As for reddit's size compared to digg here's the infographic: http://i.imgur.com/jiHka.png
you can google around and find other sites that go into greater detail on this.
This once again demonstrates that the Wired folks have moments of sheer brilliance, and then they fail to follow it through to its most logical conclusion. Acquiring reddit (for a rumored few millions) was a stroke of amazing luck for Wired/Conde Nast. But, now that everyone can look at the situation and do apples to apples comparisons with Digg and see that it's a far superior community and technology in pretty much every measurable metric, and worth at least as much as Digg, the reddit guys are struggling to pay for enough engineers and machines to keep the thing running smoothly and fast. Part of that problem is I think that the guys best equipped to grow it (Steve and Alexis) have both moved on; the remaining guys are very smart, but I think they were hired for their engineering abilities rather than entrepreneurial strengths. And, I imagine they left partly because they were dissatisfied with their ability to grow and lead from within the Conde Nast organization.
Another way to think of it is that neither digg nor reddit are actually worth that much -- lots of traffic, yes, but no way to monetize it. Conde Nast might just be doing things right, financially, with regards to reddit.
I can't wrap my head around the idea that 300 million deeply interested eyeballs every day is not "worth that much".
It's at least worth more than a staff of six.
Though, I do think Digg has been pretty much valued out of any reasonable exit by raising too much money, and the lack of vision on the part of leadership as exhibited by the tepid new version of Digg (which caters to marketers and major media to the point of absurdity for a "social" site) pretty much insures there's no way to build to something dramatically more valuable. Even if they were to learn from their mistakes, with a staff and infrastructure that big, they'll run out of money before they find their way.
In the case of reddit, it's userbase is very difficult to monetize -- they've said as much themselves. I think the less you can monetize something the more likely you'll have a lot of users; once you start doing things to monetize your userbase they get annoyed and simply move on.
I think any one of these sites is bad investment because those 300 million users can come and go in an instant. Digg could simply be over now and just takes a few people a few months to throw out the next big thing.
I agree with you, somewhat, but I will play devil's advocate and point out that for the first half of the Internet age, search was considered "very difficult to monetize". So much so, that all the major players started building portals and other BS to make their search more monetizable. This shift left a huge gaping hole for Google to fill, because there were almost no pure search engines left! Digg has gone down a similar path...building up and out to try to send tentacles out into more monetizable spaces, rather than having a focus on their value to their users. reddit remains extremely valuable to its users.
I don't know how they'll monetize it, but I can't help but think that whenever someone does figure out how to monetize a community of that size, it will be pretty serious cash.
Reddit also has a non-technical community manager (though I wouldn't be surprised if they got him programming by now). http://www.reddit.com/user/hueypriest
Hacker News could actually really benefit from one of those.
