Does Quora Really Have All the Answers?

Quora founders Charlie Cheever (left) and Adam D'Angelo at their Palo Alto headquarters.
Photo: Joe Pugliese

Craig Montuori, Caltech class of 2008, knows he should devote every waking moment to the startup he cofounded last year. Yet he compulsively spends two or three hours a day on Quora, a question-and-answer website he describes as “very addictive.”

Michael Wolfe, an entrepreneur deep into his fourth startup, also can’t help himself. If Quora sits open in his browser, he feels its tug. Someone will pose a question in one of his areas of expertise—the Silicon Valley startup scene, for example, or venture capital—and “it’s Pavlovian,” he says: He feels compelled to respond immediately and with enough authority that votes from fellow users push his answer to the top. Wolfe has forced himself to stop using the site at work. “If I didn’t limit myself, I’d check Quora relentlessly,” he says.

George Kellerman discovered Quora last fall. At first, Kellerman, who consults for startups looking to do business in Japan, didn’t know what to make of it. Tentatively, he answered a couple of questions. People were encouraging. He answered a few more; soon he was hooked. “I spend practically every free moment I have on Quora,” he says. “It’s the only thing I find intellectually stimulating on the Internet anymore.”

Quora’s founders were both star engineers at Facebook, a fact that might help explain how their young site has hooked so many users—some 200,000 people currently visit the site each month. The Facebook factor was also enough to draw scores of would-be investors before anyone knew a thing about the startup. The company has yet to earn a dime in revenue and won’t anytime soon, even as it has raised more than $11 million in financing and could drum up four times that with a few phone calls. One of its early funders, Keith Rabois, a so-called superangel who has invested in more than 60 companies, believes Quora could be the most important startup since Facebook and Twitter. Max Levchin, a PayPal cofounder and the brains behind Slide, a media-sharing site that Google snapped up last summer for $179 million, has said pretty much the same, tweeting that Quora may one day rank among the web’s 10 most valuable businesses. If Quora can fulfill its vision—getting experts to engage in its rollicking conversation and thus generate searchable and authoritative answers to thousands upon thousands of questions—then it may someday grab more pageviews than Wikipedia by filling in the gaps that no encyclopedia could ever address.

On many sites, people value the funniest or snarkiest answers; at Quora, the coin of the realm is honest intelligence and wisdom.
Photo: Joe Pugliese

Yet the love affair between tech-industry insiders and Quora isn’t just about the payday they foresee for its founders and, in a few cases, themselves. The pull is far deeper, and odder, than that. It’s hard to think of any website that has ever inspired this level of personal ardor among entrepreneurs and investors, not just as admirers or enviers but as users. These men and women (mostly men) don’t merely spend hours every day, despite their all-consuming work schedules, posing and answering questions on the site; they indulge in rhetoric that floats high above the typical boilerplate about startups changing the world. Quora is “a micro-university,” says Chris McCoy, an entrepreneur from Sunnyvale; it’s “the modern-day equivalent of the Library of Alexandria,” says Ari Shahdadi, a New York-based lawyer who works with startups. Savvy users like them know from personal experience that most companies fail, that new websites flare up and fizzle out like fireworks. And yet they somehow have come to see Quora as far more than just another online venture: It’s nothing less than an extended family, a virtual salon, a potential revolution in knowledge.

For that revolution to succeed, Quora will need to achieve something even more implausible. It will need to replicate—in hundreds of communities and fields of expertise far from San Francisco Bay—the same kind of fervent engagement that it has sparked among Silicon Valley insiders. The site has already shown what it can accomplish inside a small biosphere of like-minded people with high IQs and outsize ambitions. That was the easy part. The big question now is: Can Quora really hope to answer everything?

In 2005, The Onion imagined a new product from Google called Google Purge. Its purpose was to delete from our brains any information the search giant could not index. What’s the use of harboring private experiences, after all, if they can’t be cataloged and accessed via search?

