A method for generating advertising content includes: during a content creation period, receiving a video advertisement from an entity; packaging the video advertisement with a pointer to the entity and a checkout portal for content linked to the video advertisement to generate an augmented video advertisement; during a live period succeeding the content creation period, for a first instance of the augmented video advertisement accessed at a first computing device associated with a first user, associating a first purchase completed within the checkout portal of the first instance of the augmented video advertisement with the entity based on the pointer; and, for a second instance of the augmented video advertisement accessed at a second computing device associated with a second user, associating a second purchase completed within the checkout portal of the second instance of the augmented video advertisement with the entity based on the pointer.