Jack Dorsey, who stepped down as Twitter’s CEO this week, holds the dubious distinction of being one of Silicon Valley’s most important woolgathering sages. Speaking with him can be incredibly disorienting, the journalist Ashley Feinberg once remarked, “not because he’s particularly clever or thought-provoking, but because he sounds like he should be.” That echoes my own experience: Dorsey is quiet and reserved in interviews—a departure from the usual chief-executive bravado—and he seems genuinely interested in giving thoughtful answers, also rare. Yet however earnest his engagement, he almost never gives a straight or satisfying response. Press him to account for specific problems on his platform, and he’ll launch into a game of tech-founder Mad Libs that takes the conversation nowhere.
I don’t think Dorsey means to stonewall by meandering; rather, he’s expressing, in his elliptical way, the disconnect between his lofty ideals for social media and the toxic discourse it creates. It’s as if he has a perfect version of Twitter in his head but lacks the language to describe it. Now, with his departure from the company, that tension can at last be swept aside. Like other Big Tech leaders, he’s pivoting away from his teenage, problem-ridden platform in the hopes of getting to a better, different kind of place. Imagine a version of the distracted-boyfriend meme in which the guy in the middle is a CEO, and he’s ogling a decentralized metaverse.
Dorsey has always had a reputation as an ideas guy. After Twitter’s storybook launch, in 2006, he set to work on another company, one to help democratize mobile payments, which became Square. His tech “visionary” status meant that Dorsey could be eccentric, which he capitalized on by fasting, drinking a concoction of suspect nutritional value called “salt juice,” walking five miles to work, and sporting a trademark beard and nose ring. Visionary status also allowed him to juggle two part-time CEO jobs, and it provided cover when, a few years ago, he began tweeting intensely about cryptocurrency. In August, Dorsey claimed that bitcoin would eventually “unite the world.” This could well be the context for his next big idea in tech, and his next multibillion-dollar company. But also, it was @jack being @jack.
Being at the helm of Twitter in 2021 is hard. In early 2020, Elliott Management, the activist investor, took a sizable stake in the company and pressured Dorsey to hit growth targets. And although Twitter is working on some new products, the platform is, to a large degree, mature. Leading a mature company—especially one that has an outsize influence on politics and culture—involves a lot of maintenance work. It’s also kind of a nightmare. In the past 18 months, Dorsey has had to navigate a flood of COVID misinformation across his platform, multiple testimonies before Congress, and a deeply contentious election season, which culminated in his executive decision to ban the sitting president of the United States. I’m not suggesting that we shed a tear for this billionaire, but I’ve been tagged in enough of Dorsey’s mentions to know that part of his management experience is absorbing justified criticism from, well, basically everyone. Not exactly what a visionary wants to do all day.
Legacy tech platforms make plenty of money from their hundreds of millions, if not billions, of users, but they’re also riddled with problems. Those problems must feel quotidian to the people who dreamed the platforms up. Rolling out new products, updates, and rules is a logistical challenge, and users are cranky and resistant to change. The successes of Web 2.0—the social internet—are no longer playgrounds of possibility; they’re not the future. That’s why many venture capitalists, programmers, and Silicon Valley CEOs such as Dorsey are eyeing Web3.
To put it in simple terms, Web3 refers to a third generation of the internet where online services and platforms have been transitioned to a model based on blockchains and cryptographic tokens. In theory, that means they are decentralized, and anyone who owns tokens has some amount of ownership or voting control over them. This model of the web represents a financialized vision of the internet, backed heavily by investors and speculative currencies. It is also the kind of chaotic space to which developers and creatives instinctively flock. Blockchain-based projects are sometimes confusing, they can have barriers to entry (like requiring a crypto wallet), and they seem to generate their own, varied countercultures. There is an immense amount of money to be made. It’s exciting—a new playground.
Dorsey is among the crypto world’s best-known evangelists. At a conference in Miami this summer, he remarked on bitcoin’s supposedly unlimited potential for good. “For me, bitcoin changes absolutely everything,” he said, extolling its ability to be a universal asset and a utility for unbanked people in the developing world. He described having spent November 2019 in Nigeria, Ethiopia, and Ghana with entrepreneurs, and said he’d learned that the technology is transformative, even beautiful. In an act of foreshadowing, Dorsey added that he would be working fully on bitcoin if he weren’t the CEO of Twitter and Square.
Dorsey’s bitcoin musings hit familiar notes for him: They are full of hope and possibility, but they are also extremely vague. “What I’m drawn to the most about it,” Dorsey said of cryptocurrency, “is the ethos, is what it represents, the conditions that created it, which are so rare and so special and so precious. 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.”
Dorsey’s vision for bitcoin, much like his vision for Twitter, is confidently idealistic. In 2019, when he was confronted about Twitter’s harassment features, he offered mumbly, circuitous responses. And now, when he is confronted with bitcoin’s problems —such as the environmental impacts from “mining” cryptocurrencies—his answers are just as opaque and unsatisfying. “I believe fully that bitcoin, over time and today, does incentivize more renewable energy,” he told the crowd in Miami. “And I think it does incentivize more awareness around how we’re getting that power and gives people more freedom to convert unused, wasted power into something that provides value for billions of people around the world.”
I believe that Dorsey believes what he says. Of all the major tech CEOs, Dorsey has always been the most responsive to criticism and has pushed Twitter to tackle important harassment problems. But his visions for bitcoin, like his past hopes for Twitter, take for granted that somebody will eventually solve the biggest problems facing a piece of technology. It’s a nice idea, the kind you might expect from an “ideas guy.” But the parallels are clear between his vision for Web3 and, say, the free-speech idealism he espoused before a sitting president used his platform to deny the results of an election. Web3 is, in theory, more egalitarian and inclusive than our current, messy internet. The way we get there, according to the Web3 prophets, is to trust the process and follow their lead. The logistics will work themselves out.
In that respect, Jack Dorsey’s departure from Twitter and embrace of crypto resembles Mark Zuckerberg’s rebrand of Facebook in favor of the metaverse. Big Tech’s founders have jettisoned the escape pod from their bloated, boring second incarnations of the internet and set off for a new frontier. Their ambitions would be admirable if not for the harms that their platforms have already wrought. Dorsey and company may, in fact, be visionaries—city planners who can deftly sketch the thoroughfares and public spaces we will eventually traverse. But city plans don’t make a city, nor does a collection of parks and avenues. Cities are the result of a meticulously managed infrastructure. They need a sanitation department to make sure that garbage doesn’t pile up in the streets, and transit authorities to keep the trains on time. They need bureaucrats, not visionaries.
It makes sense that Dorsey, a man with a vision so grand that he could barely articulate it, would find bureaucratic work to be stifling. If anything signals the end of the second iteration of the internet, it’s the dreamers moving on.