But the celebrities didn't get a true glimpse of Twitter either. They were ignorant of the disputes between Jack and Ev. Even the fund-raising had been a cl.u.s.ter f.u.c.k-at least behind the scenes, where it had become another internal tug-of-war gone awry: Ev pulling on one end, Jack on the other, Biz trying his best not to get caught in the middle.

While Ev had been leading the funding talks, Jack felt excluded from the conversations. Wanting to prove to Ev that he could handle the task, Jack tried to negotiate with investors on his own. As a result, one minute a venture capitalist would get a call about a meeting from Ev, the chairman. The next, the phone would ring with Jack, the CEO on the line, hoping to set up the same meeting. To the venture investors, it just came across as a slight misunderstanding. To Jack it came across as being slighted.

One afternoon Jack got on the phone with one of the venture capitalists and negotiated a deal that would value Twitter at one hundred million dollars with the latest fund-raising. Proud of himself, he trudged off to tell Ev. But it was too late. Ev had already decided that he wanted to use another firm. The lead investor would be Spark Capital, and Bijan Sabet, a well-respected and kind partner at the Boston-based firm, would be joining the board of Twitter after it closed its eighteen-million-dollar round of investing in June 2008, which would value the company at eighty million dollars.

From Jack's perspective the deal that he had struck was a better one than Ev's, and he was once again irate that Ev was going above him to make decisions.

Though Jack didn't know it at the time, for Ev the funding round hadn't just been about the money or the valuation of the company. It had been about a bigger goal, fixing the company the best way Ev knew how: by taking more control of its daily operations.

f.u.c.k f.u.c.k f.u.c.k ....

Bijan's fingers moved on the keyboard in a repet.i.tive motion. Back and forth he typed, one single word, like a parrot with Tourette's syndrome. "f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k." Then he hit "send," catapulting the words in an e-mail to Fred Wilson's in-box. Nothing else, just the word "f.u.c.k," eighteen times.

He didn't need to add anything to the message. No explanation was needed. Fred knew exactly what had just happened.

Bijan buried his head in his hands, closed his eyes, and repeated the word one last time to himself. "f.u.c.k!" In Twitter's eighteen-million-dollar round of financing in June 2008, Bijan's company, Spark Capital, had invested fourteen million, with Jeff Bezos of Amazon and Fred Wilson investing the majority of the other four million-along with several angel investors. The large sum put in by Bijan's company had secured him a seat on the board of Twitter, along with Fred Wilson. Over the next couple of months Bijan had started to become entrenched in the company, attending a few meetings, raising his hands for a few critical infrastructure votes. And now here he was, f.u.c.king it all up already.

He sat for a moment, pointlessly trying to reason whether he could somehow, by some means, any means, delete an e-mail he had accidentally sent to Jack a few minutes earlier. It was impossible, he knew. You can't resurrect the dead or delete an e-mail that has traveled eighty-five thousand miles per second across from Boston to San Francisco.

After a few seconds trying to calculate the incalculable, Bijan sat up and frantically began typing another e-mail.

To: Jack. "Please call me when you get this message," he wrote, noting that he wanted to clear up his previous e-mail. "Out of context this could be really confusing."

It had all started in July 2008, when Twitter purchased its first company, Summize, which used Twitter's third-party tools to allow people to search everyone's public tweets. People had taken to the feature as quickly as they had taken to Twitter itself. Before long, so many people were using Summize that Twitter found itself competing with the company for page views. Rather than snuff it out, Twitter decided to purchase Summize and its small team of highly competent engineers.

The sale had been relatively painless. The initial negotiation between Fred and John Borthwick, an investor who was on Summize's board, occurred while the two were standing next to each other at a bathroom urinal. "Why don't we just join these companies and call it a day?" John said as he peered over at Fred, a tinkling sound emanating from their respective urinals.

Fred agreed. After a couple of in-person meetings, a deal was struck (not in a men's room, thankfully).

July had already been a busy month as Twitter had also moved into new offices: a fancy, modern, loftlike s.p.a.ce with lots of windows and room to grow. Among the fun features they had added to the office (a living-room setup with a couch and video games, a large red phone booth, and a fully stocked kitchen with cereal and other snacks), Jack had suggested putting in a Radiohead room. "It can play Radiohead twenty-four hours a day!" he said excitedly when suggesting the idea.

