What is Jack Dorsey thinking?

We have some questions about what's going on with Jack Dorsey. It started in December when Dorsey and Marc Andreessen started scrapping on Twitter. That was bad enough, but now it seems like Elon Musk's Twitter bid has made Dorsey even more honest. Now he’s calling himself a “Block Head," which, well, OK then!

Dorsey ostensibly shouldn’t care about Twitter, right? He announced last year he’d step off the board and end his relationship with the company completely by next month. He’s also said he’s dedicating his life to bitcoin, and his work at his companies — make that company, singular, now — was only relevant to him if he thought it advanced that cause. Because bitcoin, Dorsey believed, would bring about world peace.

But now? Dorsey seems like a man who has run out of cares to give. Except when he's not dropping the occasional hugging emoji, that is.

• In a recent tweet, he posted a video of one of Kurt Cobain’s last interviews. Cobain describes the main character of a novel: “Every time he smells human … he’ll just get really disgusted and hide. He tries to stay away from people. I can relate to that.”
• In the category of “people Jack Dorsey can’t relate to”: Salesforce co-CEO Marc Benioff. Dorsey razzed him about posting his latest magazine cover, and asked the Time magazine owner if he’d bought that title, too. (There’s somehistory here: The two billionaires fought over a local tax measure in San Francisco years back.)
• Also: Robinhood CEO Vlad Tenev! Dorsey called him “thirsty.” The issue here seems to be that Tenev likes cryptocurrencies that aren’t bitcoin, and that’s not OK with Dorsey, who’s extremely pro-bitcoin and nothing else in cryptoland.
• Also: the American political system! In a testy exchange with the official House GOP Twitter account, he said, “No one’s buying a two-party system is good for the people either, but here we are.”

The most serious feud may be with Twitter’s board. And that’s not a great thing, given the upcoming showdown with Musk, who’s lined up financing for his bid to buy Twitter.

• Dorsey joined other directors in welcoming Musk onto the board, which made it awkward when Musk rejected the board seat. Dorsey also voted along with his other directors to adopt a poison pill plan to block Musk’s hostile bid.
• In response to Microsoft’s Tren Griffin quoting the observation that “Good boards don’t create good companies, but a bad board will kill a company every time,” Dorsey responded “Big facts.” Twitter’s board, he added, has “consistently been the dysfunction of the company.”
• “Are you allowed to say this?” a Twitter user asked Dorsey. “No,” he replied. Asked to elaborate by CNBC’s Scott Wapner, he said, “So much to say … but nothing that can be said.” If this is Dorsey censoring himself, we can’t imagine what it would look like if he really let go.

The thing is, Dorsey does have a day job, and it’s running Block. The company formerly known as Square has serious issues, like increasing competition in point-of-sale systems and the challenges of integrating its Afterpay acquisition.

• Under Dorsey’s redirection, Block changed its name to emphasize the importance of cryptocurrency to its business. Square and Cash App are the moneymakers, but Block also has a number of new crypto technology initiatives.
• Some of Dorsey’s recent tweets are about Block; he’s praised the new Square Stand and Cash App’s marketing, for example.
• But his feuds, particularly those about Web3, highlight a problem: What if Dorsey’s interests are diverging from Block’s? (We asked a Block representative if the board remained confident in the CEO in light of his recent tweets, and didn’t get a response.) At the very least, there needs to be an objective discussion about whether Cash App’s crypto-trading business would be stronger if it weren’t limited to bitcoin, whatever its CEO’s personal views are.

It may be uncomfortable, but the way Dorsey uses Twitter is always worth watching. One of the changes Ev Williams made after he fired Dorsey as CEO was to change the prompt on Twitter’s website from “What are you doing?” to the more impersonal “What’s happening?” Dorsey’s vision of Twitter was as an updated version of AIM’s status message, a real-time view into people’s emotions, hopes and fears. Williams, who also created Blogger, saw it more as a place to dispassionately observe the world. (Twitter’s rumored “Vibe” status feature is a throwback to the Dorsey version of Twitter.) So Dorsey’s lashing out on Twitter may at times be unbecoming. But it’s also very real. Maybe Dorsey’s not OK. Maybe none of us is OK. And that’s OK. Let’s all stop and hug.

— Owen Thomas (email | twitter | dog’s instagram)

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