Jack Dorsey: the exiting Twitter CEO with an artist's vision

Photograph: Anushree Fadnavis/Reuters

The 45-year-old who could have been a dressmaker steps down as social media industry becomes ever more competitive

    Jack Dorsey likes to keep things simple, at least for a 45-year-old multibillionaire. He eats one meal a day, fasts at weekends and tries to meditate for two hours daily. The post that launched Twitter, and ultimately a million pile-ons, was equally austere: “just setting up my twttr”.

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    Dorsey was born in St Louis, Missouri, in 1976 and was a self-taught computer programmer, using a Macintosh computer that his father bought for him. In 1999 he dropped out of New York University and moved to California where he dreamt up the idea of a Twitter prototype while co-founding an online courier and taxi dispatch firm. The company later failed.

    The Twitter story began to take shape when Dorsey was hired as a coder at Odeo, a podcasting startup run by a future Twitter co-founder, Evan Williams. This is where Dorsey appears in Sarah Frier’s award-winning history of Instagram as one of the peripheral figures in the story, trying to make his way in Silicon Valley like so many others.

    “Dorsey, a 29-year-old New York University dropout with an anarchist tattoo and a nose ring, considered himself to be more of an artist. He would sometimes dream, for instance, about becoming a dressmaker. He was an engineer, but only as a means to an end – to create something out of nothing, with code. Also, so he could pay rent.”

    There was enough hard-edged business sense within Dorsey, however, for him to co-found Twttr – soon renamed Twitter – with Williams, Biz Stone and Noah Glass in 2006. Dorsey became chief executive, for the first time, in 2007.

    Indeed, Dorsey’s artistic mindset was cited, pointedly, when he was removed as chief executive for the first time in 2008. Williams said to him: “You can either be a dressmaker or the CEO of Twitter,” according to Nick Bilton’s book Hatching Twitter. “But you can’t be both.” Dorsey would apparently intersperse his chief executive duties with breaks for hot yoga and sewing classes.

    Dorsey leaves the company with 210 million daily active users and annual revenues of $3.7bn

    Dorsey came back as executive chairman in 2011, having set up payment company Square – today worth $100bn – in the meantime. Twitter struggled in the wake of its 2013 flotation, which made Dorsey a billionaire, and he replaced Dick Costolo as chief executive in 2015 while relinquishing the executive chairman role.

    Dorsey leaves the company with 210 million daily active users and annual revenues of $3.7bn. According to the Bloomberg Billionaires Index, he is worth $12.3bn, ranked 174th among the ranks of the world’s super-wealthy. He still owns 2.3% of Twitter.

    But unrest had been building about Dorsey’s priorities. In 2019 Dorsey surprised staff and investors by announcing plans to move to Africa for up to six months a year. Announcing the move during a month-long trip to the continent, he tweeted, from Addis Ababa: “Sad to be leaving the continent … for now. Africa will define the future (especially the bitcoin one!). Not sure where yet, but I’ll be living here for 3-6 months mid 2020. Grateful I was able to experience a small part.”

    Dorsey, who remains a cryptocurrency enthusiast, dropped the plan after coronavirus arrived. But it wouldn’t have dissuaded the activist investor firm Elliott Management from its view that Twitter was a business in need of more focus at the top. Elliott took a stake in Twitter last year and is still the 13th largest shareholder in the business, according to the financial data company Refinitiv, with a stake of just over 1%. At the time of the stake-building move, Elliott’s billionaire owner, Paul Singer, was reported to have been concerned by the fact that Dorsey had two chief executive jobs – at Twitter and Square.

    By the end of last year it appeared that Dorsey had survived the pressure. In November a committee of Twitter directors said it had “confidence in management and recommended that the current structure remain in place”.

    Much of the innovation shown by Twitter under Dorsey’s leadership in recent months has been more to do with safety than making money, however. It has launched trials warning users that they are about to enter a heated conversation and is testing a “safety mode” that blocks accounts for seven days if the tech firm’s systems spot them using harmful language or sending repetitive, uninvited replies and mentions. In the context of Frances Haugen’s Facebook revelations and the upcoming Online Safety Act in the UK, social media companies know they have to focus on protecting users.

    On the money-making side, in the US the company launched Twitter Blue, a product that for $2.99 a month offers a range of services including a 60-second grace period to amend a tweet before it is fully posted. Expect more money-making initiatives under the new boss, the chief technology officer Parag Agrawal, who has to hit ambitious targets: to increase the company’s daily average users by more than 50% to 315 million; and more than double revenue to $7.5bn by 2023.

    According to one California-based analyst, now is a good time for Dorsey to leave, with the social media industry becoming ever more competitive.

    “Dorsey is a pillar of the social media world,” said Dan Ives, managing director of the investment firm Wedbush Securities. “These are big shoes to fill.”

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