Google Purge was a joke, of course, but buried inside the satire was a kernel of seriousness. Two decades after the invention of the web, there are vast areas of knowledge and experience that are still not online, let alone searchable. Wikipedia, which just recently celebrated its 10th birthday, is astonishing in its breadth and scope, but there’s only so much that any encyclopedia, limited to verifiable facts about discrete nouns, can capture within the entirety of human knowledge. On the other end of the spectrum, sites like Facebook and Twitter allow people to describe their lives and to make personal observations, but on such networks it’s hard to separate the informed opinion from the pure speculation.

The large expanse between the two approaches—the purely objective and the purely subjective—is the terrain that Quora hopes to occupy. What was it like to live in Silicon Valley in 1998? What goes on neurologically when a song lodges inside a person’s head? What should the Winklevoss twins have done to protect their idea for Facebook? Will human consciousness ever be transferable to a computer? Those are questions no encyclopedia could ever hope to answer fully, and yet in each case, there are people who can tackle them with a fair bit of authority. For years, blogs have occupied this territory, but their idiosyncratic and diaristic style has left their insights largely inhospitable to search. By creating an environment for members to post and answer questions, as well as rate the quality of others’ answers, Quora is building a searchable repository of information while it also builds a community.

“Ninety percent of the information people have is still in their heads and not on the web,” says Charlie Cheever, one of Quora’s cofounders. According to Cheever, Quora’s goal is to capture as much of that subjective knowledge as possible. “There’s no place where you can put all this wisdom you accumulate over your life or these things that you just know,” he says. “And that just seems such a valuable piece of what people have to share. It seemed a shame not to have someplace to share that.” Quora’s other founder, Adam D’Angelo, Facebook’s first CTO, calls it “experiential knowledge.” Unlike with Wikipedia, whose searchable trove has been built on the backs of tireless amateur researchers, Quora hopes to attract so many users that their inherent knowledge will construct a comprehensive picture of the world.

The site’s design is fairly simple, though not as intuitive as it could be. You can begin with the page—framed as a question, naturally—about getting started on Quora. Or, if you’re not one for reading the manual, you can begin by sifting through random questions that are displayed in the center of the screen. Up on top there’s a big search bar. Using keywords, you can find questions that others have already posed or choose topics to follow so that the site can begin serving up queries more suited to your interests. You can also start following people. That way the questions they ask, answer, and follow will show up in your feed, not unlike on Facebook. You can vote up answers you think are helpful (“helpful,” along with “authentic,” being the favored compliments among Quora loyalists) and vote down those that aren’t. All of that activity shows up in your feed as well. Like on Facebook, real names are mandatory, so there’s a social cost to acting the fool. (The service does allow for anonymous posts, however, which helps when asking about a personal health issue, say, or responding about your own experience as a fellow sufferer.)

Browse topics within the tech industry and it’s easy to see why the rhetoric about Quora has been so high-flown. The amount of knowledge that has been poured into the site is phenomenal. Users ask questions about raising capital, or about booting a cofounder who fails to pull his weight, and almost immediately a discussion sprouts up among seasoned engineers, investors, and CEOs. Sometimes, it’s almost comic how questions will draw cameo appearances from the exact person who can offer the most insight. How did Friendster blow it? Jonathan Abrams, the company’s founder, is among those who posted answers. Why did AOL make a particular decision? Here is former CEO Steve Case weighing in with his perspective. Netscape cofounder Marc Andreessen has dropped in to answer questions; so, too, has Reed Hastings of Netflix and Rob Glaser, founder of RealNetworks.

Quora co-founder Charlie Cheever 
Photo: Joe Pugliese

Stray from the startup scene, though, and Quora can look disappointingly like a ghost town. Marc Bodnick, who works in product marketing at Quora, insists the site isn’t just about Silicon Valley; he points to movies, where the site is supposedly “amazing.” Yet a search for five seminal films from throughout Hollywood history (On the Waterfront, Wall Street, Raging Bull, All About Eve, Annie Hall) yields nothing at all. Quora’s Oscar coverage, Bodnick says, was similarly amazing. But look forThe Fighter, a film that saw two actors take Academy Awards in February, and all you find is a single question (“Is that Christian Bale’s real hairline?”) with a correspondingly trite answer—a best guess, really, by someone whose only stated credential is being a devoted viewer of Bale’s films.

