This week on The Upswing, WTMJ’s Jeff Sherman talks with Ryan Laessig, executive director of Milwaukee’s East Side BID #20, about how the neighborhood is evolving while staying true to what makes it special. A Milwaukee native, Laessig shares why he sees the East Side as “a beacon for what Milwaukee stands for,” how investments like bike lanes are improving safety and access, and what it means to say goodbye to longtime staple Beans & Barley while supporting the businesses shaping the future. The conversation also highlights the Oriental Theatre, partnerships with Milwaukee Film, and big ideas for East Side events in 2026 — all centered on making the neighborhood work better for residents, artists, and businesses.

🎙️ The Upswing is presented by Horicon Bank.