It took a great deal of time and almost as much disappointment in the process, but Andrew Winistorfer is finally making a living as a music writer. Since coming on as the Editorial Director for Vinyl Me, Please, Winistorfer spearheaded the record subscription service’s music coverage and assembled a staff of skilled contributors to assist him. Along the way, he helped put together two ambitious coffee table books—including the just-released The Best Record Stores In The United Statesalong with contributing liner notes to celebrated reissues and handling A&R for VMP’s new “Classics” division. In many ways, it’s a dream job for Winistorfer. Especially when taking into account the long and uncertain road that brought him to this point.

Shortly before the book’s release, My First Band host Tyler Maas stopped by the Midwest office of Vinyl Me, Please in downtown Madison to talk about the exciting things Winistorfer is doing now and to take a trip down memory lane. The two reminisced about their time working together on their college newspaper (The Advance-Titan at UW-Oshkosh), compared horror stories about the difficult and ever-changing world of entertainment writing, and chronicled their separate paths to the ultra-rare distinction of making a career in modern journalism.

During the extensive conversation, Winistorfer told the story of playing a college house party with his one and only band, admitted he came close to quitting music writing to become a manager at Target, and talked about how writing about his record collection in alphabetical order would ultimately change the course of his life.

My First Band is sponsored by Boulevard Brewing and Mystery Room Mastering. The show is edited by Jared Blohm. You can listen to My First Band on iTunes, Stitcher, Spotify, and wherever else you get podcasts. Music used in this show comes courtesy of Devils Teeth (“The Junction Street Eight Tigers”) and—the title track from Vinyl Me, Please’s Classics record for the month of December—B.B. King’s (“Lucille”)

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