Certainly it would be unfair, less than two years into Quora’s existence, to judge the site by what’s missing instead of by what’s there. But Hollywood is an instructive example, because it highlights not just the gaps in the site’s breadth but the huge challenge Quora faces in filling them. Let’s stipulate right off the bat that the film equivalent of tech CEOs—the Martin Scorceses and Natalie Portmans of the world—won’t be showing up to answer questions very often. But to replicate for movies what the site has accomplished in tech, Quora will at least need to lure the producers, the critics, the film scholars, the gaffers, and so on: experts from overlapping but very different communities, some of them far-flung around the country or the world. And that’s just for movies; now imagine that same problem multiplied by a hundred or by a thousand.

Quora wants to replicate the exhaustiveness of Wikipedia, but to do so it would need to achieve the ubiquity of Facebook. The odds against emulating either web titan are steep; the odds against both, enormous.

The basic concept for Quora was born in the fall of 2008, when D’Angelo had already left his CTO gig but Cheever was still working as an engineer. Over Chinese food near Facebook’s offices, the two discussed what they called “latent markets”—areas of online behavior in which consumer demand was clear but existing solutions were lacking. Maybe the biggest example, they realized, was sites devoted to answering questions. A sizable portion of Internet searches are framed as questions; Yahoo Answers, the Q&A site created by Yahoo in 2005, attracts more than 50 million users in the US every month. But few searchers can be satisfied with Yahoo Answers, where the silliness of the questions (a recently featured question of the day: “What if you ask a woman if she’s pregnant and she’s not?”) is exceeded only by the inanity of the replies, which tend to be wild guesses offered by people with absolutely no knowledge of the subject. Cheever and D’Angelo found something perversely inspiring about Yahoo Answers and other similarly mediocre Q&A sites like Answers .com. “These other sites were a mess, but they were still popular,” D’Angelo says. “That told us that we were onto something.”

In the Q&A format, they realized, there was an opportunity just as ripe as the one that had made Facebook a billion-dollar business. The early leader in social networking, Friendster, had terrible technology. The advertising-heavy MySpace, which dethroned Friendster, was a bit like Yahoo Answers: chaotic and low-rent, prone to spammers and scams. Yet both were immensely popular—until Facebook came along and figured out how to do social networking right.

D’Angelo and Cheever seemed almost destined to be part of Facebook’s rise to dominance. The former’s relationship with Zuckerberg dates back to high school: The two became friends at Phillips Exeter Academy, where both had been late arrivals, transferring to the school in the 11th grade. D’Angelo might have been the better programmer—according to the fall 2001 Exeter Bulletin, he took eighth place in that year’s USA Computing Olympiad. When D’Angelo was a junior at Caltech, he put his studies on hold to spend a semester helping his friend during the early days of Facebook. After completing his degree, he immediately headed north to Palo Alto to become the site’s VP of engineering, and Zuckerberg soon created the role of CTO for him.

Quora co-founder Adam D'Angelo 
Photo: Joe Pugliese

Meanwhile, Cheever—whose claim to fame was heading up Facebook Connect and Facebook Platform, which have entrenched Facebook’s dominance by integrating it with millions of other websites—had in his low-key way been Zuckerberg before Zuckerberg. Three years ahead of the soon-to-be-billionaire at Harvard, Cheever had his own brush with the admin board after he wrote a program that let people search the university’s student directory. It seemed harmless enough, but technically, Cheever, like Zuckerberg, had violated university policy. Unlike Zuckerberg, he took his admonishment without protest—and he graduated.

As far as Cheever can recall, the two men met only once at Harvard—when his future boss tried out for his Ultimate Frisbee team. “He only came to, like, one practice,” Cheever says. By the time TheFacebook was founded, Cheever was living in Seattle and working for Amazon.com, but because he still read the Harvard Crimson (he had helped design its website), he was in the first group of 1,200 to sign up. In late 2005, when a Facebook recruiter emailed him to ask about coming to work for the company, he was 24 and couldn’t imagine working for someone younger than himself. But he soon changed his mind when two Harvard friends in Seattle told him at a party that they were leaving their jobs at Microsoft and heading to Facebook. Still at the party, Cheever fished out the old email and replied to the recruiter.