After the company had signed the paperwork with Summize and divvied up Twitter stock as part of the sale, Jack got on the phone with Greg Pa.s.s, the engineer who had been running the tech side of Summize.

"Hey, so we're thinking that, since we don't really have any real leadership here on the engineering team, that you can run all of it," Jack said.

Greg sat silent for a moment, processing what Jack had just said, immediately realizing that something must be amiss at Twitter, as he heard the CEO utter the words "no leadership" on the engineering team. "Um, okay," Greg said, but before he had a chance to ask what Jack meant, he was interrupted.

"And," Jack said, "how about you run the operations side too?"

The operations side of the company included managing the so-far-disastrous scaling of Twitter's servers. "Um, I don't have any experience running operations," Greg said.

"Well, there is no one here that can run it better than you," Jack replied matter-of-factly.

When they got off the phone, Greg was shocked. And he wasn't the only one. Jack sent an e-mail to the company announcing that there would be a management switch, that Greg was now director of operations, or "ops" for short, and overseeing all of engineering. (Jack planned to focus his time on product development.) When the message arrived in Ev's in-box, he was livid. "You're just going to put someone in charge of engineering and ops for the entire company and not discuss it with me or the board?" he said to Jack in pure frustration.

It was the "enough's enough" moment for Ev. But also for Fred and Bijan. And in several secret calls and meetings, they decided it was time to figure out what was going on inside Twitter.

Fred and Bijan, now the two investors on the Twitter board, flew out to San Francisco from New York and Boston on the red-eye. They set up meetings with Goldman, Biz, and Jeremy. For what? "Oh, just to talk. We want to get your thoughts on how things are at Twitter." It was partially true. But in reality, Fred and Bijan wanted Jack out. So did Ev. The main purpose of the meetings was to learn how such a move would go over with employees. Twitter's senior staffers didn't need much cajoling.

One by one, Goldman, Biz, and Jeremy were shuffled away from Twitter's office and into coffee shops and gently interrogated. Then the most senior employees were told that Fred and Bijan, with the full support of Ev, were going to demote Jack, removing him as CEO. "What do you think?" they asked, even though the decision had essentially been made.

Bijan and Fred soon found out that Jack had been incompetent with the company's finances too. Although revenue was still at zero, expenses were quiet the opposite, with growing server fees, text-message bills, and payroll. Jack, who had been managing expenses on his laptop, had been doing the math incorrectly. When Ev learned about this, he asked a friend and seasoned entrepreneur, Bryan Mason, to meet with Jack and show him how to manage the company's books, but Bryan spent the entire meeting at a whiteboard with a marker explaining the basics of accounting.

When Bijan and Fred met with the engineers, they heard mostly worries about Jack. "Engineering and ops are a disaster," they consistently said. "He's a great guy. A great friend. A fun boss. But he's in over his head," another announced. "He's like the gardener who became the president." "I don't know who is in charge. Ev presents the product and vision for what's going on, and Jack just sits in the corner and takes notes."

The board members knew they had to find a new role for Jack or let him go immediately.

Everything was all set; it was all about to happen. Then the plan came to a screeching stop.

"I'll quit!" Biz said to Fred and Bijan as he folded his arms and sat back in his chair like a petulant child. "Should Jack be running Twitter? Probably not," Biz admitted, but he believed that forcing Jack out would tear Twitter in two. Although most employees would have helped pull Ev's side of the tug-of-war rope given the choice, and although Jack was completely out of his league as CEO, some Twitter employees, including Biz, still loved him. "I'm serious. If you fire Jack, I'll quit."

It was a bluff, but it worked. Fred and Bijan knew they couldn't lose Biz, especially if they were pushing Jack out too. As Biz's job as cofounder had unfurled, he had started to serve two distinct roles at Twitter. First, he had become the public face of the company. Given Jack's and Ev's strange and often quiet public posture, Biz had stepped up his gregariousness and become the guy who joked with the press, enlivened employees, and often entertained the visiting celebrities.

He had also become the moral line at the company. In late November 2007, Twitter had been used as a prop on the TV show CSI: Crime Scene Investigation: Tweets were used as clues to track down the victim of a murder. It didn't take long for fiction to turn into reality, and the FBI and other law enforcement started knocking at Twitter's door demanding information on certain people who used the service. Biz and Ev, along with Crystal, had emphatically said no, adamant about protecting people's ident.i.ties on Twitter rather than caving to some big guys with guns in suits.

