by Nick Bilton
People who used Twitter were complaining as much as the servers. In one instance, a group of Twitter’s faithful users decided to hold an online boycott. They proclaimed, on Twitter of course, that they would snub the service for twenty-four hours to show their disdain for the free site going off-line all the time. On the same day, after reading about the boycott, another group of Twitter supporters decided to send free pizzas to 164 South Park to show their love of the service.
But no amount of pizza could fix Twitter; it had been born broken.
As things worsened, Biz took to the company’s blog to address the situation.
“Twitter. Is. Slow. We are painfully aware,” he wrote on the site in a post appropriately titled, “The Tortoise and the Twitter.” “The slowness is being caused by massive popularity which makes for a bittersweet type of situation. We thought we’d let you know what we’re doing to make things more sweet than bitter.”
Its slowness didn’t stop Twitter’s growth. People kept signing up. The press kept coming—some good, some bad. The site kept growing. Every two weeks the number of people joining Twitter doubled. And as the Financial Times noted in a story on the front page of its print paper, the “mini-blog is the talk of Silicon Valley.” There was a BusinessWeek profile. Twitter was referenced in Time magazine as one of the top fifty new Web sites. “Broadcast where you are and what you’re doing right here and right now by texting from your mobile phone,” the article said. Mainstream newspapers, television stations, and nontech blogs were picking up the story. Even though the site was not ready for its moment on the stage, it was getting it.
Twitter employees were so busy trying to keep the site alive that they were stripping things out of the site, rather than adding new ones. As this all happened, some of the loyal tech nerds on the service decided to take the lack of new features into their own hands, and two new strange characters started to appear regularly in people’s Twitter stream: the symbols @ and #.
In programming speak, @ was used by engineers to talk to other people on a server, so it was natural that it would transfer over to Twitter. The first use of the @ symbol was by a young Apple designer, Robert Andersen, who on November 2, 2006, replied to his brother by placing an @ before his name as they talked. The symbol started to slowly steep into the vernacular of Twitter. Before long, people were referencing one another not by their first names but by their Twitter @ names. The new communication method grew so popular on the site that in early May, Alex Payne, a Twitter programmer, added a new tab to the Twitter Web site that showed people’s @-replies.
Then there was the hashtag, the pound symbol that until then had primarily been used on telephones while checking an answering machine. On Flickr, the photo-sharing site, people sometimes used the hashtag symbol to group similar images. In one instance, people had been using Flickr to share pictures of forest fires in San Diego, California, and had started to organize the newsy pictures with a tag that read “#sandiegofire.” Chris Messina, a designer who lived in the Valley and was friends with many of the Twitter employees, started using the same symbol on Twitter, and before long it was picked up by others on the site.
One day Chris decided to stop by the offices to pitch a more formal usage of this strange-looking hashtag icon. He wandered inside and on the stairs bumped into Ev and Biz, who were on their way out to grab lunch.
“I really think you should do something with hashtags on Twitter,” Chris told them.
“Hashtags are for nerds,” Biz replied. Ev added that they were “too harsh and no one is ever going to understand them.”
Chris argued otherwise, pointing out that people were actively using them now and that they could connect conversations on Twitter with chatter taking place in the real world. But Ev and Biz weren’t sold on the idea. Instead, they said they would “come up with something better later, something friendlier.”
But it didn’t matter what Ev, Biz, or anyone else who worked at Twitter thought or said. In an example of the site taking charge where the founders could not, people continued to use hashtags to organize everything, including group chats, conferences, and discussion of news events.
Internally, amid the growing outages on the site, Ev and Goldman continued to try to forge Jack into a better CEO—a struggle that proved to be even more difficult than keeping the Web site alive.
Ev, who had since taken on the role of chairman at Twitter, pressed Jack to supervise Blaine—who was often still anarchistic and thrived on the chaos—explaining how to give him financial incentives and set up regular check-in meetings. (It turns out even anarchists like a good pay raise.) Yet this backfired when Jack started talking down to employees. Or, as Ev noted in an e-mail discussing the problem, “Jack was acting like a cowboy.”
Each step forward felt like two steps back. When Ev told Jack to send a Twitter-wide e-mail setting company goals, his first draft began with the subject line “3 things I want for Twitter.” Jack then went on to begin each milestone with the off-putting “I want to be able to …” or “I want …” or “I …” Goldman suggested “we” might be a more appropriate way to address the company. Sounding like a dictator wasn’t the best way to talk to your employees.
Although Jack really wanted to learn how to manage, how to run a company, and how to be a good CEO, he often found himself at a loss for what to do next. Although he would never admit it, pretending that he knew exactly what he was doing and that his actions were all part of a bigger, more resolute plan, he was so far out of his league that he was often speechless. When things grew frustrating, rather than confront the problem with his employees, Jack would walk out the front door of the office and then spend an hour or more walking in circles around South Park, a petulant look on his face.
