey probably loved that, too.
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