It never fails. Whenever you have a very popular free service, there will always be a minority of users who will hem and haw when you try to monetize or make money off that service. Call it an entitlement mentality or just call it an addiction to a “clean service,” but adding ads to a previously ad-free communication platform on the internet always draws some concerns from a fairly small but vocal group of users. This is the risk any service provider runs, but the truth of the matter is the more successful your service is, the more resources you would need to run such a service and the more users you have to support, costs go up. Somebody has to shoulder these costs. Venture Capital Funding can only go so far. Enter advertising.
While Skype is by no means a startup anymore, and it does have some premium services, its recent launch of “conversation ads” has ruffled some feathers on the blogosphere. Basically, the conversational ads work like this: When you are having a conversation with your buddy on Skype, to the side of your friend’s image an ad will run. The upside to this ad is that it is personalized according to Skype. At this point in time, we do not know what personalized means. It is contextual to your conversation? How would they know? Do they use the name of the person or some sort of demographic targeting? We still do not know.