The Best of The Upswing from 2025

WTMJ’s Jeff Sherman rings in the new year with a special Best of The Upswing, revisiting some of 2025’s most memorable conversations and the biggest storylines shaping greater Milwaukee — while also offering a look ahead to what’s coming in 2026. To open the show, Sherman reflects on a whirlwind year in Milwaukee sports and civic life, from the Brewers’ historic run to continued momentum in downtown development. He also highlights major data center investments, neighborhood upgrades, and new community amenities that helped make the city more connected, bikeable, and walkable. This New Year’s edition features standout segments from across 2025, including a deep dive into donuts with Colton Grebe of Grebe’s Bakery and practical AI insights from Matt Kirchner, host of The TechEd Podcast. Sherman revisits the themes that defined the year in business, innovation, and community, along with additional fan-favorite moments. Looking ahead, Sherman previews next week’s guest, Beth Ridley of Ridley Consulting Group, on workplace culture and feedback, and revisits a recent conversation with Tedd Lookatch of The ERA Group as a timely New Year’s resolution for business owners. The episode wraps with three predictions for 2026, offering insight into where Milwaukee, business, and technology may be headed next. 🎙️ The Upswing is presented by Horicon Bank.