by Nick Bilton
He sat on a couch in Campbell’s office, one hand firmly gripping his notepad and the other grasping a pen, ready to jot down Campbell’s advice. Fenton watched the two of them with excitement. Campbell leaned back in his chair and began his role: coaching. He ranted, raved, and yelled, throwing out one-liners as if he were telling Ev to rush a ball into an end zone. And he cursed. Like a hammer striking metal, the word “fuck” was used in place of the period at the end of each sentence. Fuck this … Fuck that … Fuck. Fuck. Fuck.
When it was Ev’s turn to talk, he asked his first question: “What’s the worst thing I can do as CEO to fuck the company up?”
Without skipping a beat, Campbell responded: “Hire your fucking friends!” He went into a ten-minute tirade about friends and business and how they don’t mix. Ev scribbled in his notepad.
Ev was smitten with Campbell. They shook hands and agreed to start meeting once a week. Fenton was elated. “This is going to be great!” Campbell said as he slapped Ev on the back. “Just fucking great!”
One of the reasons Fenton and the board had been pushing for Ev to see a CEO mentor was Ev’s insistence on hiring his friends at Twitter. Ev didn’t see this as a problem. Most of his friends were the few people he could relate to about technology, and they had often fit perfectly into the companies he had started over the years. He also saw his success as a lot of hard work and a little bit of luck, and he wanted to give the people he knew the opportunity to be a part of it. He had hired his sister, a chef, to run the kitchens at Twitter. His wife, Sara, had been hired to help design the new Twitter offices. Numerous friends from Google were employed working on engineering and design at Twitter.
Ev also reasoned that his friends would never betray him.
While Ev was willing to hear Campbell’s advice, he still had one last buddy to hire, his good friend Dick Costolo, whom he had met at Google a few years earlier.
In 2009 Dick was forty-five years old and lived in Chicago with his wife, Lorin, and their two young children. Although he wasn’t as young and hip as most tech founders, he was well known in the tech scene and had become close friends with Ev.
Dick had grown up near Detroit and studied computer science at the University of Michigan. During the first semester of his senior year, he decided to take an acting class to fill one of his open classes, figuring that acting wouldn’t require much additional homework. This way, Dick reasoned, he could spend his evenings focused on his computer science assignments. Yet after the first thespian session he was hooked, and he signed up for another acting class the second semester.
Before he knew it, he started ignoring his computer science assignments and instead spent his evenings on a small stage near campus performing stand-up comedy. Although he graduated with a number of job offers from big tech companies, Dick instead chose to pursue his new and improved dream of becoming a world-famous actor, comedian, or both. He packed his bags and set out to Chicago to join the Second City sketch-comedy and improv troupe in hopes of eventually making it on Saturday Night Live or getting his own TV show.
It didn’t work out that way.
Although Dick was a talented comedian, he found himself doing improv shows at night and working in a Crate & Barrel, wrapping flatware and selling place settings, during the day to pay the bills. Eventually this wore thin, and in the early 1990s he decided it was time to put his computer science degree to work and took a job at Andersen Consulting to subsidize his comedy career.
On numerous occasions he walked into work and explained to his bosses that there was this new thing they should all be paying attention to called the World Wide Web. But his superiors laughed it off, thinking it was just another Dick Costolo joke.
He eventually grew tired of the corporate atmosphere and quit. Rather than return to comedy, he corralled a small group of coworkers, and they started their own consulting firm, called Burning Door Networked Media, which specialized in building and managing Web-based projects. Before long he was creating and selling companies, three in all, and making millions of dollars in the process. One of the companies that put him on the map was Spyonit, a service that notified people when a Web site they were interested in had been changed. Finally, in 2007, Dick hit the jackpot when he sold a company called FeedBurner, which helped bloggers syndicate their blog posts, to Google for more than one hundred million dollars. Along the way he met Ev, and the two became close friends.
In 2009, after running into Dick at a party in San Francisco, Ev asked if he would be interested in managing the Twitter employees while Ev went on two weeks’ paternity leave with his first child. The conversation quickly escalated to Ev asking if Dick would be interested in a full-time job as chief operating officer of Twitter. Until then no one had held the role, but Fenton and the rest of the board had been pressing Ev to hire someone.
