The Upswing

This week on The Upswing, WTMJ’s Jeff Sherman welcomes back Beth Ridley, CEO of Ridley Consulting Group, for a timely conversation about the evolving workplace and what effective leadership will look like in 2026.

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 downto...

An annual tradition returns to The Upswing as WTMJ’s Jeff Sherman welcomed Rabbi Levi Stein, Father Joseph Simmons, and Marquette University President Dr. Kimo Ah Yun for a thoughtful and uplifting conversation on faith, community, and the holiday season. Each guest reflected on what first inspired their commitment to faith, with Rabbi Stein sharing his work supporting mental health crisis respons...

This week on The Upswing, WTMJ’s Jeff Sherman continues gearing up for the holidays with a look at some of 2025’s hottest toys and the growing success of Milwaukee’s holiday markets hosted by local bars and restaurants. Jeff first welcomes back Toy Tips founder Marianne Szymanski, a Marquette University graduate who shares how her toy-recommendation business grew from a hotline to a magazine and b...

This week on The Upswing, host Jeff Sherman explores Milwaukee’s creative and influencer community. Photographer and entrepreneur Eric “Bert Lauderdale” Halverson shares how he built his visual style, developed his “Bert Alerts” weather persona, and even inspired a new collaboration with Broken Bat Brewing. Jeff also welcomes Martin Moore of Koss Headphones to discuss influencer culture, the rise...

On this special holiday weekend edition of The Upswing, host Jeff Sherman takes a look back at some of his favorite recent conversations — but not before diving into the numbers and importance behind Small Business Saturday and why shopping local matters more than ever. Then, Jeff revisits standout moments from Milwaukee-area leaders and experts: Flory Jerez-Villasenor of Northwestern Mutual on fi...

On this episode of The Upswing presented by Horicon Bank, WTMJ’s Jeff Sherman welcomes back Marquette University President Kimo Ah Yun and Marilyn Jones, the university’s inaugural director of the Lemonis Center for Student Success. Jones, a first-generation immigrant from Costa Rica and first-generation college student, shares her perspective on building stability and upward mobility for Marquett...

As the holiday season takes off, The Upswing, presented by Horicon Bank, sits down with two guests offering distinct perspectives from the runway to the boardroom. Jet Out’s Matt Wild shares insights into the evolving world of private aviation — where accessibility, flexibility, and efficiency are redefining how business leaders and families travel. Wild also offers universal tips to make flying s...

Jeff Sherman explores Milwaukee’s holiday buzz with Marcus Hotels’ John Wise and Roundy’s dietitian Emilie Williamson — from festive dining trends to smarter grocery shopping this season.

Jeff Sherman spotlights Milwaukee changemakers — Running Rebels’ Victor and Dawn Barnett and Mumbies founder Bradley Will — who are transforming lives for local youth and dogs alike.

Marquette University President Dr. Kimo Ah Yun and Dr. Manal Hamdan, director of Marquette’s predoctoral program in oral and maxillofacial radiology, join Jeff Sherman for a conversation on technology, mentorship, and the future of education. Dr. Hamdan spotlights cutting-edge advances in dental care — including how artificial intelligence is transforming both patient outcomes and the training of...

Doors Open Milwaukee returns September 27–28, giving the public a rare chance to explore some of the city’s most iconic and exclusive spaces. Jeff Sherman is joined by Ray Hill, executive director of the Dr. Martin Luther King Jr. Drive BID, and Grace Fuhr, events director at Historic Milwaukee, to preview this year’s event. Hill explains how Business Improvement Districts fuel neighborhood growth...

In this episode, Jeff Sherman sits down with Colton Grebe, fourth-generation co-owner and chief strategy officer of Grebe’s Bakery, to talk tradition, innovation, and the launch of Grebe’s “store within a store” concept now open at Metro Market. Colton shares the bakery’s 1937 origin story, lessons from the International Baking Expo in Las Vegas, and how Grebe’s balances Milwaukee favorites like c...

From Restaurants to Our Schools, WTMJ's Jeff Sherman talks to Milwaukee Journal Sentinel Food Critic Rachel Bernhard and Hunger Task Force's Jonathan Hansen

This week, WTMJ's Jeff Sherman was joined by Tamara Key, an Army veteran, owner of The Herbal Key Apothecary and the Wisconsin ambassador of the CJ3 Foundation, a nonprofit that provides services to wounded and disabled first responders, veterans, and current military service members. In response to increased customer demand for holistic and alternative health solutions, The Herbal Key Apothecary...

Join Jeff Sherman as he talks with local restaurateur and entrepreneur Jesus Gonzalez about his food truck park and new venture that makes bringing food trucks to events as easy as pie.

Jeff Sherman meets some of the vendors at Summerfest this year including Mae'Rose Naturally Rooted, Howdy Hat Bar, Bandit MKE and Unfinished Legacy.