Cheever is tall and slim, with blue-eyed, Lifetime-channel good looks and scruffy hair. He’s polite, coming across as thoughtful and sincere but also shy, and has an engineer’s habit of employing superas an all-purpose adjective. (“I was super-glad I didn’t get in the movie,” Cheever says of The Social Network. “It wasn’t super-flattering.”) D’Angelo, who fills the role of company CEO, comes off as similarly modest. Also tall and thin with tousled hair, he has an easy, toothy smile that he flashes often, but he isn’t exactly comfortable talking about himself. When called upon to do so, he tugs at his midsection, clasps his hands between his knees, and contorts in his chair.

By the time D’Angelo left Facebook, in the summer of 2008, he felt that he was “in a good position to start a company,” he says, though nothing jelled right away. But when Cheever left in March 2009, the pair immediately started working on a project they called Alma Networks, after the street in Palo Alto where Cheever lived. That summer they made their first two hires—Rebekah Cox, a top designer at Facebook, and Kevin Der, an engineer—and set to work building their online service.

That fall, the four were ready for users to try out the site. They launched as a private beta and gave out the invitations to friends and friends of friends. As a result, Quora’s earliest heavy users tended naturally to be fellow players in the startup game. Very quickly the beta site grew into a fascinating reflection of the collective Silicon Valley psyche. Try as some might (and The Social Network did) to sell the startup life as a world of clubbing and party houses lubricated by appletinis and dope, the reality is both more sober and more emotionally fraught. The real young denizens of Facebook and other startups, Quora included, have little time to do much beyond work, sleep, and banter about one another’s companies. Cheever’s existence, for instance, is basically confined to a tiny patch of Palo Alto; he usually works till 2 or 3 am before he trudges the five blocks home to his bed.

Most of Quora’s early users were no different, and they immediately began asking questions drawn from the same hopes and fears that fueled their manic days. In response, they’d hear from a veritable who’s who of big Valley names stopping by to voice an opinion or share a story.

In just 15 months, Elevation Partners’ Marc Bodnick posted 3,500 questions—and answered another 1,200 himself.

“You would think that people with critical thinking ability and not a lot of free time would be perfectly immune to this kind of thing,” says Levchin, the PayPal cofounder. Levchin admits to spending the better part of a day sifting through old diaries and looking up domain registration dates, all because a stranger asked him on Quora to describe the four startups he founded before PayPal. “I think the lesson of Quora,” he says, “is that successful people are just as vain and just as interested in praise for a good answer as anybody.”

One of those who “begged an invite,” as he puts it, was Marc Bodnick, cofounder of Elevation Partners, a Silicon Valley-based private-equity firm. Elevation makes large, late-stage bets (typically $50 million or more) on technology companies. It was Bodnick who steered his fellow partners toward early ownership stakes in Facebook and Yelp, and he was determined to see what Cheever and D’Angelo were up to. When he started reading the Harry Potterbooks to his kids, he felt he was missing some of the nuance of the series, so he posted a few questions on Quora about the books. Soon it became a nightly ritual: After the kids went to bed at 8, he’d spend the next four hours on the site, posting and answering on all manner of subjects and even suggesting corrections to other people’s posts. All told, Bodnick—a managing director at a $2 billion fund whose other partners include Bono and VC legend Roger McNamee—posted 3,500 questions in 15 months, or an average of eight per day, and answered another 1,200 questions himself.

At the end of January, just a week before I met him for this story, he informed his partners that he was leaving Elevation Partners to become Quora employee number 18. “There are people who think I’m crazy,” Bodnick says. But how can he help himself when he believes that the company has the promise to transform human knowledge?

In an age of 140 characters, so much of the conversation throughout the Internet now takes place in short, timely bursts. Quora, by contrast, has a way of encouraging answers that are thorough and in-depth. On other sites, people tend to value the funniest or snarkiest answers, but in Quora’s community, the coin of the realm is your honest intelligence and wisdom.

