Articles on the site primarily focus on dining and entertainment, as well as daily briefs and blogs.

[6][7] According to WISN-TV in February 2019, the magazine was looking for black history stories from African Americans in the area.

The writer of the article also questioned if Jeff Sherman and Andy Tarnoff were joking when they said they wanted to buy the Milwaukee Record.

[9] In 2020, after being with OnMilwaukee for over twenty years, Jeff Sherman sold his interest in the media company and left the organization completely.

[10] In January, 2024, founder Jeff Sherman joined 620 WTMJ where he launched the radio program The Upswing which focuses on the world of business, communities, and commerce in the greater Milwaukee area as well as across Wisconsin state.