New York Times’ Randall Stross wrote a piece yesterday, outlining some of the “difficulties in making brand advertising work on social networking sites. Members of social networks want to spend time with friends, not brands.”

That’s a theme I’ve stressed on in posts as far back as in August, when I compared it to a Pyramid scheme. Call it what you will, but this idea of becoming pitch-men to your close friends could damage your social brand. As Randall writes:

And when they try to take advantage of new “social advertising,” extending their commercial message to a member’s friends, their ads will be noticed, all right, but not necessarily favorably. Members are understandably reluctant to become shills.

Why is Twitter different

However, in my estimation, Twitter may be immune to such ad targeting hardships primarily because of the inherent promiscuity in following and lack of intimacy with the nodes in the network that Twitterers exhibit. This strangely enough, leads to your sharing an incredible amount of information about yourself as candidly as possible!

So, while I carefully prune and maintain my true social network (~230 friends), I’m followed by nearly 2000 folks on Twitter. While I’ve shared ~600 Posted Items on my social networking site of choice, I’ve shared ~4000 tweets on stuff I love and hate in half that time. Here’s a sampling of thoughts/tweets, which is less than a week old:

Subscriptions to GQ & Esquire, Ads for Gap, Banana Republic?

What’s your favorite scarf wrap? http://tinyurl.com/6rmjmf I prefer the Loophole. 4:17 PM Dec 13th

Targeted Fandango ads, please…

Such a flattering review of “The Wrestler” and Rourke’s performance by the New Yorker – http://tinyurl.com/6djqa5 3:43 PM Dec 13th

Benjamin Button LA Premiere – Variety Photo Gallery http://tinyurl.com/5mocyf 12:04 AM Dec 10th

Netflix/Blockbuster DVD ads for either Jim Carrey movies or Nolan’s Dark Knight:

The Existential Clown, Jim Carrey – The Atlantic (December 2008) http://tinyurl.com/5k6shb

Christopher Nolan analyzes his favorite scene in ‘Dark Knight’ | PopWatch Blog | EW.com http://tinyurl.com/5566oy 11:04 PM Dec 9th

Guess what? I actually bought the Dark Knight DVD yesterday. I don’t mind if I’d received ads for a Dark Knight DVD or premiere tickets to the Wrestler. Twitter is like Google in that it’s intent based – in Google (you search for stuff and advertisers find you), while on Twitter (you say it out loud and advertisers could find you). Either way, there is massive benefit for the user.

In conclusion, Twitter would be a terrific buy for a search engine, where much of this valuable information is already being indexed. And, Given Ev’s (Twitter co-founder) history with Google (he sold “Blogger” to Google in 2004), the possibility seems all the more intriguing.

What do you think is Twitter’s easiest path to monetization?

Follow me on Twitter – http://twitter.com/mariosundar