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So open it hurts

Web 2.0 visionaries Tara Hunt and Chris Messina blogged and twittered about their romance to all of geekdom as if it were one of their utopian open-source projects. Sharing their breakup has been a lot harder.

Even without the existence of Twitter, the Yahoo! party would have been a madhouse. But with 10,000 conferencegoers texting each other about where to chill out after the first full day of the Web 2.0 Expo in late April, it seems as if every geek on the West Coast has ended up in Yahoo!’s SoMa satellite office, aka the Brickhouse, celebrating nothing in particular and basking in their own fabulousness. Electronica pulsates over the massive sound system, while packs of messy-haired boys in faded T-shirts nurse Cokes—the beer stopped flowing a while ago—and fiddle with their iPhones (apparently, these geeks don’t dance). No one even tries to talk-yell to someone they don’t already know.

The only thing the Yahoo! party has in common with the one at Citizen Space, a few blocks away, is a shortage of booze. Still, a guy with an accent manages to scrounge up a couple of beers buried under some ice, shrugging, “I’m German,” as if that explains everything. This is the year the New York Times—and therefore the world—discovered coworking, defined as office-sharing with a utopian mission. As the epicenter of the most intriguing trend to hit the workplace since telecommuting in pajamas, Citizen Space is hopping tonight, too, but in a low-key, cocktail-party way. If the Yahoo! mob scene is Web 2.0 as we’ve come to know it—boisterous and buzzy, full of promise, yet cliquey and strangely impersonal—then the Citizen Space party is Web 2.0 as a few visionaries believe it can be: like hanging out in a good friend’s living room under the cozy glow of a chandelier. It’s easy to be yourself, and it feels natural to strike up a meaningful conversation with anyone who stops by.

For all the wild success of YouTube, Facebook, and other social-networking and content-sharing sites over the past three years, some young dreamers continue to see the web not as a way to get rich (or get laid), but as a working metaphor for how humankind could operate IRL—in real life. This idealism is embodied by Tara Hunt, Citizen Space’s 35-year-old cofounder and de facto camp counselor, who stops midconversation to smother me with a warm hug. Like many of her friends, Hunt holds two fundamental beliefs about the real and virtual worlds. The first is that “social networking” without actual social contact is sterile and alienating. The second is that the more everyone shares what they know, the more good things they can make happen. In digispeak, the latter view is known as open-source thinking, a term that originated with the open-source software movement—programmers freely trading code and ideas to develop better, cheaper, more innovative technology accessible to all—and has come to describe a whole philosophy of life.

In Hunt’s case, this passion for openness extends to pretty much everything. Thanks to her blog, Horsepigcow.com, and her frequent “tweets” on Twitter (instant messages broadcast to a whole social network at once), I know more about her day-to-day existence than I do about that of some of my own friends—her body-image issues, her attempts to keep her son interested in school, her brunch plans, her love life. To a lot of people, this is the definition of TMI (too much information), especially coming from a well-regarded marketing consultant with an ascendant career and some serious projects to promote. But Hunt doesn’t care—she’s committed to living as transparently as possible, even if the result is a bit messy sometimes. “The more I’ve opened myself up, professionally or personally, the more I have benefited,” she emails me after the party. “It really is the key to community. We can’t watch out for and help one another if we don’t know what the other person is doing.”

When I first met Hunt last fall, her hair was chocolate brown with a stark blond stripe running through it. Tonight, she sports a sexy bleached-blond bob—breakup hair. She wears a white eyelet blouse with billowy sleeves that makes her look like a SoHo fashionista. The guy who helped inspire this new sleekness, her ex-boyfriend Chris Messina, is surrounded, as usual, by a coterie of geeks who revere his work on such high-profile open-source projects as OpenID, a centralized web log-in system that’s been adopted by the likes of Google. Blond, bespectacled, and borderline brilliant, the 27-year-old Messina exudes a nerdy charisma, like a cross between James Van Der Beek (Dawson in Dawson’s Creek) and Bill Gates. He and Hunt are cohosting the event, but they keep a careful distance from each other.

