The Accidental Activist: Part I
April 2011 Issue

Twitter Was Act One

Considering that he invented Twitter and is about to launch another potential game changer with his new company, Square, Jack Dorsey has one of the lowest profiles in tech. But from his childhood obsession (city maps) to his dream job (mayor of New York City), Dorsey’s eclectic, ascetic vision has focused on the flow of human interaction. David Kirkpatrick gets the press-shy visionary talking about his taxicab inspiration, his ejection as Twitter’s C.E.O., and his ambition to make Square the payment network of the future.
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Photograph by John Huba.

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The tale of Twitter begins in 1984, in the bedroom of an eight-year-old boy in downtown St. Louis.

Little Jack Dorsey was obsessed with maps of cities. He papered his walls with maps from magazines, transit maps, maps from gas stations. His parents had resisted joining the emigration to the suburbs, and their shy, skinny son supported them by becoming a passionate proponent of city life. He was mesmerized by locomotives, police cars, and taxis. He would drag his younger brother Danny to nearby rail yards, where they waited just to videotape a passing train.

When their father brought home the family’s first computer that year—an IBM PC Jr.—Jack immediately took to it. He had a talent for both math and art, and began to design his own maps using a graphics program. Soon, he taught himself programming to learn how to make little dots—representing trains and buses—scoot around the maps. He spent hours listening to police and ambulance radio frequencies, then plotted the emergency vehicles as they moved toward an accident or a hospital. As he evolved into a talented teenage programmer, he came to an oddly poetic view of this precise, orderly urban grid. “I wanted to play with how the city worked, so I could see it,” Dorsey recalls.

His obsession with cities—and with programming—never abated. By early 2006, having dropped out of N.Y.U. and bouncing between jobs, he found himself working for a San Francisco software start-up called Odeo, which was going nowhere. One day he proposed an idea to his boss based on a notion that Dorsey had been noodling over for years. He was fascinated by the haiku of taxicab communication—the way drivers and dispatchers succinctly convey locations by radio. Dorsey suggested that his company create a service that would allow anyone to write a line or two about himself, using a cell phone’s keypad, and then send that message to anyone who wanted to receive it. The short text alert, for him, was a way to add a missing human element to the digital picture of a pulsing, populated city.

Odeo’s Evan Williams embraced the idea, and named the 29-year-old Dorsey the founding C.E.O. of a new company, Twitter. The rest has become a peculiarly prominent part of Internet history. Twitter, celebrating its fifth anniversary, is now one of the signature social platforms of our day, drawing 200 million users. Google, Microsoft, and Facebook have all reportedly been vying to buy the company for more than $8 billion. And Twitter is so central to modern culture that when popular uprisings swept through the Middle East this year many of the protesters coordinated their movements by tweeting. Indeed, Dorsey’s invention is helping transform communication and political life across the globe.

So why have you heard so little about this man who is one of the visionaries of the Digital Age? Why don’t you know that in 2000 he dropped everything to pursue a career in botanical illustration? Or that he studied for a year to become a certified massage therapist, or more recently took classes in fashion design (making an impressive pencil skirt), or has already set his sights on his dream job: mayor of New York City?

Well, first off, Dorsey is reserved and modest and, until now, has avoided cooperating for a full-scale profile. Over the years, he has tended to view himself more as a craftsman than an entrepreneur. His was an idea for a service, not a company. He launched it from inside a somewhat disorganized corporate culture, owned by someone else. Plus, back then, Dorsey was not the greatest manager. Williams and the board pushed him out within two years. And although Dorsey remains chairman of the company, he was out the door by the time Twitter had become a cultural force. What’s more, Dorsey and Williams, to this day, rarely speak to each other beyond occasional exchanges at board meetings.

Jack Dorsey’s belief in the power of Twitter, however, has never waned. (One incentive: he’s the second-largest individual shareholder in the company.) Several months ago, Dorsey re-ignited his relationship with Twitter’s management, though only after Williams, 38, had agreed to step down as C.E.O., last October. That said, Dorsey has a lot on his plate. In 2009 he discovered something that excited him just as much as Twitter. That’s when he co-founded Square, where he is now C.E.O. Square is a service that allows any individual or small business to easily accept payment by credit card; users simply download an app, attach a plastic square to a tablet or a mobile phone, and then swipe a card through a slot. Just as Twitter made anyone a broadcaster or pundit or diarist, Square can make anyone a merchant.

