1 > back at twttr Jack Dorsey's time had finally come. Standing in the cafeteria of Twitter's headquarters on San Francisco's Market Street on June 11, 2015, he watched eagerly as Dick Costolo, a former entrepreneur who had been hired four years earlier to lead Twitter out of turmoil, delivered an unexpected message to hundreds of Twitter's workers during their regular all-hands meeting. Costolo was resigning as CEO. He had been quietly confiding in friends since the start of the year that he had grown anguished with his role at Twitter and was ready to leave. The person to replace him, at least on an interim basis, was the man standing next to him who had helped start it all: @Jack. Dorsey had strategized for years to complete his Steve Jobs character arc. He was unceremoniously fired as Twitter's chief executive in 2008 and had plotted a route back to the top job ever since, allying with board members and engineering a narrative in the media that framed him as the sole visionary behind the social media service. His comeback would be triumphant-the driving creative force behind Twitter's previous successes, back at last-just as it had been when Jobs returned to Apple. To Twitter employees, Dorsey was a man returning from a winter in the wilderness. He stood in front of them with a new executive title and a thick brown beard that descended past the collar of his shirt and framed his lean, angular face and icy eyes. Although he had served as the chairman of the company for years and was renowned as a cofounder, few employees had ever seen him in person. They sized up the former model and meditation enthusiast before them and couldn't help but view him with trepidation as he spoke in his distinctive monotone about changing the company. Twitter needed that change fast, because it was in the dumps. There was little product innovation, no user growth-the key metric by which any meaningful social internet company is judged on-and a snowballing sense that the company couldn't succeed. The history of dysfunction and backstabbing among the company's founders, and the game of musical chairs in leadership, contributed to the feeling that Twitter was going nowhere. Dorsey had instigated some of the early missteps, and chaos was becoming an accepted part of Twitter's culture. With good reason, the workers wondered: Was Jack the solution? Could he turn this company around? Or would he flame out once again? >>> Born in 1976, Dorsey grew up in St. Louis, raised by a liberal mother and a conservative father, alongside two younger brothers. As a teenager, he became interested in the inner workings of dispatch services-an early sign that he would gravitate to building complex systems for transporting information. He attended college in Missouri and New York, but dropped out before finishing his degree. Dorsey moved to the Bay Area in 1999, on the eve of the dot-com bust. - It was a heady time to be in tech. The visionaries and pioneers of the internet and personal computer had governed themselves with an open, collaborative ethos that relied on loose anarchic consensus combined with unfettered technical expertise. That democratic culture appealed to Dorsey, a punk aficionado who once had blue hair. Upon arriving in the Bay Area, he moved into the Sunshine Biscuit Factory, a warehouse buried deep in the gritty eastern side of Oakland known for housing artists and hosting underground music shows. He tinkered with online programs to dispatch taxis, bike messengers, or even first responders. Unlike a lot of the scraggly coders who flocked to Silicon Valley in pursuit of million-dollar paychecks, Dorsey was interested in aesthetics-his own and that of the products around him. He toyed with the idea of abandoning tech altogether in favor of becoming a fashion designer. He liked to change his appearance, piercing his nose or using castile soap to turn his hair into dreadlocks. His shape-shifting presentation and interests would stick throughout his life, leaving some of the people around him wondering if he was just looking for a place to fit in. "I actually got the nose ring because there was just an impulse thing-I thought that might look really cool," Dorsey later said on 60 Minutes . "There was no real statement that I was trying to make." Having taken a few freelance coding gigs around the Bay Area, including one building a dispatch service for the ferries to San Francisco's Alcatraz Island, Dorsey came across Odeo, a podcasting start-up that web entrepreneur Ev Williams was building in San Francisco, in 2005. Williams had made a fortune two years earlier by selling his publishing platform Blogger to Google, and Odeo was his next act. With Blogger, Williams had taken pride in delivering publishing to the masses, allowing anyone to post their own content online with a single click. He eschewed content moderation, viewing it as an impossible task, and let most posts remain on his platform. The twenty-eight-year-old Dorsey sent Williams his résumé and was offered a freelance