CEOs who can't sit still: Jack Dorsey's Twitter departure is a sign

Jack Dorsey, who is stepping down after six years as Twitter's chief executive, is one of the tech leaders who seem to have grown tired of managing their empires

In 2015, when Jack Dorsey rejoined Twitter as its interim chief executive, he raved about the app with quasi-religious fervor, calling it “the closest thing we have to a global consciousness.” 

But on Monday, Mr. Dorsey left the pulpit. He resigned, saying in an email to Twitter employees that he believed the company should “stand on its own, free of its founder’s influence or direction.” He announced that Parag Agrawal, Twitter’s chief technology officer, would take over as C.E.O., while Bret Taylor would become its board chair. 

In some ways, Mr. Dorsey’s departure is far from surprising. He has faced pressure for more than a year from the activist investor Elliot Management to boost Twitter’s growth and improve its financial performance. He’s also been running Square, the fast-growing financial services company he co-founded, and it always seemed that at some point he would decide that one C.E.O. job was enough. (In his email, Mr. Dorsey said that leaving Twitter was his choice.) 

But there’s something else going on with Mr. Dorsey and some of his fellow tech moguls. They seem to be getting bored and restless with their jobs, and they’re striking out in search of adventure. 

Jeff Bezos’ wanderlust led him to step down from Amazon this year and fulfill his childhood fantasy of going to space. Google’s founders, Larry Page and Sergey Brin, stepped down in 2019 and have since been investing in futuristic projects like airships and flying taxis. Mark Zuckerberg is still running Facebook, but it’s called Meta now, and the company’s big metaverse pivot seems to be designed in part to infuse some novelty and excitement back into a staid, big-company culture. 

As Recode’s Peter Kafka wrote this year, this year’s big wave of tech executive departures partly reflects the fact that the biggest Silicon Valley giants are so huge and profitable that they no longer need visionary founders in charge — just competent managers who can keep the money-printing machines running and avoid any catastrophic mistakes. 

But it also hints at how little fun the titans of tech seem to be having. The founders of today’s biggest tech giants are growing tired of managing their empires, which are increasingly burdened by political controversy and hard-to-fix problems like misinformation and hate speech. They don’t see an easy way out, and they’re more excited by building new things than fixing old ones. So they are turning those empires over to others and heading off in search of new frontiers. 

It seems obvious what Mr. Dorsey’s next frontier will be. He’s obsessed with Bitcoin (it’s the only thing in his Twitter bio), and he talks about cryptocurrency and the decentralized web with the kind of zeal he once used to describe Twitter. 

“I don’t think there’s anything more important in my lifetime to work on, and I don’t think there’s anything more enabling for people around the world,” he told the audience at a Bitcoin conference in Miami in June. 

Mr. Dorsey, whose oracular beard and quirky wellness routines have made him something of a cult figure in Silicon Valley, has become a crypto influencer in recent months. Bitcoin fans cheered his resignation on Monday, assuming he’d be spending his newfound free time championing their cause. (A more likely scenario is that he’ll continue to push crypto projects at Square, where he’s already started building a decentralized finance business.) 

Mr. Dorsey didn’t respond to a request for comment, so I can’t be totally sure what’s behind his exit, but it’s easy to see why he would be getting restless at Twitter after more than 15 years of involvement. He cut his teeth during the internet boom of the late 2000s and early 2010s, when being a co-founder of a hot social media app was a pretty great gig. You got invited to fancy conferences, investors showered you with money and the media heralded you as a disruptive innovator. If you were lucky, you even got invited to the White House to hang out with President Barack Obama. Social media was changing the world — Kony 2012! The Arab Spring! — and as long as your usage numbers kept moving in the right direction, life was good. 

Today, running a giant social media company is — by the looks of it — pretty miserable. Sure, you’re rich and famous, but you spend your days managing a bloated bureaucracy and getting blamed for the downfall of society. Instead of disrupting and innovating, you sit in boring meetings and fly to Washington so politicians can yell at you. The cool kids no longer want to work for you — they’re busy flipping NFTs and building DeFi apps in web3 — and regulators are breathing down your neck. 

In many ways, today’s crypto scene has inherited the loose, freewheeling spirit of the early social media companies. Crypto start-ups are raising tons of money, attracting huge amounts of hype and setting off on utopian-sounding missions of changing the world. The crypto universe is full of weird geniuses with unusual pedigrees and big appetites for risk, and web3 — a vision for a decentralized internet built around blockchains — contains lots of the kinds of complex technical problems that engineers love to solve. Those factors, plus the enormous sums of money flowing into crypto, have made it a tempting landing spot for burned-out tech employees looking to get back in touch with their youthful optimism — and maybe for C.E.O.s, too. 

“Silicon Valley tech is the old guard, distributed crypto is the frontier,” Naval Ravikant, another crypto booster and an early Twitter investor, tweeted this month. 

Square, which builds mobile payment systems, has always been the most natural outlet for Mr. Dorsey’s crypto dreams. But he has tried to incorporate some of Bitcoin’s principles into Twitter. The company added Bitcoin tipping and started a decentralization project called Bluesky last year, with the goal of creating an open protocol that would allow outside developers to build Twitter-like social networks with different rules and features from the main Twitter app. (Mr. Agrawal, who is taking over for Mr. Dorsey at Twitter, has been closely involved with these initiatives, meaning they probably won’t disappear when Mr. Dorsey does.) 

One cynical interpretation of what’s happening with Mr. Dorsey and his peers is that they’re simply trying to evade responsibility — shooting themselves into space and fooling around in crypto while other people clean up the messes they made at their old jobs. 

Still, there’s something to be said for knowing when to pass the torch. And after he has seen what it’s like to wind up in the center of power, it’s hard to fault Mr. Dorsey for wanting to decentralize the internet, starting with himself.