Everyone's talking about selling subscriptions via auto-renew, but just yesterday I heard a new spin on this: selling online ads via auto-renew. The publisher (who asked not to be named here, lest his/her competitors get any ideas) told me they used to try for a three month sale. Now they try for a month-to-month sale, with a three month minimum tostart. "You can cancel at any time," the reps tell advertising prospects, "it's so easy." Then the publisher sits back and relies on the "power of inertia" to keep revenues streaming in. According to the publisher in question, his/her ad revenues are up nearly 100% since the auto- ad-renew program began a few months ago.
Naturally this only works for ad deals in which the amount is small enough to be charged on a credit card, and the marketplace is one, such as small biz, where the credit card in question is often a company leader's. My suggestion is to try it if you have an online or emailed directory that vendors can put paid listings into. It's enough of a lead-gen placement that they won't cancel ads as quickly as they would branding spots in these economic times.
Overture does this, to some extent, as once you open an Overture account for paid search engine listings they automatically charge your card $20 a month, plus listings fees, until you cancel the account.
Speaking of which, if you'd like to make some money selling paid search listings from your site, I've heard Search123 is offering this as a co-branded service. It would be perfect if the search were primarily searching your own site's pages so you could sell search ads against your own content, but I suspect it simply takes visitors off to other places, which probably isn't your goal.
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