This Is Why Your Startup Failed: The Magic of Quora

by Adrianne Jeffries

I used to write for a tech blog that got a hundred pitches for no-name apps and companies every day. Sure, some of these emails would start with “Dear Sir/Madam” and continue: “We developed an innovative concept: a set of two connected lamps called Ping!” But most of the pitches I saw were from tech entrepreneurs pitching all the wonderful social networks, web sites and productivity tools you’ve never heard of. Some even sounded interesting, even if the sender was usually either insecure and desperate (“It would great if you could give us some exposure, because we don’t have any investors”) or delusional and PUMPED (“ called us ‘Twitter meets Groupon!’”) The thing would vanish regardless of whether we wrote about it, so you can scratch “insufficient enthusiasm in tech blogosphere?” off that sticky note you stuck to the mirror during your post-failure introspection. So why do so many startups fail so hard? Students of failure, I have found the answers, exquisite in detail, right here on the Internet! is a question and answer site similar to Yahoo! Answers, but much smaller, more feature-rich and way less dim.

The site was founded in 2009 by some former Facebook employees who have convinced people it’s worth somewhere upwards of $80 million. They raised $11 million earlier this year. Quora’s well-connected founders were able to get high-profile investors, entrepreneurs and personalities (Ashton Kutcher!) to sign up early, turning the site into a salon where techsters in Silicon Valley could talk inside baseball, like “Did Caterina Fake quit Hunch and if so, why?” (answered by Fake, who founded Flickr) and “Why has Craigslist innovated so little with its product?” answered by Craigslist founder Craig Newmark and 9 others (we’re all Craigslist experts now), and filed under the topic Questions That Contain Assumptions.

Other common constructions with their own topics on Quora include Is X Profitable, How Does X Make Money, and How Much Did X Acquire Y For, which is a wonderful catalog of cutesy startup names and Valley gossip, with queries like “How much did Kabam acquire Wonderhill for?” and “Is Adult Friend Finder really going around the valley begging VCs to invest in them?” (Ohhhhh shit!)

Regular people could care less, right? But one popular Quora topic holds interest for anyone interested in the human condition: Why Did X Fail. Quora now contains referenda on the likes of Google Buzz, Google Wave, Facebook Places, Friendster, “personalized news startups,” witch burning and “Studio 60 on the Sunset Strip” (actually, Why Did X Television Show Fail has its own sub-topic, but the only other question is about “Arrested Development”).

The Why Did X Fail questions often attract long thoughtful reflections by X’s founders. The question “Why did Jumpcut fail?,” referring to the video startup acquired and shut down by Yahoo!, elicited an earnest 830-word answer from a member of the Jumpcut team, mostly whining about the fact that Jumpcut never got hooked up with Flickr. But the answers come in from all over the web. Questions about failures at Kmart and Google elicited responses from former employees. The question about personalized news startups yielded a discussion so extensive and high brow, it was hard to believe it came from the Internet. Entrepreneur Nik Black wrote an extremely thorough 2,025-word pre-requiem, complete with 12 citations, for a company called Six Apart. Developer Eston Bond ruminated on memes, self-expression, novelty and penises for 1,925 words, in answer to a question about the decline of Chatroulette, the site that lets users video chat with random strangers.

These long-winded answers usually leave the impression that each startup was the victim of a perfect storm of problems.

Last week, News Corp hinted in an earnings call that it will shut down MySpace if the site doesn’t turn a profit, or at least stop bleeding money, soon. The suits are probably wondering the same thing posed on Quora: “Why specifically did MySpace fall so fast and so far?”

Here is a summary of the multi-step punch that knocked MySpace down: Users escalated their “freedom of expression,” a.k.a. sparkly animations, on their profiles until most of the site was painful to look at. For this and other reasons, including its immense popularity with 13-year-olds, MySpace got a reputation as a “cultural ghetto.” Then because of its bad rap, lack of stock options after News Corp bought it, and the facts that it was built on unsexy technology and based in L.A., MySpace had an “inability to recruit top-tier talent.” At the same time, MySpace was too focused on “young, alternative music lovers,” which drove away other demographics, and its “broad population of teenagers” began to flee. Then News Corp slowed down the company and squashed innovation with its “advertising priorities.” Also, Facebook came along (addressed more in a separate question under the less popular Why Did X Succeed).

Other companies were felled by some combination of PR stumbles, lack of resources, divisions within management, greed, strong competition, poor technology, being overrun by penises (Chatroulette) or users seeking “cyber pleasure” (Second Life), failure to recognize trends, lack of focus, etc.

However, I realized all the reasons for failure listed on Quora can be grouped into the following three basic explanations:

• People didn’t use it (it sucked, insufficient enthusiasm from the tech blogosphere, etc.).
• Incompetent management (greed, not enough resources, outdated technology, etc.).
• Got acquired by Google or Facebook and shut down.

The end.

Now that we’ve figured out why companies fail, consider this interesting twist. The ultimate Quora obituary would have to be for Quora itself. Why Did X Fail, the metameme. Every user on the site could offer a theory (confusing nested comments, encourages me to sign up with my Facebook account and I hate that, it’s a downer, not enough pretty pictures, etc.).

Of course if Quora fails, that’d be the most graphic answer of all — and the saddest, barring Quora and future failed startups from this ritual of public catharsis. Hang in there, Quora.

Adrianne Jeffries is a freelancer in New York City and person on Twitter.