Described techniques enable a particular user to automatically share a piece of content with a group of users. To share the content, the particular user navigates to a Website or the like to identify the desired piece of content. The particular user then chooses to share the piece of content by actuating a button, an icon, or the like displayed within the content (e.g., Web content) or displayed within the browser's toolbar. In some embodiments, the users with whom the piece of content is then shared each include the particular user within a contact list. This document also describes techniques capable of enabling the particular user to allow a third party to select and share a piece of content. In some instances, the piece of content comprises an advertisement. This piece of content may be shared with a group of users that include the particular user as a contact.