When he was 16, Evan Williams loved reading business books. The first one he read was about real estate, and at the time, he lived in Clarks, a town in central Nebraska that today has a population of 379 and a median home value of $34,900. Williams wasn’t particularly interested in investing in property in Clarks or anywhere else, but he reveled in the fact that it was so easy to learn about building businesses and making money. “I realized I could go buy books and learn something that people had spent years learning about,” he recalls. “I was very intrigued with the idea that there’s all this stuff out there to know that you could use to your advantage. It was written down in these books, and no one around me was using it.”

Today, Williams is half a continent away from Clarks, in San Francisco; no longer just reading about business, he’s the founder of Obvious, the Web-product development company that owns the popular microblogging service ­Twitter. At 35, without a college degree, he has become a bootstrapping, improvisational businessman whose decisions are influenced by what he describes as “hallucinogenic optimism.”

Williams became mildly famous in Silicon Valley during the first dot-com boom, after he cofounded Blogger in 1999. Blogger made it very easy for people to publish their thoughts on the Web in personal weblogs, as blogs were known at the time. In 2003, Google acquired Blogger for a sum the entrepreneur declines to disclose (although he says it was less than the $50 million that Valleywag, a ­Sili­con Valley gossip blog, has reported). It was, in any case, a significant amount: Williams worked at the Googleplex in Mountain View for a little more than a year before he left with the cash to conjure more winning ideas.

At first, he struggled to find something that would fully engage his energies. But Twitter seems to be it. The idea behind the service is simple: people compose 140-­character updates about themselves, ostensibly answering the question “What are you doing?” Users can post their updates by text-­messaging from cell phones, by logging on to the ­Twitter website, or by using desktop software such as instant-­messaging tools. Messages (also known as ­twitters, twits, and tweets) can be private, sent only to friends or groups of friends, or they can appear on Twitter’s home page for all to see. ­Twitter has been so successful that last April, ­Williams spun it out into its own company.

Resources:
www.blogger.com
www.twitter.com
www.twittervision.com

Twitter’s headquarters is in South Park, a tiny San ­Francisco neighborhood south of Market Street that attracts a mixed crowd. During the week, hipsters sip coffee in cafés on South Park Street, a one-way path that bounds the oval park; homeless men guard shopping carts near the park’s entrance; and entrepreneurs and computer programmers gather inside offices that line the green, trying to build the next big thing.

I visited Twitter’s loftlike office to meet Williams on a warm July afternoon. He has a spare frame and a handsome face that retains a youthful softness, and he was wearing his standard outfit of plain white T-shirt and jeans. The simplicity that made Blogger so attractive to Google, he told me, is similarly driving Twitter’s growth. Williams matter-of-factly described how the companies came about (both serendipitously) and explained what he sees as their appeal: they fill people’s need to stay connected with one another.

By the largely noncommercial standards of social-­networking startups, Twitter is a success. (Whether the company can become a profitable business is another matter, one much debated among those who follow the social-­networking industry.) Twitter took off in March, around the time it won a Web Award for best blog at the South by Southwest Interactive Festival in Austin, TX. Since then, the number of registered Twitter users worldwide has been steadily rising. Twitter doesn’t reveal the actual numbers, but TwitDir.com, a third-party Twitter directory, estimates that there are nearly 500,000 public users, who allow their profiles and updates to be searched. In August, Twitter received about $5 million in funding, much of which came from Union Square Ventures, a New York venture capital fund. The company is in talks with Hollywood studios about using Twitter for promotional purposes, and MTV used the service to promote its annual Video Music Awards in September. Perhaps the biggest indicator of Twitter’s success is the sudden appearance of “me-too” startups boasting that their services offer Twitter’s features and more. (For a review of Twitter and its competitors, see “Trivial Pursuits”.)

According to Williams, Twitter is catching on for a simple reason: “It’s social, and people are social animals.” But ­Twitter is a different way to be social, he says. Though Twitter updates have elements of blog posts, instant messages, e‑mails, and text messages, they’re often shorter, can be broadcast more widely, and require no immediate response. “It’s a no-brainer,” Williams says. “People like other people. So hearing from them, and being able to express yourself to people you care about in a really simple way, is fun, and it can be addictive.”