In a world not known for its epic romances, ChrisandTara used to be Web 2.0’s version of Brangelina. They lived together, worked at adjoining desks, finished each other’s sentences, guided each other’s dreams. Personality-wise, they were yin meets yang meets a whole lot of Venus and Mars. But in many other ways, they were two pieces of the same puzzle. Ultimately, the core tenet of open-source culture is that the sum is exponentially greater than the disparate parts—and the same could be said of Hunt and Messina’s union. In both work and love, they pushed each other to thrust the ideals of open source, including transparency and collaboration, into real life. In just two years, through the coworking movement and myriad other projects, the ripple effects of their partnership could be seen around the globe. “It was sort of magical,” Hunt says. “Just really powerful to have his more technological side and my more human side, and bring them together.”

Then, just as their efforts were hitting the mainstream, Hunt and Messina broke up. True to their principles, they pushed themselves to be extraordinarily candid about what was happening—­­as they continued to work as business partners and occasional cohosts in the same once idyllic, now heartbroken community. But it’s been a deeply painful struggle. Comparing their tentative interactions at the Web 2.0 Expo party with their potent partnership just a few months earlier, I wasn’t sure which I felt more strongly: admiration for their determination to stick it out, or pity for how exhausted they must be. True, no one ever said living an open-source life would be easy. But did they—or anyone—have any idea that it would be this hard?

One afternoon in the summer of 2005, Chris Messina and six of his hotshot geek pals were talking about an invitation-only retreat sponsored by tech impresario Tim O’Reilly. What would happen, they wondered half seriously, if they started their own grassroots version, open to everyone—and, more intriguing, what would it look like? “Conferences are these nebulous, overproduced affairs, and yet the problem you’re trying to solve is getting people together in a way that facilitates conversation and sharing,” Messina recalls. “So why not design a conference to accentuate that? I like to look at a design problem and figure out how to solve it.”

A mere six days later, the same weekend that Foo Camp (for Friends of O’Reilly) was getting underway in Sonoma County, BarCamp (the name is based on a joke that’s comprehensible only if you speak hackerese) made its debut in Palo Alto. “We had no money, no sponsors, no venue, and no idea if just the five of us or 50 random folks would show,” Messina wrote on his blog, Factoryjoe.com. In fact, hundreds of people turned out, attracted by the organizers’ goal of making BarCamp “a demonstration of the decentralized organizing potential of the Web 2.0 Generation” and by Messina’s ability to get people excited about his ideas. Though he hasn’t generated many headlines—he hasn’t started a series of companies or made a billion dollars—Messina is a dyn­amic presence in the open-source world. Says frequent collaborator Scott Kveton, founder and ex-director of the Oregon State University Open Source Lab, “He’s one of those personalities that creates a reality-distortion field that stays with you even after they leave.”

What made BarCamp so interesting, and quickly turned it into a worldwide underground phenomenon, was the way it incorporated open-source and related principles. While the term means many things to many people, to Messina open source is “both an attitude and a methodology. It’s a practice for how you work. You build an idea by being transparent and by offering up the blueprints, by allowing other people to modify that work so they can spawn their own individual project.”

For the first BarCamp, Messina and his buddies devised a simple system that let attendees, rather than organizers, create the day’s agenda on the spot. Anyone could claim a room and lead a talk. The result was a user-generated “unconference” where collaboration and serendipity ruled. Meanwhile, Messina and his pals documented every step using Web 2.0 tools that enable openness, including blogs, photos, and a wiki site, so that anyone, anywhere could take the idea and run with it. Three years later, hundreds of BarCamps have been held in places as far-flung as Mauritius, off the coast of Africa, and Baku-Lankaran, Azerbaijan, tackling subjects as diverse as education, healthcare, public transportation, and personal finance. Even the Web 2.0 Expo, sponsored by O’Reilly, now has a BarCamp-esque component (Web2Open) that Messina and Hunt helped organize. BarCamp’s transformation “is like Darwinian evolution,” Messina marvels. “That’s one of the greatest things about open source—it embraces the way that natural systems evolve over time.”

Messina is soft-spoken and intense, with a tendency toward flip or grandiose statements that can make him seem callow, especially in writing. But in person, he is earnest and likable, with the magnetism of a natural leader. As he explores an idea, you can practically hear the synapses firing; even mundane questions about office space or social networking lead to fascinating discourses on civic engagement and personal freedom. The only time he flounders is when I ask about his feelings, but he’s candid about them in his own way, too: He confesses that as much as he believes in openness, he has a hard time sharing his emotions with anyone but close friends. Partly to deflect from the personal and partly because he’s obsessed with the topic, he leads everything back to a metaphysical rumination about open source.

