In my experience we are either viewed as some not very serious country, thanks largely to the way Italian politicians have represented us around the world, or simply totally ignored.
At the same time, the feeling I got from with Dave Winer, while he was visiting a couple of weeks ago, is that our country doesn't look any worse than most western countries, and while we Italians tend to harshly criticize our own country, most stuff seem to be working pretty regularly to an outsider.
Then there is ignorance. Most of the world has a very fuzzy idea about us, in part thanks to popular but not very Italian imagery (the Sopranos, for example), and while I agree that Italy should not be put in the same league as India and Korea (I wish we had their resources and growth rate!), I don't think that with his remark Robert was expressing an opinion about our Country.
It would be interesting to hear a comment from Marc Canter, who is spending a couple of months in Trieste with his family and apparently is enjoying the experience (also if it's not clear if it's just about the food...).