Some of his coworkers, including Biz and Crystal, believed that the company’s problems weren’t Jack’s doing or undoing, that no one could keep Twitter afloat in these tumultuous seas, especially with the influx of new people joining each day. But Ev didn’t care whose fault it was or wasn’t. His personal money was invested in the company and his name, again, was on the line. It didn’t matter if it was Jack’s fault or the Easter Bunny’s. Ev wanted to stop the site outages, fix the lack of management, and settle the overall chaos of the company. As 2007 wore on, Ev was growing increasingly impatient with the reality that these issues weren’t being fixed and they were actually growing worse.
The Dressmaker
It was late in the afternoon when Jack and Ev walked up the stairs to the conference room that had been nicknamed Odeo Heights. Their feet moved in sync, like two programmed robots, stair by stair, upward to the second floor. They opened the door to the dinky meeting room, pulled back the chairs across from each other, and sat, hands clasped.
Jeremy watched them ascend the staircase as they had done a hundred times before. As did Blaine. And a few others in the office too. But no one paid them much attention. Just a normal meeting between the CEO and chairman of the company. They had no idea—until much later, at least—that Jack would walk up those stairs as one person and walk down as somebody completely different. Two different Jack Dorseys.
Things often don’t break; they bend. Relationships rarely just splinter apart; they slowly start to bow, curving in another direction, distorting, and eventually separating. The relationship between Ev and Jack had been doing just that for some time, bowing like wet wood, moving between good and bad, but right now, as they shuffled into their seats in the conference room, it was about to break in two forever.
Ev immediately dropped the gauntlet.
“You can either be a dressmaker or the CEO of Twitter,” Ev said. “But you can’t be both.”
Although Jack worked hard, coming into the office well before anyone else arrived, he often left at around 6:00 P.M. to attend to one of his extracurricular activities. For a while he had taken drawing classes, sketching nudes in his notepad. He attended hot yoga classes, rushing off after work to contort his body into downward dog and
sweat out the stresses of the day. He had also been taking classes at a local fashion school to learn how to sew, still contemplating a future career in fashion. He loved sewing and enthusiastically set out to learn how to make an A-line skirt for his first class assignment. The eventual goal was to make his own pair of dark jeans, maybe even end up working for his favorite jeans maker one day, Earnest Sewn in New York City.
Jack’s social life had also grown exponentially, just as Twitter had. People had started to invite him to parties, lots of parties. He was taken to baseball games by affluent bigwigs like Ron Conway. Girls were paying attention to him, including one, a twentysomething blonde named Justine, who had gained a reputation in tech for dating several well-known start-up founders.
Jack was also feeling his first glimpse of fame as a Z-list celebrity in San Francisco, being written about in the media in Twitter-related articles and blog posts. For the first time in his life, the invisible boy from St. Louis was being recognized by tech enthusiasts at local coffee shops who showered him with their love of Twitter (when it worked). People who used Twitter were also starting to be given ranking based on the number of followers they had on the site. And who better to be the king of the nerds than user number one: Jack Dorsey.
But there was one person who was not Jack’s biggest fan: Ev. He believed Jack didn’t work hard enough. Wasn’t in the office enough. Was distracted by his hobbies. Was too lackadaisical with his management style. Was … was … was.
When Ev was in the office, he demanded quiet. Jokes and chatter among coworkers were often met with a long “Shhhhhhhhh!” from Ev. Biz, the always-on jokester, often laughed off the shushing, but Jack took such requests personally.
Jack had been trying to befriend his employees, organizing movie nights and dinners on a regular basis. He had also started a new ritual called Tea Time: a weekly event for Twitter staff that was held on a Friday afternoon to discuss the company’s latest news. Although people were supposed to drink tea at the discussion, they instead showed up with beer and other spirits.
But Ev didn’t care about Tea Time or movie nights. He was concerned with the company. A company that was in trouble.
The continual site outages had started to take their toll on Twitter. For a few weeks sign-ups had started to slow slightly, and Ev had sent e-mails sounding alarms.
“You leave the office too early,” Ev said. “You go off to your dressmaking classes and yoga, and to socialize, and we have all these problems with the site and growth is slowing.” Ev went on listing Jack’s flaws. Jack was furious but didn’t respond. He didn’t know how to respond. He didn’t know if he could respond. Could a CEO argue with a chairman?
It was unclear what Jack could and couldn’t say to Ev, as their relationship and the power dynamic between them were full of twists and turns. They had started out as employer and employee, with Jack reporting to Ev, then became cofounders and friends as they started Twitter together. Then the roles of employer and employee had switched as Jack became the CEO and Ev, although the lead investor in the company and chairman of its board was technically an employee reporting to Jack. Now they were two people at odds with each other.
It hadn’t always been this way. For a time they had become very close, bonding over Noah’s exodus, over winning at South by Southwest, and over drinks—which always helped them both loosen up. In late 2006 Ev, Jack, and Sara had even gone skydiving together for Sara’s birthday, thrusting themselves out of a perfectly good airplane and bonding over the experience of falling to earth at 125 miles per hour. They’d even gone camping. But as quickly as they had become friends, their camaraderie had fallen apart.
