Part IThe Story
Gulp
The room was the size of an aircraft hangar, and before the doors opened it was empty. In March 2010, the organizers of South by Southwest in Austin had booked their largest hall for the conference's star speaker, the co-founder and chief executive of the messaging service that had become the defining digital phenomenon of the moment. In a private minute before the crowd arrived, Evan Williams took out his phone, photographed the endless rows of vacant chairs facing the stage, and posted the picture to the service he ran. He added one word.
"Gulp."
What came next has the grim symmetry of a parable. Williams sat onstage and talked about building a twenty-first-century business, about Twitter's founding principle (the Google-like injunction to "be a force for good"), about corporate experimentation. He did not perform. He did not do bits. He talked, carefully and at length, in the voice of a man who has thought about a question longer than the person asking it. One by one, members of the audience began groaning and leaving. The chairs he had photographed empty began to empty again.
"They wanted Ev Williams," a Twitter staffer said later. "They got Ev Williams."
The irony was too large for anyone to miss, and nobody tried. Here was the man who had, more than almost anyone alive, built the machinery by which ordinary people could address the world, and he could not hold a room in Texas. He had co-created Blogger, which turned anyone with a browser into a publisher. He now ran a service with 175 million registered users, up from 503,000 three years earlier and 58 million just the year before; it was adding roughly 370,000 accounts a day. It had been used by protesters in Iran and Moldova, by Oprah Winfrey, by the State Department. The fingers that typed "Gulp" were, his friends noted, almost always in motion: fiddling with a keychain, shredding toothpicks at a bar. Before big public appearances, staff handed him a drink and an espresso to loosen him up.
Seven months after Austin, on October 4, 2010, Williams announced on the company blog, under the hashtag #newtwitterceo, that he was stepping down as chief executive. Dick Costolo, the chief operating officer, would take his place. Williams would focus on product. He was 38.
The press called it a demotion, and the New York Times put the word in a headline. Williams offered something closer to a confession. "I've been studying this stuff for a really long time," he said, "and I've screwed up in many, many, many ways in terms of managing people and product decisions and business."
That sentence is a decent summary of a career that spans four companies and three revolutions in the way human beings put words in public. It is also, strangely, the most confident thing he said that year.
To understand why a man so uneasy in front of crowds would spend his life building tools for addressing them, you have to go back to a field in central Nebraska, a magazine rack in a shopping mall in Grand Island, and a paperback about a seagull.
By the Numbers
The Quiet Man's Megaphones
379Population of Clarks, Nebraska, his hometown
1M+Registered Blogger users when Google bought Pyra Labs in 2003
40404SMS short code chosen for Twitter for 'ease of use and memorability'
110Twitter employees at the end of 2009, despite $150M raised
175MRegistered Twitter users when he stepped down as CEO, October 2010
$2.56BValue of Williams's Twitter stake at the close of IPO day, November 7, 2013
Ninety Miles and an Eternity
Clarks sits on Highway 30, one of the towns that appear every ten miles along it, about a hundred miles west of Omaha. When Williams was growing up there in the 1970s and 1980s it had 379 residents; a later count put the median home value at $34,900. He did not live in town. He lived outside it, on a farm, "90 miles and an eternity" from Lincoln, as he put it, and as a teenager he was responsible for irrigating the field to the west of the house. He and his sister rode modded John Deere bikes. There was a shed with a slanted roof that served as a ramp.
The rest of the picture comes into focus by subtraction. His high school had fewer than sixty students. They were all white. All the boys played football except him. He had the same twelve to fourteen kids in his class from preschool through high school, and together, he later wrote, they "reinforced each other's ideas and assumptions about the outside world (which we had very little experience with)." He did not see the ocean in person until he was 20. He did not leave the United States until he was 29.
His older brother was the counterweight, the figure against whom everything else was measured. "My brother was the consummate Nebraska boy," Williams told the Times in 2010, "the football star who went to the university, was president of his fraternity, hunted with my dad all the time. I just didn't feel at home there."
In junior high, he began dressing strangely, listening to music his friends hadn't heard of, taking up hobbies for the express purpose of being different. An older cousin from Kansas City — "the Big City," Williams called it, with an affection that does not quite hide the awe — noticed his struggle and assured him there was a bigger world out there. The cousin gave him a copy of Jonathan Livingston Seagull, Richard Bach's fable about a gull bored by the conformity of his flock, who pushes himself to learn everything he can about flight and is expelled for it. He keeps flying. He finds a higher plane.
It is worth pausing on the bird. Williams would spend the next three decades among birds of one kind or another — a T-shirt with a bird on it was part of his uniform at Twitter, and the company's logo, a piece of clip art by the British designer Simon Oxley later redrawn into a cartoon called Larry the Bird, would become one of the most recognized marks on earth. But the first bird was a gull who left the flock.
— Evan Williams, to The New York Times, 2010I had a fierce desire to create things, to be independent and prove myself, which caused me to reject authority, but never in a sort of rebellious way. It was more like, 'I'm going to show you by doing it all myself.'
The escape, when it came, came through print. He was indifferent to the books assigned at school ("mostly kind of made up stories that I didn't see the point of"), but the library was different. He checked out a book on juggling, went home, and learned to juggle. "I'm not very good at juggling," he said at the XOXO festival in Portland in 2013, "but it impressed my friends. And I learned it from a book, and I thought, 'Aha, this is power.'" He read a biography of Benjamin Franklin — inventor, publisher, idea man, which is to say a preview. At 15 or 16 he bought a book about making money in real estate, "because that seemed like a reasonable thing to do for a 16-year-old in rural Nebraska with no money," and had what he describes as an epiphany. "I realized I could go buy books and learn something that people had spent years learning about," he told MIT Technology Review. "It was written down in these books, and no one around me was using it."
Then the magazine. Around 1993, at the Conestoga Mall in Grand Island — "where we get our duds" — he stood in front of a rack holding the neon-colored second issue of Wired. Inside was an article about a man named Dave Hughes whose life's mission was to "hook up all 5.5 billion brains on this planet." Williams was not yet a programmer. "I was mesmerized by that," he told a Nebraska audience two decades later. "It blew my mind... this article painted a future that I wanted to be a part of."
In 2022, writing in the Times, Williams described his own mind as a house he has been building for five decades — rooms well lived in and rooms barely touched, dusty programming books on a shelf, an even dustier piano. He began building it, he wrote, in the style his neighbors used. Then he found reading. "I was physically limited," he wrote, "but mentally free."
He would spend his adult life trying to give that particular freedom to everybody else, and then, much later, wondering what everybody else had done with it.
