Dorsey Morning Future
Imagining Best Practice 14 September Sep 2018 0830 14 September 2018

Jack Dorsey: the bad boy of Silicon Valley who got Twitter off the ground

Careerist, arrogant and not even that bright: that’s how many see the man in charge. And yet, he seems to be the only one able to get the little blue bird in the air

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Careerist, arrogant and not even that bright. That’s what everyone is saying and writing about Jack Dorsey, 41, founder of Twitter. Many see him as Silicon Valley’s dark side. The first of many to describe him as such was the exceedingly reliable New York Times. In 2013, Nick Bilton, one of the publication's leading reporters and now a special correspondent at Vanity Fair, published a book about the creation of Twitter. From this reconstruction of events emerges a story of betrayal, opportunism and violent back-stabbing, for the most part inflicted by Dorsey upon his three partners, Evan Williams, Biz Stone and Noah Glass, who, it seems, he literally kicked out of the company.

And the reputation of Twitter's CEO is not exactly the cleanest. Legend has it that, at the company’s launch party, Dorsey was so drunk that he fell and fractured his skull. Various sources - including Bilton’s investigative book - attest that the startup’s Board fired Dorsey in 2008, for being too unruly: they say he worked too few hours, leaving the office for yoga or to attend courses in fashion design (one of his great loves in life is fashion).

I saw the rise of Instagram here [on the bus], the rise of Vine and Snapchat, and how many more people were using Facebook versus Twitter

Jack Dorsey, CEO of Twitter

This party-animal image is one that the young multimillionaire is struggling to shake off. While his peers, the other founders of his generation - from Facebook creator, Mark Zuckerberg, to the founder of Reddit, Alexis Ohanian - have spent recent years posting photos of their families and pushing their philanthropic initiatives, Dorsey is still the one who lives for the most exclusive parties, on his several-million-dollar yacht, always dressed immaculately and accompanied by a different top model. Not, then, an exemplar of moderation. Even if you look closely at his Instagram profile, which depicts a very different person to the one the newspapers describe: several pictures of his family, his godson’s christening and various photos of public transport, because, as he explains, this plays into his market research. “I saw the rise of Instagram here [on the bus], the rise of Vine and Snapchat, and how many more people were using Facebook versus Twitter. It’s amazing. Like, look - anyone reading magazines, newspapers, books?”
The day-to-day that his social media accounts portray are far more normal than anyone would expect from him, as if he were trying to say, “I’m not bad, they’re just trying to make out that I am.”
Who, then, is Jack Dorsey? The unscrupulous careerist that gave his friends the boot in order to regain control of the company? Or the boy next door, christening his best friend’s son?

A tale about the American Dream

According to sources, Dorsey was not the real genius among Twitter’s founders. Bilton, in his book Hatching Twitter does not try to conceal his belief that Dorsey got lucky.

Yet Dorsey’s story is not one of someone who simply had a lot of luck. He was born in Saint Louis to a staunchly Catholic, working-class American family. His father was an employee at a manufacturing company and his mother a housewife. Dorsey went to the city's Catholic school and, at the age of 14, began to nurture an early interest in programming, for a taxi dispatch system. He carried this interest with him to university, first heading to the University of Missouri–Rolla and later transferring to New York University. But after just a semester he left. It was as an open source software developer that he found a job after abandoning his studies. This work went so well that various companies still use some of that software today.

Having left university, Dorsey moved to the West Coast, to California, and trained as a professional masseur - because if there is anything the young multimillionaire does well, it’s making confused and unpredictable decisions. Perhaps this is why he fails to gain people’s trust. Dorsey never practised as a masseur, because, in California, he began working with a media company that produced podcasts and it changed his life forever.

Twitter was born

It seems unlikely that a story of universal success such as Twitter’s could begin with failure, but that is exactly what happened. In 2000, Dorsey moved to Oakland, the city on the other side of San Francisco Bay. Here, at just 23 years old, he founded his first communications company, for ordering taxis and requesting emergency services online. Drawing on the idea of instant messaging, it was during this experience that he began to consider a service that would allow users to share their statuses with friends. It was an embryonic form of social network, before they even existed. On this basis, he created Odeo, where he met the people who would become his future partners. The Company was, in fact, interested in developing a system for creating and managing podcasts. It worked in a very similar way to personalised voicemail.

But at that point, the first iPhone and the new iTunes were released, pulling the carpet from under the feet of any potential competitors - Odeo included. The company closed and the four boys threw themselves into a new venture: they adjusted the research and development they had carried out for Odeo and in two weeks launched a prototype that would later become Twitter. On 21 March 2006, they bought the domain for 7,000 dollars: the little blue bird had begun to tweet.

The only one who could get Twitter to take off

At 30, Dorsey was named CEO of Twitter. He removed his nose piercing to secure some credibility in his new position as a businessman. The platform enjoyed immediate success. Users liked it and straight away it attracted the attention of the big Silicon Valley investors. The big turning point was in 2007 at South by Southwest, one of the largest creative festivals in the US: use of the social network tripled over the festival weekend, from 20,000 to over 60,000 Tweets per day.

Dorsey was the group’s undisputed leader for two years, the face of the social network, until he was suddenly replaced in October 2008. The motivation behind this move was his lack of focus on Twitter’s strategy. Bilton writes in his book that the Board believed he dedicated too little time to work. Evan Williams replaced him, a humiliating fact that Dorsey could not forgive, not even having been appointed Chairman of the Board, a position that requires a representative rather than strategic input. During this period, Dorsey drifted from the company’s operational work and launched a new startup, Square, a payment system that enables small businesses to accept card payments. The initiative increasingly gained success. Dorsey took up the position of CEO and, in the meantime, tried to regain control of the reigns at his other creation.
In March 2011, he got back behind the wheel at Twitter, this time as Executive Chairman, after Williams was replaced as CEO by Dick Costolo. Bilton believes this move was a Dorsey strategy to regain control, although Dorsey himself has never confirmed this. “Was I thinking, Screw Ev?” he asked during an interview with the New Yorker. “Emotionally, was I asking that? I don’t know. Maybe.” The result, however, is unquestionable: with Williams out of the game, Dorsey was back in charge. In 2015, he once again took up the role of CEO, which reversed the negative trend Twitter had been suffering for some time. Two years later, share prices soared by 30% and the little blue bird was worth 33.97 million dollars.

Perhaps Dorsey’s is not the most transparent reputation in Silicon Valley and opinions about him remain divided. But to date, one thing is clear to see: the only one who has been able to get that little blue bird off the ground has been him.

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