But more pressing than their opinions of how well the company was being run, Ev and Jack had fundamentally different views of what Twitter was and how it should be used. Jack had always seen Twitter as a status updater, a way to say where he was and what he was doing. A place to display yourself, your ego. Ev, who was shy and had been shaped by his days building Blogger, saw it as a way to share where other people were and what other people were doing.
Ev saw it as a way to show what was happening around you: a place for your curiosity and information. This was the debate that had originated with the concept of Twitter as a news source after the earthquake months earlier.
“If there’s a fire on the corner of the street and you Twitter about it, you’re not talking about your status during that fire,” Ev said during one of their unending discussions about the topic. “You’re Twittering: There’s a fire on the corner of Third Street and Market.”
“No. You’re talking about your status as you look at the fire,” Jack replied. “You’re updating your status to say: I’m watching a fire on the corner of Third Street and Market.”
To many this might sound like semantics. Yet these were two completely different ways of using Twitter. Was it about me, or was it about you? Was it about ego, or was it about others? In reality, it was about both. One never would have worked without the other. A simple status updater in 140-character posts was too ephemeral and egotistical to be sustainable. A news updater in 140-character spurts was just a glorified newswire. Though they didn’t realize it, the two together were what made Twitter different.
They also disagreed over the importance of mobile versus the Web. Jack was adamant about focusing on mobile development, devoting resources to building new SMS tools, allowing more countries to sign up for the service using text messages, and focusing energy on mobile applications. Ev was more focused on the Web and was constantly pushing the team to expand features on the Twitter Web site. He also worried that an emphasis on text messaging was going to bankrupt the company. Each month Twitter was being forced to pay cell-phone carriers tens of thousands of dollars in SMS bills. And each month the bills were higher than the last.
The only thing that Ev and Jack agreed on was that there was very little Ev and Jack actually agreed on.
Jack believed he had been growing and changing. He had even started to look more the part of a CEO, getting his hair cut, tucking his shirt in, and, in the boldest move yet, taking out his nose ring, the same nose ring he’d proudly worn under a Band-Aid years earlier rather than remove it at the behest of an employer. He’d wanted to lead Twitter enough to make that concession and others, but they weren’t enough for Ev.
Jack’s bond with another employee of Twitter had also deteriorated. Earlier in the summer Crystal’s relationship with her boyfriend had fizzled. Although Jack now had lots of girls to choose from, he was still sweet on his first Odeo crush. He had planned to ask Crystal out, to organize something special—maybe an old movie, a gesture that could move him from friend territory to kissing territory. But his courage had failed him when he lost her forever in Las Vegas.
He knew exactly when it had happened. It was the weekend of September 7, 2007. Twitter had struck a deal with the MTV Video Music Awards, where celebrity tweets, including those from rapper Timbaland and the band Daughtry, would be integrated into the channel’s on-air programming during the awards show. To help with the festivities and ensure that the nontechie musicians knew how to tweet properly, most of the team flew off to Las Vegas to help. But Jack couldn’t attend, as a prior commitment took him elsewhere. At the end of the long weekend, the employees came back with dreadful hangovers and lots of stories of partying with the stars. Crystal, though, came back from Las Vegas with a new boyfriend: Jason Goldman.
Jack must have been devastated. His one chance with Crystal had been stolen from him by one of Ev’s best friends and one of the board members of Twitter. “Jack versus Ev” was now “Jack versus Ev and Goldman.” And as Jack probably saw it, Crystal was on the wrong side.
Goldman wasn’t deterred by Jack’s reaction to his new love affair. He was, after all, one of “Ev’s boys,” not Jack’s. What’s more, Crystal could date whom she wanted.
Any resentment toward Goldman over Crystal couldn’t compare, though, to his feelings toward Ev as he was told he could eithe
r be a dressmaker or the CEO of Twitter.
There was no cursing during the meeting between the two that day. No screaming or fists banging either. But with each critique slung across the table, Jack was seething.
When the meeting finally ended, they walked down the stairs. As Jack sat at his desk, fuming at the things Ev had said to him, Ev grabbed his things and walked out. Jack shook his head at the irony. After railing against him for leaving the office early, Ev had done just that.
And in that moment, the click of the beige front door, the departure of Ev, the relationship between Jack and Ev was no longer bending. It had just broken.
Rumors
The rumors had been circling the Valley for weeks. Twitter was raising its next round of funding.
“Love it or hate it, Twitter, a service that embodies our narcissism, is one that we can’t stop talking about,” Om Malik wrote in a blog post on May 21, 2008. “That buzz is turning into a bidding frenzy for the company’s next round of venture funding.”
And a frenzy it was. Everyone wanted a piece of the company. In the outline that was sent around to investors at the time, Twitter laid out its stats: The company was now made up of fifteen employees. There were 1,273,220 registered users on the service. Those people were sending almost fifteen million status updates a month. The outline noted that updates were global, coming from all over the planet. But while the document showed rising numbers everywhere, there was one digit that hadn’t changed since day one: Revenue = $0, the presentation said. They were still paying the bills with the first round of financing from Fred Wilson and other investors a year earlier, but that money was quickly running out.