Williams himself can seem addicted to continuous self-exposure. One night last August, he twittered, “Having homemade Japanese dinner on the patio on an unusually moderate SF evening. Lovely.” He’s not alone in his addiction. That same night, a Twitter user named Itiswell posted, “I am having problems with the computer with missing software components.” And I wrote, “Sense of accomplishment: never has my bathtub been this clean.”

Some experts, including Elizabeth Lawley, director of the social-computing lab at the Rochester Institute of Technology, see such posting as a completely new form of communication. “Because it focuses on the minutiae, it’s almost as if you’re seeing a pixel of someone’s life,” Lawley says. “When you see all of those little pieces together, it gives a much richer portrait. With other forms of communication, we don’t tend to share those everyday things, but the question ‘What are you doing?’ is exactly the thing that we ask people we care about. Otherwise we only get the big events, the things that are worth sending an e-mail about.”

To others, of course, twitters seem banal, narcissistic, and excruciatingly dull. Detractors believe, too, that the company is doomed because it lacks a clear path to profitability. A comment on the popular blog TechCrunch combines both sentiments: “Twitter is a worthless app for the most self-absorbed among us. There is no money involved and it will be extremely hard to insert any sort of advertising. A pay model won’t fly either because the mobile networks will just launch an application themselves if Twitter tries that path. Furthermore, most blogs are really boring (perhaps even my own). Twits are even worse. ‘I ate a cheese sandwich.’ Yawn. Fail.”

The criticism doesn’t seem to bother Williams, in part because he’s heard it before. “Actually, listening to people talk about Twitter over the last few months, you hear that almost all the arguments against it are the exact same arguments that people had against Blogger,” he says. “ ‘Why would anyone want to do this?’ ‘It’s pointless.’ ‘It’s trivial.’ ‘It’s self-aggrandizing bullshit.’ ‘It’s not technically interesting.’ ‘There’s nothing to it.’ ‘How is this different from X, Y, and Z that’s existed for the past 10 years?’” Indeed, there were blogging tools available when Blogger was released, and others have emerged since–including TypePad from Six Apart, which offers more features. But none has the simple appeal of Blogger, and none is as easy to use. These were the reasons Blogger was such an important force in the blogging revolution.

At first, Williams doesn’t seem the type to dedicate himself to changing human communications. He fits a certain Midwestern stereotype: he’s a thoughtful man of relatively few words. But the trajectory of his life defies that stereotype; growing up in Clarks left him dissatisfied. “Not to bad-mouth it,” he says. “It’s just not like people are striving to be their best. Doing something that’s different doesn’t occur to people. Looking around me, I think I did not want to be like most of the people I saw. I was always looking for a way out, to be different, to be exceptional.”

Williams enrolled at the University of Nebraska right after high school but dropped out after a little more than a year. He was in Lincoln in 1994, just as the Web was becoming a mass phenomenon. Guessing that the Internet would be important, he decided to build a product around it: a video that explained the ins and outs of using a command line to connect computers across the network.

The video made a profit, and Williams started a full-fledged Internet company, with a variety of ideas for businesses and products. (“It was when the Internet was new enough that you could just say you were an ‘Internet company’ and didn’t have to be more specific,” he says.) The company failed spectacularly. “It was sort of a train wreck in terms of management,” he admits. “I had lots of ideas for things that were potentially interesting products, but I had no idea what I was doing, either in terms of managing a company or on the technology side. If we could have written software, we would have been in a better position. We tried to hire people who could write software, but I couldn’t manage them, and they didn’t know much about what they were doing.” After a year or so, Williams fired his employees and shut the company down. In 1996, he moved to Northern California.

Williams is vacuuming the rug…he’s still vacuuming the rug…he’s thinking and vacuuming the rug…he’s finished vacuuming the rug!
Credit: Toby Burditt

The late 1990s were heady for entrepreneurs in San Francisco, who worked long hours, racing to build the websites that would make their fortunes. “It was a pretty wild time,” recalls Meg Hourihan, Blogger’s cofounder. “You’d finish coding some feature for a product at 10 o’clock at night and then walk over to the party next door for free food and drinks.”

Hourihan, an English major with an aptitude for computers, was a technology consultant at the time, and she craved an entrepreneurial adventure. Meanwhile, Williams was becoming interested in collaboration software that helped people work on joint projects more effectively. In the summer of 1998, he and Hourihan both attended a networking event in San Francisco. “I ended up sitting down next to Ev and talking to him,” Hourihan says. “Somehow we started talking about the Web and computers, and I felt like he was the first person I had met who saw the potential on the Web that I saw, that it was a life-changing thing.”