One of Messina’s early influences was an obscure Lithuanian philosopher named Andrius Kulikauskas whose manifesto, “An Economy for Giving Everything Away,” argues that the best way to find the answer to a problem is to look at what other people are doing, then share your data so that others can benefit. “The value,” Messina says, “is no longer in having monopolistic control over the entire conversation.”

He stumbled on the paper during high school in Manchester, New Hampshire, where he was a bright, restless kid with a libertarian streak. “I rejected the way that school was done,” he recalls. “In class, we did rote exercises. I thought, ‘All of these problems have been solved before; why not work on things that enrich the world?’” He was artistic, with an innate grasp of all things tech—“I had no fear of destroying computers and putting them back together again, much to my parents’ chagrin”—so web design was a natural outlet. But when Messina created a web page for a gay student group, he was suspended. “It gave me the feeling that I couldn’t trust these institutions,” he says. Traditional modes of protest, like the rallies he attended as an ACLU volunteer in college, left him even more cynical. Harnessing the Internet to spread ideas was “a better use of energy then yelling at someone you don’t like,” he decided.

More than anything, Messina wanted to make technology accessible to people like his parents and customers in his first job, as a troubleshooter for an Internet provider. “They would have the same problems again and again, and it was so humiliating to want to connect with people but have the technology get in the way. I thought it was unfair that as the world was moving toward increased technology, a great number of peo­ple were being left behind.”

Open-source developers, meanwhile, were working together to make technology easier to use—more democratic and empowering. “With proprietary systems, they are closed, they are black boxes, you have no idea how they work inside,” Messina says. “This leads to a stagnation in web design and development.”

During and after college (he was a communication design major at Carnegie Mellon University in Pittsburgh), Messina worked on Howard Dean’s 2004 presidential race through CivicSpace, a project that developed open-source software for political campaigns. That led him to Mozilla, a Mountain View foundation that was developing a new web browser, using open-source code, to challenge Microsoft Internet Explorer. As a volunteer on the grassroots marketing team, Messina designed a two-page ad that ran in the New York Times for the launch of Firefox in 2004 (he also helped raise $220,000 in 10 days to pay for the ad). The project was a life-altering experience. “Rather than hiding stuff, here was a collective of people who had come together to create something where transparency was central to how they did their work,” he rhapsodizes.

Before long, he was blogging: “We need to open source all infrastructure…including our economic system, including education, including government…and the entire legal system.… Civilization will advance not with open source, but because of it.”

Messina was determined to live by these principles, too. Unlike some Silicon Val­ley wunderkinds, he wasn’t motivated by money—indeed, keeping stuff proprietary, à la Microsoft, is the antithesis of open-source idealism. Every idea was given away. Every project was made accessible through his blog, on unrestricted listservs, or on wiki sites where any netizen could edit the content. As he put it, rather impatiently, in his blog’s tagline: “This can all be made better. Ready? Begin.”

Tara Hunt settles into her pea-green sofa and puts her feet up, a mug of tea in her lap. Late-afternoon sun streams into her living room, which looks out over a happening stretch of Second Street near AT&T Park. The apartment’s walls are awash with cheery color: peach, lemon yellow, avocado. Even the front door is a yummy cherry red.

Fifteen-year-old Tad pops his head into the room. An artsy kid with a fondness for skateboarding and video games, he has long, dark hair and is dressed mostly in black. “Mom? Did you see my report card?” he asks, handing her a slip of paper.

Hunt scans the printout and pours on the unconditional support. “That’s so awesome, hon,” she beams. “I’m so proud of you. Yeah, that ROTC sucks, huh? But hey, you got an A, too! Keep up the good work.”

After he leaves, Hunt confides that like her son, she also had her “floaty years”: “I struggled through high school because I just didn’t think it was really important.” But her doting parents (her mother is an artist, her father a veterinarian) never stopped applauding, as she morphed from shrill high school environmental activist to teenage single mom to determined guerilla marketer. She says her parents’ support—plus growing up on a farm in Sundre, Canada (population 2,167), where everyone knew her business anyway—made sharing her failures and successes instinctual, a habit she’ll never be able to kick.

“She doesn’t do it for shock value,” says Celeste Evancio, a friend since college. “It’s not to be offensive or bold or to call attention to herself. If it’s not appropriate, she won’t say it. She’s just being honest.”

