Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal

by Nick Bilton

  Jack started saying “No one has ever done this before” about his products, an exact quote from a Jobs interview in early 2010 at a conference. Jack then adopted Jobs’s terms to describe new Square features, words like “magical,” “surprise,” and “delightful,” all of which Jobs had used onstage at Apple events.

  Before long, like someone undergoing minor plastic surgeries until he resembles his idol, Jack no longer looked and acted like Jack Dorsey: He began acting like the second coming of Steve Jobs. The Beatles, the Gandhi references, the “editor” title, the design ethos, the daily uniform, and the quotes all contributed to what happened next.

  The tech blogs, now believing that Jack had founded and built Twitter on his own, that he had come up with the idea when he was just a child—which Jack insinuated to dozens of media outlets—and that he possessed the same principles as Jobs in both design and management, started asking: “Is Jack Dorsey the next Steve Jobs?” (They inevitably answered: “Yes.”)

  It wasn’t a grand master plan by Jack to copy Jobs. Rather it was dozens of little plans that added up to a re-creation.

  In many respects it was Steve Jobs who helped create Jack Dorsey. Jobs was notorious for denying access to reporters. He had trained the media to behave exactly how he wanted them to—when he spoke, they listened, which was his best magic trick of all. So when he took a leave from Apple after falling ill in 2009, the media went in search of the next Steve Jobs. Jack walked like that duck, used the same quotes as that duck, wore the same glasses, had the same principles, and the same astounding theories on design as that duck. He even listened to the Beatles!

  But for Jack, cultivating Steve Jobs 2.0 wasn’t just about creating an aura of visionary; it also had the unintended consequence of lighting a fire that Jack had been trying to start since he had been ousted from Twitter. A fire that would smoke Ev out of the company too.

  On a late afternoon in mid-2010, Mike Abbott, who was vice president of engineering at Twitter, asked Jack if he could stop by the Square offices to chat. Abbott had no idea that Jack’s title as chairman of Twitter was a veneer. Along with the rest of the world, he believed Jack was powerful in high-level decisions at the company. And like most of Silicon Valley, he believed that Jack Dorsey was the heir apparent to the Steve Jobs mystique.

  They began meeting on a regular basis, discussing design and projects within Twitter. And then one afternoon the opportunity presented itself.

  “I need your help,” Abbott told Jack. “We have no direction at Twitter, and I don’t know where the company is going.” Abbott explained that he didn’t like working with Greg Pass, now Twitter’s chief technology officer, that he didn’t think Ev had solid direction, and that he needed Jack’s help and guidance. “I don’t know what to do,” Abbott admitted.

  It was the moment Jack had been waiting for. Fenton had always been on Team Jack. But the other board members, specifically Fred and Bijan, were still very wary of Jack, believing that he had almost sunk Twitter with his inability to lead in the early days of the company.

  Now a senior executive at Twitter was asking Jack for help. Like Jobs, Jack understood that he could whisper in one person’s ear and those murmurs would turn into shouts somewhere else. So Jack began speaking softly.

  “I consider the vice president to be the equivalent to the CEO, and if you’ve spoken to Ev and it’s not going anywhere, you need to go to the board,” Jack told Abbott. “Talk to Fenton, talk to Bijan, to Fred—whoever—about your concerns. Talk to the other senior execs.”

  Abbott did just that, calling the board to raise his concerns about Ev and Goldman and voice his fears that the company wasn’t heading simply in the wrong direction but in no direction at all.

  Abbott started telling other vice presidents at Twitter to meet with Jack too. The whispers eventually made it to Ali Rowghani, who had been hired as the chief financial officer at Twitter and was also frustrated by Ev’s slow decision making. Ali set up a meeting with Jack at Blue Bottle Coffee near Square’s offices. There, amid the aroma of five-dollar cups of coffee, Ali lamented the state of the company. Adam Bain, who was building revenue at Twitter, traipsed off to meet with Jack too. And then Dick followed too.

  It wasn’t that the company was falling apart. Quite the contrary. Twitter had secured the search deal with Google and Bing and was also now experimenting with advertising ideas, creating a new type of business experience where people could turn tweets into advertisements. The site was also finally on the mend. The engineering team had come up with an extensive long-term plan to rebuild the entire back end of Twitter, fixing the legacy problems that had plagued the company since its inception.

  The problem was Ev. He was still unable to make a decision. He communicated infrequently with the board and senior staff. Some, like Mike Abbott, took it personally when they were not included in high-level conversations and decisions.

  Ev was running a company that even the most experienced executive would have struggled to manage. What had been small problems at a tiny start-up like Odeo were big problems in a company that had grown as quickly as Twitter. Those big problems, when shown to the board under Jack’s magnifying glass, would prove to be fateful for Ev.

  At the time, Ev had set out to completely redesign Twitter, giving it a much-needed face-lift. He recruited his most trusted employees and set up what they nicknamed the war room in one of the conference rooms to brainstorm ideas. Each day, Ev huddled up with his small group of designers and programmers, with pictures and inspirations hung all over the wall, redesigning the site.