While Bijan and Fred were whisking employees away, Jack suspected something was amiss-secret closed-door meetings, quiet phone calls from Ev in the conference room-but he had no idea about the severity of the situation.

What's more, Jack had no idea that Biz's threat to quit was Jack's second reprieve in recent weeks. Another pardon had taken place earlier in the month after a disastrous attempt by Jack to break bread with Ev, whom he barely spoke to anymore.

The two cofounders had agreed to meet for dinner to talk about the turmoil. Jack thought the purpose of the meal was to mend some broken bridges. He suspected Ev wasn't happy, but as neither of them was direct about his views and feelings, they had been skirting around the conversation.

They met at Bacar, a California fusion restaurant, in early August. The smell of burning wood drifted through the air as they both doused their uncomfortable feelings with a few large gla.s.ses of alcohol. After long stretches of silence that were punctured by short bursts of small talk, they got down to business. "What's going on?" Jack asked Ev as they waited for their meal to be served. "You don't seem happy."

Ev explained that the company's problems-the blackouts, the lack of communication with him and the board, and the text-messaging bills that were approaching six figures-were all hurting the growth of Twitter. Ev noted that over the past few months the Twitter company blog had been one post after another explaining that the site was down-all of this, he said, was an embarra.s.sment to Twitter.

"Do you want to be CEO?" Jack interrupted, point-blank. Ev was caught off guard by the question. "Do you?" Jack asked again, in a rare stern moment.

"Well, I've been thinking about things," Ev replied, taking a sip from his martini, then swerved and jumped back into a slew of other problems the company was going through: the lack of hiring, the costs, the chaotic culture.

Jack interrupted again. "You're not answering the question. You have to tell me if you want to be CEO. I don't want to leave this table without knowing your intent; I do not want to work under a cloud."

Ev paused briefly. He had not planned to tell Jack that evening about the board's plan to demote or remove Jack, but he was now being pressured to answer. He hadn't even told Goldman what was going on, fearing that such a conversation would be told to his girlfriend, Crystal, and eventually come back to Jack. Finally Ev took a deep breath and replied. "Yes. I want to be CEO. I have experience running a company, and that's what Twitter needs right now."

"Fine," Jack said, a look of anger and disgust on his face. "I want to move immediately on this. I want to tell the management team tomorrow."

After an extremely awkward dinner, Jack walked home panicking about what to do. When he opened the door to his apartment, he paced, his feet tapping the brown hardwood floor as he tried to clear his head. Then he dropped down onto his white couch, slipping his laptop out of his Filson bag and quickly rattling out an e-mail to the senior management team telling them there would be an emergency meeting the following morning. Then he sent another message, to Fred and Bijan, describing the conversation with Ev.

Jack then tried to go to sleep but found himself lying awake in bed, tossing and turning as he replayed the evening's conversation in his head. He suspected that this was all some elaborate ploy by Ev to take power and control of the company and that the moment Fred and Bijan read the news, they would stop the miscreant chairman.

The next morning in the office, everyone filtered into a conference room for this emergency meeting. As Jack and Ev stood a few feet from the conference-room door, about to walk inside, they both received a text message from Bijan saying that they should call him immediately, together. Do not do anything, Bijan said. "Call me now."

They walked out of the conference room, where the management team now sat utterly confused. And although they were about to get on the same conference call, Jack turned in one direction, entering the Radiohead room, and Ev walked into another separate conference room, both to call Bijan.

"Look, we've heard what's going on and we don't want you to do anything yet," Bijan said. "Just hold off for now."

While Jack listened, he paused for a moment as he heard Radiohead lyrics floating in the background in the tiny conference room, his iPhone pressed up to his ear trying to block out the faint music. He looked in the direction of the speaker, briefly registering the irony of the song "Karma Police" playing while he was embroiled in this confusing power battle with Ev.

Bijan continued, "Fred and I are gonna fly out there next week and meet with you both and the management team," he said.

The call ended, and Bijan hung up the phone, relieved that he had held off the switch from one CEO to another. Ev and Jack opened their respective conference-room doors simultaneously, paused briefly as they looked at each other as in a dramatic romantic-comedy scene, then walked briskly across the concrete floor in the same direction to sit awkwardly and silently across from each other.