They started dating but after two months decided they would be happier as business partners. In the fall of 1998 they began to work together on Pyra, a Web-based project-­management application. The goal was to create an online “worktable” that would keep track of project changes, questions, meetings, and more. The Pyra team became a company called Pyra Labs when a friend of Williams’s from Nebraska, Paul Bausch, joined to help write the code. In order to keep tabs on the status of Pyra’s features, the three employees posted updates on an internal blog they called “Stuff.” Both Williams and Hourihan had been early bloggers, so it seemed a natural way to communicate. Stuff became the central nervous system for the company. “That was really how we communicated and collaborated, which is ironic because we were building this collaboration tool that was much more complex,” Williams recalls. “We joked semiseriously many times that we should just make Stuff our product. I had a little bit of a thought that there was something to it, but it was just so ultrasimple that I didn’t seriously consider it.”

Then a slight modification to Stuff made Williams reconsider. One day, Bausch wrote a piece of code that made it possible to transfer an entry from Stuff to Pyra’s public Web server using something called a file transfer protocol, or FTP; the entry would then be visible to anyone. “That was really the genesis of Blogger,” Williams says. “The simplicity of having an application that ran on the Web that would then FTP a static file to your server was the key thing. Once we did that, we thought people would use that.”

Eventually, it became clear that Blogger, not the more complex Pyra, was what people wanted: Williams had found a simpler, more valuable communications product inside the more diffuse company. The team raised money in a small round of funding. Yet Williams’s colleagues were nervous because Blogger was a free service, and it still didn’t have a business plan. And Williams, who was the CEO, struggled to raise more funds. “We started running out of money,” says Hourihan. “We couldn’t stay ahead of the infrastructure we needed to keep growing. Then the market collapsed, and it seemed like we couldn’t raise another round.”

The team, which had grown to six, bitterly disbanded. Williams “just took the servers back to his house and kept it going, a one-man show, for a while,” says Hourihan. “Then things started to come back, and he was able to hire some people back and slowly get its legs under it again.” ­Hourihan stayed away, but Williams was successful enough to negotiate the sale to Google in early 2003.

After leaving Google, Williams took time off to find startup ideas. Instead, a startup found him. A friend, Noah Glass, was working on software to help people create, distribute, and search for podcasts, and he and Williams began to talk about the product. Williams started spending his days advising Glass, and eventually he invested in the new company, Odeo. At first, Williams wanted to maintain his distance in order to pursue other projects, but in February 2005, he was asked to unveil Odeo at TED, the yearly, invitation-only conference of technology, entertainment, and design. At TED, his name quickly got attached to the company. “I sort of had an ego thing going on where I was like, ‘This is my next thing.’ But that wasn’t my intention in the beginning,” he says. “I was excited and glad to help out, but I wasn’t ready to start a new thing, and it wouldn’t have been that.” There was a lot of excitement surrounding Odeo, Williams recalls, and he got caught up in it, against his better judgment.

Odeo had plenty of funding up front (after Blogger, it wasn’t hard for Williams to attract investors), but the company’s prospects weren’t really very healthy. No one had a clear sense of what its main product would be, and in June 2005, Apple released a version of iTunes, its audio software, that offered podcasting functions nearly identical to those Odeo was developing. “It sort of shocked us,” Williams says. “Apple did it all, and they’re on millions of desktops. All this stuff that we built was kind of irrelevant once Apple launched their product.”

The problem wasn’t just Apple’s beating Odeo to market, he adds. Odeo’s product demanded a more traditional approach to the media business, one that relied on distribution and media deals as opposed to viral growth, and that wasn’t the type of business model that appealed to Williams and the company’s engineers. “We just weren’t a company that was going to excel in those things,” Williams says. Realizing this, he went to the board in October 2006 and bought the company with his Google money. Among Odeo’s assets was an early version of Twitter–at the time, merely a side project.

Liz Lawley of the Rochester Institute of Technology was initially skeptical of Twitter when she started using it in February. “My first reaction was that I don’t need another place to post things, yet another user name and password to remember,” she says. “I have four blogs, and it didn’t seem to me that I needed to do anything different.” But by March, she was twittering on a regular basis. Now she tends to twitter mainly when she’s traveling, when something unusual is happening, or when a lot is going on in her life. “It’s easier to update people that way rather than figuring out who to send e-mails to,” she says.