Hunt’s openness extends to new experiences and forms of community. After high school, she spent a few years hanging out with a bunch of bike messengers in Calgary, then did an about-face and joined a sorority in college (among other things, it gave her a new appre­ciation of female friendship and provided a gaggle of babysitters for little Tad). The resulting support network freed her up to study cultural issues and communications, design web pages, and develop a safe-sex curriculum that wasn’t well received, because she included transgendered people. As happened to Messina, Hunt’s turn as an activist left a lasting impression. “I just didn’t ever feel like politics changed anything,” she says, “that it took so long to change politics, so let’s change the world around you directly.”

Things didn’t always work out as she expected, like her decision to try a career in marketing because the movies made it look glamorous (and, she admits sheepishly, she loves to shop). She quickly became disenchanted with the explicit product flogging and old-school marketing strategies—“stupid messages about stupid stuff [that people] don’t give a damn about”—that seemed out of touch with the way the Internet was reshaping culture. Then she stumbled on The Clue­train Manifesto, a book-length treatise, available for free online, that explored the way the web has changed the relationship between markets and consumers. Companies, Hunt concluded, should think of their customers as members of a social network and build credibility by embracing transparency—for example, by letting them talk to each other about problems they might be having with a product, instead of pretending the problems didn’t exist. A marketer’s role was to double as a consumer advocate and community organizer, and let the dollars flow from there. Says her friend Brad Neuberg, a technologist and open-source advocate who works at Google, “Tara’s marketing is about knowing what your values are and putting them out there.”

Hunt’s route to the Bay Area was filled with detours that crystalized her ideas about business and culture. At 28, she started her own firm, Rogue Strategies—she was known as Miss Rogue at her favorite karaoke bar in Calgary—before she moved to Toronto and discovered how hard it was to thrive with no social network. “All of a sudden, I had no reputation,” she says. When the tech bubble burst and left her nearly broke, she took a job with a human resources association for a few years to make ends meet, but kept in touch with her Cluetrain-inspired ideas—which she has variously dubbed “Pinko marketing,” “marketing of the people,” and “geek marketing”—by blogging. (She took the name of her blog from a phrase her mom coined “to avoid embarrassment when she called someone by the wrong name.... Something like, ‘Hi James, Jake, HorsePigCow, Jason. How are you?’” Hunt likes the term because it’s a way of saying, “‘Hell, I’m human and I screw up, but let’s move on.’”)

In 2005, a fellow blogger referred her to a Redwood City startup called Riya, now an image search engine, which hired her as its online marketing director. Out here, she discovered, her ideas weren’t considered foreign or outlandish at all. Putting theory into practice, she blogged about everything from the details of her transfer to the Bay Area to the not always pretty realities of working at a startup (“We don’t know what we are going to do next”); she also joined every social network ever invented. “I achieved amazing results,” Hunt wrote in one post. “And what I found was the most bloody incredible thing ever.... I found community.”

Hunt and Messina met in San Francisco at a BarCamp spin-off in the fall of 2005. He liked her style—a little art school, a little Critical Mass—and when he overheard her mention that she wanted a T-shirt from the blog news site Technorati, he walked up to her, wordlessly handed her a shirt that he’d picked up earlier for himself, then disappeared into the crowd. “That’s when I started to notice that he was pretty cute,” Hunt confides.

A few days later, Hunt and Messina found themselves hanging out with mutual friends. Fueled by “too much beer,” Hunt told Messina that she’d like to get to know him. “I just sent you an email saying the same thing,” Messina responded. They talked until 4 in the morning.

Before long, they were linking to each other’s blogs (Hunt later told Messina that “links is love”) and referring to each other as “partners in crime.” They posted snapshots of themselves together on Flickr and changed their relationship status on Facebook to reflect their budding romance.

Even their first fight went public when they blogged about it. What started as Hunt fretting that she couldn’t check her Technorati ranking (her popularity in the blog­­osphere, as measured by the number of links to her site) because the site was down escalated into an argument about the meaning of life. Messina’s postfight reflections left her more smitten than ever. “Wow,” Hunt wrote in response to his post. “I mean, Wow.”

