Hatching Twitter Part 7

"Hey," Ev said to Jack as he walked over to his desk. "Let's talk outside." Goldman followed them.

"So?" Goldman asked as they stood on the sidewalk. "What's the number?"

"Twelve," Ev said bluntly, his arms folded as he toed the edge of the sidewalk with his sneaker.

"What's twelve?" Goldman asked, now slightly confused. Jack started to giggle.

"They offered us twelve," Ev said, his voice pitched higher with slight disbelief.

"Twelve million dollars?" Goldman asked, his eyes widening slightly when he said the number aloud to himself.

"Yep," Ev said. "Twelve million dollars."

They weren't upset by the offer, as investors were begging to fund the company, but they did think it was comical that Yahoo! would offer such a low number.

"We should really take the deal," Jack said sarcastically as they all laughed.

The comical tone was interrupted as Ev told them what Bradley had said on the phone: that he believed Yahoo! could easily build the technology behind Twitter, that it was "simply just a messaging service" and "a few engineers could do the same thing in a week." He had concluded that if Twitter didn't sell, Yahoo! planned to build and release a compet.i.tor.

It was a typical relations.h.i.+p offering in the Valley: Either you f.u.c.k us, or we'll f.u.c.k you.

But hearing such an offer, followed by the fearful threat of attack by a much bigger company like Yahoo!, was also a relief. Now that they knew they weren't going to sell Twitter, they had a clear path. They could move forward and raise their first real round of venture capital, money they needed right away to expand the servers and hire engineers to help with the company's growth. Before the Yahoo! meeting, they had already decided that their first choice for investment would be Fred Wilson. This was partially because Ev and Jack believed Fred understood what Twitter could be. But more important, Fred didn't care about a business model and wouldn't pressure the founders of Twitter to come up with one-that, he told them, would come later.

As Goldman, Jack, and Ev walked back into the office, there was a rare esprit de corps among them. In a single day they had almost sold their company, then found out the suitor was now coming after them. Although they didn't know it yet, it was one of the few moments they would agree on a direction for Twitter. By the end of the coming summer, it would no longer be Twitter versus its compet.i.tors. It would be Twitter versus itself-Jack on one side, Ev on the other.

"Twelve million?" Goldman asked again as the door closed behind them.

"Yep," Ev said, laughing. "Twelve million dollars."

Is Twitter Down?.

The blog post appeared on the Twitter Web site at 11:53 A.M. on Thursday, July 26.

"First, Twitter was a fun side project, then it was cared for lovingly at Obvious until it was time to form Twitter, Inc.," Jack wrote in the blog post. "Today, we're excited to announce an important moment for Twitter. We've raised funding from our friends in New York City at Union Square Ventures." Fred Wilson, a partner at Union Square, would be leading a five-million-dollar round of funding that would value Twitter at just over twenty million dollars.

Then in a separate blog post, Fred explained why his firm was investing in a company with no income. "The question everyone asks is 'What is the business model?' To be completely and totally honest, we don't yet know," Fred wrote on Union Square's Web site. "The capital we are investing will go to making Twitter a better, more reliable and robust service. That's what the focus needs to be right now." Revenue would have to come later.

Fred was right. There was no time to worry about business models while Twitter was in its current state: broken.

Each morning had been the same for the Twitter employees. A scene of Jeremy's wife finding him on the couch at home in the same position as the night before, his laptop still glowing a warm blue haze on his chest, a small waterfall of drool coursing down the side of his cheek, his fingers lying on the keyboard as if he had been shot in a break-in gone awry. Blaine was found in the same position at his apartment.

They had both been working through the night, trying to keep Twitter up and running-but often to no avail. The Web site was continually breaking and nothing could be done to stop the outages.

Because of the way the site had been built-hacked together over two weeks-the influx of people on Twitter was making it fall apart. It wasn't just one aspect of the service that was breaking; it was every aspect of it. Posts weren't showing up in the timeline. Accounts were disappearing. The site was off-line for hours or sometimes more than a day at a time. The servers were collapsing. And because everything was in such disarray, the employees were revolting. Twitter had been built as a small rowboat designed to carry a few people across a pond; now the same vessel was being used to carry the same number of pa.s.sengers as a cruise s.h.i.+p across an ocean.

As a result, it was sinking.

The outages also had a domino effect, with the failure of one aspect of the site knocking down everything else. The third-party tools Twitter gave to developers were being harnessed by hundreds of companies and apps that used Twitter's content (Twitterrific, Twitteroo, Twitterholic, Tweetbar, Twittervision, and Twadget, to name a few). This influx of applications was straining resources away from the Web site. The site itself, which was still stuck together with the digital equivalent of plastic wrap and Scotch tape, would often bring down the servers. The servers would get clogged up with all the tweets waiting to be sent to the Web site and, bringing it back around to the beginning, the third-party tools would stop working. Almost daily, the entire operation would just come to a halt.