At first Bijan and Fenton were not interested in hiring Dick, noting that he was just another friend of Ev’s. Fenton was particularly sceptical and believed that the wrong appointment would cause chaos. Bijan agreed, questioning whether they should go outside to fill the role rather than hire another of Ev’s friends.
Still, Ev didn’t give up. “We’ve been friends for a couple years, and I think he’d be a great complement to myself and the team,” Ev told the board in an e-mail. “I have a high degree of trust with Dick that I wouldn’t have bringing in an outsider, no matter what their experience.”
For Dick the prospect of being Twitter’s COO was a redux of the opportunities he had missed by pursuing his improv career instead of taking a job at a big tech firm after college. Twitter was changing the world, and Dick wanted to be a part of it. Here was his chance to be back on the stage, a global stage.
After he underwent extensive interviews with Biz, Goldman, Bijan, Fred, and Fenton, the Twitter board agreed to hire him, although Ev didn’t leave them much of a choice. In contrast to his inability to make smaller decisions, when Ev made up his mind about something big, it was going to happen. As he had been the time he had driven to Florida to get a job with the advertising guru, Ev was determined: Twitter would hire Dick.
In early September 2009, the day before Dick arrived for his first day at Twitter, he thumbed his first tweet as an employee of the company. It was a joke that made people laugh, including Ev. But it would later haunt Dick.
“First full day as Twitter COO tomorrow,” he wrote. “Task #1: undermine CEO, consolidate power.”
Jack’s Gone Rogue
We need to talk,” Biz said to Ev. “Jack’s gone rogue.”
“What do you mean, he’s ‘gone rogue’?” Ev asked, laughing.
Biz turned his laptop around and slid it across the table so Ev could see.
“Jesus,” Ev said, shaking his head with disbelief as he started reading. “Again?”
As 2010 began, here was another article about Jack, touting him as the founder, inventor, architect, and creator behind Twitter, another article that made Jack seem like the only employee at the company, even though there were now nearly a hundred people toiling away on the site. Jack not among them. It had been growing worse by the day. Since Jack had been pushed out, he had taken on almost any press asked of him. Blogs, newspapers, TV, magazines, public talks. Yes, yes, yes, and yes. He would do them all.
Even Biz, who rarely got upset, was starting to grow more impatient with Jack’s media junkets. Not only was he taking on press, but he was also failing to mention anyone else’s involvement in the creation of Twitter. What’s more, Biz was increasingly upset that Jack was giving interviews about moral issues related to Twitter. Biz had always been clear that Twitter employees and executives should not take on interviews where Twitter was being cast as the catalyst in a social issue. Discussing how Twitter was being used as a tool for war, politics, or major news events was strictly off limits for anyone who worked for or with the company. “I don’t want it to seem like we’re taking a side in anything,” Biz often said.
Jack believed this rule didn’t apply to him, and wh
en he did talk about these issues, he often got them wrong. During a taped interview with the famous artist and protester Ai Weiwei about digital activism in China, Jack was asked about Twitter’s stance on trying to open the service in China. With no knowledge of Chinese politics, he fumbled, and appeared unaware that Twitter had been blocked in the communist country.
At the time, Ev asked Sean Garrett, who had been hired as the director of communications to help with the unrelenting Twitter media onslaught, to talk to Jack and give him some media tips. “If he’s going to go out and do this press, he should at least know what he’s talking about,” Ev said.
Publicly, Jack couldn’t explain some of the decisions that were taking place inside the company, and even if he could, he often didn’t agree with them. He was convinced that Ev was too focused on the Web and not paying enough attention to the mobile aspect of the service. And he completely disagreed with a major alteration Ev made in early November 2009—one of the biggest to the Web site since Jack’s departure.
Ev had finally changed the question in the Twitter box, from Jack’s “What are you doing?” (which he’d always seen as a question about ego) to “What’s happening?” which he believed gave Twitter more of a bloglike feel. It was a win by Ev in the debates between the two founders in the early days, with Jack’s saying that Twitter was about your status, Ev’s touting it as being about the status of the events taking place around you.