Dorsey may belong to Gen X, but he is a throwback to a kind of heartland idealism we associate with earlier generations. His optimism flows mostly from a St. Louis-bred spirit about our common life, democracy, and human potential. He claims his inventions all aim at the same goal: a society that works more efficiently and humanely. “My role as an observer and as a technologist,” he says as he strides through a San Francisco rainstorm, holding a big blue umbrella, “is to show everything that’s happening in the world in real time and get us to that data immediately, so we can change our lives even faster, with better knowledge.” (Urban strolls are one of Dorsey’s favorite activities, and he has specifically asked to be interviewed while meandering around San Francisco and New York.)

The minimalism of Twitter—each tweet can be no longer than 140 characters—reflects Dorsey’s own terseness. “What makes Jack magic is his precision,” says his friend Ashton Kutcher, who spent a week with Dorsey on a State Department-sponsored trip to Russia. “When he speaks he makes every syllable count.” Dorsey is also close to actress (and avid Twitterer) Alyssa Milano, who, like Kutcher, is struck by what Dorsey doesn’t do. He can easily captivate a room full of celebrities, she says, but not because he seeks attention. “He never really says what he does for a living,” she explains. “I’m usually the one bragging about his achievements.”

Dorsey’s is the highly considered life of a purist. His ardent asceticism has only recently been leavened with a dollop of luxury. For years he gave away the software he wrote as shareware. His apartment in San Francisco’s Mint Plaza area is spacious but austere and immaculate. It wasn’t until a few months ago that he bought his first car—a BMW M3, whose design he admires. Lately, he has become partial to Prada suits, worn with a white shirt and dark tie. His iPad case is not the functional microfiber Apple model, but an envelope of hand-sewn gray felt. When he shops, he seeks the ne plus ultra in quality and durability because he expects to keep each item for life: a Filson leather-and-canvas shoulder bag; a Shaker bench; a Rolex, because its maker is one of the few watch companies, he says, that manufacture their own parts.

And how many tech nerds admire Balanchine and Diaghilev? “I’ve learned a lot from ballet,” reports Dorsey, whose most recent serious relationship was with Sofiane Sylve, a principal dancer with the San Francisco Ballet. “I appreciate the coordination and the discipline. Making something simple is very difficult.” (He is currently single and remains mum about his personal life, devoting most of his waking hours to his two companies.)

A black, nine-inch tattoo, in the shape of a thick S, runs down Jack Dorsey’s left forearm. But one can ignore the outlaw implications: this is a man whose first act each day is to text his mother. Dorsey intends the tattoo as a reference to his interests in math, music, and anatomy. First, it represents an integral. “It symbolizes integrating everything,” explains Dorsey, somewhat cryptically. He also sees it as the musical notation for F-sharp (“When I was small I played the violin,” he says) as well as a human clavicle (“the most graceful bone in the body”). Observes Roelof Botha of Sequoia Capital, who just led an investment of $27.5 million in Square, “People who know what an integral is would generally not have tattoos. It sums up what makes Jack an interesting entrepreneur—his ability to blend ideas.”

One brisk December day, Dorsey, 34, is leaving Third Rail, an artisanal coffee shop he frequents in New York’s West Village. As he walks, he is unusually effusive. “I just had a meeting I’ve been wanting to have since I was 14,” he says gleefully, “with the taxi-and-limousine commissioner.” Their topic: “Technology in cabs. Making transactions faster and easier and more informational. I said, ‘Anything you guys need. This was my first passion. I’m happy to help.’ ” He thinks the city ought to rip out the intrusive, noisy, balky video screens in the backseats of cabs and instead install Apple iPads equipped with a credit-card reader from Square.

His interest in New York City government goes surprisingly deep. And although he currently lives in San Francisco, his ultimate aspiration is to become mayor of New York. He’s even spoken to Michael Bloomberg about it. (According to Dorsey, the current mayor’s advice—no surprise—was to make a lot of money first. Dorsey’s personal wealth may well exceed $300 million.) He knows this all sounds a bit ridiculous, but he’s not apologetic in the slightest. Dreaming of running America’s largest metropolis is a way of keeping himself focused on what matters to him. “What gets me really energized,” he says, sitting on a bench near the fountain in Washington Square, “is thinking about activity within a city. Like, even this intersection at the end of Fifth Avenue, seeing all the taxicabs turn. There’s such a rush of energy constantly coursing through.”

By the time Dorsey was in high school he was writing rudimentary software programs that could be used to dispatch taxis, ambulances, or delivery couriers. His mother, Marcia Dorsey, owned a small coffee shop in town. One day someone from a local software company came in and mentioned that he was desperate to hire new programmers. “My son loves computers,” she told him. Jack, then 15, was soon standing in the firm’s reception area.