  Ev buried his head in Twitter’s redesign, ignoring most of the daily chores of a CEO. And across town, just a few blocks from the Twitter offices, Jack was offering friendly advice to the people not involved in the project: You should talk to the board. You should talk to Fenton. Tell Fred. Bijan. Tell them all that Ev isn’t doing a good job. Tell them your fears for the future of Twitter. Jack even ensured that some people voiced their concerns to Campbell, Ev’s coach.

  Although it was not normal for a CEO coach to come to board meetings, Campbell would often arrive unannounced at Twitter board meetings and insert himself into the goings-on of the company. People were confused by the spectacle, but given that he was not a normal CEO coach, they simply stood back and watched.

  With the whispers now entering Campbell’s ear, he too was starting to voice concerns about whether Ev was the right CEO for the job. But he didn’t tell Ev; instead he spoke to Fenton about the private coaching sessions going on between Ev and Campbell. Fenton then told Jack about those sessions. Like a snowball rolling down a mountaintop, accumulating every speck of dirt it encountered and growing darker and larger with each tumble (with each meeting, with each call to the board), the case against Ev started to gather an unstoppable momentum.

  Russian-Roulette Relations

  The snipers started showing up in the early morning. Dressed in all black, they climbed to the roof. Then, standing on gray concrete slabs, they unpacked long metal rifles and fine-tuned their scopes. Walkie-talkies could be heard giving off spurts of static as the masked men spoke to each other in Russian.

  For two weeks, black suits had been sporadically appearing at the Twitter offices at all times of the day. They swarmed around cubicles like ants in search of food, checking every nook and cranny of the building. Their shiny sunglasses concealed their eyes; handguns were shrouded underneath dark blazers. Some had ferocious-looking dogs that sniffed the building for explosives.

  They peeked out of windows, quietly pulling back the blinds to peer down at the busy San Francisco streets below.

  “We will need a map of all of the exits and elevators,” one of them said in his thick Russian accent to a Twitter employee. The elevators would need to be shut down for the visit. “We will put the metal detectors at the entrance of the offices.”

  After Dick had joined as COO, the company had gone on a hiring spree. By late 2009 Twitter had grown its workforce from 30 to
almost 120 employees, including freelance contractors. So in November of that year the company moved into a new office at 795 Folsom Street, occupying the sixth floor of a large beige building that had been the home of several start-ups. By June 2010 that office housed almost 200 employees.

  At a recent Twitter conference called Chirp, which was organized by the company, Ev had announced that more than one hundred million people had signed up for Twitter and three hundred thousand new people were joining the site each day. Ryan Sarver, who ran the company’s third-party tools, told the audience that one hundred thousand applications were on Twitter too. Those apps, he said, were interacting with the site three billion times a day. The cherry on top of these Twitter numbers had also started to scare Google: People were now searching Twitter six hundred thousand times a day.

  Sara had been recruited to redesign the new office space. The funky look featured a large red @-shaped light that hung above a blue, modern couch, lots of bird-related stickers, and hip designer accents like three wooden deer heads. There was even a DJ booth in the company’s dining room.

  Increasingly, government officials had been making the rounds at Twitter. John McCain had come in on a weekend, taking a tour of the office and meeting with executives to understand more about Twitter’s role in government—and how to use it to not lose elections. Gavin Newsom, then mayor of San Francisco, had started showing up on a regular basis, coming for town-hall discussions and meetings with Ev. And Arnold Schwarzenegger had stopped by for a Web chat.

  But June 23, 2010, was different. Dmitry Medvedev, the president of Russia, would be arriving at Twitter’s headquarters to take a tour of the office and, as he put it, to “see with his own eyes” the hottest start-up in Silicon Valley. He also planned to send his first tweet.

  It was a stark example of how the world’s stage was changing. On previous visits to the United States, leaders of other nations would meet with newspaper and magazine editors. Now, rather than fly into New York City and make the rounds at Esquire, Time, or Newsweek, officials were dropping in to Silicon Valley to see the companies that were changing the way the world communicated.

  Twitter would be the first part of a three-day trip to the United States by President Medvedev to bolster relations between America and Russia. He planned to stop by the Valley for a few meetings, including one with Steve Jobs. (Medvedev’s hope was that he could explore how to build a Silicon Valley equivalent in Russia.) Then, after meeting with the nerds, he would be off to Washington to meet the suits: first President Barack Obama, then Secretary of State Hillary Clinton, Vice President Joe Biden, and other high-level U.S. generals and economic advisers, to discuss national-security issues, counterterrorism efforts, nuclear treaties, and the global economic crisis.

  But first, before anything, Medvedev had something more important to do: He had to tweet.

  There was, however, one slight problem.

  For the past few months Twitter had been drawing more attention than ever before. The office had become Grand Central for celebrities, who often arrived unannounced, then proudly tweeted their locale for all to see. Visiting the company’s offices had become a pilgrimage. As a result, Twitter’s every breath was being picked up by press outlets from San Francisco to the Vatican. There was barely a publication on earth that hadn’t mentioned Twitter.

  Just a couple of weeks before the Russian president had announced he was stopping by the company for a visit, Twitter had been the cover story in Time magazine. The article had been titled, “How Twitter Will Change the Way We Live.”

