The Upswing

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.

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.

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.

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.

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.

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.

This month on Marquette on the Move on The Upswing, WTMJ’s Jeff Sherman welcomes back Marquette University President Kimo Ah Yun and Tim Rabolt, manager of recovery at the university. The conversation addresses recent vandalism at the Church of the Gesu and how the campus community is responding, along with reflections on Marquette men’s basketball and continued student engagement. They also highlight student achievement beyond athletics, including undergraduate research showcased at Madison Square Garden. Rabolt shares insights into Marquette’s collegiate recovery program and efforts to build a wellness-focused campus culture, including the idea of “sober tailgates” and the growing role of non-alcoholic options. Dr. Ah Yun discusses the university’s approach to artificial intelligence through a Jesuit lens and how Marquette prepares graduates for life after college through strong alumni networks and career resources.

As Milwaukee prepares for the 58th Annual St. Patrick’s Day Parade, The Upswing host WTMJ’s Jeff Sherman sits down with two guests helping bring the celebration — and its economic impact — to life. Stacie Callies, executive director of the Westown Association, discusses how the parade continues to thrive through corporate partnerships, downtown collaboration, and the growing momentum around Milwaukee’s central business district. She also highlights the impact of the Baird Center expansion and shares details on upcoming events like the Milwaukee Night Market. Later, Kelley Cramer, vice president of marketing for the Water Street Brewery Group, talks about how some of Milwaukee’s most iconic bars — including Trinity Three Irish Pubs, The Harp, and Vagabond — prepare for parade weekend. He also shares insights into changing nightlife trends, from mocktails and non-alcoholic beers to the growing demand for curated experiences when people go out. 🎙️ The Upswing is presented by Horicon Bank.

Change can be hard — but it can also open the door to new opportunities. This week on The Upswing, WTMJ’s Jeff Sherman talks with Tina Quealy, CEO of the Betty Brinn Children’s Museum, about plans to find a new home for the beloved Milwaukee institution. She explains why expanded classrooms and outdoor space are part of the vision, what the multi-year relocation process could look like, and why access to high-quality learning should be a statewide priority. Later, in this month’s edition of The Future of Almost Everything, Jeff welcomes Martin Moore of Koss to discuss affordable new tech like the MacBook Neo, the idea of Milwaukee as a testing ground for innovation, AI regulation in social media, and why authenticity still matters for leaders online. 🎙️ The Upswing is presented by Horicon Bank.

Jeff Sherman likes to say that in greater Milwaukee, “seven degrees of separation” feels more like 1.5 — and this episode proves it. Jeff brings together James Shiparski of Hot Spell Sauna and Moshe Katz of Yellow Wood and Atid Properties for a conversation about health, wellness, retail, real estate, and community — only to discover the two guests already knew each other from regular sauna sessions. What follows is a story of serendipity, small-business resilience, and the powerful intersections between commerce and connection in Milwaukee. Moshe reflects on 11 years of building Yellow Wood into more than just an outdoor gear shop, while James shares how Hot Spell is growing a modern sauna and cold plunge movement along the lakefront. The episode closes with a note on Winter Break at Havenswoods State Forest. The Upswing is brought to you by Horicon Bank.

This week on The Upswing, WTMJ’s Jeff Sherman welcomes Marquette University President Kimo Ah Yun and Judge Derek Mosley, director of Marquette Law School’s Lubar Center, for another edition of Marquette on the Move. In recognition of Black History Month, Judge Mosley reflects on 15 years of sharing daily social media posts highlighting lesser-known Black history and how digital platforms shape the way we learn. The conversation also explores public health, community responsibility, unconscious bias, and Marquette’s efforts to foster inclusion. The episode touches on the landmark House v. NCAA case, upcoming campus initiatives, and personal reflections as the Lenten season begins — closing with anticipation for Give Marquette Day on March 3.

This week on The Upswing, host Jeff Sherman explores innovation in food access, co-working, and the future of communities. First, Michael Hostad of Fork Farms explains how indoor hydroponic Flex Farms are expanding access to fresh food in schools and communities — and why healthy food access should be a priority in Wisconsin’s 2026 governor’s race. Then, longtime guest Steve Glynn of Experience Milwaukee shares lessons from transforming the Wantable Café into a co-working hub, insights from a recent tech tour of Phoenix, and thoughts on where Milwaukee’s innovation ecosystem is headed. The episode wraps with a discussion about return-to-office trends and why a meaningful “return to local” may have the greatest impact. 🎙️ The Upswing is presented by Horicon Bank.