Lawley represents only one type of Twitter user. Some people are hypergraphic, posting incessantly. Others rarely post but follow the updates of people they don’t know. A few writers are experimenting to see how storytelling changes when it’s produced in 140-character increments, while others are creating charming haikus. People are also using Twitter to send clues for scavenger hunts and other games. And individuals aren’t the only users. In fact, the service has proved useful for advertisers, news outlets, and even fire departments.

These uses aren’t surprising to Jack Dorsey, the Odeo engineer who proposed Twitter to Williams in 2006. Dorsey, now Twitter’s CEO, had always been fascinated with real-time communications and dispatching systems–the kind that send taxis around cities and ensure that ambulances quickly arrive at the right place. “Back in February of 2006, we were having a bunch of conversations about how to change Odeo into something that we loved,” he recalls. “We wanted something a little bit different. Texting was getting big, and in a meeting I brought up the idea of Twitter. It was the simplest thing we could do: send what you’re doing to your friends, and that was it. Everyone started thinking about that, and a week later Evan gave me the go-ahead to build a prototype.”

Just like Blogger, Twitter was a simple communications product salvaged from the impending implosion of a more complex project. In both cases, Williams didn’t really know what he was doing. With both ventures, his genius–if that is the word–derived from what the English poet John Keats, in a letter to his brothers, called “negative capability”: “that is when man is capable of being in uncertainties, Mysteries, doubts without any irritable reaching after fact & reason.”

With the help of another engineer, Dorsey built the basics of Twitter in about two weeks, using a popular Web programming framework called Ruby on Rails. At Twitter’s core is a simple messaging distribution machine that is, in the jargon of communications, “device agnostic.” After a twitterer composes a 140-character update and clicks a button on a Web page, in an instant-messaging program, or on a cell phone, the tweet is almost instantaneously routed to the people who have elected to receive it. They in turn will read the message on the Web, with an instant-­messaging program, or on a cell phone, according to their preferences.

Crucial to Twitter’s popularity was the release in September 2006 of its application programming interface, or API, which allows outside programmers to build applications that plug into the company’s information infrastructure. Once the API was available, geeks everywhere started to create innovative Twitter tools. “A ton of our usage is through our API,” says Williams. And the API is relatively simple: “It’s not the most powerful development framework, but it’s encouraged a ton of people to play with it. This means that a ton of interfaces and tools were built and plugged into Twitter because of that simplicity.”

Among the tools that third-party developers have built are desktop interfaces. An example is Twitterrific, a downloadable program for Macs, which makes twitters pop up on the Mac OS desktop and then fade into the background. Another way people have tapped into Twitter’s code is by redisplaying the public posts in interesting ways: in a program called Twittervision, for example, a globe displays twitters as they are posted all around the world. It is the diverting spectacle of the human race (or at least that part of it that twitters) talking to itself. Bots–automated program–can also post twitters with content extracted from some information feed. There are news and weather bots, and little programs that update users with earthquake information from the U.S. Geological Survey.

By letting programmers build twittering tools that appeal to a broad range of people, Twitter has gained many more users. And this could be just the beginning. “Another way to look at it is as a platform for device-agnostic real-time messaging,” Williams says. “And that has broader implications. People have contacted us about emergency broadcasting systems. We like the idea, but we’re not anywhere near saying that we want to be counted on for that.” For emergency use, Twitter would need to be reliable, a goal that seems elusive. This past summer saw many Twitter outages, both planned and unscheduled, and it’s not uncommon to have a twitter or two dropped.

Williams, Dorsey, and another Twitter cofounder, Biz Stone, are betting that by shoring up the service’s infrastructure, they’ll be able to fend off the mounting ranks of competi­tors. These include Jaiku, Plazes, Kyte, Yappd, Pownce, and ­Facebook (which has a feature that lets users update their “status” in a way that resembles twittering). All of these services differ: Jaiku has more functions than ­Twitter–users can add pictures to their posts, for instance–but it’s a bit complicated to use, and it doesn’t yet have as many users as Twitter. Pownce, which is still in its beta-­testing phase, allows invited users to share different types of files with different groups of people: users can create lists that allow them to send information to one person (as in an instant message), to a few of their contacts, or to all of them. And Facebook is “in a much stronger position” than Twitter, Williams says, because for social applications, the number of users is crucial.