The Van, the CD-ROMs, and the Spam
He moved to Columbus for his senior year of high school, graduated from Columbus High in 1990, and enrolled at the University of Nebraska–Lincoln that fall. He joined the FarmHouse fraternity. He lasted through his sophomore year — a year and a half, more or less — and the university's own student paper later recorded that he put off his self-paced Keller Plan courses until the last minute. "I went because it seemed like something to do at the time," he told students when he came back to campus in April 2009 as Twitter's chief executive. "But I always knew that college wasn't for me."
He went to Florida and did freelance copywriting. His father, Monte, gave him an old van to take with him. Asked about it years later, Monte Williams sounded like every farm father whose son has done something incomprehensible and turned out fine: "I never doubted him. But I'm surprised he got this big this quick."
He came back to Nebraska in 1993 and the following year started his first internet company in Lincoln, financed by his father. It built websites for local businesses and made CD-ROMs about Nebraska football and the internet. It turned out, among other problems, that football fans were not using CD-ROMs. The business failed. He could not repay his father.
There is a relic of this period that Williams has shown on stage, with the evident pleasure of a man who has survived his own youth. In a basement in Lincoln, he and a friend made a VHS tape to teach people how to use the internet, which they agreed was going to be huge and was currently impossible to use. On the tape, a slick-haired young Williams discusses growth figures while his friend intones: "Indeed the internet has finally come of age." They sold the videos "mostly through spam on CompuServe."
"And that's how I started to be an internet entrepreneur," he told 750 people at the Big Omaha conference in May 2014. His first lesson, he said, was to just start. Later in the same talk he added a note of unease that would have been unthinkable in that basement: "I'm less convinced than I was in 1994 that the internet has truly come of age. It's more complicated now."
In 1997 he went west for good, to a marketing job at O'Reilly Media, the technology publisher in Sebastopol, California. Tim O'Reilly remembers a young man who was "just very frustrated, and he had ideas for how we could do things differently and better. He had a little bit of attitude, a chip on his shoulder, but always with good spirit." At O'Reilly he taught himself to code, and began to see the web not as a place to visit but as something you could build on. He left after seven months.
"I was bad at working for people," he said.
It is a striking thing for a person to know about himself at 25. It would take him considerably longer to discover the corollary: that he was also, for a long time, bad at having people work for him.
When It Was Just Me
In January 1999, at the height of the dot-com bubble, Williams started Pyra Labs with Meg Hourihan, his former girlfriend. Paul Bausch, a friend from high school, joined soon after. The company was building web-based project management software, and somewhere in the course of building it, the team started keeping an internal log of their changes. The tool for posting those notes was a feature called Stuff. A few people, Williams among them, had already been writing small scripts so they could publish to their personal weblogs without having to FTP into a server and hand-write HTML each time. The insight was that the side feature — the thing for posting a quick dated note to a web page — was more interesting than the product.
"No one had blogs at this time," Williams recalled in Omaha. "We thought maybe others would want to use that, but the important thing was it just had to work."
Blogger was one of the first web services to automate blog publishing. It made the public web writable by people who did not know what FTP was, and the questions that greeted it — Why would anyone blog? Why would anyone read a stranger's blog? — would be asked again, almost word for word, about his next creation. In a TED talk in 2009, Williams described the lesson he took: "I learned to kind of follow hunches even though you can't necessarily justify them or know where they're going to go." Blogger had been a side project that "took over the company and his life."
Then the bubble burst. By January 2001 Pyra had run out of money. Williams told his five employees, Hourihan and Bausch included, that he could no longer pay them and that he would run the company alone. When he couldn't raise money to buy badly needed servers, Pyra asked its users for help, and they donated more than $10,000 — a modest sum that, in retrospect, looks like a down payment on the whole participatory internet. He kept Blogger alive with what one account calls "life-sustaining deals" and a paid tier, Blogger Pro. In June 2001 it began making money by charging for added features. He hired again. In February 2003, Google bought Pyra Labs for a sum Williams has declined to disclose, though he has said it was less than the $50 million a gossip blog reported. Blogger had more than a million registered users.
It is a heroic story, and it is also, depending on who tells it, a different story entirely.
Several people who had worked at Pyra said they made no money on the Google sale because Williams had never submitted the paperwork needed to allocate their stock options. Williams says that group hadn't been at the company long enough to vest. Hourihan, who did earn millions from the sale, gave the Times a verdict so blunt it reads like a diagnosis written in advance:
— Meg Hourihan, Pyra Labs co-founder, 2010I don't think he took care of the people who got him to where he was. It was bitter, horrible and tough. He's not C.E.O. material. It doesn't play to his strengths. He's a better inventor; he's better at coming up with ideas.
Williams's own reading of the episode is more interesting than a defense. He says all successful businesspeople make enemies. But he also says this: "I was trying to do everything myself when we were going through hard times. When it was just me, I was happier, which I think is a sign of failure of working with people."
When it was just me, I was happier. The sentence carries the whole Clarks childhood inside it — the boy who would show them by doing it all himself, the gull flying alone above the flock. It is also the kind of thing a person can only say after he has stopped being able to live that way.
He went to work at the Googleplex in Mountain View, continued to run Blogger, and met his wife, Sara Morishige, there. MIT Technology Review named him to its list of young innovators for having "fueled the expansion of blogs across the Web," noting that he was "a survivor." He believed blogs would become "an accepted part of the media ecosystem." In October 2004 he left Google, intending to take time off.
He did not take time off.
Fuel Poured on the Floor
His neighbor was a man named Noah Glass, and Glass was working on a podcasting company. Podcasting was the obvious next frontier — if Blogger had made text publishable by anyone, someone would do the same for audio — and Odeo was meant to be that someone: a place to find, record, and share podcasts. It began in November 2004. Williams came in as an adviser.
What happened next he has narrated with unusual candor, most memorably at the Future of Web Apps conference in San Francisco in September 2006, in a talk he billed as "My five best Odeo screw-ups." It had cost about $70,000 to build the first version — Glass and a couple of contract developers. Then came an opportunity to announce Odeo at TED. Williams joined the company full time and put in another $100,000. The TED appearance produced a big New York Times article, which produced more press, which produced more attention. Angel fundraising went well: over a million dollars committed in a month. Then the venture capitalists came calling, including Charles River Ventures, and offered a valuation roughly three times what the angels were paying. Odeo took the VC terms and rolled the angels into the round.
"Think of money like fuel," Williams told the room. You need an engine to put the fuel into. Otherwise "you can pour it on the floor and light a fire and do nothing." Odeo had no proven product and no proven market. It had a fire on the floor.
