Bad metaphor applied to a wilful mis-characterisation
I am no fanboy for Web 2.0 as a term, but you seem to think it is all about AJAXy interfaces, which is clearly false. O'Reilly talks about an architecture of participation in pursuit of collective intelligence, and his recent business-friendly exposition of the subject was, I think, intended to counter-balance the consumer start-up build-to-flip direction that most "Web 2.0 companies" have taken.
The Communist analogy is also a bit weird given we are talking about distributed systems and collective intelligence. If anything, existing enterprise software is closer to the Communist (well ... Stalinist) model and Web 2.0 is structurally closer to political movements such as Al Qaeda, unpalatable as the comparison may sound.
Tito, aside from being an extremely impressive leader, will be remembered as somebody who held together a diverse set of national interests with a powerful set of ideas under a clever collective brand. It worked wonderfully well during times of plenty, and within the context of a wider conflict between major powers, but became harder to maintain outside of this context. Perhaps the Yahoo CEO might want to bear this lesson in mind, but I think you are stretching the point by comparing Tim O'Reilly with Tito.