The basic deets

The story first leaked to CNBC, and the company soon made it official. Dorsey made public his email to Twitter employees, where he said:

• He doesn’t believe in founder-led companies, which is “severely limiting and a single point of failure.”
• Parag Agrawal—who “leads with heart and soul, and is someone I learn from daily”—will make an excellent successor: “My trust in him as our CEO is bone deep.”
• He will also quit his seat on the board around May—to “give Parag the space he needs to lead.”
• He’s a super humble guy, ICYMI: “And there aren’t many founders that choose their company over their own ego.”

Parag who? The 37-year old IIT-Bombay and Stanford graduate joined the company as a software engineer more than a decade ago—after research internships at AT&T, Microsoft and Yahoo. He became the Chief Technology Officer in 2017—and has mainly overseen the strategy to use artificial intelligence to create an open social media platform (more on the Bluesky Project here). As Economic Times notes, the two most powerful people at Twitter will now be India-born—the other being Vijaya Gadde, its policy and safety lead director.

The quirky history of Jack Dorsey

Unlike many of his Silicon Valley peers, @Jack’s road to great success has been full of twists and turns:

• He was a whiz kid from St Louis who wrote software for taxi services as a high school student. And like many tech titans today, he never graduated from college—dropping out of New York University to join his first startup.
• Dorsey was soon fired and went back home to dabble in… botanical illustration. He even became a licensed masseur and only dropped the idea after returning to San Francisco and discovering that “everyone was a massage therapist.”
• Dorsey first built the prototype of what would become Twitter in 2000—but his enduring obsession for the longest time was… fashion design!
• A month before Twitter launched in 2006, Dorsey told his co-founder: “I’m going to quit tech and become a fashion designer.” And he cut out early from work to take “drawing classes, hot yoga sessions and a course at a local fashion school.”

Point to note: Much has been written about Dorsey’s eccentric lifestyle—which led New York Times to dub him as the Gwyneth Paltrow of Silicon Valley:

“During the year of soul-searching after his ousting from Twitter, he turned to meditation and the practice still remains an essential part of his morning routine today. He wakes at 5am and only eats one meal a day: dinner. His daily wellness rituals have been known to include ice baths, cryotherapy pods and infrared saunas. He journals and tracks his sleep. His life is spartan, almost monastic.”

The In & Out CEO: That sense of always being distracted by something other than Twitter has dogged Dorsey all through his career—and frequently cost him his job. 

• He was first pushed out of his CEO job in 2008, when co-founder Evan Williams took over—uttering the famous line: “You can either be a dressmaker or the CEO of Twitter. You can’t be both.”
• Down-but-never-out Dorsey used his time to found the payment services company Square—which he leads to this day.
• He returned to Twitter in 2011 as executive chairman, got absurdly wealthy from the IPO in 2013—and was restored to the CEO throne in 2015.
• But over recent years, the same old concerns about a lack of focus have grown. This time around, it’s Dorsey’s increasing obsession with cryptocurrency—which is the focus of his other company Square.
• In 2019, he announced plans to spend six months a year in Africa, tweeting: “Africa will define the future (especially the bitcoin one!).”
• The pandemic canceled that plan—but one of Twitter’s investors Elliott Management soon tried to push Dorsey out of his job in 2020.
• A truce was reached… or perhaps not. A year later, Dorsey is once again out of his CEO job.

The big question: Did he quit or was he fired?

Likely a bit of both.

One: The truce agreement with Elliot Management already included a “CEO succession plan”—and many predicted that Dorsey’s tenure was on a timer. Also, Elliot is led by a rabid rightwinger Paul Singer—who may not have taken kindly to Dorsey’s decision to ban Donald Trump from the platform (though the call was made by subordinates when Jack was chilling in French Polynesia, which again likely irked Elliot even more). 

Two: Most founders stick around as board members even after they quit the CEO job. Unnamed employees told Vanity Fair that he has been shunted out completely this time—to ensure he never finds a way back in. Another says Dorsey just saw the writing on the wall: “I think Jack knew that his performance as CEO wasn’t up to par, and that while he had held off being ousted before, he knew that it was only a matter of time before other investors, or his new board, would force him out as CEO.”

Three: Also likely: @Jack just lost interest in Twitter, and wants to focus on Square—which doesn’t come with the headache of running a social media platform:

“While Twitter’s financial success is mostly limited to its ability to sell digital advertising, a market dominated by Google and Facebook, Square has a grip on the entire consumer payment system. Square is enmeshed with brick-and-mortar sales, e-commerce, peer-to-peer, and increasingly the crypto market. While Twitter is building new revenue streams, particularly through its subscription offering, Square simply has more chips on a table with generally lower risk and better returns.”

Square is also a better fit for Dorsey’s big crypto ambitions—unlike Twitter which has never been keen on virtual currencies.

The bottomline: Back in 2020, New York Times podcast host Michael Barbaro said to Dorsey: “Twitter doesn’t seem to like you exactly. And you don’t exactly seem to like Twitter.” Maybe this was just a divorce that was long overdue.

Reading List

New York Times has a profile of Agrawal. Quartz explains why Dorsey chose Square over Twitter. Vanity Fair has all the insider gossip on whether Dorsey was fired. Wired predicted Dorsey’s departure last year. Wall Street Journal (paywall) and this recent Bloomberg News op-ed lay out the problems that Agrawal will inherit. For profiles of Dorsey’s quirky career track and management style, read CEO magazine, CNBC News and Wired. MoneyControl has the full text of Dorsey’s resignation email.