The other screw-ups on the list read like a negative image of everything Blogger had gotten right. Odeo tried to build too much from the start. It built for people unlike its makers: it turned out that not many people wanted to use a podcast creation tool. It didn't adjust fast enough. And — the fifth — Williams didn't listen to his gut.
The final blow came from Cupertino. When Apple built podcast support into iTunes, the most powerful distribution channel in digital audio became, more or less overnight, somebody else's. Williams has admitted that his own passion for podcasting had waned. The board grew frustrated. There were layoffs. In the middle of all this, Williams did something that in hindsight looks like either desperation or genius and was probably both. He told everyone at Odeo to hatch new ideas.
The previous year, before Odeo's collapse was obvious, he had written a list of ten rules for web startups. Rule one was Be Narrow: "Focus on the smallest possible problem you could solve." Rule nine was Be Agile: "Ebay was going to sell auction software. Initial assumptions are almost always wrong." There was a bonus eleventh rule, which was also the most self-aware: Be Wary. "Overgeneralized lists of business 'rules' are not to be taken too literally."
Odeo had broken most of the ten. It was about to be rescued by the eleventh.
A Short Burst of Inconsequential Information
One of the engineers Williams had hired at Odeo was Jack Dorsey, who had spent years tinkering with an idea about status — the simple, almost embarrassingly small notion of letting people broadcast what they were doing. Odeo was already playing with SMS. One day, sitting on a children's slide in a park and eating Mexican food, Dorsey laid out to colleagues a way to send status updates by text message.
Work began in February 2006. The founders discussed the concept on February 26 and 27. Glass, who would later receive almost none of the credit, came up with the name: twttr, five characters, the length of an American SMS short code, with the vowels dropped Flickr-style because twitter.com was already taken. The developers considered 10958 as the service's short code before switching to 40404, "for ease of use and memorability." Dorsey later explained what the full word meant when they found it in the dictionary: "a short burst of inconsequential information," and "chirps from birds." "And that's exactly what the product was."
On March 21, 2006, at 12:50 p.m. Pacific time, Dorsey sent the first message: "just setting up my twttr."
Dorsey and Biz Stone built the prototype in two weeks. During that stretch, Stone was ripping up the carpet in his Berkeley house when the phone in his pocket vibrated. It was a message from Williams: "Sipping pinot noir after a massage in Napa Valley."
It is hard to imagine a less consequential sentence, or a more consequential one. The carpet, the buzz in the pocket, the wine country indulgence — it is the whole product in miniature, the inconsequential made ambient. Williams would later say the founders compared Twitter to ice cream: not that useful, but "a fun thing for family and friends when they are not in the same place."
The service launched publicly on July 15, 2006. Om Malik wrote what appears to be the first news story about it. On August 3, a mild earthquake — magnitude 4.4 — rolled through California, and users tweeted about it in real time, each from a different vantage, and the team glimpsed something that was not ice cream at all. In September, a planned splashy debut at the Love Parade produced roughly a hundred signups.
Then, in October 2006, Williams made the move that defines him in the eyes of his admirers and his detractors alike. With Stone, Dorsey, and other Odeo staff, he formed a new company, Obvious Corporation, and acquired Odeo — including Odeo.com and Twitter.com — from its investors and shareholders. He dipped into his own funds to cash those investors out. He came away with a controlling stake in what would become Twitter.
He also fired Noah Glass.
Glass said nothing in public about his role in Twitter's founding for nearly five years. When the story finally surfaced in 2011 — The Atlantic ran it under the headline "Twitter's Fifth Beatle Tells His Side of the Story" — Williams responded, characteristically, in under 140 characters: "It's true that @Noah never got enough credit for his early role at Twitter. Also, he came up with the name, which was brilliant."
There is no satisfying way to reconcile those two facts — the buyback that made a fortune and the firing that erased a founder — and the honest thing is not to try. The investors who were cashed out had been sold a podcasting company that was failing; they got their money back. Williams had bet on a side project nobody yet understood. That is one story. Another is that the man who knew best what Twitter might become arranged to own it before anyone else realized it was worth owning. Both stories are about the same afternoon.
In March 2007, at South by Southwest — the same festival where, three years later, the chairs would empty — Twitter found its audience. The company placed two 60-inch plasma screens in the conference hallways streaming nothing but tweets. Daily volume jumped from 20,000 to 60,000. The blogger Scott Beale said Twitter was "absolutely ruling" the conference; danah boyd said it was "owning" it. Twitter won the festival's Web Award, and the acceptance speech was, inevitably, a joke about brevity: "We'd like to thank you in 140 characters or less. And we just did!"
In April 2007, Twitter was spun out as its own company. Dorsey was chief executive. Stone was creative director. Williams was chairman, though he spent his days running Obvious, the incubator, and was not focused on Twitter. In June, Union Square Ventures led a $5 million round that valued the company at $20 million. In August, a user named Chris Messina proposed using the pound sign to group conversations — "how do you feel about using # (pound) for groups. As in #barcamp?" — and the hashtag was born from outside the building. A developer named Blaine Cook suggested "tweet." The @-reply, Williams would later tell a TED audience, "was completely invented by users. We didn't build it into the system until it already became popular, and then we made it easier."
The company's users were writing its spec. It was a lesson he would take seriously, and later, perhaps, too seriously.
The Coup in Plain Sight
Williams joined Twitter full time in the spring of 2008. It did not go well.
He and Dorsey were, the Times reported, "much quieter men whose only bond was their work." Stone, the outgoing showman, was friends with both and socialized with both. Williams and Dorsey were not friends. They were two introverts running the same company, and the company was beginning to break — the site crashed constantly under its own growth, and the whimsical error illustration that appeared during outages, Yiying Lu's drawing of eight orange birds hoisting a whale out of the sea in a net, had acquired a nickname, coined by a web designer named Jen Simmons in September 2007: the fail whale. In 2007 Twitter had about 98 percent uptime, which sounds fine until you realize it means six full days down. The 2008 Macworld keynote brought it to its knees.
That same year, Facebook tried to buy Twitter. Financiers asked Williams whether he wanted to sell. He said he wanted to sleep on it. The next day he sent them a long email explaining why Twitter should stay independent.
"He's got this ability to be patient in this very productive way," said Bijan Sabet of Spark Capital, which had invested in a June 2008 round alongside Jeff Bezos's personal fund. "It was not just this flip e-mail but very thoughtful — what we could accomplish by when, why there's still so much we have left to do. It was pretty inspiring."
