The Upswing

620 WTMJ
  • 5.0 (3)
  • DAILY NEWS
  • UPDATED DAILY

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.

  1. The Future of the CFO

    11H AGO

    The Future of the CFO

    This week on The Upswing, WTMJ’s Jeff Sherman welcomes Martin Moore of Koss to the studio for another edition of The Future of Almost Everything, exploring the latest in technology and innovation. They dive into emerging AI platforms like Moltbook, debate the impact of AI-related Super Bowl commercials, and discuss how artificial intelligence is reshaping creative industries and consumer expectations. The conversation also touches on local developments, including what’s next for Bayshore Town Center and what leadership qualities matter most looking ahead to Wisconsin’s next governor. Later in the show, Jeff is joined by Tedd Lookatch, consulting partner at ERA Group and president of the Frank L. Weyenberg Library board in Mequon. They discuss business challenges from a CFO’s perspective, practical advice on vendor contracts and phone plans, and how modern libraries are evolving as community hubs — including a preview of Library Legislative Day on Feb. 10. 🎙️ The Upswing is presented by Horicon Bank.

    43 min
  2. Marquette on the Move: Mentorship

    JAN 31

    Marquette on the Move: Mentorship

    As National Mentorship Month comes to a close, The Upswing host WTMJ’s Jeff Sherman welcomes Marquette Mentors’ Radtke Director Dan DeWeerdt and Marquette University President Kimo Ah Yun for this month’s edition of Marquette on the Move. The conversation reflects on the legacy of Marquette mentor and actor Pat Finn, the importance of presence and connection in mentoring, and the reopening of the Church of the Gesu on campus. They also discuss leadership within Marquette men’s basketball, college affordability, and how mentoring helps students navigate financial and professional challenges. The episode closes with a look ahead to the 2026 Wisconsin governor’s race and a reminder that mentoring can start with a simple step: asking and listening. 🎙️ The Upswing is presented by Horicon Bank.

    38 min
  3. Treasures of Milwaukee's East Side

    JAN 24

    Treasures of Milwaukee's East Side

    This week on The Upswing, WTMJ’s Jeff Sherman talks with Ryan Laessig, executive director of Milwaukee’s East Side BID #20, about how the neighborhood is evolving while staying true to what makes it special. A Milwaukee native, Laessig shares why he sees the East Side as “a beacon for what Milwaukee stands for,” how investments like bike lanes are improving safety and access, and what it means to say goodbye to longtime staple Beans & Barley while supporting the businesses shaping the future. The conversation also highlights the Oriental Theatre, partnerships with Milwaukee Film, and big ideas for East Side events in 2026 — all centered on making the neighborhood work better for residents, artists, and businesses. 🎙️ The Upswing is presented by Horicon Bank.

    37 min
  4. Community and Foodie Minded

    JAN 17

    Community and Foodie Minded

    This weekend on The Upswing, WTMJ’s Jeff Sherman welcomes Arthur Ircink, a Milwaukee-area creative and community leader whose work spans food media, local government, and community-building. Ircink shares behind-the-scenes insight into the Emmy Award-winning Wisconsin Foodie and what it means to spotlight Midwest culinary innovators, including Indigenous chef Sean Sherman. He also discusses Shorewood initiatives such as the new Shorewood Feast dining event, upcoming infrastructure improvements, and his vision for a more walkable, connected community. The conversation wraps with a look at the 2026 Wisconsin gubernatorial race and the importance of bridging the divide between urban and rural communities. 🎙️ The Upswing is presented by Horicon Bank.

    38 min
  5. 2026 Workplace Trends

    JAN 10

    2026 Workplace Trends

    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.

    37 min
  6. The Best of The Upswing from 2025

    JAN 3

    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.

    37 min
  7. A Priest, Rabbi and University President Walk Into a Bar...

    12/20/2025

    A Priest, Rabbi and University President Walk Into a Bar...

    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 response alongside the Marquette University Police Department. As Christmas and Hanukkah approach, the group explored what these sacred seasons mean in Milwaukee and Wisconsin today—emphasizing compassion, understanding, and meeting people where they are. The conversation also ventured into sports, resilience after tragedy, grief, and the challenge of living faith authentically rather than just following rules. The episode closed with warm reflections on holiday traditions, generosity, and the shared joy of giving to others.

    41 min
  8. Toys at the Store & Toys at the Bar

    12/13/2025

    Toys at the Store & Toys at the Bar

    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 beyond. She explains why certain classic toys never leave store shelves, how generational differences influence holiday shopping, and why tariffs affect what families buy. She also breaks down how TikTok and YouTube “unboxings” now shape what kids ask for. Next, Jeff sits down with Marla Poytinger, President and CEO of Bars & Recreation, whose first bar, Splash Studio, began as a fusion of her and her husband’s passions for beer and art. She discusses building bars around Wisconsin traditions, the vision behind Newfashioned in the Deer District, insights from a successful holiday market, and the challenges of running multiple local venues. Looking ahead, Bars & Recreation plans to expand its catering operations in 2026. 🎙️ The Upswing is presented by Horicon Bank.

    38 min
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5
out of 5
3 Ratings

About

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.

Information

  • Channel
    620 WTMJ
  • Creator
    620 WTMJ
  • Years Active
    2024 - 2026
  • Episodes
    500
  • Rating
    Clean
  • Copyright
    © 2025, Good Karma Brands, LLC
  • Show Website
    The Upswing

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