Romenesko graduated from Marquette University and went to work for the Milwaukee Journal, serving as a police reporter for the newspaper.
From 1982 to 1995 he worked as an editor for Milwaukee Magazine, where he wrote features and an award-winning column that covered the local media called "Pressroom Confidential".
In 1998 he began the website Obscure Store and Reading Room, which linked to odd news stories, and which earned him the reputation of a "witty Matt Drudge.
[11] [12][13] Romenesko has also been mentioned as a predecessor to Gawker for having "opened the first and biggest hole in the sacred wall between news and gossip in reporting about the media.
In the process of reporting, the online chief of the Poynter Institute, Julie Moos, was contacted and noted that this behavior had occurred since 2005.
Moos placed Romensko's blog on hold while the issue was being investigated, and following investigation ordered that all of Romenesko's posts be approved by an editor prior to post and to follow the Poynter Institute's attribution guidelines of placing quotation marks with any text used in the original article.