By the end of 2008, Williams had made a different kind of argument to the same board. He suggested that Dorsey be pushed out. With the exception of Dorsey, directors agreed unanimously, according to several people involved. Williams had run three companies; they figured he'd do a better job.
The announcement came on October 16, 2008. Williams would become chief executive. Dorsey would become chairman, a move the board made deliberately to keep close a founder who still held a large stake and had conceived the idea. Fred Wilson of Union Square Ventures gave the official rationale: "We all think Ev is a better fit to lead the company from a product perspective, an operations perspective, and a business standpoint." Stone put it more simply: "We had two very strong leaders here and we really needed to choose one." Williams's blog post praised Dorsey for taking Twitter "through an order of magnitude of growth and two major rounds of financing, while safely navigating some very rocky waters." On his personal Twitter stream, he wrote two words.
"Big day."
The change shocked employees. People close to Dorsey say he felt betrayed. "There was a feeling that Ev wanted to take control after he realized the potential importance of Twitter," an employee who lived through it told the Times. Williams's own account of the arrangement, two years later, was strikingly unguarded: "It's hard and confusing. I think there's few cases in history where the C.E.O. steps down and is also the founder and reports to someone and that works."
He was describing Dorsey's situation. He could not have known he was also describing, with some precision, his own future.
The particular economy of Williams's language is worth noticing across these episodes. "Gulp." "Big day." The tweet about Glass. A man who has made a career of short-form publishing tends, at moments of maximum consequence, to say almost nothing. Philip Kaplan, a close friend, described the pattern in social settings: "Often there will be a room with five people having a conversation and he says the least, but when he does talk, everyone listens intently, and it's a gem." The anonymous chief executive of a Silicon Valley social company described the same quality from the other side of a negotiating table: "Ev is very difficult to work with because he has a tough time making a final decision on products."
Patience and paralysis are, it turns out, the same trait viewed from different chairs.
Hanging On by Our Fingernails
In 2009, Twitter went from 5 million registered users to 71.3 million. Nothing in Williams's life — not Blogger's million users, not Odeo's money — had prepared him for this.
In February, Benchmark Capital and Institutional Venture Partners led a $35 million round. On April 17, Williams sat beside Ashton Kutcher on The Oprah Winfrey Show to explain Twitter to Oprah's audience; Kutcher had just become the first user with a million followers. A week earlier, on April 10, Williams had gone home to the University of Nebraska–Lincoln, where, as chief executive of the third-most-popular social media application in the world, he answered questions from about 250 students and told them about his "hallucinogenic optimism." That morning he had tweeted that he'd met his wife five years earlier to the day. Asked whom he liked to follow, he named three accounts: Biz, his wife, and P. Diddy. On April 30, he and Stone were named to the TIME 100. Twitter won the Webby for Breakout of the Year.
In June, during the protests over Iran's disputed election, Twitter had scheduled maintenance for what were off-peak hours in California and peak hours in Tehran. A State Department official emailed. The company pushed the downtime back a day. Newspapers speculated that Washington had leaned on a startup. In August, on the BBC's Newsnight, Kirsty Wark asked Williams directly whether he had acted on the government's request. "There were many people asked us to do that, including someone from the state department, but that's not why we did it," he said. "We did it because we thought it was the best thing for supporting the information flow there at a crucial time, and that's kind of what we're about."
The Newsnight interview, billed as his first British television appearance, became something of a cult object — the Guardian transcribed it under the headline "Read it and weep" — mostly for what Wark chose to ask. She asked about Demi Moore. She asked whether Twitter created "a false sense of self." She asked about an archbishop who feared it dehumanized social life. ("I think it's kind of silly.") She asked how Twitter verified that the real Demi Moore was the real Demi Moore, and Williams explained the new verified-account badge, and then gave an answer that captures the absurd, hand-built scale of the company in mid-2009 better than any statistic:
"In Demi's case, I've actually talked to her personally."
She asked if Twitter might be a fad. "The only reason Twitter itself would be a fad," he said, "is if someone comes along and does it better."
Behind the cameras, the company was barely holding together. It fielded dozens of calls a week from corporations, celebrities, and politicians — CNN, Oprah's producers, the State Department. Its first office was classic startup: a keg in the kitchen, a pair of big green concrete deer, a communal table where employees ate take-out burritos. Big-name chief executives sat on frumpy couches because there was no proper conference room. A video crew once walked through the unlocked front door without permission and began filming employees.
— Evan Williams, on Twitter in 2009We were just hanging on by our fingernails to a rocket ship.
What the company needed was simple: people to do the work. It had raised $150 million in venture capital by the end of 2009. It had 110 employees. "The mistake I made was definitely underhiring, both in quantity and in experience, in several areas, for a long time," Williams said later. He attributed it to the daily distractions of running the place and to not anticipating how big it would become. The man who had once preferred running Blogger alone had built a rocket ship and staffed it like a canoe.
He was, at the same time, rethinking what the rocket was. The founders had talked about Twitter for years with a kind of awe, "as if it had a life of its own and they were mere bystanders," freely admitting they didn't know how people would use it or how it would make money. Around 2009, Williams later said, "we made the distinction internally and in the way we started talking about that — rather than a social network, it was a real-time information network." In a 2013 interview he put it more fully: "It didn't replace anything. There was this path of discovery with something like that, where over time you figure out what it is." The ice cream was gone. In its place was infrastructure.
Researchers that August categorized a sample of 2,000 tweets and found 40 percent of them to be "pointless babble." danah boyd replied that the babble was better understood as "social grooming" and "peripheral awareness" — the human need to know what the people around you are thinking even when you can't be near them. Both readings were right, which was the strange genius of the thing. Williams had built a system in which the pinot noir and the protest ran through the same pipe.
On April 13, 2010, Twitter announced Promoted Tweets — "ordinary tweets that businesses and individuals want to highlight to a wider group of users." The company now sold ads to Starbucks, Ford, and Microsoft. Costolo, then chief operating officer, spearheaded all of it.
Williams turned his own attention to something stranger: the problem of scale itself. Twitter's executives became preoccupied with the "Dunbar number," the roughly 150 relationships a single person can maintain. "I've never seen a company so focused on avoiding the Dunbar number," said Adam Bain, who had just arrived from News Corporation as head of global revenue. "You can tell Ev planned it out." Each time employees logged into their computers, they were shown a photograph of a colleague, with clues and a list of hobbies, and had to identify the person. Notes from every meeting were posted for everyone to read. The company that was building the world's largest machine for glancing interactions was engineering its own employees, login by login, into intimacy.