Although the site's problems should have slowed the flood of people signing up, they were only making it worse, adding bad press that would pique more curiosity about this Twitter thing-"If everyone else is signing up and breaking it, then surely I should see what this thing is about"-a pile-on of hundreds of thousands of people on one tiny little company.

When the site reached one of its daily snapping points, the biggest problem was that the engineers had no idea where the breakage had originated. To solve this problem-or at least try-Jeremy and Blaine built code into the servers that would notify them via text message and e-mail when the site was suffering from one of its many issues. Like a patient put on life support, tubes and wires and cords sticking out and beeping about his health, the new code was designed to help engineers determine where the patient had fallen ill. Then they could go in and operate. This worked for a short while, but as they soon found out, the road to chaos can be paved with good intentions.

In a matter of days the notifier was sounding a series of alarms that couldn't be turned off, and the engineering team was inundated with bulletins. Their phones woke them in the middle of the night-sometimes every few hours, other times every few seconds-vibrating, ringing, and buzzing on the nightstand, with Twitter begging for help, as it had flatlined again. On several occasions, the problems were so severe that Jeremy and Blaine woke up to find more than a thousand text messages from Twitter servers complaining about a problem that had shuttered the site.

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 t.i.tled, "The Tortoise and the Twitter." "The slowness is being caused by ma.s.sive 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 b.u.mped 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 d.i.n.ky 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. Relations.h.i.+ps rarely just splinter apart; they slowly start to bow, curving in another direction, distorting, and eventually separating. The relations.h.i.+p 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 cla.s.ses, sketching nudes in his notepad. He attended hot yoga cla.s.ses, rus.h.i.+ng off after work to contort his body into downward dog and sweat out the stresses of the day. He had also been taking cla.s.ses at a local fas.h.i.+on school to learn how to sew, still contemplating a future career in fas.h.i.+on. He loved sewing and enthusiastically set out to learn how to make an A-line skirt for his first cla.s.s a.s.signment. 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 shus.h.i.+ng, 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 cla.s.ses 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 relations.h.i.+p 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 pus.h.i.+ng 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 s.h.i.+rt 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 relations.h.i.+p 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 either 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 relations.h.i.+p 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 doc.u.ment 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.

The venture capitalists didn't care about the bills, which were flowing in. Each month's user growth was higher than the one before; the projections for the coming months, higher still. The charts accompanying the presentations looked like stairways to heaven.

Ev noted in his presentation that the company hoped to raise ten million dollars in capital at a rate that would put Twitter's valuation at fifty million dollars. But by early May, amid the frenzy and excitement of investors hoping to attach their name to Twitter, the valuation of the company had jumped to sixty million. Then it spiked to seventy million a few days later. In the end, when the news finally broke, the company was worth eighty million.

It didn't matter that Twitter still had no business model or even the faintest sign of one. Or that the site was broken. Everyone still wanted a piece of the fledgling company because it was gaining so much attention. Investors wanted their names a.s.sociated with the Next Big Thing, and they believed they could help fix its problems.

From the outside looking in, it appeared that Twitter was just growing too quickly. The venture capitalists lining the streets, ready to hand over millions of dollars, believed that with the right check and the right investor guidance, the company would be able to hire new engineers and scoop up a few new servers, and all would be right in the world. Of course, what happened inside the company was often very different from how things were perceived on the outside.

Inside, it was complete disarray.

In April 2008 Jack fired Blaine, seemingly in an attempt to show Ev his control of the company. Internally it was a typically ugly exit, with Blaine being sacked while he was on vacation. Yet externally the tech media believed it was just an oh-shucks-it's-time-to-move-on-and-we're-still-friends story. Then Jack fired Lee Mighdoll, another senior engineer who had been hired only a few months earlier. After Blaine was fired, the site's problems only worsened. Blaine had been the core programmer of Twitter, and without him Jack struggled to fix certain issues.

Since the site's inception, when Twitter went down, people were greeted by a picture of a cat doing something funny. "I is in your komputer," one notification proclaimed, a picture of a sleepy kitten curled up inside an old PC. As the company had grown up slightly, Biz decided the cat pictures were too jokey and went in search of something more serious. He soon came across an ill.u.s.tration on a stock-photography site by Yiying Lu, an artist and designer from Sydney, Australia, of a whale being lifted from the sea by some birds. This became the new image people saw when Twitter crashed. As the site was going off-line so much, it didn't take long for the whale to garner its own nickname: the Fail Whale.

There was also the bittersweet problem that celebrities were now using Twitter, bringing more followers and sign-ups with them. In a trend that would continue indefinitely, some of those celebrities would randomly show up at the office. The pilgrimage to the great blue bird. One morning, when a couple of engineers strolled into the office and walked into the kitchen to get their morning coffee, they found a member of the band blink-182, half-asleep and half-drunk, pouring a small bottle of gin into a bowl of Fruity Pebbles cereal, then chowing down on breakfast. At other times, the rapper MC Hammer would show up out of nowhere with his entourage and just hang out.