Today, 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 biggest greater Milwaukee storylines, and looking ahead with a few predications for 2026.
Looking back at greater Milwaukee’s year
To open the show, Sherman reflects on a whirlwind year in Milwaukee sports and civic life, from the Brewers’ historic run and heartbreaking finish to continued momentum in Downtown development. He also explores major data center investments, neighborhood upgrades and new community amenities that helped make the city more connected, bikeable and walkable.
Best of 2025 conversations
This New Year’s edition of The Upswing features standout segments from across 2025, including a tasty donuts deep-dive with Colton Grebe of Grebe’s Bakery and practical AI insights from Matt Kirchner, host of The TechEd Podcast. Sherman highlights the themes that defined the year in business, innovation and community, along with additional moments from other fan-favorite guests.
Looking ahead in 2026
Sherman then previews next week’s guest, workplace culture expert Beth Ridley of Ridley Consulting Group, focusing on how her approach to feedback, tough conversations and everyday team dynamics can strengthen any organization. He also revisits a recent conversation with Tedd Lookatch, consulting partner at The ERA Group, citing it as a new year’s resolution every business owner can put into practice.
Finally, Sherman shares three forward-looking predictions for 2026, offering a quick roadmap for where business, technology and Milwaukee’s momentum may be headed next.
The Upswing is presented by Horicon Bank.
