I am allergic to generalizations, so I felt a bit sick when I read that "the real limit is the mentality that MOST young Italians have: risk aversion, fear of failure, sense of self-entitlement, fatalism, cynicism and envy". I'm not a hater here, I hate haters :P Just trying to show the other side of the coin. Moreover in the post you (implicitly) focus on tech/web startups. What about traditional startups in Italy? Btw thank you for your response.
I've actually been part of ISS for a while, and am familiar with the great minds that it attracts. I even talked about it on Stacktrace: http://stacktrace.it/2011/01/25/intervista-con-stefano-berna...
Unfortunately, it's still a group of 3000-4000 people only, from which you can't really draw conclusions about a country of 60M people.
On the bright side, it's a light in the dark and one of the most exciting communities I've seen in Italy.