The first issue of Outbound magazine appeared in August 2002 printed on glossy magazine stock and in convenient pocket size. While some refered to it as the new "bar rag" (a term based on a long-ago Milwaukee activity guide called RAGG), the magazine featured articles, news, and activity calendars. The magazine was a much needed venue for businesses to run glossy color advertisements, a capability never previously available to LGBT businesses in Wisconsin. The magazine was the brainchild of lovers Jim Dawson and James.

Outbound magazine had an excellent regular feature, in virtually every article, which focused on a particular organization or business (usually bars)- typically featuring same on the cover, and having a brief article inside about that organization or business. This had the effect of giving various groups and businesses exposure they might not otherwsie have.

The publishers of Outbound briefly also published a monthly newspaper, Outbound News, to attempt to fill the gap left with the demise of the In Step newspaper a few years before. Unfortunatly, in the same month they launched that paper, another newspaper also started up. Outbound News was folded one year later, to allow the staff to focus on maintaining the high quality of the monthly magazine and web site.