As he walked onstage at the Bitcoin 2021 conference in Miami, Jack Dorsey was still technically the chief executive officer of two publicly traded companies, but he looked more like a beachside bartender. He wore a sunburst tie-dye shirt, with his head shaved and his long, graying beard untrimmed. He’d flown to South Florida, even though the official policy at one of his companies, Twitter, was that employees weren’t supposed to travel for work, and even though a group of activist investors had spent the better part of the previous 18 months trying to oust him for being unfocused.
No matter: Dorsey had resolved to enjoy himself in the most Jack Dorsey way possible. He went to the beach with a twentysomething model, Flora Carter, had dinner with Dave Portnoy, the professionally obnoxious sports media entrepreneur and stock trading enthusiast, and hung out with Floyd Mayweather, the professionally obnoxious boxer-turned-crypto-promoter. (Mayweather was in town on behalf of EthereumMax, a new cryptocurrency, and for an exhibition fight against bro influencer Logan Paul.) Onstage, Dorsey was heckled by Laura Loomer, the far-right conspiracy theorist who’d famously handcuffed herself to the doors of Twitter’s New York office after her account on the social media service was banned in 2018. Dorsey had called her protest “brave,” and now, when Loomer jeered that Dorsey was the “king of censorship,” he replied earnestly. He said he hoped to remove the “corporate-ness” from Twitter, making it more open and decentralized, like Bitcoin.
Dorsey had lots to say about Bitcoin—in fact, a lot more than he had to say about either Twitter or Square, his payments company. He predicted Bitcoin would replace banks, bring economic opportunity to entrepreneurs in the developing world, and incentivize investments in renewable energy. “Bitcoin changes absolutely everything,” Dorsey stated matter-of-factly. “I don’t think there’s anything more important in my lifetime to work on.”
Five months later, Dorsey resigned from Twitter Inc. and announced that he was renaming Square. Henceforth the company, which helps local coffee shops and other small businesses process payments, would be called Block Inc., which brings to mind the main technology underlying cryptocurrencies: blockchain. Officially, Block is Dorsey’s full-time job, but almost everybody in his orbit knows he has a pretty serious side hustle. While he was running both Twitter and Square, his employees often joked that Twitter was his “favorite child.” Now it appears—based on conversations with more than 30 current and former employees who’ve worked for him—the favorite child isn’t so much Block; it’s Bitcoin.
Over the past two years, Dorsey, who declined to comment through a spokesperson, has fashioned himself as the currency’s unofficial spiritual leader and public defender, promoting it constantly from his Twitter feed and taking swipes at tech’s venture capitalists who are funding rival crypto projects. Last year, at a different crypto event alongside Elon Musk, Dorsey said he believed Bitcoin could bring about “world peace.” (Musk, the world’s richest person, became Twitter’s largest shareholder in March, deepening an alliance with Dorsey that has developed over several years.) During his dinner with Portnoy, Dorsey told him he wanted to focus exclusively on the digital currency. “He is as bullish on Bitcoin as anybody I’ve ever heard,” Portnoy said on his podcast.
Dorsey’s enthusiasm has implications for Block—which has grown in part thanks to a feature that makes it easy for regular people to buy Bitcoin from their phones and which has spent $220 million buying Bitcoin to keep on its balance sheet—and for the future of the cryptocurrency itself. Dorsey can be iffy as a manager, but as a futurological weather vane, he’s rarely wrong. As a former Twitter employee, who like others quoted in this story requested anonymity to avoid angering a former boss, puts it, “Jack hasn’t met a cult he didn’t wanna lead.”
The best way to understand what Dorsey is thinking about at any given moment is to follow his tweets. Twitter is where he posts everything, including what music he’s listening to and the social issues he cares about. Although Dorsey can be cryptic—the day before he resigned as CEO, he posted “I love twitter” without any other context—his missives typically offer a glimpse into what’s on his mind.
Judging by this, Dorsey’s interest in Bitcoin took off after a monthlong trip to Africa in November 2019, after which he started tweeting about the currency nonstop. The trip included stops in Ethiopia, Ghana, Nigeria, and South Africa. He met with local entrepreneurs, many of whom were building companies focused on Bitcoin. That fact “amazed” and “inspired” him, and he walked away convinced Bitcoin could change the financial systems on the continent. Dorsey’s employees (he’d been joined by several Twitter executives) didn’t think much of the trip at the time, but after he was headed home, tweeting from the airport in Addis Ababa right before he boarded his flight, things seemed to get more serious. “Sad to be leaving the continent … for now. Africa will define the future (especially the bitcoin one),” Dorsey tweeted. “Not sure where yet, but I’ll be living here for 3-6 months mid 2020.”
