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The Upswing

620 WTMJ

Hosted by Jeff Sherman, The Upswing is everything business. Jeff is a prominent figure in the business world, and is formerly the CEO and founder of OnMilwaukee, creator of the podcast series “The Hopcast,” and currently is the CMO of Okanjo. Jeff brings his expertise to The Upswing to discuss the ever-changing world of business and commerce in Milwaukee and across the state of Wisconsin.

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27 episodes
weekly
Avg 37 min
English

Episodes 27

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May 16 · 36 min
The Upswing celebrates National Nurses Month
It’s National Nurses Month, and this edition of Marquette on the Move on The Upswing brings together leaders helping shape the future of healthcare and nursing education. WTMJ’s Jeff Sherman is joined by Marquette University President Kimo Ah Yun, Children’s Wisconsin CEO Gil Peri, and Madeline Schmidt from Marquette’s College of Nursing for a conversation about workforce demand, mental health, technology, and the human side of patient care. The group highlights the strong partnership between Marquette and Children’s Wisconsin, the growing demand for nurses, and why many students see nursing as both a career and a calling. The episode also explores how innovation and community partnerships are helping healthcare evolve while keeping relationships and compassion at the center. 🎙️ The Upswing is presented by Horicon Bank.
May 9 · 36 min
The Upswing: Local Food, Family Business, and a Lot in Common
This week on The Upswing, WTMJ’s Jeff Sherman sits down with two family-owned food businesses from southeastern Wisconsin — and the similarities in their journeys stand out. First, John and Maria Ranieri of Sheboygan Pasty Company share how they grew their business out of a family bar during the pandemic, built key distribution partnerships, and continue to expand with new products. Then, Hannah and Tami Kopplin of Tots on the Street talk about building a mother-daughter business focused on scratch-made, locally sourced food and growing their reach through partnerships across the region. It’s a conversation about entrepreneurship, family, and the power of supporting local. 🎙️ The Upswing is presented by Horicon Bank.
May 2 · 37 min
The uncertainty of downtown's nighttime economy
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Milwaukee Alderman Bob Bauman for a wide-ranging conversation on the future of downtown. They dive into the nighttime economy, including Water Street, food truck curfews, and efforts to balance safety with a vibrant entertainment district. Bauman also shares updates on housing development, long-term plans for The Hop streetcar, and how policy decisions shape the trajectory of neighborhoods across Milwaukee. Jeff also opens the show with a look at evolving coffee culture — from national brands to local players like Stone Creek Coffee — and closes with a recommendation for an offbeat new Netflix series. 🎙️ The Upswing is presented by Horicon Bank.
April 25 · 39 min
The Upswing Pops Out of the Trees
This week on The Upswing, WTMJ’s Jeff Sherman opens with his “Two Up” segment, highlighting a new boutique hotel in Hartland and Brian Williams’ return with a Netflix podcast. From there, Jeff explores cultural shifts — including more young men returning to church and declining alcohol consumption among younger generations — and what those trends could mean for community and local businesses. He also touches on lighter topics, from an electric vehicle patent for an in-car toilet to a unique collaboration involving Children’s Wisconsin. Later, Greg Marshall of CI Design joins the show to discuss storytelling as a marketing tool, emphasizing authenticity, emotional intelligence, and why context matters — especially in today’s fast-moving digital landscape. The conversation also dives into brand messaging, including Nike’s recent Boston Marathon controversy, and wraps with a look at Marshall’s upcoming show in Milwaukee. 🎙️ The Upswing is presented by Horicon Bank.
April 18 · 43 min
The Year of Housing continues to build community
This week on The Upswing, WTMJ’s Jeff Sherman tackles one of the biggest challenges facing Milwaukee and communities nationwide: housing. From rising first-time buyer ages to the need for real solutions, Jeff explores what it will take to move from conversation to action, drawing on insights from a recent Greater Milwaukee Committee panel. He’s joined by Luke Knapp from the Mayor’s Office to break down Milwaukee’s 2026 housing toolkit, including updated TIF policies, down payment assistance, and efforts like Homes MKE — along with the role of public-private partnerships in expanding access to homeownership. The episode also features the “2-Up” segment, local business updates, and a look at challenges facing Milwaukee’s restaurant workforce. Jeff shares thoughts on youth sports pricing, the city’s coffee scene, and the need to invest in downtown infrastructure — plus a simple closing challenge: take a few minutes to unplug and let your mind wander. 🎙️ The Upswing is presented by Horicon Bank.
April 11 · 38 min
Is it closing time for grocery store bars?
WTMJ’s Jeff Sherman goes (mostly) solo this week on The Upswing, diving into a little bit of everything Milwaukee. From new restaurant openings like Nino’s Southern Sides in Fox Point to rising gas prices and MCTS’s new tap-to-pay system, Jeff explores how daily life in the region is evolving. He also looks at changes in local retail, including Metro Market’s shift away from in-store bars, and reflects on taking his son to vote for the first time — and why connecting with candidates still matters. The episode also touches on Milwaukee’s role in America’s 250th birthday, major local investments like Rockwell’s new New Berlin facility, and the importance of aligning talent and infrastructure to support growth. Along the way, Jeff crowdsources the best sandwich spots across southeastern Wisconsin and wraps up with WTMJ’s Sandy Maxx, previewing what’s ahead for What’s on Tap and this week’s “Maxx-perience.” 🎙️ The Upswing is presented by Horicon Bank.
April 4 · 36 min
The Upswing: The future’s so bright, you have to pay for sunshine?
This week on The Upswing, WTMJ’s Jeff Sherman and Martin Moore of Koss dive into the fast-moving world of tech, culture, and consumer trends. From Apple’s evolving AI strategy and the future of Siri to OpenAI shutting down Sora, they break down what’s next in artificial intelligence — and what’s already changing. The conversation also explores everything from phone-free dining and stadium beer prices to bold ideas like “sunlight on demand” and growing legal pressure on social media platforms. It’s a wide-ranging look at how innovation, business, and everyday life are colliding in real time. 🎙️ The Upswing is presented by Horicon Bank.
March 28 · 36 min
The Upswing: 50 years of simple, good neighborhood food
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Steve “Saz” Sazama, founder of Saz’s, as the Milwaukee staple celebrates its 50th anniversary. Saz reflects on opening day in 1976, the relationships that helped build the business, and how a neighborhood bar grew into a beloved institution. He shares the stories behind iconic menu items like Mozzarella Marinara, memorable moments from State Fair and Summerfest, and the pride of seeing former team members launch their own successful ventures. The conversation also looks ahead to “Festa Sazama” during Brewers Opening Weekend and Jeff closes with insights on community building and the evolving role of AI. 🎙️ The Upswing is presented by Horicon Bank.

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