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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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20 episodes
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Avg 37 min
English

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Yesterday · 36 min
Alverno College President on Preparing Students for the Future
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Alverno College President Christy Brown for a conversation about the future of higher education and Alverno’s role in greater Milwaukee. Brown discusses preparing graduates to contribute from day one, building AI and problem-solving skills, and why Alverno’s distinctive ability-based learning model remains relevant today. She also addresses the college’s financial challenges and long-term sustainability, along with new partnerships with Milwaukee-area schools and employers. Brown shares how her commitment to women in leadership and expanding access to education shapes her vision for Alverno’s future. 🎙️ The Upswing is presented by Horicon Bank.
August 21 · 37 min
How Acquisitions Are Shifting Wisconsin's Manufacturing Landscape
This week on The Upswing, WTMJ’s Jeff Sherman welcomes back Milwaukee Business Journal senior reporter Rich Kirchen to break down some of the biggest business stories shaping southeastern Wisconsin. They discuss the Wisconsin Center District’s search for a new CEO and what it could mean for downtown development, along with challenges at Molson Coors, UMB’s Milwaukee footprint, and recent activity involving local manufacturers. Rich and Jeff also examine the uncertainty surrounding tariffs, including whether companies like Harley-Davidson could receive refunds — and whether any savings might eventually reach consumers during the holiday season. 🎙️ The Upswing is presented by Horicon Bank.
August 15 · 36 min
Best of The Upswing: Restaurants, Murals, and Natural Resources
This week on The Upswing, WTMJ’s Jeff Sherman takes a look back at some of his favorite conversations from 2026 so far. Revisit Cheryl Nenn on Milwaukee’s push to become a swimmable city, Martin Moore on who deserves to be represented in downtown murals, and Tedd Lookatch on the collaborative spirit that gives Milwaukee an edge. The show also returns to Steve “Saz” Sazama’s reflections on 50 years of Saz’s, plus recent conversations with Tristen Shorter about the future of Milwaukee County Parks and Purslane chef Mary Kastman on earning national recognition for her East Side restaurant. It’s a celebration of the people, businesses and ideas helping move Milwaukee forward. 🎙️ The Upswing is presented by Horicon Bank.
August 8 · 35 min
Top Local Dining and Saving Our Parks
This week on The Upswing, WTMJ’s Jeff Sherman spotlights two Milwaukee success stories centered on long-term investment and community impact. First, Purslane chef-owner Mary Kastman discusses her restaurant’s recognition as one of America’s top Mediterranean destinations, the realities of running an independent restaurant, and why Milwaukee continues to be a great place to build a culinary business. Then, Tristen Shorter of the Milwaukee Parks Foundation shares the organization’s vision for investing $10 million in Milwaukee County Parks by 2029, expanding community engagement, and ensuring the parks remain vibrant for generations to come. Jeff also closes the show with insights into evolving social media trends and a note of gratitude following the latest U.S. News & World Report Best Hospitals rankings. 🎙️ The Upswing is presented by Horicon Bank.
August 1 · 37 min
Paving, Parking Lots, & Pickleball
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Ryan Laughlin, CEO of PLM Paving, and Mike Blaney of America Sports Construction for a conversation about the business behind the surfaces we often take for granted. From parking lots and drainage systems to the growing demand for pickleball and padel courts, they explain how quality construction, long-term planning, and strong customer relationships drive their work. The discussion also explores workforce challenges in the skilled trades, the growing role of AI in construction, and how technology is improving everything from GPS precision to site planning. Jeff wraps up the show by revisiting last week's conversation on the future of murals in downtown Milwaukee. 🎙️ The Upswing is presented by Horicon Bank.
July 25 · 36 min
The Future of Netflix, Downtown Murals, and a Big Return to IRL
This week, The Future of Almost Everything returns to The Upswing as WTMJ’s Jeff Sherman and Martin Moore explore how technology, media, and culture are shaping the future. They discuss the rise of artificial intelligence, whether it’s time for a “return to IRL,” Netflix’s evolving strategy, and why the Milwaukee Bucks’ return to local television could strengthen the team’s connection with fans. The conversation also examines Milwaukee’s public art, the lasting legacy of Giannis Antetokounmpo, the need for more murals honoring influential women, and whether nonfiction storytelling can continue to thrive in the age of AI and podcasts. 🎙️ The Upswing is presented by Horicon Bank.
July 11 · 36 min
Milwaukee Dives into the Global Swimmable Cities Alliance
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Milwaukee Riverkeeper Cheryl Nenn to discuss Milwaukee’s new membership in the Global Swimmable Cities Alliance and what it means for the city’s future. Nenn explains how years of improving water quality have positioned Milwaukee to join the international movement, while outlining efforts to make local waterways safer and more accessible through projects like additional safety ladders and greener riverfronts. She also shares how residents can play a role in protecting Milwaukee’s rivers and beaches, reinforcing that creating a swimmable city is a community-wide effort. 🎙️ The Upswing is presented by Horicon Bank.