coding gig at Odeo, where he quickly fell in with the other cyberpunks on staff. But even among that oddball crew, Dorsey stood out. He was exceptionally quiet, preferring online chats to talking in person. He faded into the background when the group worked on projects or went out for drinks. And even though he was working for the renowned Blogger founder, Dorsey did his own journaling on a competing blogging platform, LiveJournal. For the early days of the social web, Dorsey was a prolific poster. And while his personality came out more in his LiveJournal posts, he felt like he needed something more. On both platforms, a user needed so much intention to post-drafting sentences and paragraphs of a blog or uploading and editing images from their digital cameras-before publishing. There needed to be something quicker, more stream-of-consciousness, where someone could post and share effortlessly and instantly without much thought. "Real-time, up-to-date, from the road," Dorsey said. His vision would mimic status updates on AOL's instant messaging service, where users posted notes about what they were up to, what they were thinking about, or cryptic song lyrics that revealed their mood. In July 2000, he had sketched the idea in a legal pad with a blue ballpoint, calling it My.Stat.Us, surrounding the product name with curlicued doodles. In the sketch, Dorsey's status was "reading," but other options included "in bed" and "going to park." At the time, Dorsey frequented South Park in San Francisco, a small oval of green space in the city's South of Market district, nestled among tech offices and apartment buildings. The idea stayed rooted in the back of his mind as Odeo sputtered along. The start-up was struggling to get users, and when Apple added podcasts to iTunes in 2005, Odeo was dead on arrival. Dorsey saw an opportunity and started pitching his status update concept to Williams and other leaders at Odeo. One of them, Noah Glass, thought the pinging of a status update felt like a twitch. He thumbed through tw- words in the dictionary until he landed on twitter, the excited chirp of a bird. Twitter had a breathless, intriguing air about it. The Odeo leaders shortened it to Twttr , in keeping with the trend of vowel-less start-up names that launched in the early 2000s and making it compatible with text message short codes so that its users could send status updates from their cell phones. (The word tweet would come in 2007 from enthusiastic third-party developers who were looking to coin a verb for what they were actually doing when they posted.) In March 2006, an early version of the service was ready to go. "just setting up my twttr," Dorsey wrote. It was the world's first official tweet. The service had plenty of skeptics. But Dorsey led by example, posting short missives about his travels, the champagne he drank, and the meals he ate. His quiet manner inspired loyalty, and he seemed to listen to and trust his coworkers, rather than seeking to overrule them or order them around. "I'm happy this idea has taken root; I hope it thrives," Dorsey wrote later, reflecting on Twitter's beginnings sketched in his notebook. "Some things are worth the wait." Twitter did thrive. In keeping with his terse way of speaking, Twitter users were limited to 140 characters per tweet-a format that also made it possible to send tweets via text message, a necessity in the pre-smartphone era. Dorsey lost the nose ring and was named the company's chief executive, while Williams, who was its largest shareholder after supplying much of the early financing, served as chairman. Williams retained a 70 percent ownership stake and gave 20 percent to Dorsey. They eventually shuttered Odeo and began focusing on Twitter full time, which exploded after being named best start-up at the 2007 South by Southwest conference in Austin, Texas. It grew so fast that it often overworked the infrastructure Dorsey, Williams, and a small team of their former Odeo coworkers had pulled together with the digital equivalent of duct tape and prayers. Outages became a regular occurrence, and during downtime, Twitter users were greeted with an illustration of a whale being airlifted by a flock of birds known as the "fail whale." But most of the time, when it was working as intended, the site was governed by a simple principle: the tweets must flow. Some of them were outright pornographic. Some were threats against other users. Twitter stuck with the philosophy that had worked at Williams's Blogger-there wasn't time for content moderation, and even if there was, no one on the team had the patience to sift through questionable tweets. Dorsey was supportive of this laissez-faire approach but ducked the obligation of conveying Twitter's stance to the public. He left that job to one of his cofounders, Biz Stone, and other early employees who had worked together at Blogger and believed they could replicate its approach. Besides, Dorsey was overwhelmed with the onslaught of responsibilities he faced as a first-time