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.

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.

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.

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.

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 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.

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.

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.

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 of micro-influencers in Milwaukee, and why authenticity matters more than ever. In “The Future of Almost Everything,” Jeff and Martin look ahead to holiday shopping trends, AI’s growing role in business, and the tech and TV picks getting them through winter. The Upswing is presented by Horicon Bank.

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 finding purpose in finance, giving back, and smart budgeting for the holidays. Brian Dranzik, Milwaukee Airport Director, on Spirit Airlines’ exit and the continued benefits of flying local. Emile Williamson, Dietitian at Roundy’s, on the protein craze and what shoppers should know about balancing their diets. John Wise of Marcus Hotels & Resorts on beverage trends shaping Milwaukee’s hospitality scene.

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 Marquette students. Together, she and President Ah Yun discuss the university’s continued focus on student success retention — and how the Lemonis Center turns those goals into action with tutoring, mentoring, and wellness support under one roof. The conversation also highlights Marquette’s Jesuit mission of inclusion and community, extending beyond campus into Milwaukee. And, as Thanksgiving approaches, the guests share their personal traditions that remind us what connection and gratitude truly mean. PLUS: Quick Two Up business headlines and a price check on The Upswing Coffee Index

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 smoother for everyone: avoid connections when possible, sit near the front, and plan ahead to reclaim valuable time on the road (or in the sky). Then, Milwaukee Mitchell International Airport (MKE) Director Brian Dranzik joins host Jeff Sherman to preview the busy holiday travel season from a commercial standpoint. Dranzik discusses MKE’s ongoing improvements — including a new parking guidance system and the soon-to-open Central Standard Craft Distillery Crafthouse & Kitchen — and reminds travelers that choosing their hometown airport saves more than just money: it saves time, builds community, and reduces stress. Tune in for practical advice, hometown pride, and a look at how Milwaukee continues to elevate its travel experience — one flight at a time.

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 tomorrow’s dentists at Wisconsin’s only dental school. Dr. Ah Yun shares Marquette’s broader commitment to preparing students across disciplines for an AI-driven future and discusses his Charting Our Course tour, a nationwide rollout of his vision for the university. Plus, Jeff closes the show with the latest on coffee prices in The Upswing Coffee Index and news of a new exclusive coffee brand debuting at the Baird Center.

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 and shines a light on the development momentum along Historic King Drive. Fuhr highlights standout buildings on this year’s tour — including the Wisconsin Club and the Uplifting Mansion — and shares how Milwaukee takes cues from other cities to keep Doors Open exciting and fresh.

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 crullers with large-scale icons like Wisconsin State Fair Cream Puffs. Plus, Martin Moore from Koss joins Jeff to break down post-Apple-event iPhone wishes, Southwest Airlines’ seating shakeup, creative tactics in luxury real estate, smarter inbox habits, and quick-hit ideas to keep Milwaukee moving forward.

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 is relocating and expanding its operation and services to 117 N. Thompson St., in Oconomowoc. A grand opening event is scheduled for Saturday, Sept. 13, 2025, from 9 a.m. to 5 p.m. Jeff Sherman also was joined by Rich Kirchen, senior reporter at the Milwaukee Business Journal. The Upswing is presented by Horicon Bank.

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.

Jeff SHerman was joined by Stacy Bartsch and Sarah McManus from Milwaukee's Betty Brinn Children's Museum on new exhibits and how they educate children. PLUS: Koss Headphones' Martin Moore to talk about the latest technology trends.

My Office? Your Office!

A lot of development is going on between Milwaukee and Madison and WTMJ's Jeff Sherman is talking to the people making it happen. Michael Luckey is the Jefferson County Administrator and Deb Reinbold is Thrive's Economic Development President and they explained why business is booming along I-94

Jeff Sherman was joined again by Marquette University President Dr. Kimo Ah Yun and Marquette's first-ever CHief Wellness Officer Luis de Zengotita to talk more about Mental Health Awareness Month..

What is this sleeping giant that helps with job and housing development? Jeff talks to Clarence Johnson from Wisconsin Community Services to get the inside scoop. PLUS: Martin Moore joins to talk summer movies, splintering in social media and MORE!

"Small business" is a bit of a misnomer.