He told a group of new hires in the spring of 2010 that Twitter had three goals: to change the world, to build a business, and to have fun. "You can succeed by only building a business, and many companies do," he said. "We won't consider it success unless it's all three."
He still described the company, that fall, as "a 6-foot-tall sixth grader — there's a lack of maturity, despite size and the perception of outsiders."
The Man Who Demoted Himself
The decision to step down came after Williams spent months conceiving and working on "New Twitter," the redesign rolled out in September and October 2010, which let users see photos and videos without leaving the site. He had spent the summer doing what he was good at. It clarified, apparently, what he was not good at.
Dick Costolo was, in temperament, Williams's opposite: wiry, restless, a former improv comic who had run companies three times and sold the last one, FeedBurner, to Google in 2007. The Times called him "all about the details of making money and getting things done." Williams, characteristically, gave the cleanest description of the arrangement himself:
"Dick is hard-charging and very focused on urgency and executing now, and I tend to be very contemplative. My weakness is probably taking too long to make a decision, and his is being too hasty."
Steve Blank, who teaches entrepreneurship at Stanford, read the move generously: Williams was "the type of entrepreneur who knows when to pivot," and this might be "wonderful signs of entrepreneurial wisdom." Read against the Pyra story, it looks like something more personal — the moment the man who once said when it was just me, I was happier chose, on purpose, not to be the one in charge. "The thing I've learned that's much different than any other time in my life," he said, "is I have a team that is really, really great." Meg Hourihan had said in effect the same thing eight years earlier as an accusation: he's a better inventor than chief executive. Now he was saying it about himself, as a strategy.
It did not stay as tidy as the announcement. By the time Costolo took over, the office had locked doors, a receptionist in a sunlit lobby — where the green concrete deer now stood, promoted along with everyone else — a chef cooking for 300 employees, sixty percent of them engineers. A whiteboard near the executives' desks bore headings like "commit," "invest," and "leverage." While Williams was away, the Times reported, "Mr. Dorsey and Mr. Costolo forged a close relationship." In March 2011, Dorsey returned to Twitter as executive chairman focused on product. Within weeks Williams confirmed he was no longer involved in day-to-day operations. He remained on the board.
There is an obvious symmetry here, and nobody involved has ever pretended otherwise: the founder Williams had moved aside in 2008 came back and took the product role Williams had kept for himself in 2010. In 2009 Williams had said that the founder-who-steps-down-and-reports-to-someone arrangement rarely works. He had now demonstrated it twice, once from each side.
Twitter went public on the New York Stock Exchange on November 7, 2013. Seventy million shares were priced at $26 the night before by Goldman Sachs; they closed the first day at $44.90, valuing the company at roughly $31 billion. Williams, still the largest individual shareholder, saw his stake valued at about $2.56 billion. Dorsey's was worth about $1.05 billion. The farm boy who couldn't repay his father for the CD-ROM company was, by the arithmetic of a single trading day, a billionaire.
He did not stay quiet about the company he had left. In December 2014, when Instagram announced 300 million monthly users and commentators rushed to declare Twitter beaten, he gave Fortune the most quoted sentence of his public life: "If you think about the impact Twitter has on the world versus Instagram, it's pretty significant... important stuff breaks on Twitter and world leaders have conversations on Twitter. If that's happening, I frankly don't give a shit if Instagram has more people looking at pretty pictures." Two months later, at the Code/Media conference: "Wall Street does not have a sophisticated understanding of what creates value in this world."
When Costolo stepped down in 2015, Williams helped search for a successor and offered, unprompted, to get out of the way. "I will say personally if the right C.E.O. would prefer one less C.E.O. on the board I'd be happy to — it's more important that we get that person than I'm on the board." Asked whether Twitter should stay independent, he declined to give a real answer, and said so with a candor that most board members would never risk in public: "There is incredible potential in Twitter and blah blah blah… the board will do what it's supposed to do."
Dorsey came back as chief executive. Williams left the board in 2019.
The Internet Is Broken
He could not stay away from the text box.
"It was one of those things that I couldn't stop myself from doing," he told John Battelle. "I left Twitter about five years ago. I was immediately thinking about this area — it's all I think about — publishing platforms, the future of media and the web. I didn't necessarily want to get into that again." Looking at the state of blogging software after Twitter, he found it barely changed. "It feels like these blogging tools haven't really evolved in a decade," he told David Carr. "When I looked at that, I thought, 'Do I really want to get into this again? Am I just stuck in a rut?'"
In 2012, with Biz Stone among the founders, he launched Medium, which he introduced as "a beautiful space for reading and writing — and little else. The words are central." The Atlantic summarized his career in a line he liked enough to repeat: "Ev makes text boxes that we pour our souls into." Medium had no comment section. Readers could leave notes pinned to particular words. Posts carried an estimate of how many minutes they would take to read. It commissioned some professional work — Walter Isaacson, Emily Gould, Ben Smith, even Elon Musk published there — but by 2014, more than 95 percent of its 1,000 to 1,200 daily posts came from nonprofessionals. It had 13 million monthly visitors and, for a while, nobody quite agreed on what it was: platform, publisher, "platisher." Williams himself insisted it was a platform and worried that its professional content "may have set the bar too high." The Twitter lesson about networks was baked in: "your posts link to each other, your ideas bump into each other, and instead of living on an island somewhere out on the web, you're part of a dynamic whole."
The texture of his thinking was changing. In a long conversation with Om Malik at the end of 2010, Williams had already been worried about "the web of infinite information" and had said something that, read now, sounds like a wish made against the grain of his own invention: "I want Twitter to be an antidote to infinite information, not a cause of it." At XOXO in 2013, he gave his theory of the whole medium. "The internet is a giant machine designed to give people what they want," he said. It was "an engine of convenience." He had looked up the Latin root of convenience and learned that it meant assembling and agreeing. "Isn't that what the people who created the internet did?" Convenience was only bad, he said, if we focused "on the clicks and the connections and the retweets and the likes for the sake of more and more connections."
By 2017, the tone had curdled into something close to grief. "I think the internet is broken," he told the Times that May, and it was "a lot more obvious to a lot of people that it's broken." He offered an image so plain it lands like a slap. You're driving and you see a car crash, and of course you look; everyone looks. "The internet interprets behavior like this to mean everyone is asking for car crashes, so it tries to supply them." His goal with Medium was to break the pattern: "If I learn that every time I drive down this road I'm going to see more and more car crashes, I'm going to take a different road." In January of that year, he had abruptly pivoted the company away from advertising and laid off about a third of its staff — roughly 45 people.
