Farewell to Jack Dorsey, the weirdest CEO in Silicon Valley. Twitter is a reflection of his nature

Silicon Valley just got a little less weird. Jack Dorsey, the raggedy-bearded, nose-ring-sporting chief executive of Twitter, has announced his resignation from the social network he co-founded 15 years ago. More than a sea change for his company, it marks the end of his tenure as quite the oddest person to run any major US tech firm.

Silicon Valley is a weird place, but nowhere in its top players will you find any CEO who could so fairly be described as a space cadet. Not Amazon founder Jeff Bezos, and certainly not his replacement as chief executive Andy Jassy; not Google’s Sundar Pichai, nor Microsoft’s Satya Nadella and Brad Smith. Not even Netflix boss Reed Hastings gets there – despite his bizarre cyber-Maoist management style built around radical transparency and self-criticism.

Sure, Facebook’s Mark Zuckerberg has his eccentricities: the year where he challenged himself to kill every animal he ate (at one point knifing a goat and serving it to Dorsey for dinner), for example, or his perennial fixation on Augustus Caesar, the first Roman Emperor. But with classic rich-man hobbies such as wakeboarding and skiing, he’s not a patch on Dorsey.

The only serious competition is Elon Musk, who once blasted a Tesla car into space in tribute to the late sci-fi author Iain M Banks and named his child with pop star Grimes X Æ A-12 (before publicly correcting her about its meaning). Yet so often, Musk’s weird actions feel affected and try-hard, undertaken with a knowing wink to his fans and seemingly calculated to stir up controversy and gain likes and retweets on the social network Dorsey built.

Dorsey, by contrast, has never seemed to care about his Twitter following – or, at times, about Twitter itself. What other Big Tech chief executive has been fired from his own company for doing too much yoga? Dorsey was ejected from Twitter in 2008 for, among other things, leaving the office around 6pm to de-stress and attend night courses in fashion and drawing. "You can either be a dressmaker or the CEO of Twitter, but you can’t be both," his fellow co-founder Evan Williams told him.

He never quite gave up those interests, telling another co-founder just before Twitter’s launch in 2006 that he was "going to quit tech and become a fashion designer". Before Twitter, he pursued botanical illustration and massage therapy, only dropping the latter after coming back to San Francisco and finding that "everyone was a massage therapist". He eventually regained the CEO seat in 2015.

Then there was the claim by rapper Azealia Banks that Dorsey had once sent her a lock of his beard hair so that she could create a magical amulet to protect him from Isis, supposedly in exchange for promoting her album (he did not). "A lot of articles said I put a hex on him but I didn’t," Banks said in 2018. "We made a spiritual pact... and he left me hanging. He will pay for that." Though Dorsey has flatly denied this, the fact that it was plausible speaks volumes about his image.

There was also Dorsey’s mocking, cynical, occasionally candid performance while testifying remotely before the US Congress this March, in which he was often visibly checking his phone. As legislators harangued the witnesses with theatrical yes-or-no questions, he created a blank Twitter poll asking users "yes" or "no", then responded to a congresswoman’s cheeky question about it by saying "yes".

Later he retweeted a Big Tech lobbyist’s tweet criticising the quality of the questions. In his kitchen in the background, a special "clock" could be seen displaying the real-time exchange rate of Bitcoin to US dollars.

All of this would be trivia if Dorsey’s oddness had not filtered down to his company. Yet for some of Twitter’s most crucial years he appeared to be dreaming at the helm, telling journalists about his daily routine – ice baths in the morning, fasting until the evening, walking more than an hour to work through rainy, foggy San Francisco – while new features and reforms languished in development.

He was, after all, running two companies: not only Twitter but also Square, the payment provider he founded after his firing in 2008, which will now be his focus once again.

These were the years when nation states used armies of Twitter bots to manipulate foreign elections; when online extremists gamed Twitter’s algorithms to boost their messages into the headlines; when organised harassment became a daily reality for many users; when Donald Trump used his knack for controversy to win the presidency and turn Twitter into a megaphone that would later help instigate the Capitol insurrection. Dorsey’s responses rarely seemed to rise above blue-sky pontificating about free speech and "healthy conversations".

All that started to change around 2019. Someone seemed to have lit a fire under him and the company, resulting in a rapid stream of new features and unusual levels of corporate transparency. Twitter began releasing huge public data dumps about disinformation campaigns that it had discovered, and explaining more than other companies, both to journalists and to the public, about its rules and how they were enforced.

When Twitter, Facebook and YouTube all banned Donald Trump after the Capitol riot, Dorsey gave the most candid and detailed explanation. "I do not celebrate or feel pride in our having to ban [Trump]," he said. "A ban is a failure of ours to promote healthy conversation... [It] sets a precedent I feel is dangerous... [and] in the long term it will be destructive to the noble purpose and ideals of the open internet."

And while Facebook’s internal research into its own problems had to be leaked to journalists as the "Facebook files", Twitter released full details of studies showing that its content ranking algorithms had a bias toward right-wing news sources and that its photo-cropping algorithms were biased against dark skin.

Even Twitter’s pipe dreams were dreamier than most. Many contemporary tech CEOs claim to believe in "openness" and "decentralisation" because they grew up in the anarchist-tinged hacker culture of the nineties and noughties. Most now pay these ideas only lip service in their statements and actively oppose them with their actions.

But Dorsey, by far the biggest cryptocurrency backer of all Big Tech CEOs, kept talking about creating an open marketplace for Twitter users to build and sell their own ranking algorithms, or moving Twitter to a new open tech protocol that would release it from centralised control. These may never happen, and might just end up as hot air, although Dorsey’s replacement Parag Agrawal is also a believer.

For many people, all of this will be too little, too late, and Dorsey’s chief legacy will be the extremism, polarisation and anxious cultural neuroticism that Twitter helped ignite. Even so, its faults and its virtues directly mirror the peculiarities of a tech baron who almost became a dressmaker and never stopped talking – and talking, and talking – about his hacker ideals.

Io Dodds is a tech reporter based in California