Jack Dorsey and breaking up the cult of the founder

Dorsey’s farewell note is a warning shot to all founder CEOs … especially you-know-who.

Jack Dorsey

“There aren’t many companies that get to this level. And there aren’t many founders that choose their company over their own ego.”

Photo: Getty Images

In his note Monday announcing his departure from Twitter, Jack Dorsey delivered a warm welcome to the company’s new CEO, a fond farewell to the tweeps he’s leaving behind and a quick shout-out to his mom.

He also fired a warning shot at certain other founder-CEOs who shall remain nameless.

“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 wrote. “There aren’t many companies that get to this level. And there aren’t many founders that choose their company over their own ego.”

Whether that’s the real reason for Dorsey’s departure after nearly 16 years as a company leader and two stints as its CEO remains in question, and maybe even in doubt. Until today Dorsey was, after all, the simultaneous CEO of two publicly traded companies — one of which he was nearly ousted from last year — and his apparent new calling in life, bitcoin, has precious little to do with a social network for sharing quippy takes on pop culture and global catastrophe. That there are other dynamics at play in Dorsey’s decision to hand over the CEO role to Twitter CTO Parag Agrawal, effective immediately, is almost certain.

But Dorsey’s point about founder-led companies is still well-taken: Maybe, he seems to suggest, the people responsible for dreaming up what a company could be at the beginning aren’t always — or even ever — the best people to run it after it has become something else entirely.

The company Dorsey leaves behind is almost unrecognizable from the one he co-founded in 2006, or even the one he returned to as CEO in 2015. That June, when Twitter announced Dorsey’s encore as CEO, his biggest obstacle was finding a way to jumpstart sluggish growth. Less than one week later, Donald Trump descended an escalator inside Trump Tower, announcing his bid for the presidency and resetting the agenda of Dorsey’s next six years.

Suddenly, Dorsey was grappling not just with demands from investors — though those continued — but also with the world’s first Tweeter-in-Chief, who used the platform for years to prolifically spew hate and conspiracies with little interruption from Twitter and who, in doing it, wrote a playbook for global strongmen and fringe politicians to follow. Under Dorsey’s lead, Twitter initially took a hands-off approach, crafting new rules that allowed elected officials to say just about whatever they wanted. When you’re a global leader, Trump’s presidency proved, they let you do it.

Trump’s election ushered in a new era of scrutiny for social media companies, Twitter included. As the extent of the information warfare playing out on tech platforms became clearer, Washington wanted Twitter and others to do something about the bots and the trolls and, depending on who you asked, the censorship — or lack thereof — of some conservatives.

These are the problems Agrawal now inherits — problems Dorsey and his co-founders couldn’t have imagined in Twitter’s earliest days. To Dorsey’s credit, Twitter has made progress on some of these fronts. In 2019, Dorsey embarked on an apology tour of sorts, taking seemingly every interview as a chance to lament Twitter’s failures and commit to making the platform a “healthier” place.

The company seems to have earnestly sought to deliver on that goal. At a time when Google was firing its top AI ethicists and Facebook was disbanding its civic integrity team, Twitter was recruiting top tech critics to oversee its ethical AI work and expand the team with Dorsey’s direct blessing. The company has also experimented in plain sight with tools that discourage toxic conversations before they start and enable auto-blocking of hateful tweets. It’s opened up its full archive to researchers so they can study the platform from the outside in. And of course, early this year, after wallpapering his account in warning labels, Twitter finally banned Trump for life.

But far from relishing in the decision, Dorsey described the ban as “a failure of ours ultimately to promote healthy conversation.”

“Having to take these actions fragment the public conversation. They divide us,” Dorsey tweeted at the time. “They limit the potential for clarification, redemption, and learning. And [it] sets a precedent I feel is dangerous: the power an individual or corporation has over a part of the global public conversation.”

Dorsey made much the same argument then that he is now: That no one person, including himself, should have so much power — and certainly not the one person who, by virtue of having founded a company, may be the most blinkered to its failures.

Plenty of prominent tech founders have stepped down from leadership roles at their companies: Larry Page, Sergey Brin and Bill Gates, to name a few. That leaves Mark Zuckerberg as the last obvious Big Tech target of Dorsey’s admonitions. Zuckerberg has also often lamented the concentration of power in his hands, but only to urge governments to impose light, industry-approved regulations, not to advocate for his own removal.

As recent leaks from Facebook whistleblower Frances Haugen have shown, Zuckerberg remains deeply, personally involved in everything from annual staffing decisions to whether Facebook should bow to pressure to censor dissidents in Vietnam.

These and other revelations have led to constant calls for Zuckerberg to step down and let someone else lead the global behemoth that was once a dorm-room experiment. Though he didn’t name him outright, Dorsey’s note does seem like yet another not-so-thinly veiled dig at Zuckerberg.

Of course, it was the cult of the founder that brought Dorsey back as CEO of Twitter in 2015. Even though he was simultaneously CEO of Square, a position he still holds, hopes were high that Dorsey’s ties to Twitter’s roots would help him more clearly envision its future. Six years later, he’s stepping back only now that he has another dream to chase — and another company to run.

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