In early 1998, Jeff Sherman and Andy Tarnoff met for a drink at the Nomad Pub. With a noble idea, minimal coding background, and an overriding love for their city, OnMilwaukee.com was launched that September. Sherman and Tarnoff were kind enough to welcome host Tyler Maas—who can identify with being part of a web-only upstart—to their conference room to discuss the site's origin, its evolution, difficulties sustained along the way, and what OnMilwaukee is doing to stay ahead in an increasingly digital market. Laughs were had, insight was bestowed, and they also (jokingly?) offered to buy Milwaukee Record.