chief executive, floundering as he struggled to manage employees, balance budgets, and oversee Twitter's brittle infrastructure. He was more than willing to let others tackle the thorny issues of content moderation, as he preferred to work on Twitter's interfaces and technology. He liked convincing people that his pet project could transform their conversations-and, eventually, their lives. By 2008, the site's constant outages and mounting expenses were unsustainable. Twitter had more than a million users, but it often crashed when people tried to sign up or publish tweets. The problems needed to be fixed-in fact, fixing them was long overdue-and Dorsey wasn't moving fast enough. In a coup that October, Williams and the Twitter board, which consisted of two venture capital investors, fired Dorsey. He was given a consolation seat on the board but none of the voting rights that normally would have come with it. Williams took over as CEO. With Dorsey on the sidelines, the site he had helped create continued to explode in popularity. In 2009, Iranians flocked to Twitter to protest their country's presidential election, cementing the company's reputation as an online haven for free speech. Twitter became the fastest-growing website that year, skyrocketing from 1.2 million visitors in May 2008 to 18.2 million in May 2009. Williams, Stone, and Twitter's other leaders took a permissive approach, and the service became fundamental in the Arab Spring as protesters across the Middle East used Twitter and Facebook to protest their governments and organize themselves politically, toppling dictatorships across the region. The company occasionally took down illegal content, like child exploitation material. But in most cases, Twitter stuck to its maximalist approach to speech. Executives nicknamed their start-up "the free speech wing of the free speech party," a clear and unapologetic middle finger to anyone who criticized the company for refusing to take down tweets. On the fringes of the company, Dorsey began plotting a comeback. When he wasn't staring frostily at Williams in board meetings, he tinkered with solutions to a problem that small merchants faced when trying to accept credit card payments. Dorsey began work on a digital payments processor, tapping some of his old interests in relaying and dispatching information, and developed an elegant credit card reader, reminiscent of Apple products in its design, that could be plugged into an iPhone's headphone jack. He gave the project a simple name: Square. After its founding in 2009, Square was quickly adopted by small businesses. But despite his success at Square, Dorsey couldn't take his eye off Twitter. He still was bitter toward Williams and dreamed of going back. While he was able to apply his artistry to Square, it didn't hold the cultural sway of Twitter. Its logo wasn't splashed across the chyrons of national news outlets. Presidential candidates, world-famous actors, and Dorsey's favorite musicians didn't rely on Square. And even though creating Twitter had been a group effort, it was his idea, his notebook sketch, his vision. The first step to return to the throne was to get rid of Williams. Dorsey waged a whisper campaign, telling board members and senior Twitter employees that Williams wasn't up to the task of running the company. Indeed, Williams was struggling. "We were just hanging on by our fingernails to a rocket ship," he later said. By 2010, Dorsey's story had taken hold. The board removed Williams as chief executive and replaced him with Dick Costolo. It was payback from Dorsey, who had been ousted by Williams two years earlier. Dorsey eventually succeeded Williams as the board's executive chairman, giving him back some control over the company, while Williams was shunted into a new role overseeing product. From there, it was just a matter of Dorsey getting himself from the boardroom to the corner office. In 2013, the company went public, valued at more than $18 billion. By then, Dorsey's stake had been diluted to less than 5 percent as the company had taken on additional investors over the years. Williams's ownership had been whittled down to 12 percent. Twitter had yet to earn a profit. The company boasted 218 million monthly active users and, in the six months leading up to its 2013 public offering, it had run up a loss of almost $70 million. But Costolo had figured out how to weave some ads into the timeline and analysts thought Twitter showed promise in taking on Facebook. Dorsey, clean-shaven in a crisp white shirt and black suit jacket, beamed as Twitter celebrities including the actor Sir Patrick Stewart rang the bell at the New York Stock Exchange, launching his company onto the public market. Excerpted from Character Limit: How Elon Musk Destroyed Twitter by Kate Conger, Ryan Mac All rights reserved by the original copyright owners. Excerpts are provided for display purposes only and may not be reproduced, reprinted or distributed without the written permission of the publisher.
