No one wants to admit it, but those ads *sucked* on top of all of the brand dilution crap. I mean, seriously, ticket arbitrage sites and various supplements were the most common ads and they were never relevant. I say this of all of the ad networks ESPN has used since I started working there until today.
The other part of this, though, is having mature, state-of-the-art systems to manage internal ad runs. This is something that ESPN, through the Walt Disney Internet Group, did well. Medium-sized publishers often end up with ad nets and sponsored link units because they don’t have the kind of smart inventory management that larger companies have.
I have high hopes for self-service tools like Google Ad Manager as a potential way of bridging the branded advertising/genero network idea.
I found this Calacanis’s blog, and he has other advice for online companies. Worth reading, as well as the linked post.
Update: clarified the second paragraph. I lumped in startups because they/we use networks like Adsense, but for different reasons (no ad sales person). The point about infrastructure was about sites that haven’t crossed into the very large group.