A friend of mine just joined AskJeeves...he asked me what I thought about Ask. I said I haven't visited it and haven't been given a reason to visit it. You can take that as a reflection of their PR or promotions group. I don't watch TV so I missed all the ads he spoke about. I've always liked the concept of AskJeeves. Natural language queries instead of assuming that the world can be inarticulate with just a few words and solved with popularity based solutions.
Back on the topic, he asked me what I think Ask should do. I started on the NL rant, but he redirected my nicely by asking "well what do you think of Ask using Google for search ads?". My initial reaction was 'why give money to your competitor?'. The natural answer was better monetization via query coverage (ie: size of advertisers base). Well then beat them at it because they don't have 100% query coverage AND their matching isn't all that great. Random ass idea: if queries are perishable then you might as well give away some query ads for free just to get advertisers in the door. That wouldn't be a loss because you weren't making bank on it anyways. Scared of loosing G-dollars? Then do A/B or just do backfill with free ads. They will obviously have to validate the advertisers (ie: credit card check) to avoid abuse and crappy targeting. They should reward based on relevance.
Of course the other camp would say, focus on what you are good at: user interface. Well is Ask UI so ass-kickingly good that they are taking search share?
For him it is just a place to ear a paycheck but not a place to stay.