“If you look at Pownce and Twitter and Facebook today, they’re all conceptually the same, but they’ll evolve in different ways,” Williams says. “We know there are lots of features and functionality that we want to add and will add, but we don’t want to make it more complicated, because we do think that much of the beauty is in simplicity.”

Staying static for too long on the Web is risky, however, especially for the first company with a new type of technology. In 2002, a social-networking site called Friendster quickly became successful, gaining droves of users who created profiles that linked to their friends’. Friendster’s social-networking preëminence didn’t last long: in 2003, MySpace entered the picture. Now MySpace, which is owned by Rupert Murdoch, has around 100 million registered users, and it’s growing. Friendster still operates, but at a smaller scale than MySpace. (See “Friend Spam,” by Friendster founder Jonathan Abrams.)

Williams says that he thinks about Friendster’s fate, especially when Twitter’s service falters. “We’re doing okay now, but when we were doing really poorly, the Friendster ­analogy came up,” he says. This is why it’s crucial to focus on improving reliability and making the interface even more foolproof, he adds. “I think if we can make it perform and make it obvious how to use it and just get it in front of people, we’ll do well.”

Williams believes that building a healthy infrastructure is also the key to eventually making a profit, so that’s what he hopes to do with the money from Union Square Ventures. Fred Wilson, a Union Square managing partner, says, “I think with a lot of these kinds of services, the big looming question is ‘How are we going to make money?’ In the case of Twitter, we felt if they could build a communication system that was easy to use and was used in lots of different ways by lots of different services, then they could become a piece of the infrastructure of the Internet.” At that point, Twitter would possess enough “messaging volume” to get paid by someone: “probably by other people who want to participate in that volume–maybe wireless carriers,” Wilson speculates.

“Our advice was to not focus on generating revenue on day one,” he adds, “but focus on getting as many people and as many services as you can to use the underlying Twitter infrastructure to build messaging services.”

Crucial to this plan is ensuring that Twitter’s technology–that is, the structure of the system’s underlying code–can support new users as they join the service. Technologists say that a network “scales” when it can take on an increasing number of customers. A good portion of the company’s recent funding, Williams and Wilson say, will go toward making Twitter “scalable.” If that doesn’t happen, opportunities for profit may go unrealized.

When I last saw Williams, he had just returned from his honeymoon, a safari in Kenya. (In Africa, predictably, he twittered using his cell phone: “Touring Nairobi.” “Having drinks after a day of game drives and relaxing.” “Watching lions. Shhh.”) Over breakfast at a restaurant in San Francisco’s Mission District, he told me that he’s taking a few steps back from Twitter: he’ll sit on the company’s board but leave coding to the engineers and the day-to-day management to Dorsey. Before his wedding, Williams explained, he had spent a lot of time writing code for features and slogging through the daily maintenance of the service. Now he feels the company is in ­capable hands without him.

So do his venture capitalists, it turns out. Williams “seems a little more thoughtful and willing to live with ambiguity more than most of the entrepreneurs I know,” says Fred Wilson. “That’s a big positive, but it could be a big negative, too. It’s a positive because startups need to have ambiguity around for a while, but a lot of the time things need to be decided, which is why I think it’s good he’s letting Jack [Dorsey] run the company. Jack is probably a little more decisive.”

Now Williams says he wants to work more on Obvious, which, for him, is a different type of venture; he describes it as a kind of incubator for products that solve obvious problems. Obvious (which upon its founding in October 2006 absorbed Odeo) wasn’t created with a product or even a technology in mind; it was conceived as a company where ideas are fueled until they either catch fire or simply fade away. But as of our meeting, Williams was the only employee, and it’s clear that he doesn’t know how Obvious will operate.

Williams has some technological problems he’d like to explore, including his old preoccupation at Pyra: the question of how companies can communicate more effectively, both internally and with other companies. He has at least one person in mind to do some coding, too. Still, he seems uncertain how any solution could be turned into a product, let alone a viable business.

In fact, he tells me, he doesn’t have any solid plans. At the end of 2007, Williams finds himself in the same state that he has so often been in before: uncertain, without any irritable reaching after fact and reason.