The thing is, one of the most fraught questions for CommYou is advertising. I'm tentatively inclined to have a *little* of it, at least for non-members, to firm up the income flow. And I really quite like Gmail's model of advertising: just a bit, based on the text of what you're reading, with an eye towards maybe being useful. I intensely dislike the advertising-all-over look of many websites -- frankly, I think it's kind of dumb and counterproductive, with the saturation-bombing by some advertisers leading me to tune them out entirely. If all you're going for is awareness it might be okay, but I rarely click on the ads. By contrast, I *do* occasionally click on Gmail ads, because they're more likely to be quirky, interesting and relevant. (Even sometimes fun.) Seeing an ad for HDMI cables when I'm *talking* about HDML cables is far more useful to me than yet another advertisement for Microsoft.
The problem, though, is that I don't much trust the advertisement aggregators, and that's where the ads would necessarily come from. I mean, yes, Google (the likely supplier) tries to "Do no evil", and I think that for the moment they're mostly sticking to that. But I have every confidence that that will slowly erode over time, and I think most of their competitors are further along down the evil curve than they are.
In particular, the issue that I dislike is tracking. I mean, the data I would send them would be as anonymized as I can make it -- just the text contents, nothing personally identifying. (That probably weakens the value prop slightly, but I don't much care: the whole point of running a lean company is that I can do things like that.) But they can still get at your IP address, and that's gold to advertisers: they try to correlate every bit of data they can get their hands on. Granted, nearly every website participates in this giant data-mining operation, so it's not like CommYou would be *unusual* in it, but I can't say that I love the idea of being part of that. From a privacy viewpoint, it makes me decidedly uncomfortable.
So I like the bill that's being proposed in NY, which (according to the article) targets exactly that -- it would theoretically give you a way to get the data-mining to back off. (Whether it would succeed or not remains to be seen, but I like the principle.) Indeed, the possible consequence that I would *love* to see is a more nuanced attitude towards data retention and mining in general. If it forced Google to have the internal mechanisms to *not* retain any user data in some cases, then it wouldn't be such a big leap for them to permit it on a site-by-site basis. And I would be *much* more comfortable buying ads from Google if I could stipulate that they cannot retain any data that I send to them. Yes, it might mean I get a little less money -- but again, I can live with that.
We'll see where it all goes -- it'll be some months yet before any of this is relevant. But the tension between advertising and user privacy is one I'm going to have to be very careful about...