Another problem is that in general there is no trust in the idea that you can create business in the Internet. In part this is due to the fact that the online advertising market in Italy is smallish at best, that users are rarely willing to pay for services, and other stuff like that.
But... I think italians too often overlook what is good about Italy, and if there was not this cultural brake we could do much more interesting things. For instance there is a model where it is normal for a son to stay in the home of the parents up to 30 years old or more, without the need of earning at all. This means that you can use a few years to develop your startup without any required money.
Also in my opinion Italy is a place with many talents. It's not hard to find good people, there are many programmers as in the 80s home computing and electronic was a real boom here as an hobby, and schools are still in decent shape.
So what should Italian entrepreneur do? It's hard to focus on the italian internet market as it's small, but it is either not very easy to penetrate the US market from Italy. It's a very hard question. I would say that probably it makes sense to still beat on the US market for a technological company, but perhaps not just with finished products for the end user, but also with business to business technology, or electronics (things like Arduino).
Unfortunately some fields where we could be very successful require money that is hard to find, otherwise Italy could be the "Apple" of all the things apple is not doing, mixing good design and technology. From alarm clocks to other kind of appliances that are usually poorly designed and ugly to see.
Well just a number of random ideas...