This week on The Upswing, WTMJ’s Jeff Sherman welcomed Ryan Laessig, Executive Director of Milwaukee’s East Side BID #20. A Milwaukee native who has worked with other local BIDs, Laessig shares how his role – through constant change – is helping the East Side feel different while still honoring what makes it special.
He calls the neighborhood “a beacon for what Milwaukee stands for” and pushes back on old narratives and misconceptions about North Avenue, noting how investments like new bike lanes are making the East Side safer and more accessible for residents, businesses, and visitors. Jeff and Ryan also talk about the upcoming closure of the iconic Beans & Barley and what it means to grieve a staple while still showing up for the local spots that are here now — and those yet to come.
The conversation highlights the Oriental Theatre, the BID’s collaboration with Milwaukee Film, and how this “North Star of Milwaukee” anchors a flourishing destination for arts and culture on the East Side. Looking ahead to 2026, Ryan shares big ideas for events at Ivanhoe Plaza and Black Cat Alley, plus his platform for the year: improving traffic so it better supports businesses, artists, and residents on the East Side and across Wisconsin.
The Upswing is presented by Horicon Bank.