It helps that users can vote an answer up or down, the better to push quality to the top and push down (if not off the page entirely) the frivolous and poorly conceived. A button was even added that allows users to deem an answer “not helpful”—a signal to the Quora team or one of the site’s 100-plus volunteers that perhaps they should consider deleting it.

Contributing to Quora can leave some people with bruised feelings. Unlike on Facebook, everything you write can be trimmed, corrected, or otherwise massaged by one of the rigorous volunteers. “An answer isn’t written for the person who added the question,” as D’Angelo puts it. “It’s written for the world, and for anyone who has that same question for the rest of time.” Volunteers often send answers back to their authors marked up with suggested cuts and changes. Questions, too, can get extensively reworded. And heaven help the newbie who starts taking wild guesses at answers, as if Cheever and D’Angelo’s Olympian creation were nothing but Yahoo Answers with superior graphic design. One user publicly “banned himself” from Quora because he was tired, he wrote, of warring with the “petty bureaucrats” who police the site with their “arbitrary” rules and “righteous” attitude.

Food commissary at Quora HQ
Photo: Joe Pugliese

Michael Wolfe, who started using Quora when it was in beta, is one of those so-called bureaucrats. He knows he and his fellow volunteers can come off as pedantic. Their lectures about respecting the community, he acknowledges, “drive some people crazy.” But he doesn’t care. “The community is somewhat unforgiving,” he says. “But if the site appealed to the lowest common denominator, it would become a cesspool of crazies—and then a lot more people would get turned off.”

A precise and friendly man with short-clipped reddish hair, blue eyes, and a bland expression, Wolfe boasts a résumé that would be extraordinary if he lived anywhere other than the Bay Area. A company called Kana he cofounded in 1999 went public; in 2007, he sold his next company, Vontu, to Symantec for $350 million in cash. Wolfe was working as an entrepreneur-in-residence atBenchmark Capital, a top-tier VC firm, when he got his invitation to Quora. As a married 42-year-old with two kids, his expectations were low. “I’m not a social networking, Meetup, Twitter kind of guy,” he says. He logged in to Facebook maybe once a day. But with Quora it was immediately different. “Some days I check my Quora account before my email, I’m embarrassed to admit,” he says.

The question Wolfe can’t quite answer is exactly why he does it. A good response can take an hour or more to write, he says, and in a year’s time, he has posted more than 500 responses—that’s more than 12 weeks of full-time work. Given his family responsibilities, his new startup, and a fitness habit that already eats into a large part of his free time—he’s been competing in triathlons for 15 years, occasionally taking first place in his age group—he knows Quora is a huge and probably unjustifiable time sink. Wolfe is nothing if not a disciplined person; Quora is clearly, for him, a deliberate decision. He sees it as not only better than watching TV (“it’s more engaging, it’s more relaxing, and it’s obviously more rewarding”) but as a benefit to the professional community to which he belongs. “I’m constantly answering questions I wish someone answered for me 10 years ago,” he says.

In fact, Wolfe beams when he describes what all of his, and others’, answers amount to: nothing less, he believes, than the fullest road map ever drawn for starting a company in Silicon Valley. Maybe contributing to Quora, he says, is like the urge some successful people have to teach a course at a local college. Quora is even better, though, because the experts get to interact with fellow experts and to learn (for better or for worse) how their insights are received.

“This will be a party for the ages,” Wolfe says on a cold Saturday evening this past January, shortly before we join roughly 150 other revelers at the Old Pro, a restaurant and sports bar in downtown Palo Alto, for Quora’s super-user party. He’s wearing a dark sports coat over a plaid pink shirt, and every hair has been groomed into place. A 23-year-old software engineer who has been following Wolfe’s posts for the better part of the year (and who wanted nothing more, according to one Quora post, than to become “obscenely rich”) comes over, and the two continue a debate they’ve been having online. Soon, Wolfe gets a solid 15 minutes with D’Angelo, who, in stark contrast to Wolfe, is hosting the affair in programmer-casual attire: T-shirt and light jacket.