In addition to creating the Radiohead room, Ev and Jack had agreed to sit in the same place in the new office. Their desks b.u.t.ted up against each other, back to back, like conjoined twins. As they shuffled into their seats after the call, their frustrated scowls were obscured by two large monitors that stood on the desks like sandbags piled high on a battlefield to hinder enemy fire.

Although the call with Bijan had stopped his execution, Jack now knew there were larger forces at work than just Ev. He sat, playing the things Bijan had said over in his head and trying desperately to figure out what was going on. Words like "yet" and "not now" spun in circles but didn't offer clues to the future.

It was a week later that Fred and Bijan flew out to Twitter HQ. The plan all along had been to fire or demote Jack and put Ev in as CEO. But when it came time to pull the trigger, Biz protected him, temporarily. So Bijan and Fred were left with no other option but to keep Jack in his current role. They sat him down and gave him an ultimatum. "You've got three months," they told him. "Three months to fix things and take control of the company."

Of course, they knew Jack couldn't fix anything in three months, or three years. He was incapable of running the company. It was like watching somebody try to build sand castles underwater.

The two investors flew back to New York and Boston and started organizing a way to remove Jack, sending e-mails back and forth discussing a possible new job for him at the company. It was then that Bijan made his heinous error.

First thing in the morning, his coffee cup still full next to his computer, and weary from a night without much sleep, Bijan accidentally pressed the "reply to all" b.u.t.ton on his computer instead of replying just to Fred.

"I believe Jack would take a 'pa.s.sive' chairman role," Bijan wrote. "It would then really be up to Ev to decide if he could live with Jack's new t.i.tle." He hit "send" before he realized what he had done.

Seconds later, he looked up at the exchange and uttered a word he was about to write eighteen times in an e-mail that he then sent to Fred: "f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k f.u.c.k."

He then quickly rattled off the e-mail to Jack: "Please call me when you get this message. Out of context this could be really confusing."

But it was too late. Jack knew what was about to happen.

Building Sand Castles Underwater.

The summer of 2008 was coming to a close, the seasons changing as August rolled into September and Jack's three-month reprieve began.

Although Jack had spoken to Bijan after the accidental e-mail, he believed he could somehow save himself from being thrust out of the company. So he immediately went into panic mode and held a meeting with Twitter's leadership team to announce his battle plan.

"Before we start, I want to take a moment to address the events of last week," Jack said. "For me, it was a wake-up call." He took responsibility for the problems at Twitter, admitting that there was a lack of strong leadership. He also laid some of the blame on Ev and Goldman, noting that he needed to execute his own vision for the company, not theirs. And he admitted that Twitter needed to "think bigger," as Ev had been saying since day one.

But Jack's idea of thinking big wasn't to fix Twitter's endless thirty-hour-long outages. It wasn't to resolve the bank-robbery-size SMS bills. It was, as Jack outlined in an e-mail to Fred and Bijan, to "be at the forefront of this historic 2008 Presidential elections [sic]."

"As we've been pointing out consistently in the past, events, ma.s.sively shared and immediate experiences, capture the essence and engagement of what Twitter has to offer the world," Jack wrote to the board. "And the biggest shared event we can plan for already has traction with our users, is right under our noses, will deliver us to mainstream usage, and is rapidly approaching." Then, beating the rallying drum, he announced: "Twitter will be at the forefront of this historic 2008 Presidential elections [sic]. Whether we do anything or not, it's going to be huge for us. Imagine how big it could be if we fully embraced it as a company?"

As they read, none of the team members were in support of this idea. Fred: This won't solve our problems! Bijan: Oh, Jack. Ev: WTF! Goldman: What the h.e.l.l is he thinking?

Blogger had been down this road before. Four years earlier Goldman had set out to the Democratic National Convention in Boston to try to persuade the media and attendees to blog. There he had seen firsthand that if people were going to use these new technologies, they did it of their own accord, not because a company willed them to.

Goldman remembered the 2004 election vividly. He had hopped on the phone with Noah, who was in California, and explained the scene in Boston, recording a podcast that described the apocalyptic setting with thousands of Boston police and protestors.