Of course, members of the Web 2.0 generation—aka the see-through generation—are notorious for blathering endlessly about themselves all over the Internet, much to the consternation of cultural geezers who sternly warn that they’ll regret it one day, just like they’ll regret all those tattoos. But Hunt and Messina were different, or so they claimed: open not in a reflexive, navel-gazing, exhibitionist way—their posts weren’t at all sexually explicit, for example—but to make a philosophical point. In a podcast entitled “Bloggers in Love,” Messina extolled the virtues of “putting everything out there and letting the source flow and using the building blocks in whatever ways make sense.” Blogging about his personal life was also a form of rebellion, he admitted. “It’s like, ‘Fuck Hallmark.... We don’t want your brand of love.…’ When you’re putting [your relationship] out there, you’re [saying] we don’t buy into the mainstream definition of love that has everyone unhappy by the fifth year of marriage.”

In their work-obsessed world, the business partnership Hunt and Messina built seemed especially romantic. Within a month of their first date, they flew to Paris, where they talked and talked while sipping wine at cafés and taking long walks. During one of these strolls, as they paused in front of a glowing fountain, Hunt persuaded Messina to start taking charge of the projects he felt so passionate about. “Chris had a can-do attitude but a can’t-take-credit attitude,” she recalls. “He was like, ‘I have this idea and I’ll just give it to somebody else to lead, and I’ll help support them and they can grow it.’ I was like, ‘You’re a leader, just freakin’ take the leap!’”

"That’s when I realized I wasn’t going to be effective by outsourcing my own dreams,” Messina concurs.

Hunt, meanwhile, felt emboldened by Messina. He wanted to solve the world’s problems, big and small, and convinced her that she could take risks, too. “I want people to transform like I transformed after I met Chris,” she says. “From ‘Oh, that would be so cool, but there’s no way I can do this on my own’ to ‘I can do it.’”

Other couples go away for the weekend to a spa or B&B; Hunt and Messina took off for their own personal LifePlanningCamp. Back in San Francisco, they imme­diately began collaborating on WineCamp—bringing together geeks and nonprofits—and discovered that they made a great team. Soon, they moved in together, quit their jobs, and launched a web consulting company called Citizen Agency (he was “citizen executive officer,” she was “citizen marketing officer”). Thanks to their solid reputations, they had no trouble lining up clients, like the messenger-bag company Timbuk2 and the social-bookmarking site ma.gnolia. “Rather than just going out there and flogging our name, they were showing us how to build something that people would come to care about and love,” says ma.gnolia’s founder, Larry Halff.

One of Hunt’s favorite projects was something she called Government 2.0—trying to get transit systems, for example, to use simple tools like Twitter to communicate with their network of riders about delays in service and the like. Getting rich wasn’t the goal—in fact, after working with ma.gnolia for more than a year, Hunt and Messina decided their collaboration with the company had been so mutually beneficial that they stopped billing him, Halff says. Hunt explains their philosophy: “I mean, I love being able to pay for this beautiful apartment and continuing to travel and stuff. But it feels more right to do awesome things and then see what comes of them. I figure if instead of concentrating on making money, I concentrate on making the world a better place, and the money doesn’t come—well, it wouldn’t have come anyway. But it has come, which has been really cool.”

Less cool was how male-dominated geekdom sometimes responded to Hunt, whose down-to-earth girliness—even her website has a frilly quality—made her an anomaly. In a world where killer apps are more valued than killer people skills, and hyperan­alytical thinking trumps touchy-feeliness, Messina was seen by some as the more important figure (Hunt’s Wikipedia page was deleted while his was not; a reporter gave him all the credit for organizing Web2Open, although she did more of the work), which made them both furious.

“We had a lot of discussions early on about…his privilege as a young, white, educated male,” Hunt told me last December. “Chris really latched onto this idea and spent a lot of time educating others in the tech industry about why it is important to consider diversity.” Messina agrees: “Wherever you have discrimination or a lack of diversity, you cut yourself off from what could be important. Now the first thing I do is look at the diversity quotient of an event, which will tell me whether this is something that can teach me things or will just reinforce my assumptions and stereotypes.”

Gender equality was their calling card. Last fall, in a blog post titled “The Future Is Feminine,” Hunt wrote about the importance—in business and in life—of devaluing “the aggressive, competitive, dominating, quan­titative, competitive sides” and giving greater weight to feminine qualities (which just so happened to bear a striking resemblance to open-source values). She also discussed the response she frequently gets after a presentation on her male/female spiel. “So many people come up to me afterwards to say, ‘Thank you for telling me it is okay to have a different perspective.’” But she wasn’t always comfortable voicing her own views, she blogged, adding: “Chris did that for me.”