— Evan Williams, to The New York Times, 2017I thought once everybody could speak freely and exchange information and ideas, the world is automatically going to be a better place. I was wrong about that.
It is an unusual thing for a founder to say, and an even more unusual thing for this founder to say. The boy who discovered that books were "power," who read an article about connecting 5.5 billion brains and felt his mind blown, had spent his life acting on a single premise — that lowering the barrier to speech would make people smarter. "I got excited about the internet in the first place because I thought it was going to make us smarter," he told Battelle. "It's questionable whether or not that's the case." You can trace the arc of his thinking in his own words across two decades: the Lincoln basement in 1994 (the internet has finally come of age), Big Omaha in 2014 (I'm less convinced), the Times in 2017 (I was wrong).
Twitter, meanwhile, went on without him, and then went somewhere else entirely. On April 25, 2022, its board accepted Elon Musk's $44 billion offer. At a Fortune dinner in San Francisco two days later, Williams, by then without formal ties to the company beyond his shares, called Musk "clearly a genius who thinks on another level," and then made the more interesting observation: "I think what we're also seeing is people project either their hopes and dreams or their worst nightmares." He declined to pretend he knew how speech should be policed — "I don't know what should be censored or moderated on a daily basis" — and offered a farmer's metaphor instead: let people choose between pools with rules against public urination and pools without. "Choose your pool." He called the clamor over an edit button "overblown." He later told an interviewer the purchase had made him sad. "He's brilliant," he said. "But no one's brilliant on everything."
The deal closed on October 27, 2022. Musk fired the chief executive, the chief financial officer, and the top lawyers that day, dissolved the board, and laid off roughly half the 7,500-person workforce within the week. On July 23, 2023, Twitter became X. The bird — Larry, redrawn in 2012 by Douglas Bowman to resemble a mountain bluebird — was retired, replaced by a double-struck capital letter. A Times columnist said the brand value had been "wiped out." In March 2025, Musk's AI company acquired X; in February 2026, SpaceX acquired the AI company. A startup called Operation Bluebird petitioned to claim the abandoned Twitter name, and X sued to stop it. Twitter never left, the company insisted, in a legal filing about a word that the company itself no longer used.
Williams had moved on to other things: Obvious Ventures, an investment firm for what he calls "world-positive" companies; and, most recently, Mozi, a social network whose stated purpose is to help people meet in person the people they care about — a tool for being somewhere physically rather than everywhere at once. "You can set a goal to run a marathon," he told Tim Ferriss in 2025. "You can't do that to invent the computer or Twitter or create amazing art. You can't plot it." He has two sons. He lives mostly in the Bay Area.
At Big Omaha in 2014, before he got to any of the hard parts, Williams put a satellite photograph of his family's farm on the screen behind him. Seven hundred and fifty people looked up at it. He pointed to one rectangle of land, a field to the west of the house, flat and green and squared off by the geometry of center-pivot agriculture, and explained that when he was a teenager it had been his job to water it.
Part IIThe Playbook
What follows is less a formula than a set of recurring moves — some of them deliberate, some of them discovered after the fact, several of them learned at real cost to Williams or to people around him. Williams himself would warn against taking any of it too literally; his own list of startup rules ended with the instruction to be wary of startup rules. The principles below are drawn from the record of four companies — Pyra and Blogger, Odeo, Twitter, Medium — and from the unusually candid way Williams has narrated his own mistakes.
The principles
- 1.Watch the side project, not the roadmap.
- 2.Buy the asset nobody else values yet.
- 3.Don't pour fuel without an engine.
- 4.Rename the category before the market names it for you.
- 5.Let users write the spec, then pave the path.
- 6.Remove steps from an ancient desire.
- 7.Sleep on the acquisition offer.
- 8.Treat underhiring as a decision, because it is one.
- 9.Engineer intimacy against your own scale.
- 10.Demote yourself before the board does.
- 11.Pick your metric, and defend it profanely.
- 12.Audit your founding optimism in public.
E
Four Companies, One Pattern
Each venture began as one thing and became another; the outcomes varied sharply.
| Company | Original plan | What it became | Outcome |
|---|---|---|---|
| Pyra Labs (1999) | Project management software | Blogger, from an internal note-posting feature | Sold to Google, 2003 |
| Odeo (2004) | Podcast discovery and creation | A shell that incubated Twitter | Failed; bought back by founders |
| Twitter (2006) | SMS status updates to friends | A real-time information network | IPO 2013; sold for $44B, 2022 |
| Medium (2012) | "A beautiful space for reading and writing" | A network for ideas, repeatedly re-pivoted | Survived; one-third laid off, 2017 |
Principle 1
Watch the side project, not the roadmap
Twice in Williams's career, the most important product his company built was not the one on the plan. At Pyra, the team was building project management software when an internal tool for posting dated notes turned into Blogger. At Odeo, a podcasting company facing Apple's arrival in its market, an engineer's long-running fascination with status messages turned into Twitter. In both cases, the main product was failing or about to, and the side project was what the builders themselves kept using.
Williams has framed this as instinct — "I learned to kind of follow hunches even though you can't necessarily justify them" — but the pattern is more specific than a hunch. In each case the side project was small, cheap, and built by the team for the team. The Twitter prototype took two weeks. It was first used as an internal tool among Odeo employees. The signal was not market research; it was the fact that Williams was texting Biz Stone about pinot noir in Napa and Stone, mid-renovation, was reading it.
The corollary matters as much: Williams told Odeo staff to hatch new ideas before the company's failure was final. He created the conditions for the side project rather than waiting for one to appear.
Tactic: When your core product stalls, list the internal tools your own team uses voluntarily every day — one of them may be the company.
Principle 2
Buy the asset nobody else values yet
In October 2006, Williams formed Obvious Corporation and used his own money to cash out Odeo's investors, acquiring Odeo and Twitter.com in the process and emerging with a controlling stake in what became one of the most valuable consumer internet companies of its era. At the time, Twitter was a side project with negligible traction; its launch at the Love Parade a month earlier had produced about a hundred signups. The investors were being handed an exit from a failing podcasting company. Few people, possibly including Williams, could have priced what was inside.
This is the move that made him a billionaire, and it should be studied with clear eyes. It worked because Williams had information — daily use, internal enthusiasm, his own instinct — that outside shareholders did not weight. It also coincided with the firing of Noah Glass, who named the product and was silent about his role for nearly five years. Williams's 2011 acknowledgment that Glass "never got enough credit" is the coda that makes the lesson complete: concentrated conviction can be an asset, but the people you leave out of the cap table become part of the story whether you tell it or not.
