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I have explored the MSN and Microsoft website and found no mention of how to become a featured site, although they say that some of their featured sites are MSN advertisers. I e-mailed their advertising people with the question of how to be a featured site, but got no response. I was just wondering if anyone has done it.
I have also written their advertising department about the "featured listings" but never heard anything back. From what I have heard from others these listings can be a great way to go. If you are really serious about them and you send enough emails to them I am sure you will hear back eventually.
However, if you don't want to deal with MSN or feel their pricing is a bit high you can surprisingly trump them and go right to LookSmart. LS offers "top pick" (butterfly) listings that miraculously are listed higher than MSNs paid featured listings and you can often get them for a fraction of the cost.
More or less whenever an ad rep tells you there's a huge minimum he/she is playing hard ball. If you can make a compelling pricing argument based on what works for your roi you can normally get an ad reps ear. Do the reasearch and be persistent and it can pay off HUGE.