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, was launched that September. Since that fateful day, the online magazine’s traffic and local influence have skyrocketed, its staff has grown exponentially, and the product of that bar room chat now resides on the 11th floor of a downtown office. Love ’em or hate ’em, OnMilwaukee was ahead of the digital media curve in Wisconsin, and they continue to thrive today.

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 relevant in an age that find far more outlets vying for page views. Laughs were had, insight was bestowed, and they also (jokingly?) offered to buy Milwaukee Record.

As always, this episode is brought to you by our friends at Ale Asylum, who we can’t thank enough for supporting On The Record since day one. Music in this episode comes courtesy of Piles (“Blue Glue”) and The Scarring Party (“A Church In The Wild”). Subscribe to On The Record via iTunes or Stitcher (for free!)