As the 2008 presidential election approached, people were no longer talking about podcasts or blogs. A new word had obliterated the vernacular of politics and media: "Twitter."

Outside, protesters were using the service to organize ma.s.sive demonstrations against the police. Inside, a young senator from Illinois named Barack Obama was using Twitter to try to disrupt politics and gra.s.sroots campaigning and, he hoped, win the election. And the media, including the Huffington Post, had set up Twitter accounts to update live snippets from the 2008 conventions.

The reality was, Twitter didn't need to do anything to ensure that it kept growing. It was already on its way to becoming a "personal newswire," as Biz explained it.

Twitter continued to compress time, often reporting news more quickly than news outlets that had been in the business for more than a century. As more people joined the service, it moved even faster. During the 2008 conventions, the 1.4 million people who were actively using Twitter sent more than 365,000 tweets from both the Republican and Democratic conventions. Such numbers showed that the elections were important, Ev agreed, but they weren't more important than growing the tiny team of twenty-two employees and getting the site working properly.

Like rolling blackouts in a country already starved of electricity, the site had continued to go off-line daily. The Fail Whale took over the site almost hourly. Some outages lasted a few minutes, others more than a day. The fire hose, the name given to the stream of all the tweets coming through the service for third-party applications, would often turn off.

As Jack got to work designing a dedicated elections page, Ev said nothing, waiting for Jack to fail. And it didn't take long.

At the next board meeting, after going through the slides announcing the number of new sign-ups, Fred and Bijan asked Greg Pa.s.s, who was now running engineering and operations, to present a plan for how to fix Twitter's outages. It was an altogether impossible task, like asking a mechanic to figure out how to replace the engine of a moving car filled with 1.4 million pa.s.sengers.

The sun shone brightly through the conference-room window when Greg walked in. He sat down slowly, methodically, like a doctor about to deliver bad news to a patient.

Greg began by explaining that he had built software to detect what was wrong with the site, to find out why it continued to go off-line. As he opened his laptop and began talking, Jack sat silently. Ev too. They had both been warned by Greg what he was about to say to Fred and Bijan.

"We have a bit of a problem," Greg began. While he had been running tests on the site, he had discovered that there was no backup of Twitter. "If the database goes down right now, we would lose everything," Greg said awkwardly. Every tweet, every user, everything. Gone.

"You're f.u.c.king kidding me," Fred said with almost comical disbelief. "Well, what the f.u.c.k are you doing in here?"

As Greg rushed out of the room to figure out how to back up Twitter, everyone looked in Jack's direction. And although he didn't know it at that moment, they all did: Successful election site or not, Jack Dorsey's days as Twitter's CEO were numbered.

Calling My Parents.

The week Jack Dorsey was fired from Twitter began much like any other. Monday started with the usual Jack routine. He got up and made his white bed. Showered. Dressed in his dark blue Earnest Sewn jeans and black cardigan. Grabbed his keys and bag and ran down the stairs.

At some point that morning, Jack checked his e-mail and was greeted by dozens of messages that had filled his in-box throughout the night. There was one message that stood out like police lights on a dark city street. It was from Bijan and Fred, and it had been sent at 7:41 A.M. on the East Coast. The subject line simply said: "Breakfast wed morning."

Why were Bijan and Fred asking to get breakfast on Wednesday morning? They weren't supposed to be in San Francisco that week. Did Ev know about this? Jack thought.

He opened the e-mail. "Can you meet with me and Fred before the board mtg," the message from Bijan read. "Why don't we meet for breakfast Wed morning at 7:45am at the Clift Hotel. Let me know if that works." Jack glanced up at the time, where the numerals showed that it was 7:15 A.M. Pacific Time. Fred and Bijan wanted to meet exactly forty-eight hours later.

Routine interrupted.

Anxiety welled up in his chest. He knew almost immediately that this wasn't a good sign.

As his mind raced with scenarios, he wrote a response. "That works. I'll see you there." He hit "send" and the e-mail made its way to Fred and Bijan.

He spent his commute on the Muni train preoccupied with the meeting. The metal wheels clicked and screeched against the tracks as he tried to replay past conversations with the board in his mind. He glared out of the window, asking himself why Fred and Bijan wanted to meet. He was like one of Agatha Christie's fictional detectives trying to decode a meeting two days from now, his only clue a forty-three-word e-mail.