By mid-2006, Hunt and Messina were feeling a little hemmed in. Their apartment, which they shared with Tad, was home, office, and hub for their growing list of side projects. They needed real office space and a place to host events. The year before, their technologist pal Brad Neuberg had essentially started the coworking movement, coining the term and running a space two days a week in the Mission district. But he was ready to pass on the idea to someone who had time to nurture it.

Messina immediately saw the connection to his larger vision. He remembered his time with the Dean campaign: “Our civic spaces—places where you can meet and talk, and where you don’t have to buy your way into the space by being a consumer—were diminishing. I thought that it was really too bad that while I was organizing people on a grassroots level, we didn’t have spaces to bring them together.”

What Messina and Hunt had in mind would be much more than the typical shared office space, where everyone divvies up the rent and the monthly tab for fair-trade coffee, then retreats to separate cubicles, iPods in ears and noses to grindstone. They imagined a new kind of work environment, in which people from disparate backgrounds and fields—maybe a videographer for nonprofits, a freelance reporter, and a web consultant who plays in a rock band where all the members dress like clowns—would work in close proximity, talking to each other, brainstorming, and creating moments of “accelerated serendipity” (which Hunt defines as “everyday magic…that stuff you couldn’t have planned in a zillion years but is exactly what needs to happen to get to the next level”).

By now old hands at bringing new ideas to fruition, Hunt and Messina dove in with typical gusto, organizing a series of public meetings and posting the notes and business plans on a coworking wiki site. After a brief trial in a live/work loft in Dogpatch, they found a permanent space in SoMa, a few blocks from their apartment. They slapped some celadon-green paint on the walls, brought in some furniture from IKEA, laid down bamboo flooring, decorated the bathroom like a tiki lounge, and dangled a chandelier, which Hunt found on eBay, in the conference room. A group of rent-paying tenants got their own desks and keys to the building, but anyone could drop in. The Wi-Fi, tea, and snacks were gratis—you just had to call ahead to make sure someone was there to let you in.

Amazingly, the whole arrangement seemed to work beautifully. “One day, I was having a problem with WordPress—I was trying to put video on my blog, but it kept breaking and it was so frustrating,” recalls Lee Rodrigues, an early tenant. “And the guy across the table said, ‘Did you check this?’ I said, ‘How do you know so much about WordPress?’ And he says, ‘Well, I helped create WordPress.’ That’s why coworking is so great—you don’t know who you’re going to meet.”

It was an idea—social networking meets real life—that seemed to capture a moment and a yearning. As word spread, dozens of similar spaces popped up from Philadelphia to Perth, Australia, with Hunt and Messina fanning the excitement in any way they could think of, including an event last December that they called CoHopping. Hunt decorated the office for the holidays; Messina gave a speech envisioning a network of spaces that would let coworkers “travel around the world...learn a little bit more about each other, find out what other cultures are experiencing, and maybe raise the stature of civilization through mutual understanding.”

“Lofty goals!” Hunt interjected, to laughter. Then, toting glasses of wine, the group boarded a biodiesel bus for a tour of coworking spaces around the city.

A week later, I met Hunt and Messina for lunch in South Park, where they bubbled with enthusiasm for their many projects, the people who made them possible, and the underlying motives that help sustain any group endeavor. “Without community, we’d be nothing,” Hunt said. “I learned early on that one person can only accomplish so much. But community is not just full of altruistic people who are just nicey-nice. Human beings are selfish naturally. If a community is working well, everyone is contributing to their own end. Otherwise, you’re going to feel trapped.” Messina nodded in agreement, adding, “That’s our payoff—being able to connect with people who share similar passions, which gives us the energy to do what we’re doing.”

But they didn’t agree about everything that afternoon. There was a squabble about their travel plans to Canada for the holidays, then about a mundane detail of the coworking listserv. At one point, Hunt remarked that Messina inspired her deeply, but he was more sparing in his praise. “She’s a good marketer,” he mumbled. I remembered hearing Hunt nag Messina the week before about helping her arrange the space for CoHopping, which he did only halfheartedly.

Somehow, the fissures are always easier to see in hindsight.

On New Year’s Eve, Hunt and Messina and some of their friends each picked a “theme word” for 2008—one that would resonate in the year ahead. Thinking of all the projects she was wrapping up and the new ones she hoped to launch, Hunt chose transitions. Mes­sina announced that his word was “conduct (in all its meanings),” though he didn’t explain why.