June 27 · 36 min
A Tech-Forward Summer, Through the Drive-Thru
This week on The Upswing, WTMJ’s Jeff Sherman explores two stories centered on growth and innovation. First, Tommy Pennington and Kevin Schmoldt, franchise owners of 7 Brew, discuss the drive-thru coffee chain’s expansion across Wisconsin, their community-first approach to site selection, and how new locations can help drive business for surrounding retailers. Later, Thomas Fisher of Platform94 joins the show following Summerfest Tech to discuss helping companies scale internationally, what Milwaukee can learn from its sister city of Galway, Ireland, and what it will take for the region to become an even stronger technology hub. 🎙️ The Upswing is presented by Horicon Bank.
June 20 · 36 min
College Town Aspirations Meet the City of Festivals
This month on Marquette on the Move, WTMJ’s Jeff Sherman welcomes Marquette University President Kimo Ah Yun, Rose Howard, and Sarah Pancheri for a conversation about the unique connection between Marquette and Milwaukee. The group explores how the city’s festival culture, volunteer spirit, and sense of community create opportunities for students to engage beyond campus and become active citizens of Milwaukee. They also discuss the impact of mentorship, the value of first jobs and internships, and recent investments supporting Marquette students, including a new endowment honoring former Brewers owner Bud Selig. The episode wraps with Summerfest memories, plans for the summer ahead, and reflections on what makes Milwaukee such a special place to live, learn, and connect. 🎙️ The Upswing is presented by Horicon Bank.
June 13 · 37 min
Making Music and Decisions When Resources Are Limited
This week on The Upswing, WTMJ’s Jeff Sherman welcomes back Tedd Lookatch, managing partner at the ERA Group, for a conversation about business, community, and making smart decisions in a changing economy. They discuss the opportunities and challenges that data center growth presents for Wisconsin businesses, the pressures facing nonprofits, and why Milwaukee’s collaborative culture continues to be one of its greatest strengths. Drawing from Lookatch’s experience as a music reviewer, the conversation also explores the health of Milwaukee’s music scene, the return of the Gobbler Theater in Johnson Creek, and the role local venues play in building community. The episode closes with practical advice on reducing phone costs and getting more value from the technology we use every day. 🎙️ The Upswing is presented by Horicon Bank.
June 6 · 36 min
Housing Is a Public Health Issue...and Opportunity
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Milwaukee Habitat for Humanity CEO Brian Sonderman for a conversation about one of the region’s most pressing challenges: housing. Sonderman explains why housing is fundamentally a public health issue and discusses the collaborative efforts among nonprofits, businesses, developers, and government to expand homeownership opportunities in Milwaukee. He also shares his unique journey from CPA to minister to nonprofit leader, along with insights into Habitat’s work helping families achieve the dream of homeownership. The episode also highlights Habitat’s longstanding partnership with the Milwaukee Brewers, volunteer opportunities throughout the community, and how supporting Habitat ReStores helps local families in need. 🎙️ The Upswing is presented by Horicon Bank.
May 30 · 37 min
Hire a Damn Artist: The Future of Creativity
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Martin Moore of Koss Headphones for another edition of The Future of Almost Everything. The conversation explores the intersection of creativity, leadership, and artificial intelligence, including why human imagination still matters in an AI-powered world and where businesses should draw the line when using generative tools. Jeff and Martin also discuss Milwaukee’s recent recognition as one of America’s most creative cities, the future of consumer technology, and whether original ideas can still thrive in a culture dominated by sequels and remakes. The episode wraps with summer bucket lists, Wisconsin burger talk, and a look at how rising costs are shaping everyday decisions. 🎙️ The Upswing is presented by Horicon Bank.
May 23 · 36 min
Confidence, Community and the Next Generation
This week on The Upswing, WTMJ’s Jeff Sherman welcomes Tina Jones, executive director of Girls on the Run Southeastern Wisconsin, for a conversation about confidence, mentorship, and the connection between physical activity and mental well-being. Jones shares how the organization helps girls build resilience through movement, previews the upcoming non-competitive 5K at American Family Field, and reflects on the importance of positive female role models during adolescence. Later, Wisconsin Brewing Company Brewmaster Kirby Nelson joins the show to discuss the legacy of Schlitz, brewing the final batch of the iconic beer in Verona, and how beer culture and preferences continue to evolve across Wisconsin. Jeff closes the episode with a business and career takeaway inspired by The Devil Wears Prada. 🎙️ The Upswing is presented by Horicon Bank.
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.

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