The message caught employees by surprise. Dorsey had already been promoting the idea of remote work internally, but in promising to spend half the year halfway across the world, he’d accidentally handed a gift to a business adversary, Paul Singer. The founder of Elliott Management, Singer is known for taking stakes in public companies and then pushing for sweeping management changes. The company had viewed Twitter as a ripe target for years, partly because its business had underwhelmed, and partly because Twitter, unlike Google and Facebook, hadn’t given its founders so-called supervoting shares that would’ve allowed them to control the company. This created an opportunity for activist investors to gain a foothold, and there was nothing Dorsey could do to stop them. Around the time of Dorsey’s trip, Elliott made a big Twitter investment and, by early 2020, had more than $1 billion in the company’s stock, according to a person familiar with the purchase.
Three months later, in February 2020, the investment company’s stake became public. In a letter sent to Twitter’s board, Elliott outlined a series of issues with Twitter’s business and corporate governance, alerting the company that it planned to nominate four new directors. The most notable complaint from the activist investor: Twitter’s CEO was splitting his time with another company. Dorsey’s tweet wasn’t the only motivation, but it gave the activist investors plenty of cover to attack him. Not only did he have two jobs, but he didn’t seem particularly interested in doing either of them.
Twitter’s board and executive team scrambled to find investors who would support Dorsey in case of a shareholder vote. The board briefly discussed adding as a director Laurene Powell Jobs, a Dorsey friend and the widow of Apple Inc. co-founder Steve Jobs. (She now runs Emerson Collective, an investment firm.) But after less than a month, Twitter settled with Elliott, avoiding a proxy battle. The company added three new board members, including Elliott managing partner Jesse Cohn, and made changes to its corporate governance. Dorsey wasn’t fired, but his job wasn’t safe, either. As part of the deal, he agreed to adopt aggressive goals for expanding the company’s user base and increasing revenue.
The pandemic meant Dorsey’s Africa relocation had to be put on ice, but his antics continued to make his position as CEO awkward. He worked remotely—in Hawaii mostly, but also Costa Rica and French Polynesia—keeping his physical whereabouts secret from employees. People close to Dorsey say this was for security reasons, though that didn’t stop employees from trying to guess where he was by looking for clues in the background of his video calls. Sometimes staff could hear chickens clucking off-camera. During an interview at a Goldman Sachs Group Inc. conference shortly after the Elliott deal was announced, songbirds chirped nearby as Dorsey spoke.
There were other discordant moments. As the world was hunkered down in April 2020, Dorsey logged on to Google Meet and read aloud from Happy Birthday to You by Dr. Seuss. “Today you are you, that is truer than true. There is no one alive who is youer than you,” Dorsey said, holding up the book to the camera and moving the page back and forth to show a pop-up birthday cake. It was Dorsey’s turn for “storytime,” a weekly video call where Twitter’s senior executives took turns reading children’s books to staff and their kids.
To those on the call, the moment summed up Dorsey perfectly. For all his faults, he could make employees feel appreciated. When he had returned to Twitter in 2015, he lowered the stage that was used during company all-hands meetings so he wouldn’t be standing above his staff. He offered up $200 million of his own stock to the employee equity pool after the company had layoffs. At the beginning of the pandemic, he implemented “days of rest” at both Twitter and Block—bonus vacation time for employees to take a mental break from their job. He regularly includes his own parents in companywide events. One former Block employee recalls the CEO catching him napping at the office one day after a long night of work. The employee braced for a reprimand; the CEO simply told him to go back to sleep.
But much like his tweet about Africa, the Dr. Seuss reading caused some employees to worry that Dorsey didn’t appreciate the gravity of the moment. Less than two months earlier, Elliott had made a run at his job, and he was now on what amounted to probation. Most CEOs would’ve been fighting for their business life. Dorsey didn’t seem concerned. Five days after he read Dr. Seuss, Twitter reported disappointing earnings. Its stock price fell 8%.
For someone with a lot of power, Dorsey has been oddly averse to wielding it. Those who have worked under him at Twitter and Block say he doesn’t like making decisions and considers it a failure of leadership if he must. It’s not uncommon for Dorsey to go an entire meeting without saying more than a few words, and he prefers to leave employees with thought-provoking questions or abstractions instead of concrete directives.