Tactic: When you buy back an asset from discouraged investors, document the terms transparently and settle credit and equity for every early contributor before the asset becomes valuable.
Principle 3
Don't pour fuel without an engine
Odeo's first version cost about $70,000. A TED announcement led to a New York Times story, which led to over a million dollars of angel commitments in a month, which led to venture capitalists offering roughly three times the angel valuation. Odeo took the higher price. Williams's later post-mortem is one of the clearest statements of the premature-scaling problem on record: money is fuel, and "you can pour it on the floor and light a fire and do nothing." Odeo had neither a proven product nor a proven market. "The best scenario," he concluded, "is probably to have the fuel waiting around until you are ready to burn the fuel."
Notice the contrast with Blogger, which survived the dot-com crash on about $10,000 in user donations and a paid tier, and with his 2005 rule Be Greedy: charge within six months, because "the give-everything-away-and-make-it-up-on-volume strategy stamps an expiration date on your company's ass." The scarcity at Pyra forced focus. The abundance at Odeo encouraged the team "to build too much stuff from the get-go."
Tactic: Before accepting a higher valuation, write down the specific, already-working mechanism the new money will accelerate; if you can't name it, raise less.
Principle 4
Rename the category before the market names it for you
For its first years, Twitter was described as a social network, as microblogging, as status updates, and — by its own founders — as ice cream: "not that useful, but a fun thing for family and friends." Around 2009, Williams and the team made an internal decision to describe it differently: "rather than a social network, it was a real-time information network." That reframing was not cosmetic. It changed how Twitter was marketed in new countries ("marketing Twitter as an information network, not a social one, from the get-go," as Costolo put it in 2010), justified building trending topics and search, and gave Williams the frame for defending Twitter later: "important stuff breaks on Twitter and world leaders have conversations on Twitter."
The power of this move is that it lets a company stop losing comparisons it was never meant to win. Measured as a social network, Twitter was smaller than Facebook. Measured as an information network, it was the place news broke.
Tactic: Write one sentence describing what your product actually does in the world today, ignoring what you originally called it, and test whether your strategy and metrics follow from that sentence.
Principle 5
Let users write the spec, then pave the path
Some of Twitter's most defining features came from outside the building. The @username reply, Williams told a TED audience, "was completely invented by users. We didn't build it into the system until it already became popular, and then we made it easier." The hashtag came from Chris Messina's August 2007 suggestion. The word "tweet" emerged as Iconfactory's developers searched for a verb and Twitter's Blaine Cook proposed it. Third-party developers built the first mobile clients and the first URL shortener on top of a public API released in September 2006. By March 2010 there were more than 70,000 registered applications.
The discipline here is in sequence: watch behavior, wait for it to become popular, then formalize it. It is the user-centered approach Williams preached in 2005 — "User experience is everything... Obsess over it" — applied not to design but to the product's grammar. The cautionary half of this lesson came later: between 2010 and 2012, Twitter made a series of developer-hostile moves, including launching its own URL shortener in competition with partners, that cost it the trust of the community that had invented much of it.
Tactic: Keep a running log of user workarounds and invented conventions, and promote the most widespread ones into official features rather than replacing them with your own.
Principle 6
Remove steps from an ancient desire
Williams's mature theory of the internet, stated at XOXO in 2013, is disarmingly simple: "The internet is a giant machine designed to give people what they want." People do not want new things; they want to do the things they have always done — learn, connect, tell stories — with fewer steps. Blogger removed FTP and hand-coded HTML from publishing. Twitter removed composition itself, shrinking the unit of expression to whatever fit in an SMS. Medium removed formatting choices; its most important feature, one critic wrote, "may be all the stuff it leaves out."
The 140-character limit belongs here. It was not an aesthetic choice but an inheritance from SMS that turned out to be a feature: the constraint lowered the cost of posting so far that the inconsequential became publishable. Williams defended it hard; in 2009 he said Twitter would not let people go beyond 140 characters. (Twitter doubled the limit in 2017, after his tenure.)
Tactic: Map every step a user takes to do the core thing your product enables, then cut the step that requires the most thought — not the most clicks.
Principle 7
Sleep on the acquisition offer
In 2008, Facebook tried to buy Twitter. Asked whether he wanted to sell, Williams said he wanted to sleep on it, and the next day sent a long email explaining why Twitter should stay independent — "what we could accomplish by when, why there's still so much we have left to do," as board member Bijan Sabet recalled. Sabet called it "patient in this very productive way."
The value of the overnight pause is not just emotional distance. It forces a founder to translate a gut reaction into an argument that a board can evaluate. Williams's 2005 rule Be Picky made the same point at smaller scale: "You can almost always afford to wait if something doesn't feel just right, and false negatives are usually better than false positives." The risk, which critics have also documented, is that this deliberateness becomes a general slowness on product decisions. The trait that saves you in an acquisition negotiation can strangle you in a product review.
Tactic: Never answer an acquisition approach the same day; respond in writing the next day with a dated case for what independence achieves and by when.
Principle 8
Treat underhiring as a decision, because it is one
By the end of 2009 Twitter had raised $150 million and had 110 employees, while registered users had grown from 5 million to 71.3 million in a single year. The site crashed often enough that its error illustration became a cultural joke. Williams later named this directly: "The mistake I made was definitely underhiring, both in quantity and in experience, in several areas, for a long time." The company eventually hired a recruiter and people to run human resources, payroll, and brand consistency — "mundane but important big-company tasks."
The deeper lesson is about how founders misread inaction. Not hiring feels like prudence, especially to someone who once ran a company alone and liked it. But leaving key seats empty during hypergrowth is an active choice with compounding costs — downtime, lost partnerships, exhausted staff — and it was made by default rather than design.
Tactic: During any quarter where usage grows faster than headcount, review open roles weekly and require an explicit decision to leave each one unfilled.
Principle 9
Engineer intimacy against your own scale
At Twitter in 2010, Williams built small rituals designed to keep a growing company human. Each login showed employees a photo of a colleague along with clues and hobbies, and asked them to identify the person. Notes from every meeting were posted company-wide. Executives talked openly about the Dunbar number. "I've never seen a company so focused on avoiding the Dunbar number," said Adam Bain. "You can tell Ev planned it out."
The irony was not lost on observers: the company whose product encouraged "a multitude of ever-growing — and largely glancing — interactions" was fighting glancing interactions inside its own walls. But the move fits Williams's other stated values — he said he started companies "because he didn't believe in aligning himself with institutions" — and his three-part definition of success: change the world, build a business, have fun. The last of the three is the easiest to lose as headcount grows, and he built mechanisms to defend it rather than relying on culture to persist on its own.