Jim McKelvey, who owned the company (which archived documents onto CD-ROMs) and who today is Dorsey’s partner in Square, recalls that first meeting in 1992. “I was sitting at a terminal entering all this data, and this kid walks up behind me, with his arms straight at his sides. He was like [McKelvey speaks in a robotic voice], ‘Hi, I’m Jack.’ I said, ‘Yeah, I’ll be with you in a minute,’ and I turned around and completely forgot about him until I had to get up to pee. Jack was in exactly the same position. He’d been motionless for 45 minutes.”

McKelvey took Dorsey on as an intern and learned that this awkward teenager could swiftly master most computing tasks. When McKelvey began to worry his company could get killed by an online competitor, he found that Dorsey was the only one on his small staff who agreed on the need to migrate the business onto the fledgling Internet. McKelvey hired several freelancers for the project. “One guy asked me, ‘What’s my job title going to be?’ I said, ‘Assistant to the summer intern.’ He was basically a stick figure. I said, ‘Just do everything this kid says.’ ”

Dorsey kept improving as a programmer. His parents didn’t want him too far from home, so he enrolled at the University of Missouri at Rolla and, as a hobby, wrote dispatch software for emergency vehicles and couriers. (Dorsey is unusually good at staying focused.) In his junior year he wandered through the Web site of DMS, a large courier-dispatch company. Burrowing into its computers, he found the e-mail of the C.E.O. and wrote to him. “I said, ‘You have a [security] hole in your Web site. Here’s how to fix it. And, by the way, I write dispatch software,’ ” recalls Dorsey.

Says Greg Kidd, the nonplussed C.E.O., “I had one conversation with him, and I said, ‘I don’t want to get you in trouble with your mother, but would you come to New York?’ It was pretty clear this was a guy I wanted to have working for me.” Dorsey wasn’t yet 21. He transferred to N.Y.U. and became one of the two lead programmers at DMS—in his spare time. Kidd, like McKelvey, has remained a Dorsey friend and ally ever since.

As the dot-com frenzy grew in 1998, Kidd and Dorsey moved to San Francisco. The businessman and his coder-sidekick launched dNet, for dispatching couriers online. They raised money, hired a C.E.O., and then the tech bubble burst. In a disagreement over strategy, the new boss kicked the co-founders out. It was the first but not the last time Dorsey would find himself ejected from a firm he’d helped start.

Dorsey had always kept a journal. For a while, he’d been considering the ways in which technology might streamline that process. With one of the earliest mobile e-mail devices from Research in Motion, he tapped out brief notes to himself wherever he went. He wrote software to categorize the e-mails as journal entries. He was also an early user of LiveJournal, which let you see friends’ posts in reverse chronological order. Then, one night in July 2000, Dorsey realized that by combining these tools he could do for himself what he had spent years helping taxis and couriers do: declare where he was and what he was doing. That evening, he wrote some code that enabled him to have an e-mail re-posted to as many people as he wanted. He entered the e-mail addresses of five friends into the software, and took a walk in Golden Gate Park. In an e-mail’s subject line he wrote, “I’m at the Bison Paddock watching the bison.”

His friends weren’t impressed. “I quickly learned that, first, no one else had a mobile e-mail device, so the system was kind of useless,” Dorsey says. “And secondly, no one really cared what I was doing in the park.” Dorsey kept refining the concept, however, and in 2001 sketched out a rudimentary template for a service called Stat.us.

After the dNet disaster, Dorsey returned to St. Louis and began studying botanical illustration at the Missouri Botanical Garden. As a teenager, he had spent hours in gardens, drawing with a graphite pencil. Suddenly, he considered this hobby a possible career path. He indulged his fascination with the challenge of precisely rendering a flower’s intricate details. “I fell in love with flora of all types, especially ferns. Loved the sparse structure and repetition of shape—almost fractal.” Illustrating flowers, like programming, was a “perfect intersection of art and science.”

But shortly thereafter, deciding that illustration really wasn’t for him, his wrist started hurting. He went to a massage therapist for treatment and, in short order, became consumed by the field. After a thousand hours of training he was certified and returned to San Francisco, where he moved into a shed in Kidd’s backyard. He quickly learned, to his dismay, that the city had a surfeit of massage therapists. So, while working as a nanny for Kidd’s daughter, Dorsey started thinking again about software—and that message he’d sent from Golden Gate Park.

He did some freelance coding for a harbor-ferry service. He almost got fired for having a nose ring. He wore his hair in dreadlocks; he had earrings in both ears. When he heard that a start-up called Odeo might be hiring programmers, he e-mailed a résumé. It was a typical Dorsey exercise in minimalism. Evan Williams, Odeo’s boss, remembers it reading “Jack,” with no last name. “It had just a few words—a list of companies where he’d worked,” says Williams, who signed him to a three-week trial contract. Dorsey, however, wasn’t too enthused. “It was a podcasting company,” he says. “I had no interest in podcasting. It turns out no one in the company did, either.”