A week before the party, TechCrunch bestowed on the company its Crunchie award for best new startup, and the inevitable backlash had already begun. Most of the complaints revolve around the idea that Quora, like Facebook and Twitter before it, had become just another popularity contest, another way for people to promote themselves. The super-users at the party don’t buy that critique, though, in part because they know so many of the players personally. “This isn’t about job searching,” Wolfe says. “It’s not about raising money. Most of us who are heavy users can already do that without help. It’s a sense of sharing what we know, and it’s being part of a community.”

Rabois, the superangel, agrees. He hardly needs Quora’s help to raise money or attract talent: After stepping off the partner track at a big New York law firm, he has worked at PayPal, LinkedIn, and Slide, and he’s currently the number two at Square, a San Francisco startup trying to turn any smartphone into a credit card reader. (Square, in fact, was the runner-up for that Crunchie award.) Rabois logged in to Quora for the first time on New Year’s Day 2010 and immediately got hooked. He sees Quora as a rare oasis of intellectualism in a world dominated by the commercial and the superficial.

Not that the utility of Quora’s user base has slipped his mind. “Fifty percent of the most talented people in the Valley are here,” Rabois remarks as he looks around the party. In only a year, he has made investments in two young startups he’d learned about through Quora and has made one major hire off the site. That happened at the previous Quora gathering, held at a gallery in San Francisco. The guy was so impressive that Rabois immediately ordered him not to talk to anyone else at the party.

Among the super-users, there’s one major complaint, and it boils down to declining quality. “So many stupid people are signing up,” sniffs Ethan Gahng, the 30-year-old CEO of a company called Lazyfeed. “Their stupid questions push down my questions.” Others are less harsh in their choice of words, but they don’t disagree. Even worse, all these so-called stupid newcomers are pushing up other people’s answers, when those answers are—to Gahng and his fellow super-users—inane or off point.

D’Angelo and Cheever express the same worries a few days later at their offices above an art supply store in downtown Palo Alto. At this point, with Marc Bodnick on board, Quora has 18 employees, and all but the receptionist sit in a single room around a rectangular formation of more than 20 desks. The whole room, at least this afternoon, is pin-drop silent except for the tapping of keyboards and occasional murmuring between neighbors. Meetings happen one story up, on the third floor, where Quora has rented a larger space that includes a half-dozen offices with doors. But for now those rooms sit pretty much unused. “I think we’ll get bigger, but we’re in no huge rush,” Cheever says. These are hardly the days of the first dotcom boom, when everyone seemed to be sprinting after an IPO; now the model is Facebook, which seems hellbent on remaining private (in all senses of that word) for as long as possible.

Both founders acknowledge that the average quality of answers on Quora has ticked down significantly. The site was flooded with so many new members at the start of the year—a fivefold spike in just a month—that at one point in mid-January, half of Quora’s users had been on the site for two weeks or less.

Cheever also understands that he needs to ease Quora’s focus away from Silicon Valley and toward the wider world. He gives examples of some of the new topics burbling up on the site: Farming. Curling. Romania. “It’s been really cool seeing the circle of people growing,” he says. But he also doesn’t argue too hard with the observation, clear to anyone who spends much time on the site, that the tech scene still vastly overwhelms other areas of discussion. “It’s changing slowly,” he says. A PR person follows up with a sampling of Quora newcomers, who include a veterinarian, an economist, and a screenwriter. But the list is dominated by tech people and students, which pretty much sums up Quora as it has developed so far.

For now, then, the revolution in human knowledge will proceed at a decidedly modest pace. Cheever, for his part, says he doesn’t much care that there are so many gaps in the site’s coverage. He mostly wants to keep up with the traffic and maintain the Quora etiquette—everything else seems like noise. Ask D’Angelo where he hopes Quora will be when it celebrates its 10th birthday and he is anything but evasive or modest: “We’d like to get to the point,” he says, “and I think this will come in five years, not 10, when any question you pose to Quora will have been answered, and you’ll have confidence that it’s true.” But Cheever, asked the same question, teases back: “We tend to look two weeks out.” Ten years is 260 times too far to query.