No Entries

Sherwin explores the highs and lows of modern relationships. From emotional connection and personal growth to conflict, compromise, and the challenge of maintaining independence—Sherwin breaks down both the beauty and the struggle. Whether you're single, committed, or somewhere in between, this conversation offers real talk on what makes relationships work, when they don’t, and how to navigate love without losing yourself. No fluff, just facts and feelings.

Sherwin takes on the City of Milwaukee’s controversial goal to issue over 500,000 parking tickets. Is it about traffic enforcement—or just another revenue stream? Sherwin digs into the numbers, the neighborhoods most affected, and the broader impact on working-class residents. From questions of equity and transparency to the deeper issue of how cities balance budgets on the backs of everyday people, this episode doesn’t hold back. Buckle up—it’s going to be a bumpy ride.

Sherwin dives deep into the protest that gripped the city — unpacking the message, the movement, and the moments that defined it. From the roots of the No Kings sentiment to the voices on the ground, Sherwin offers first-hand insight into what this protest was really about, why it matters, and where it might be headed next. Whether you were there or you're just catching up, this is the episode you need to hear.

What can a zip code tell you about opportunity, health, safety, and success? In this eye-opening episode, Sherwin breaks down the stark contrasts between Milwaukee neighborhoods — from education and income to policing and public health — all based on something as simple as five digits. It’s a deep dive into how geography shapes reality in one of America’s most segregated cities. This is more than data — it’s a call to rethink how we build equity from the ground up.

Sherwin sits down with leaders, educators, and students from Milwaukee College Prep to talk about what it really takes to build strong schools and stronger communities. From academic excellence to character development, hear how this network of public charter schools is reshaping education in Milwaukee — one student at a time. It's an honest, inspiring, and forward-looking conversation about equity, expectations, and the power of believing in every child.

Sherwin takes a hard look at the looming budget cuts facing The Hop, Milwaukee’s free public streetcar. Once seen as a step toward modern, accessible transit in the city, The Hop now faces an uncertain future. Sherwin breaks down what’s behind the funding shortfall, how it could impact riders and neighborhoods, and what city officials and community members are saying.

Sherwin takes a thoughtful look at the racial diversity of fans who pack stadiums, tune in from home, and live and breathe sports culture. He reflects on how fans of color have shaped the energy and identity of sports communities—despite often being overlooked in mainstream narratives. From tailgates to bleachers, Sherwin discusses how race influences the fan experience, the barriers that still exist, and why true inclusion means more than just who’s on the field.

Sherwin tackles a troubling moment that shook the Brewers vs. Dodgers game—a fan’s racist outburst that sparked outrage both in the stands and across social media. Sherwin unpacks the incident, explores how racism still finds its way into America’s favorite pastime, and calls out the culture of silence that too often surrounds these moments.

Sherwin recounts the summer he spent working at Ernie von Schledorn's car dealership when he was just 21 years old and on break from college. He shares stories from what it was like working under Ernie, and the lessons he took with him. But the conversation also takes a turn into history, Sherwin reflects on the complexities of Ernie’s past and the contradictions of working for someone with such a controversial history.

Sherwin reads and reacts to a leaked letter allegedly written by a Republican official that contains blatantly racist language and ideology. With unfiltered commentary and historical context, Sherwin breaks down the implications of the letter, what it says about political rhetoric today, and why it matters.