Having second thoughts about programming once again, he enrolled in a fashion class at Apparel Arts, a trade school in San Francisco, and began designing and sewing clothing. “I was fascinated with jeans,” Dorsey explains, “because you can impress your life upon the jeans you wear. The way you sit imprints on the jeans.” It was another nod to the idea of maps. In the same way, botanical illustration, he points out, is the best method for rendering the details of a flower—nuances that even the best cameras can’t capture. And to properly do massage, Dorsey says, one has to map the contours of the body.

Williams had expected his business to be a directory of podcasts. But when Apple incorporated one into iTunes, Odeo’s plans went out the window. In full reset mode, Williams asked his staff for new ideas, and Dorsey laid out his vision for Stat.us. SMS texting had just begun to take off in the U.S., so the time felt right. “Meanwhile, I was still doing this fashion thing,” remembers Dorsey. “I had about 10 classes where we built, from drawings to construction, skirts. Pencil, asymmetrical, mini. I wanted to make jeans, but you start with skirts because they’re easy. Then Twitter started taking off—and I never got to pants.”

Inside Odeo, Dorsey worked closely with several others on the project, then called “twttr.” Biz Stone, Dorsey’s close friend, did the design and user interface. Stone, aged 32 at the time, had written books on blogging and worked on projects that enabled extra-short posts. Like all great ideas, Twitter had many cooks, but no one disputes that the initial brainstorm grew out of Dorsey’s singular obsession. Shortly, they had a working product, and Dorsey authored the first tweet, cogent and Dorsey-esque: “Inviting co-workers.”

Odeo launched Twitter in July 2006, but it wasn’t until the following March that the world took notice. That’s when thousands of participants at the annual South by Southwest Interactive conference, in Austin, spontaneously began using it to swarm. The best parties that year were the ones people learned about on Twitter. The Twitter feeds defined the event for tech cognoscenti, and at Odeo it became apparent that Twitter ought to be spun off as its own company.

Williams had been struggling with Odeo’s investors and eventually bought the company back from them. Twitter seemed promising, but the firm was drifting. Employees were grumbling. Williams didn’t want to run Twitter, but instead to turn Odeo into an incubator for multiple businesses. He needed a C.E.O. But Dorsey, who had headed the venture so far, was just an engineer initially hired as a contractor. “I thought, It’s a risk, because he’d never even been a manager,” says Williams. “But Twitter wasn’t a huge deal at the time, and I thought, He has the vision. He’s got the technical chops. Let’s put him in charge.”

Dorsey got serious. “I took my nose ring out after our first round of financing,” he says, matter-of-factly. Twitter raised $5 million, largely from a single V.C. firm, Union Square Ventures. But managing a new company from Odeo’s wreckage was daunting. “Suddenly I became the boss of all my peers in a very damaged culture,” says Dorsey. “The morale was low.”

Twitter usage continued growing quickly—too quickly. Dorsey and his staff struggled to keep the service from going down. Looking back, Dorsey admits he was a flawed manager: “I let myself be in a weird position because it always felt like Ev’s company. He funded it. He was the chairman. And I was this new guy who was a programmer, who had a good idea. I would not be strong in my convictions, basically, because he was the older, wiser one.” Dorsey did a poor job explaining where he wanted the company to go.

“It just got a lot bigger a lot faster than anyone expected,” says Williams. “A year and a half later we’d raised $20 million, and the servers were crashing every day It wasn’t so much that the ship was sinking, but more ‘Great job, Jack—we’ve got to up our level of experience and lay some foundation for a much bigger organization.’ ” Others say the two were barely speaking by then, and in October 2008, Williams took the C.E.O. job for himself. Dorsey became chairman, but was no longer an employee.

He was devastated to be ejected again from a company that was building a product he’d conceived. “It was like being punched in the stomach,” he says in a rare moment of candor on the subject. Fred Wilson, who had joined Twitter’s board, puts a more benign spin on the breakup: “Ev and Jack are a little like John and Paul. They made great music together for a while, but then they both kind of got ambitious about things and didn’t see eye to eye anymore.”

