Abstract: A server accepts shipping information from would-be shippers, advertising information from would-be advertisers, and correlates the two to match up an advertiser with a suitable shipper. The server contacts a carrier with the shipping information to obtain a shipping label and tracking number, and forwards this to the shipper, together with the advertisement. The shipper places the advertisement within the package, and provides the package to the carrier for delivery. The server sends one or more tracking messages to the recipient, which contain tracking information and an advertisement. The advertiser pays an advertising fee, which is used to provide a reward to the shipper for carrying the advertisement.