«10 y.o. technologies are history. 10 y.o. software without major upgrades is dead. While 10 y.o. cars are quite good and decent.»
If the web does age, and it does, that should give us some pointers on what's wrong with it.
As for the Internet improving... well, during its 40 years of age we reviewed some protocols, added some others, but I'm not sure that's what the author implies. The Internet (not the web, the Internet: http://en.wikipedia.org/wiki/Internet_protocol_suite) of today is quite the Internet of twenty years ago.
But still, if you prefer to, we can go down to algorithmic level, where things never age if they're done right.
I think iteration is very powerful, but we don't seem to have fixed the problem of when something needs to iterate beyond its old ecosystem.
I haven't said that coherently, but I mean things like WordStar or WordPerfect moving from DOS into Windows - these two huge word processing systems failed to make the transition and are now niche products used by a tiny number of geek enthusiasts. They reached a point when iteration wasn't enough, and they needed some other thing.
I mean, improvements can be gradual or revolutionary. Still it is iterative process.
Maybe Fox/Hedgehog caregorization is not applicable to such huge companies. Most likely there are departments and products where foxes are in charge and vise versa.