His feelings about authority have even started to color his own views of Twitter. Dorsey recently wrote that having companies control online content and user identity was a mistake. “I realize I’m partially to blame, and regret it,” he tweeted. It’s a view shared by Musk, who was supposedly so bothered by Twitter’s speech rules he suggested building a new service while simultaneously buying up billions of dollars in the company’s stock. (Dorsey’s aversion to corporate control also partly explains his love for Bitcoin, which is unregulated and isn’t controlled by any company.)
But having a chief executive who’s ambivalent about being chief and not crazy about executing comes with serious trade-offs. The people who work for Dorsey often feel empowered to make decisions, but his indecisiveness can also be a source of frustration, at times creating a state of internal paralysis. “If you like directions,” says one former Block employee, “you will struggle with Jack.”
Dorsey’s aversion to making decisions was why, for instance, Twitter spent years working on minuscule product tweaks, such as increasing the maximum tweet length to 280 characters. It also caused Square to miss out on opportunities, including the chance to buy Plaid Inc., a software company that lets people access their bank accounts and transfer money inside other apps. Square had been in talks to acquire Plaid for a bit less than $1 billion in 2018, and the majority of Dorsey’s senior management team favored the deal, according to two people familiar with the discussions. But Dorsey refused to make a final decision. Instead he said the team should reach a consensus one way or another. The group couldn’t, and the deal fell through. Plaid is now worth more than $13 billion.
He shines, though, in understanding and predicting the future. Dorsey can become fixated on specific trends or products years before others see them coming, his employees say, and while that might mean he ignores or disengages with more immediate issues, he’s often right. Eventually. “He’s not a product manager,” says one former Twitter employee. “He’s a product inventor.”
Dorsey came up with the ideas for both Twitter and Square, and he also created Cash App, Square’s consumer payments service akin to Venmo or PayPal. In the app’s early years, it was a major money-loser. This was still true as Square was heading for an initial public offering in 2015, when conventional wisdom suggested the company should focus on its profitable payment-processing product. But Dorsey pushed aggressively to keep Cash App alive. It now has 44 million monthly users and accounted for roughly half of the company’s profits in 2021. It’s also become an increasingly popular way for people to buy and sell Bitcoin. Customers made $10 billion worth of Bitcoin transactions through Cash App last year alone.
Dorsey was one of the earliest investors in Instagram, recognizing the app’s potential before most people even knew what a photo filter was, and he pushed aggressively for Twitter to acquire the nascent short-video app Vine in 2012 before it ever started. Even though Vine ultimately failed, a similar app—TikTok—eventually grew to become one of the most popular in the world.
Remote work was also an early Dorsey fixation. By the time the pandemic forced office workers the world over to telecommute from their living rooms, Dorsey was already moving both Twitter and Square toward the concept because he’d argued that his companies would miss out on top talent otherwise. Pre-Covid, Dorsey was already working from home a few days a week. In fact, part of his rationale for going to Africa for half of 2020 was to prove that long-term remote work was possible.
Dorsey’s admirers see his Bitcoin obsession in a similar light. “I would always pay attention to anything Jack foreshadows for the future,” says Jackie Reses, who led Square’s banking and loans business and who’s now working on her own fintech startup. “He’s more often right than wrong.” Dorsey, in fact, has been interested in cryptography since his teenage years, when he’d use an internet connection at Washington University, near his childhood home in St. Louis, and log on to Usenet chat groups, including one called alt.cypherpunks. He read the Bitcoin white paper shortly after it was released in 2008 by its pseudonymous author, Satoshi Nakamoto. “The whole thing was just poetry,” he recalled years later. The community that sprung up around Bitcoin reminded him of the internet chat rooms he’d spent time in as a kid, and Dorsey didn’t just see Bitcoin as a currency or a way to store value. He saw it as a full rethinking of the financial system that could potentially replace banks and other intermediaries. As he put it at the B Word conference in July 2021, “You see a chance to replace the whole foundation.”
After Elliott’s initial attack on Dorsey in early 2020, Twitter had a pretty good year. The U.S. election and the pandemic created an enormous appetite for news, which meant the company’s user base grew faster than it had in years. The day before the U.S. election in November 2020, Twitter issued a filing that said the board had reviewed the company’s management structure and “expressed its confidence in management.” This was code for “Jack can keep his job.”
