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My previous post on Twitter is the result of a discussion involving a couple of Silicon Valley’s thought leaders, related to what a business model for Twitter could be.

Jason Calcanis suggests what I think is the best one, that is an advertising message every “X” micro-posts (he calls it “in-feed advertising”). This is valid of course for any micro-blogging service. For Hictu, would you watch an ad-video post every X posts? I would. But more models are available. What about context-based advertising in ANY twit?

Let’s imagine a scenario like the following. I’m twittering, and chatting with some friends:

me: “I finally got my Macbook working again”
friend1: “@filos: why don’t you change you hard disk?”
friend2: “@friend1: I don’t recommend it, take it with you as is during your trip to California”

What if messages would appear like this:

me: “I finally got my Macbook working again *** Refurbished Macs - Buy a Macbook ***”
friend1: “@filos: why don’t you change you hard disk? *** PC Components *** ”
friend2: “@friend1: I don’t recommend it, take it with you as is during your trip to California *** Last minutes offering to California ***”

If properly separated from the main content, I think this approach is worth much more than what suggested by Calcanis. The reason is that the “persistence” of a Twitter message is not so long. I don’t care of every message and the probability I read an ad message is not high if I get an ad every, let’s say, 100 twits.

It’s pretty clear that not every twit would be designated to contain an advertisement, but I believe most of them would.

With context-based advertising, I’m targeting the right demographic at the right time. Nevertheless, Google teaches. Will Jaiku be the first to experiment something like what I described above?

The question is how many people will go on using Twitter given such approach. I would, since I understand that someone must pay, in the end. But how many like me?