  Steven Johnson, the bestselling book author who wrote the piece for Time, used the cover story to put to rest the common misconception that Twitter was only a place to tell all of your friends your favorite “choice of breakfast cereal.”

  Rather, Johnson noted, “as millions of devotees have discovered, Twitter turns out to have unsuspected depth.”

  “Partially thanks to the move from asking people to talk about their status to talk about what’s happening [Twitter has become] a pointing device instead of a communications channel: sharing links to longer articles, discussions, posts, videos—anything that lives behind a URL,” Johnson wrote. “It’s just as easy to use Twitter to spread the word about a brilliant 10,000-word New Yorker article as it is to spread the word about your Lucky Charms habit.”

  As a result of all of this attention, hundreds of thousands of people were joining Twitter every single day. At the peak, more than twenty thousand were signing up for Twitter accounts in a single hour. (It had taken eight months to reach the twenty-thousand-user milestone in 2006.) Even the best-engineered Web site on the Internet would have had trouble handling such attention. But for Twitter, which was still being held together by chewing gum and masking tape, the crowds had been like a whale trying to fit into a goldfish bowl.

  There were several reasons the site would disappear into its own black hole. A Twitter engineer could upload bad code that would completely disable the site. A server could fail and, like dominoes, bring down a dozen other servers. But there were more severe problems too. After the revolutions in Iran, in Syria, and elsewhere in the Middle East, Twitter was now a zone for rogue governments to attack, and bad guys with good computers were now trying to overthrow Twitter. Some hackers, proving to be deft at their trade, managed to hit the bull’s-eye on several occasions, knocking the site completely off-line. As luck would have it, the moment President Medvedev’s entourage of black cars pulled up to the beige building on the corner of Folsom and Fourth streets, one or all of the above had happened to Twitter.

  The surrounding streets were now blocked off in all directions, with San Francisco police cars and dump trucks being used as roadblocks to foil potential assassination attempts. The Russian agents and United States Secret Service emerged onto the street, surrounding the president’s car as his black, shiny loafers stepped out onto the street.

  Ev paced upstairs. He had been nervous about the president’s visit and had even dressed up for the occasion, wearing a beige button-down shirt and black blazer. Biz stood off to the side with Mayor Newsom, who was sipping from a Starbucks coffee cup so large it looked as if it would last a week.

  “Nice of you to dress up,” Ev had joked to Biz in the morning when he walked into the office. Biz was wearing disheveled sneakers, baggy, worn-in jeans, and a zip-up cargo jacket. He looked as if he had just run to the deli to pick up a carton of milk, not come to meet the president of Russia and an entourage of global press.

  Goldman, the vice president of product, was situated on the third floor with the engineering team. As one of the most senior people at the company, he had agreed to manage any problems that arose while the president sent his first tweet.

  Out on the street, President Medvedev looked up at the building as he was directed inside by his security detail. He walked past the Subway sandwich shop to his right, through the open glass doors, and across the marble-floored lobby and into the elevator. He didn’t need to wait for an elevator, because for the next several hours the only person who would be able to enter or leave the building or travel between floors would be him.

  Goldman stood like a general surveying the team of engineers who were watching over the site. As the president slowly rose through the building past the third floor, an engineer looked up at Goldman and said three dreaded words: “The site’s down.”

  “What do you mean, the fucking site is down?” Goldman asked. Like someone who had just fallen into a pool of icy water, he went numb. He started to mentally envision the worst-case scenarios.

  There had been meetings over the previous few weeks with the White House, the State Department, the San Francisco mayor’s office, Governor Arnold Schwarzenegger’s office, and the Russian embassy to play through the meticulously planned visit. The plan: After the Russian president sent his first tweet, the White House would retweet it. Barack Obama would reply, congratulating him on his tweet, as would the mayor and governor, all welcoming the Russian p
resident to Twitter and to the United States.

  But that wasn’t going to happen without a Web site. Worse, as Goldman was confined to the third floor until the president left the building, he couldn’t run up and tell Ev and Biz. He tried to text them both, but without knowing what was going on three floors above, Goldman didn’t know whether the president was there or if they could see their cell phones.

  As the elevator door opened to the sixth floor, the president emerged, shaking Mayor Newsom’s hand. He was then introduced to Ev, Biz, and Dick.

  As Biz reached out to shake Medvedev’s hand, his phone vibrated in his pocket. It was a message from Goldman, explaining the situation and urging Biz to do everything in his power to delay the first tweet.

  Biz showed his phone to Ev, who peered at the screen with a fake smile. “Shall we?” Mayor Newsom said as he led them down the hallway. Biz tried to delay, walking as slowly as possible as everyone went ahead. At one point a public-relations employee who had found out the site was off-line tapped Dick on the shoulder and said the same words that he had read from Goldman. “The site’s down.”

  Dick turned with a look of confusion and shock. “Like, totally down?” he asked as his eyes widened. Biz continued walking glacially, trying to come up with any excuse to delay the group from tweeting. “Oh, we should show him the electric bike!” Biz said as they zigzagged like lost drunks through the office.