“Twitter was originally conceived as a mobile status update service—an easy way to keep in touch with people in your life by sending and receiving short, frequent answers to one question, ‘What are you doing?’” Ev and Biz wrote in a blog post on Twitter’s Web site. “Sure, someone in San Francisco may be answering ‘What are you doing?’ with ‘Enjoying an excellent cup of coffee,’ at this very moment. However, a bird’s-eye view of Twitter reveals that it’s not exclusively about these personal musings. Between those cups of coffee, people are witnessing accidents, organizing events, sharing links, breaking news.”
They added: “‘What are you doing?’ isn’t the right question anymore—starting today, we’ve shortened it by two characters. Twitter now asks, ‘What’s happening?’ We don’t expect this to change how anyone uses Twitter, but maybe it’ll make it easier to explain to your dad.” Jack, of course, did not agree with the change, and in interviews he continued to talk about “status” as the basis for a tweet.
Internally at Twitter it was obvious that Ev was in charge of the company. Externally, some people believed Jack was running it from his “chairman” role.
The media didn’t know the difference, as news segments touting Jack as the brains behind the operation made clear. One, in late 2009 by CBS, was titled, “The Twitter Mastermind.” The segment began with the CBS anchor talking about the company. “Wall Street recently put a value on the social network Twitter at one billion dollars, even though the company has yet to make a dime,” the anchor said; then, as the screen flashed to a portrait of Jack, he noted: “Jack Dorsey was only twenty-nine years old when he invented Twitter, and now, at thirty-two, it’s clear he’s helped change the way we communicate.”
The video, which included a walk-along interview with Jack, never mentioned Ev’s, Biz’s, or Noah’s involvement. “Dorsey has become a superstar,” the CBS host said. “He was honored last month at his home town of St. Louis, where he spoke at Webster University, he got the key to the city from the mayor, and threw out the first pitch at the St. Louis Cardinals game.”
When Ev heard about the report, he just shook his head.
Each morning the Twitter employees would come into the office to find more press about Jack—articles, talks, and interviews from all over the planet. From the big, including the Los Angeles Times, New York Times, and Wall Street Journal, to tech-only outlets like GigaOM, TechCrunch, and Mashable, and then the esoteric, like AskMen, Alive magazine, as well as a number of speeches. Later Jack even gave a public talk at a New Jersey elementary school.
As Jack stacked up press like a Hollywood star on a movie junket, people who worked at Twitter were growing increasingly annoyed, and in some instances embarrassed.
The company’s investors had started to become frustrated by the press too. There were a number of meetings held at Twitter’s offices to discuss how to handle the situation. On more than one occasion, Ev debated removing Jack from the board entirely, but he thought the public-relations backlash and resulting tarnish to Jack’s image would do more to damage Twitter than Jack was currently doing.
But it wasn’t just Jack’s press junkets that were gaining the ire of his cofounders and Twitter’s investors. As he continued his development of his new company, Square, he was using his Twitter e-mail address to set up meetings with venture capitalists and the media, often saying he would be happy to discuss Twitter, when he actually intended to present his new company. When investors realized this, it started to get back to Ev, Biz, Fred, Bijan, and others at the company, and there were more meetings to decide what to do.
They were also frustrated that Jack had previously changed his Twitter bio to read “inventor” and “founder” of Twitter.
There had been decisions to fire off warning shots to Jack, telling him to stop pulling a bait and switch with his Twitter e-mail address, but as it continued, senior executives, especially Ev, decided enough was enough.
In an internal meeting, Ev, Dick, Amac (Twitter’s general counsel), Sean Garrett, and others decided it was time to shut down Jack’s Twitter e-mail address.