The stock price reached an all-time high in late February 2021, but two months later Twitter reported poor quarterly earnings, the beginning of an up-and-down year. When Dorsey resigned in late November, he tried to explain his departure in a letter to employees by arguing that being “founder-led” could be “severely limiting and a singular point of failure” for companies. A key reason he was leaving, he added, was that he wanted Twitter to “break away from its founding and founders.” It was an unconvincing explanation considering Dorsey was still running Square full time.
Those who know Dorsey say he was simply worn down by the constant pressure from Elliott, aware that a bad quarter could lead to another assault on his job. Twitter had dabbled a bit with blockchain technology, funding an effort to build a decentralized version of social media and letting users tip one another with Bitcoin. But Dorsey’s obsession with the cryptocurrency ultimately fit much better with Square. His resignation meant that Elliott got the full-time CEO it wanted for Twitter: Parag Agrawal, promoted from chief technology officer. Dorsey got to go work on crypto.
The newly renamed Block has incorporated Bitcoin into almost every one of its business units. Its internal TBD division (that’s not a placeholder—it’s the actual name) is building a technology to turn dollars into Bitcoin. There’s a separate effort, Spiral, that’s building and funding projects with the goal to “improve and promote” Bitcoin. Block is working on Bitcoin mining chips and creating its own hardware wallet so people can safely store their Bitcoin offline. And the company is involved in a venture to build a Bitcoin mine in Texas using solar panels provided by Musk’s company Tesla Inc.
In early 2021, Dorsey agreed to pay $300 million for Tidal, the music streaming service owned by Jay-Z, and later that year spent $29 billion for Afterpay Ltd., a buy-now, pay-later business in Australia. Square was even approved for a banking license in 2020 to offer small-business loans directly to customers.
The blueprint for Block’s constellation of vaguely related services, according to former employees, is Walt Disney Co., where Dorsey sat on the board from 2013 until 2018. In discussions with investors before its 2015 IPO, Block executives referred to a diagram showing Disney’s offerings including theatrical films, merchandising, and theme parks. The idea was that, just as each business line within Disney contributed to the organization’s other divisions, so would Block’s products and services reinforce one another. Today, consumers can make payments through Cash App, and businesses can accept those payments using the original Square service, while taking out a loan from Block’s banking operation.
Dorsey’s allies say this strategy was behind the Tidal purchase. Tidal had been struggling when Square bought it, leading critics to suggest Dorsey was simply paying a premium to hang out with a famous rapper. The two were seen cruising around the Hamptons on a yacht in August 2020, and Jay-Z got a seat on Block’s board of directors as part of the deal. But Dorsey has argued for a business rationale in which Block will create better ways for musicians to get paid, much like Square did for coffee shops and farmers market vendors in its early days.
And then, of course, there’s Bitcoin. Because, as he’s made clear, Dorsey believes the cryptocurrency will eventually be widely used online, it’s only natural that Block would try to carve out a niche in the crypto world. Crucially, Dorsey isn’t making many investments in competing digital coins or in the so-called web3 technologies that use blockchains to run decentralized web services. Some of Dorsey’s peers, including partners at the venture capital firm Andreessen Horowitz, are big web3 boosters, pouring tens of billions of dollars into the nascent market. (Bloomberg LP, which owns Bloomberg Businessweek, has invested in Andreessen Horowitz.) Dorsey, on the other hand, is a web3 hater. In crypto argot, he’s a “Bitcoin maxi”: He maintains that Bitcoin is the one true cryptocurrency needed and that web3 is an attempt by corporate investors and venture capitalists to take control and ruin everything. When Andreessen Horowitz partner Chris Dixon used a quote commonly misattributed to Gandhi—“First they ignore you, then they laugh at you, then they fight you, then you win”—to refer to his company’s web3 investing, Dorsey responded acidly. “You’re a fund,” he tweeted. “Not Gandhi.”
Dorsey’s willingness to beef about a major Silicon Valley investor, combined with his true believer status, only endeared him further to the Bitcoin faithful. “If he was like ‘crypto, crypto, crypto, web3,’ he would not be unique at all,” says Alex Gladstein, chief strategy officer at the pro-Bitcoin Human Rights Foundation and the man who interviewed Dorsey onstage in Miami. “The fact that he’s focused so strongly on Bitcoin is the signal.”
Gladstein is one of the many Bitcoin enthusiasts who find Dorsey’s conviction inspiring. “I’m definitely grateful that he’s out there doing his thing,” he says. “I think he’ll be remembered probably more for Bitcoin than for Twitter, in the end.”
©2022 Bloomberg L.P.