Two weeks later, Hunt was facing a transition she clearly hadn’t anticipated. “While we’ve found great success in our professional endeavors, we’ve often struggled to find a balance between love life and work life,” Messina wrote in a post cross-linked with Hunt’s blog. “And even after working at it for some time, we finally decided today to end our romantic relationship.”

Hunt was heartbroken. “I still love Chris very much…and respect him highly. He means the world to me,” she blogged the same day. “But it is something that we needed to do. Although our intellectual and professional relationship is awesome and we continue to collaborate, we hadn’t been paying much attention to the emotional side for quite some time.… This sort of neglect takes a toll on a love life, and we just didn’t want to continue to hurt one another.”

In retrospect, Hunt’s recent writings had been filled with subconscious clues that something was amiss. The upbeat posts from November, with titles like “My Seriously Serendipitous Life,” gave way in early December to “Risk, Decisions and Consequences,” in which she wrote that “the biggest risk is the one of believing in something that is not part of conventional wisdom and then pursuing the proof of that belief over a longer term. The risk is that maybe you are wrong.” By mid-December, in “Dear Head, meet Heart…and vice versa,” Hunt was stubbornly insisting, “Opposites DO attract. And they work very well together.” But two days before the breakup, she seemed uncharacter­istically subdued, reflecting on the growth opportunities presented by failure in a post entitled “The Human Body Teaches Us to Embrace the Chaos.”

Still, friends were stunned by what one immediately dubbed “Breakup 2.0,” as well as its implications for the vast and vibrant community Hunt and Messina had brought together. In the days after the announcement, the most common reaction on Hunt’s blog was the eloquently speechless “*hugs*.” Even digerati accustomed to constant tweets about friends’ every thought and action were impressed by how seriously Hunt and Messina took their self-declared responsibility to live out loud. “Chris, you and Tara both continue to inspire by your bravery, strength, and trust in openness,” a friend wrote on Messina’s blog. “I felt this announcement in my gut,” another person wrote to Hunt. “What a life/world it is to be announcing a breakup so publicly, with such an emotional impact on such a broad network that cares about you. You’re navigating something that few people have had to navigate before you. I wish you strength, support, and a large open unpodcasted space that you can fill with screams.”

At the same time, not everyone believed Messina was being been completely honest. “Why is it that it feel[s] like Chris’s post is spin control,” one commenter asked Hunt, “and your post is the emotional disclosure with notes of betrayal and pathos?”

That astute observation went to the heart of the couple’s problems, but Hunt refused to take the bait. “Knowing Chris as well as I do, I know that his message was as heartfelt as it gets,” she responded, diplomatically protecting her ex. “One of the ongoing issues in our relationship was that he had a tough time expressing himself emotionally and I had too easy of a time expressing myself emotionally. So, yes, I speak from the heart, but when I read Chris’s post, I was really impressed how much he actually did get out of his head. What you are observing is our true personalities coming through in our writing.”

She ended the post with a smiley-face emoticon.

Immediately after the breakup, Hunt and Messina put on their own game faces. They continued to work together every day at Citizen Space, and when I called Hunt in February to ask her about what had happened between them, she consulted with Messina on the answers—he was sitting a few feet away at his desk.

Within weeks, though, their hope for a smooth switch to an entirely professional partnership faded. The reason for the breakup finally emerged—Messina had started a new relationship—and the devastated Hunt, as she later described it, “let my fully human side splash all over the Internet.”

The depth of her grief was apparent in a heart-wrenching poem she posted under the headline “Body content and soul”:

my 2000 friends aren’t really here to
open their arms and pull me close and
tell me everything is going to be okay
he won’t post a sign
when did he link to her instead?
yet I continue to publish my shattered ego
over and over again
read in several continents
i’m sure they’ll love me more for it
but he won’t
his flesh and blood self is tangled in her real arms
while I send my messages off to be read from afar
I just want to be touched again
really touched
not poked or messaged or emailed
touched
I want those arms to be mine and the tangles to wrap me up

the man who related more to his machine
than my body is using his body to heal
and i’m left with my machine

Within a few days, she had recovered her equilibrium a bit. Clearly she was having second thoughts about making the poem public—“Perhaps I have lost some professional luster to some,” she conceded in her blog—but on the plus side, “The outpouring of support from my friends [online] has been overwhelming…[with comments like] ‘Keep it up. It’s helping me come to terms with my own divorce’ [and] ‘My daughter just went through a sad breakup. I’ve been showing her your tweets to help her through. It’s working.’” Nor was there much lasting fallout on the job front. “My vulnerability seemed to make me more qualified to be a community consultant. Citizen Agency had more inquiries, not fewer. I’ve had endless lunches, dinners, coffees, etc. with people who are all interested in working with me…and us.”