That afternoon Jack’s phone rang. It was Amac, who explained that they were going to disable Jack’s e-mail address because he was using it for things that could damage the image of the company. He walked Jack through a number of legal and business implications at play. Jack was enraged, calling Biz and others to try to stop the eradication of his e-mail. Then his phone rang again. This time it was Dick, who was not a fan of Jack’s at the time. He explained that Jack going on all of these press tours and using his Twitter e-mail to set up meetings for his new company was becoming detrimental to Twitter’s public image—and, possibly more important, detrimental to another aspect of Twitter that had finally and miraculously improved.
For the first time in the company’s history, a number that had been at zero since day one had started to grow: revenue. In December 2009, Dick had been instrumental in striking a deal with Google and Bing to make the nearly forty million tweets being sent across the site each day viewable on their respective search engines. In exchange Google had agreed to pay $15 million to Twitter. Microsoft would hand over $10 million. Twitter would collect $25 million total.
Jack was furious that his e-mail address was being taken from him and demanded that they reactivate it at once.
It was too late; [email protected] was gone. A bounce-back. And there was nothing Jack could do about it.
“They took my fucking e-mail address away!” he complained to Fenton, then his only ally on the board.
Fenton was furious too. “We’re going to fix this, Jack,” Fenton told him.
Once again, an attempt to mute Jack was about to backfire on Ev. Jack, together with Fenton, started to hatch a plan that would get much more than just Jack’s e-mail address back. One that would see Jack return to Twitter.
Steve Jobs 2.0
To most people it was just like any other tweet sent late in the evening on September 9, 2009: “Listening to the Beatles.”
The next one, in early December, also just flittered by. “Listening to the Beatles and working.” Then three more tweets referencing the English rock band came in January 2010. “Listening to the Beatles and working through my email.” Four during the month of March. “Working in the office and listening to the Beatles.” And so on.
No one noticed them as they bobbed in the Twitter stream, lost amid tens of millions of other updates.
But for Jack, who had sent all of those Beatles-related tweets, they were the very beginning of a thousand-mile journey, a reinv
ention of self and a transformation that would see the man from St. Louis, who just a few years earlier had arrived at Odeo wearing a T-shirt with his phone number across his chest, go through a metamorphosis into a buttoned-up, suit-wearing, perfectionist, design-guru CEO whom everyone believed resembled the greatest businessman in America: Steve Jobs.
Jack had always been an admirer of Jobs, collecting the venerable CEO’s quotes, researching his favorite designers, and trying to understand his business style—just like most young entrepreneurs in Silicon Valley. But unlike (most) other young CEOs, Jack started to take the admiration a step further.
In 2009, as Jack started building Square, he wasn’t just looking at Jobs with admiration; he was emulating him. It started simply enough by letting everyone know he was listening to the Beatles, the Apple chief’s favorite band—Jobs once told 60 Minutes that his “model for business is the Beatles.” But as time went on, Jack started to emulate Jobs’s appearance too. He experimented with Jobs’s round glasses and cloned the mantra of a daily uniform. One day he showed up to the office in blue jeans, a white buttoned-up shirt, and a black blazer. And from that moment on, he rarely wore anything else in public.
Jack began talking about Mahatma Gandhi, the nonviolent leader of Indian nationalism, after he discovered that Jobs had traveled through India for several months in 1974 in search of enlightenment. Jack made a portrait of Gandhi the screen saver on his computer and then tweeted the picture. He also started walking new Square employees along a path through San Francisco that would begin at a statue of Ghandi.
He copied many of Jobs’s decisions. He referred to “rounding the edges” in design meetings, a term Jobs began using in 1981 when he designed the Macintosh operation system. He set up the same weekly schedule for product meetings at Square that Jobs had commanded at Apple. And he started using Jobs quotes in his own speeches.
Then Jack started hiring former Apple employees at Square. But their interviews were different from those of other candidates. “Did you have the opportunity to work with Steve Jobs?” Jack would ask. “Can you tell me a little about his management style?” During discussions with former Apple employees who had been hired at Square, Jack heard that Jobs didn’t consider himself a CEO but rather an “editor.” At some point Jack started referring to himself as “the editor, not just the CEO” of Square. During one talk to employees, he announced: “I’ve often spoken to the editorial nature of what I think my job is. I think I’m just an editor.”
