Does Google have any chance at all of competing with arch-rival Facebook? Not really, former Google bigwig Paul Buchheit says. Buchheit tells us his old company will probably find it easier to land on the moon.

It's an important issue. If Google can't mount a viable challenge to Facebook, it will make the social network look all the more unstoppable to competitors and frustrated users alike. A series of privacy scandals in 2010 could not keep Facebook from reaching 500 million users, a huge milestone.

Having worked for both companies, Buchheit is in a good position to evaluate the "war" between the two companies over the social networking space. The engineer was employee number 23 at Google, where he invented Gmail and coined the slogan "Don't be evil." He left to create social aggregator FriendFeed, which he soon sold to Facebook for $50 million. He then left Facebook in November for a tech incubator.

Since then, Buchheit seems to speak more freely online. He has highlighted stories about Google's problems competing with Facebook, including a claim from a different Google veteran, quoted on the blog Mashable, that the company suffered from internal "disorganization and... teams working parallel or in conflict." He also wrote twice about how he thinks Google's ChromeOS is doomed.

Noticing this new frankness, we emailed Buchheit for more thoughts. He didn't tone down his take on Google one bit: "As for social, I expect that Google will find greater success with their self-driving car and moon landing initiatives. I think it's worth noting that the two most successful Facebook competitors, Twitter and Foursquare, were both started by people who were relatively unsuccessful at Google."

Here are a few of the questions we asked Buchheit and what he said in return.

Would it be erroneous to detect a bit of pessimism on your part about some of Google's big initiatives? Do you still think Google is innovating, on balance?

I'm actually rather optimistic about Google overall. The inevitable doom of ChromeOS is due in part to the huge success of Android. As for social, I expect that Google will find greater success with their self-driving car and moon landing initiatives. I think it's worth noting that the two most successful Facebook competitors, Twitter and Foursquare, were both started by people who were relatively unsuccessful at Google.

Good point on Android. You do sound a whole lot less optimistic about social. Why doesn't social mesh with where Google is strong, i.e. in basic engineering skills?

Well, that's a complex question, but the short summary is:

— Google's strength is in building large scale computer systems like BigTable [definition], and they reflexively try to apply that to all problems (if all you have is a hammer...)
— Facebook is also very good at what they do (unlike MySpace)
— The network effects in social are very substantial

The only good strategy I can see for Google is to create something fundamentally different from Facebook (like Twitter or Foursquare were), but Google probably doesn't have the right people doing that because of this problem.

[Buchheit is referring to the experience of Dennis Crowley, who sold his "check in" service Dodgeball to Google in 2005 and left unhappily two years later, citing a lack of support. He then started a virtually identical service called Foursquare, now valued north of $90 million and conquering a market Google considers a top priority.]

Facebook is indeed fearsome. But why would a strength and interest in building large-scale systems keep Google from building, say, a Facebook competitor? Bureaucracy? Or maybe you also mean not willing to jump into things that seem "too small," kind of a classic big company issue when it comes to emerging markets/tech?

It's a question of which skills are most highly regarded. Everyone has different strengths, and the people who are going to build the next Twitter aren't necessarily going to build the next BigTable as well. A culture that has been very successful with one strength can have difficultly recognizing others.

[Photo of Buchheit via Robert Scoble/Flickr]