“Farewell to Jack Dorsey, the weirdest CEO in Silicon Valley,“ Io Dodds wrote in 

this week as the news broke that the 45 year old Twitter founder was stepping down in order to fully dedicate himself to his other passion project: cryptocurrency.

Or, more specifically, the payments platform Square, which Dorsey co-founded in 2009. (“Tech Crunch led with the headline Jack Dorsey dials in on his dream job” ran a 

“There’s a lot of talk about the importance of a company being ‘founder-led’. Ultimately, I believe that’s severely limiting and a single point of failure,” Dorsey said in a 

Clearly, Dorsey practices what he preaches; in its 15 years of existence Twitter will now have had four CEOs, two of whom were in fact Dorsey.

, Richard Seymour sees Dorsey’s defection as the smart move. “In some ways, the choice between Twitter and Square is a straight choice between political clout and profit. Square, a payments platform co-founded by Dorsey in 2009, is worth almost three times Twitter’s current value at about $97bn (£73bn).”

It seems unlikely however that Dorsey, one of the most enigmatic and unpredictable tech CEOs around is purely doing this for the money. Also in 

, John Naughton has compared Dorsey to another tech visionary; Steve Jobs.

“There are interesting parallels between Dorsey’s relationship with the company he co-founded and Steve Jobs’s with Apple, for both were ousted at one stage by their board colleagues and were then brought back to rescue said colleagues from their incompetence” Naughton writes, before going on to point out that both men endured “sojourns in the wilderness” after being ousted from their first companies, during which time they successfully founded new ventures. (Dorsey was kicked out of Twitter but regained the top seat in 2015) “Which only goes to show that sometimes being fired is the best thing that can happen to a visionary,” Naughton says.

This time, however, it’s clear that the decision to leave is Dorsey’s alone. Either way, the occasion of his departure from one of the 21st century’s most ground-breaking tech companies offers an unmissable opportunity to recount some of the eccentric CEO’s more outlandish manoeuvres. Wherever he ends up, it seems his weirdness is destined to continue.

Jack Dorsey in 2006, at around the time he posted the world&#8217;s first ever tweet


Dorsey is a man of many talents, as he proved by dipping a toe in the tweet game and the crypto sphere simultaneously. If tech hadn’t taken off for him, his path may have been very different. Back in the heady days of 2006 he reportedly told a pal he was about to quit tech and become a fashion designer. This didn’t quite work out, but before Twitter he also studied botanical illustration and erm, massage therapy. Reportedly he only ditched the massaging because “everyone [in San Francisco] was a massage therapist”.

Californians are all about crystals and copper rings to provide good energy. Like cryptocurrency these are mercurial and their powers only exist if we believe in them. Dorsey’s interests may be even more esoteric than this, however. Back in 2016 rapper Azealia Banks tweeted that Dorsey “sent me his hair in an envelope because i was supposed to make him an amulet for protection.” 

, the tweet was accompanied by a photo depicting what looked like feathers and blood in a jar.

Apparently Dorsey sent Banks a length of beard hair for use in the amulet in exchange for promoting Banks album (Banks says he didn’t promote it in the end, FYI). “We made a spiritual pact… and he left me hanging. He will pay for that,” Banks reportedly said at the time. Funnily enough, Dorsey has flat out denied the whole story.

This March Dorsey and other tech figureheads were called before US Congress as part of an investigation into misinformation. Dorsey, testifying remotely via video hook up, was seen to visibly check his phone throughout and appeared visibly frustrated with the line of questioning. In response to legislator’s ongoing series of yes-or-no questions, Dorsey even created a blank Twitter poll during his questioning asking users “yes” or “no”.

The poll received over 71,000 tweets with Dorsey informing lawmakers that ‘yes’ was winning. He also tweeted to confirm he had been barefoot throughout proceedings.

As Elon Musk has demonstrated, tech moguls becoming heavily invested in cryptocurrencies is now par for the course. However, Dorsey is easily the biggest cryptocurrency backer of all his tech playmates and has previously touted an “open marketplace for Twitter users to build and sell their own ranking algorithms”.

What’s more, he apparently hopes for a universal cryptocurrency which, as our IRL currencies have proven, is probably nigh on impossible to achieve.

, James Ball argues that Twitter users and investors may well be glad to see the back of Dorsey, thanks in part to his outlandish ways.“ It must have come as something of a bruise to the ego of Dorsey, who cofounded the company and sent the very first tweet, to see that his parting ways with it was enough to add (for a couple of hours) $4bn to the company’s market valuation,” Ball writes.

He may have something there. At one of the early Twitter meetings Dorsey reportedly played his employees The Beatles classic Blackbird, asking them to sit in silence and listen to the lyrics. The point of which was never explained…

Ball, however, points to perhaps more mundane Silicon Valley excesses, which he labels “weird hobbies and obsessions”.

“Like many Silicon Valley men, Dorsey became a fan of intermittent fasting and also reportedly installed a custom-made ice bath in his office. Shortly before the pandemic he announced a somewhat bizarre plan to have a gap year overseas, while remaining CEO.” Perhaps, leaving Twitter, Dorsey was “only waiting for this moment to be free”.

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