Ultimately I think this comes down to two major issues with the papers. And by papers I’m referring to the top dogs like The New York Times, and small community papers and TownOnline (here in New England). In fact, I had the opportunity to interact with an exec at TownOnline/Herald Interactive and there was a sort of arrogance there – like they’re so far ahead of the rest of us that we should be so lucky. And looking at them a year + later, nothing’s changed. So actually, let me make this 3 major issues:

1. Arrogance: Just through my experience with Herald Interactive/TownOnline, and even some indirect communications with The Boston Globe and Boston.com – there’s a very old-school, conservative mentality. I have a contact at a large IBank who deals with these folks and he and I talk often about the hard-headedness of these folks. I’ve been introduced to a few people at these papers and they just can’t be bothered. At the risk of sounding bitter (maybe I’m too late), I’ll stop there.
2. Stodgy: I think there’s a lack of innovative and forward thinking leadership at a lot of these companies. Folks, it’s 2007. If you’re a newspaper and you haven’t made a big Internet play yet – you’re in deep doo-doo. I commend the NYT for making some big big changes over the past year or so. I love what they’ve done and I find myself using those features and logging in more often every week. Great job NYT! Boston.com – wish I could say the same for you. I don’t think this has as much to do with #1 and #3 as much as it simply has to do with an old-school, stodgy, good ol’ boys club mentality.
3. Techno what? Yes, no doubt there is a lack of technological initiative and strategy. But you can’t expect a newspaper with the first and second characteristics to embrace technology, can you? I haven’t really seen any major paper embrace technology in a meaningful way with a few exceptions (NYT, WSJ). Those exceptions have not only embraced technology, but they’ve also integrated into their business model – they’ve made adjustments. And as time goes on, things seems to working out fairly well.

All of this circles back to why they haven’t made a significant local-search play. The reasons for me are obvious, but I’m not a newspaper industry expert – no really, I’m not. I’m glad, too. Because there’s a market for me and Citysquares.com that allows us to make a big move. Question is, how long will it take for them to make another adjustment? I’m not too concerned, but my antennas are definitely up and tuned in.