Dorsey no longer wanted to make pants or draw flowers. He now thought of himself as an entrepreneur. And Twitter’s impact loomed large. “Twitter held all my desires in the world,” says Dorsey. He began talking with his old pal McKelvey, trying to come up with a monster concept to build a company around. “I would go, ‘That’s a great idea, Twitter should do that one,’ ” says Dorsey. “Jim was getting frustrated.” Then one day McKelvey, something of a Renaissance man, had a bad experience in his St. Louis glassblowing studio. Having handed over the reins of his software firm, he had begun to make things like hand-blown colored-glass bathroom-sink handles—for $2,000 a pair. A customer, however, had to abandon a purchase because McKelvey wasn’t equipped to accept an American Express card.

He was telling Dorsey about the botched sale as they talked on their iPhones. “I was struck with the irony,” says McKelvey. “I’m talking to my business partner on this device that has all the technology I need to solve the problem I just had.” He suddenly proposed that they build a system that would let people make and accept credit-card payments on smartphones. “I’m like, ‘Wow—this is pretty interesting,’ ” says Dorsey. “This is actually another dot that is more activity on the map.”

In time, they conceived of a business around a free device that would be dispensed to anyone who signed up: a tiny, square-shaped credit-card reader that could be plugged into the headphone jack of an iPhone, Android phone, or electronic tablet. Unlike more complex and pricier plans set up between storeowners and credit-card companies, Square would charge the same fee to everyone (from flea-market merchants to dog-walkers to kids at lemonade stands): it’s now 2.75 percent. Says Sean Parker, the founding president of Facebook and a buddy of Dorsey’s, “Maybe Square can become for Craigslist what PayPal is for eBay.”

Dorsey takes his design inspiration from Apple’s Steve Jobs, whom he reveres. And he sees himself, like Jobs, producing an integrated system in a business where others have assembled kludgy agglomerations. “Payment is another form of communication,” he says, “but it’s never been treated as such. It’s never been designed. It’s never felt magical. About 90 percent of Americans carry cards, but almost nobody can accept them. We want to balance that out and just make payments feel amazing.” Dorsey talks about how Square must be “pixel-perfect,” and staffers tell stories about him agonizing over the exact location and thickness of a line on e-mailed receipts.

Dorsey’s ambitions for Square are suitably grand. “I think Twitter is the future of communications,” he says, “and Square will be the payment network. We’re going big.”

“Jack’s biggest insights have nothing to do with technology,” says Greg Kidd. “His insights are always social first. It’s always a democratization machine. Why should you have to ask permission to take a payment? That’s how the banks treat you now.” Cory Booker, Newark’s aggressively innovative mayor, is another Dorsey fan. “Even the way he talks about Square is about social justice,” the mayor says. “Frankly, I’m in awe of him.” (Square helped Newark build a system to accept matching donations after Dorsey’s leading business rival, Facebook C.E.O. Mark Zuckerberg, gave the city’s schools $100 million.)

“We dream about backing people who have that kind of character—purity, authenticity, but just deep optimism,” says Peter Fenton, a partner at Benchmark Capital, who invested in Twitter in 2009 and has helped lure Dorsey back as a day-a-week product adviser and strategist. “This is a guy who doesn’t have a negative bone in his body.” Adds philanthropist Ray Chambers, a mentor of Dorsey’s who is the U.N. secretary-general’s special envoy for malaria, “At the core of his being, he really wants to make the world a better place.”

Jack Dorsey has spent a lot of time thinking about what went wrong at Twitter. And as Square’s C.E.O., he bends over backward to be explicit, to communicate, to guide. He hosts a “town square” company meeting every Friday, where he talks about aspirations and values. To help his 78-person staff better understand why he considers design so important, he organizes trips to visit “beautiful things.” Recently—in an inadvertent echo of an episode of Mad Men (in which employees sneak into the boss’s office to gawk at his confounding new Mark Rothko painting)—Dorsey took a group to SFMoMA, where he asked them to meet at a designated time in front of a massive Rothko, its image the shape of a square.

One recent town-square meeting, in fact, was devoted to the aesthetic virtues of the Golden Gate Bridge. “We’re the only payments company in the world that’s concerned with design,” the Prada-clad Dorsey begins. He shows a dramatic photo of the bridge taken from atop one of its towers. “This is what I want to build. This is classy. This is inspiring. This is limitless. Every single aspect of this is gorgeous. . . . So your homework this weekend is to cross this bridge, think about that, and also think about how we take those lessons into doing what we do, which is carry every single transaction in the world.”

For Dorsey, it’s all one big integrated system. Transactions are like traffic. Traffic flows over the beautiful bridge. The bridge is a point on the map. The map is an expression of the scheme, the stream, the grand flow of interactions. And he’s been thinking about this stuff since he was eight.

David Kirkpatrick is a Vanity Fair contributor and author of The Facebook Effect.