Jack Dorsey fancies himself a philosopher. He fancies himself an artist. He fancies himself a fashion designer. And he fancies himself the kind of man who can run two multibillion-dollar companies at the same time.
Twitter on Monday announced, after an embarrassingly long search, that it has hired Dorsey as its chief executive. (In what may be a symptom of the company’s internal dysfunction, someone had already leaked the news to Recode last week.) He will also remain CEO of Square, the mobile-payments startup he co-founded in 2009. This despite the Twitter board’s written proclamation in June that it would only consider CEO candidates who could commit to the job full time.
Dorsey arrives at a pivotal moment for Twitter. Billed by investors as the next Facebook when it went public two years ago, the company has struggled to grow much beyond a loyal core of users. Tweaks like a new home page for logged-out users have failed to revive its fortunes. More fundamental shifts, like Facebook-style algorithms and a rethinking of Twitter’s famous 140-character limit, are in the works but apparently still the subject of internal hand-wringing. Meanwhile, a parade of top lieutenants has headed for the exits. By all accounts, the company is crying out for a strong leader with a mandate for change.
Dorsey fits that bill. The problem is he fits a lot of other bills, too. CEO of Square is just one. Former co-founder, failed ex-CEO, prodigal son, vindictive backstabber, Jobsian hero, Vine star, fashion plate, software engineer, product visionary, self-important blowhard: Dorsey is all of these, and more. He’s a self-made billionaire, and he has helped to start and build two of Silicon Valley’s greatest success stories. He’s the kind of leader who inspires confidence—and sometimes betrays it.
Dorsey, aka @jack, co-founded Twitter in 2006 and served as its first CEO before being ousted two years later by co-founder Evan Williams over concerns over his focus and leadership skills. According to Nick Bilton’s mythmaking exposé Hatching Twitter, Dorsey was a 29-year-old unemployed NYU dropout with a nose ring when he latched onto Williams and lucked into a job as a software engineer at Williams’ struggling startup, Odeo. There, Dorsey and fellow developer Noah Glass built the messaging service that would become Twitter. Bilton makes the case that Dorsey elbowed and intrigued his way to that early CEO job, advising and consoling the troubled Glass while secretly lobbying Williams to have him fired.
Two years later it was Dorsey who was shown the door. Williams reportedly chided him for pursuing yoga and fashion design while the company’s engineers were scrambling day and night to keep the site afloat. According to Bilton’s book, Dorsey responded with characteristic maturity: He picked up the phone and called Mark Zuckerberg, reasoning that he could make his former colleagues sorry by defecting to their biggest rival.
Dorsey didn’t end up taking a Facebook job, reportedly because Zuckerberg didn’t offer him a fancy enough title. But he got a different form of revenge in 2010, when he orchestrated Williams’ own ouster as CEO and replaced him with then-COO Dick Costolo.
But the notion that Dorsey’s talents are limited to ruthlessness and self-promotion is belied by the success of Square, which he co-founded in 2009 and as CEO built it into a major success. The company was valued at $6 billion in its most recent funding round, and if it has suffered the sort of internal power struggles that have dogged Twitter, it has done a far better job of hiding them. Dorsey holds a 97 percent approval rating among Square employees, who give the company’s senior leadership an average rating of 4.3 out of 5, on the jobs site Glassdoor. (Twitter’s has plunged to 3.8.)
Found one billion-dollar startup, and you might be lucky. Found two, and chances are you’re pretty good.
When Costolo left Twitter under investor pressure this summer, Dorsey was a logical choice for interim CEO and was widely seen as a front-runner for the permanent job. But Twitter’s board was reportedly divided, with some insisting that the company needed a chief who could devote his full attention to the company. (Williams has admitted that he was among them.) As the search dragged on, however, Twitter’s inability to find someone to run it was making the company a laughingstock in Silicon Valley boardrooms. Perhaps the board gradually realized it couldn’t afford to be quite so picky. Or, perhaps more likely given Twitter’s tumultuous history and Dorsey’s reputation, there was a power struggle, and the pro-Dorsey faction prevailed.
Either way, Twitter finally has—for the first time in its history—a single, unquestioned leader. Or, at least, it has half of him.
There is precedent in Silicon Valley for a dual role like Dorsey’s. Steve Jobs famously ran Pixar and Apple. Elon Musk is running Tesla and SpaceX. But Jobs is a legend, and Musk is well on his way. The jury is still out on Dorsey.
Sometimes he sounds like a visionary. The germ of the idea for Twitter was his: a website where people could post their statuses for all to see, like a global hub for AIM away messages. More recently, he helped persuade the company to buy Vine, perhaps the best move it has made since going public. Square was born when he and his friend Jim McKelvey shared their frustration over McKelvey’s inability to take a customer’s American Express card. Both companies’ products bear the stamp of Dorsey’s eye for simple, clean design (predilections he shares with the late Jobs). “Payment is another form of communication,” he told Vanity Fair in 2011. “But it’s never been treated as such. It’s never been designed. It’s never felt magical.” The success of Square, and perhaps even more so, that of Venmo, bears that out. Other times, however, Dorsey can sound more like a parody of a visionary. A 2013 New Yorker profile found him self-consciously composing business management koans and tweeting such deep thoughts as:
I love espadrilles. And this glass of wine. And the word "asperity."— Jack (@jack) July 19, 2006
To hire as CEO a man at once so temperamental, self-important, and insecure could backfire on any company. Even as interim CEO, Dorsey was pushing hard for changes that could alter the core product and alienate longtime users.
But Twitter is not just any company. It is one that soared to great heights only to find that the sky wasn’t the limit after all. It has a thriving advertising business and a wonderful product that nearly 1 in 5 Americans uses—but its investors demand more.
If an able, thoughtful, and reliable CEO could achieve that, Costolo would have. He couldn’t, and now the company’s only option is to turn to someone who thinks so much of himself and his creative powers that he’s willing to sacrifice what made Twitter good in hopes of making it great. Jack Dorsey may not be a Silicon Valley hero, like Jobs or Musk. But neither were they, until they tried to do too much—and, against the odds, succeeded.