Tactic: Before your company passes 150 people, install at least two lightweight, recurring mechanisms that force employees to know names and read each other's decisions.
Principle 10
Demote yourself before the board does
Williams's October 2010 decision to hand the chief executive job to Dick Costolo was unusual less for its outcome than for its framing. He presented it as a division of labor matched to temperament: "My weakness is probably taking too long to make a decision, and his is being too hasty." He would focus on product strategy; Costolo would run the business. Steve Blank called it "entrepreneurial wisdom."
It is also the lesson Williams learned twice from both sides. In 2008 he pushed Jack Dorsey from chief executive to chairman and said such arrangements rarely work. In 2011, after Dorsey returned as executive chairman focused on product, Williams himself left day-to-day operations. The timeline below shows how quickly founder roles rotated, and how the "step back but stay involved" position proved unstable each time.
T
Musical Chairs at the Top
Twitter's founders traded roles repeatedly in its first five years.
2007
Twitter spins out. Dorsey is CEO, Stone creative director, Williams chairman (while running Obvious).
2008
Williams joins full time in spring; in October the board moves Dorsey to chairman and names Williams CEO.
2010
Williams announces on October 4 that COO Dick Costolo will become CEO; Williams turns to product strategy.
2011
Dorsey returns in March as executive chairman focused on product; Williams leaves day-to-day operations.
2015
Costolo steps down; Dorsey returns as CEO. Williams offers to leave the board if the next CEO prefers.
2019
Williams leaves the board, retaining only a shareholding.
The takeaway is not that self-demotion is noble but that clarity is. Williams was right about his weaknesses; what proved hard was the ambiguous middle role that followed.
Tactic: If you step aside as CEO, define in writing which decisions you own, which you merely advise on, and the date you will reassess — ambiguity in the founder's new role is the usual point of failure.
Principle 11
Pick your metric, and defend it profanely
When Instagram passed Twitter in monthly users in 2014, Williams refused the comparison. Monthly active users, he argued, had "become so abstract to be meaningless," and he noted that some competitors' definitions counted people who never opened the app. The measure that mattered was impact: "important stuff breaks on Twitter." And then, bluntly: "I frankly don't give a shit if Instagram has more people looking at pretty pictures." At Medium he pushed the same logic into business models, experimenting with ads sold on time spent reading rather than clicks.
There is a fair critique here, which Fortune made at the time: Twitter's own executives had told investors to focus on users during the IPO roadshow. Rejecting a metric after you've sold on it is harder than choosing the right one at the start. But the instinct is sound. A company that accepts its competitor's scoreboard will optimize for the competitor's game.
M
Conventional Wisdom vs. Williams
Where his stated approach diverged from standard startup practice.
| Conventional wisdom | Williams's approach |
|---|---|
| Take the highest valuation offered. | Raise only when there's an engine to burn the fuel. |
| Grow monthly active users above all. | Measure impact and depth; reject borrowed scoreboards. |
| Founders should stay CEO. | Match the role to temperament, including your own demotion. |
| Define the product and defend the definition. | Let usage reveal what it is, then rename it. |
| Optimize for engagement. | "We're not looking for addiction." |
Tactic: Write down the single metric that best captures the value your product creates in the world, and publish it internally before investors or competitors choose one for you.
Principle 12
Audit your founding optimism in public
Williams's career rests on a premise he absorbed as a teenager in Nebraska: that making it easier to share information makes people better off. "Seems like when you give people easier ways to share information, more good things happen," he said at TED in 2009. By 2017, he had reversed himself in print: "I thought once everybody could speak freely and exchange information and ideas, the world is automatically going to be a better place. I was wrong about that." He did not stop at the confession. He described the mechanism — the internet "interprets" our rubbernecking at car crashes as demand and supplies more of them — and built Medium around trying to break it, including pivoting away from advertising in 2017 at the cost of a third of his staff.
Founders rarely revise their foundational beliefs on the record, because those beliefs are the story they raise money on. Williams's willingness to do so is what separates his later work from nostalgia. Mozi, his newest company, is an attempt to use the network to get people into the same room rather than to keep them in the feed — a design choice that only makes sense if you have actually updated your view.
Tactic: Once a year, write down the core belief your company was founded on, list the evidence for and against it, and change one product decision based on what you find.
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Part IIIQuotes and Maxims
In their words
— Evan Williams, to Om Malik, December 2010I want Twitter to be an antidote to infinite information, not a cause of it.
— Evan Williams, TechCrunch Foundation interview, 2013Any big idea is going to take a while to get there. By definition, if it's big, and no one has done it before, it's not going to be 1-2-3, 'We got it!' There is going to be a dark period in there, because you don't know what the key to getting there is.
— Evan Williams, BBC Newsnight, August 2009The only reason Twitter itself would be a fad is if someone comes along and does it better.
— Evan Williams, The Tim Ferriss Show, 2025You can set a goal to run a marathon, and you can download a training regime, and you can go run the marathon. You can't do that to invent the computer or Twitter or create amazing art. You can't plot it. And to the extent you try to plot it, you shoot yourself in the foot because you cut off the possibilities that lie before you.
— Evan Williams, The New York Times, 2022I was physically limited, but mentally free.
For readers who want the founding-era story told at greater length, the young-adult biography Evan Williams, Biz Stone, Jack Dorsey, and Twitter covers the Odeo-to-Twitter years, and Evan Williams on the Future of News collects his thinking on the media problem he spent the Medium years trying to solve.
Maxims
- Watch what your team uses for free. The side project your builders can't stop using is a better signal than any roadmap.
- Money is fuel, not engine. Raising more than your working mechanism can burn just lights a fire on the floor.
- Narrow beats broad. The specialist will almost always beat the generalist, and small problems turn out bigger than they look up close.
- Let the product tell you what it is. Twitter began as ice cream and became infrastructure; the name followed the usage.
- Pave the paths users wear. The @reply and the hashtag were invented outside the building; the job was to make them easier.
- Remove a step from an old desire. People want to do what they've always done, with less friction and less thinking.
- Sleep on the big offer. An overnight pause turns a gut reaction into an argument a board can weigh.
- Not hiring is still a choice. Empty seats during hypergrowth compound into outages and burnout.
- Know which chair you belong in. Demoting yourself on purpose beats being moved by people who see your weaknesses first.
- Revise the founding belief out loud. If the premise you built on turns out to be wrong, say so and build differently.