On Messina’s side, the reaction on his blog and in his encounters with Hunt was silence. “We haven’t really talked about it,” she says now. But the need to disentangle their personal and professional relationships had become obvious. They separated their desks at Citizen Space, started seeing a couples’ therapist, and made a point of scheduling their lives so that they were rarely in the office at the same time. Hunt also banned Messina’s new girlfriend from the premises. As she told me last March, “Very few people break up and have to spend every day together, especially when there’s a betrayal involved, right?”

She sounded wistful as she reflected on what their union had allowed them to accomplish. “I don’t think we would be where we’re at today without us coming together,” she said. “Although I think we would have probably eventually gotten to our respective positions, I think it would have taken a lot longer and it would have looked a little different. I think we were really good for each other when we were together.” But until the wounds heal, she added, “It’s hard, it’s sad.”

Over the spring and summer, things got better for Hunt. She was constantly on the road, giving presentations and planning BarCamps, including this fall’s (Super)HeroCamp, a brainstorming session in Houston about ways to improve education that was inspired by her son. She finished the first draft of her first book, The Whuffie Factor, about the importance of social capital—networks, community, reputation, and so on—in marketing and business. (“Whuffie” is what Cory Doctorow called social capital in his 2003 sci-fi novel, Down and Out in the Magic Kingdom.) It will be published in November, after which she’ll embark on a book tour.

She also started a new relationship with a bioengineer in Houston whom she met at the CoHopping event last December (she recently helped him open a new coworking site in that city). She tweets about him frequently and sent around an Evite to a dinner party so friends could meet him, but rarely mentions him in her blog—her posts are mostly work-related, she tells me, and besides, it’s early in their romance. “I’m being cautious. I don’t want to jump too quickly.”

She adds that one of the great lessons she’s learned in the last few months to be more accepting of other people. “That was the problem with Chris. I was always wanting him to be more emotionally open, with me and the world, instead of radically accepting him as who he was.” He tried because he loved her, Hunt says. “I think he can breathe easy now,” she laughs.

Indeed, Messina has gone back to impersonal posts about “activity streams” and a “universal location layer for the social web.” In May, he started a full-time job for a company called Vidoop, working on DiSo, a pet project of his that aims to promote more open, interconnected, and distributed social networks. He still owns Citizen Agency and is tangentially involved with Citizen Space, but he’s hoping to start a new coworking site. He’s also juggling a slew of boundary-pushing projects such as OpenID and OAuth, which he likens to “a valet key for the web—a secure way to provide third-party websites with your information without giving them your password.” Someday, he hopes, platforms will be so open that people will be able to move as easily across Facebook, MySpace, and the like as they can from kitchen to bedroom to den.

When I ran into Messina at the Web 2.0 Expo, he told me, “I feel like I’ve aged six years in the last six months. I’m gaining a much more sophisticated understanding of both human relationships and the variety in what people expect, need, or want from technology. Through this breakup, it’s been interesting to see the degree to which Tara is able to be extremely free in her expressions, in a way that I suppose is helpful for her.”

But his own ideas about openness have changed. “I think information should be open and free and available,” he says, “but not everyone should let all information about their relationships be public all the time. Some things should be private.”

I understand where he’s coming from, of course, but it also strikes me that his experimentation with emotional transparency contributed something important to his community. As people get lost in the infinite Internet landscape, a nagging emptiness grows. As Jacob Sayles, a programmer from Seattle who started a coworking site, told me, “You have to understand what technology can do and what it cannot do. And what technology cannot do is sit and have a beer with you.”

That may be the reason why the successes and failures of Tara Hunt and Chris Messina have resonated so deeply. The two of them are a glorious reminder, in a profound moment of digital dislocation, of what it means to live passionately, to suffer enormous loss, and to rekindle hope IRL. “They stand out because they’re real,” says Erica O’Grady, a social media consultant from Texas who’s a good friend of Hunt’s. “I think it’s good for us in the world that we live in today to know that we are all human. It’s a world of humans, and Chris and Tara know how to express it.”


Bernice Yeung has written for
Mother Jones, the New York Times, and Wired.