I had actually planned a startup building something similar (+ip geolocation to pick appropriate affiliate links), however I ended up moving onto another idea b

I had actually planned a startup building something similar (+ip geolocation to pick appropriate affiliate links), however I ended up moving onto another idea because I couldn't make the numbers work out. To make the same amount of money as from CPC ads, you have to get a much higher click-through rate than CPC ads conventionally get. I wasn't convinced I could build contextual ad technology that would result in the higher CTR to make it worthwhile. Congrats if you've managing to pull that off, I'd be interested to hear what the equivalent CPC/CPM would be of your ads. My own business plan was to target sites which can't use Google Adwords, primarily sites which require logins to access content (dating sites, small social networks) or do dynamic page generation. Another good market might be blogs which don't monetize very well at the moment if your tech works well in that context. I believe jgc posted a while back saying despite his high traffic on his blog he couldn't see traditional adwords bringing in much. My plan to monetize initially was to take a percentage cut, use your affiliate code 20% of the time and the websites affiliate code the other 80% of the time. That way you avoid having to handle the payments yourself but get income very early on.