Sherwin dives deep into the controversy surrounding a Campbell Executive — who recently took a leave of absence after making public comments about the company’s product that sparked widespread backlash. Sherwin explores what went wrong, the impact on the brand’s image, and whether such company actions are justified. Expect analysis of accountability, corporate responsibility, and what executives should know before speaking out.

Sherwin tackles a topic that sparks debate every travel season: Should there be a dress code for people getting on an airplane? With airlines juggling safety, comfort, and customer experience, Sherwin explores whether attire really affects the in-flight environment. He breaks down real-world examples, listener opinions, and the line between personal freedom and airline policy.

Sherwin breaks down what it truly means to eat better and take care of your health—without the guilt, pressure, or complicated rules. From choosing whole foods to building sustainable habits, Sherwin shares simple, realistic tips anyone can use to feel more energized and in control. He also touches on mindset, daily routines, and why small changes can lead to major improvements in long-term health.

Sherwin breaks down the meaning and impact of Black buying power—how much it really is, where it goes, and why it matters. From historic barriers to modern economic opportunities, this episode explores how collective spending can influence markets, support Black-owned businesses, and drive community wealth. Sherwin also tackles myths, data, and the future of Black economic influence.

Sherwin dives into the history, psychology, and real-world impact of boycotts. From major consumer activism movements to recent viral online campaigns, we unpack why some boycotts succeed, why others fade fast, and what really drives change. Featuring expert insights and surprising case studies, this episode helps listeners decide whether boycotting is a powerful tool—or just symbolic noise.

Sherwin dives into a wide mix of topics—culture, money, relationships, world events, and everything in between. Each episode blends thoughtful analysis with candid conversation as Sherwin breaks down what’s trending, what matters, and what we’re all thinking about. Expect insight, humor, and a fresh perspective every time.

Sherwin dives into the complex world of political communication and leadership, exploring how two very different public figures—Mamdani and Donald Trump—can sometimes exhibit surprisingly parallel patterns in style, strategy, and public impact.

Sherwin takes listeners on a sharp, engaging journey through the past, present, and future of socialism in the United States. Moving beyond clichés and misconceptions, he explores how socialist ideas have influenced American politics—from early labor movements to modern policy debates—often in ways the public doesn’t realize.

Sherwin visits Milwaukee College Prep to talk with educators, leaders, and students who are redefining what high-quality urban education looks like. Through candid conversations and behind-the-scenes stories, Sherwin uncovers how the school’s culture, expectations, and community partnerships fuel academic excellence and empower young people to thrive.

Sherwin dives into a months-long investigation uncovering allegations of racial discrimination within the U.S. Coast Guard. Navigating internal documents, and historical context, he brings listeners into the heart of an institution wrestling with questions of identity, equity, and accountability.

Sherwin revisits the widely reported WWF ring boy scandal of the early 1990s, analyzing testimony, media coverage, and the industry dynamics that allowed misconduct to go unchecked. Through careful sourcing and expert commentary, he explores the pressures young workers faced, the allegations that sparked national attention, and the long-term implications for the wrestling business.

Sherwin sits down with Milwaukee Health Department official Mike Totoraitis for a clear, practical conversation about the current open enrollment period. Together, they break down key deadlines, available coverage options, what residents need to know before signing up, and how the city is working to expand access to care.

Rick and Sherwin as they sift through the chatter, headlines, and historical patterns to explore who the Democratic Party might select as its next presidential nominee. In each episode, the duo breaks down emerging contenders, analyzes the dynamics shaping the field, and discusses how party priorities and voter sentiment could influence the eventual choice.

Sherwin unpacks the political and leadership dynamics involving Donald Trump, Linda McMahon, and the broader conversations surrounding the Department of Education. Through clear, balanced analysis, Sherwin explores how political figures shape public debate on education policy, funding priorities, and federal influence.

Sherwin dives into the surprising resurgence of measles in various parts of the world. He explores what’s driving the comeback—from declining vaccination rates to misinformation and global travel—and examines how public health systems are responding.

Sherwin breaks down what many are calling “Trump 2.0” — the evolution of Donald Trump’s political influence and what a renewed era of Trump-style politics could mean for the country. From shifting voter bases to new policy priorities, Sherwin takes a steady, fact-focused look at why the Trump movement continues to resonate and what its next chapter could hold.

Sherwin dives into the complex and often misunderstood idea of entitlement as it relates to Black and White communities in America. Rather than reinforcing stereotypes, Sherwin explores how history, social systems, economic inequality, and cultural narratives shape the ways entitlement is perceived—and misperceived—across racial lines. Through honest conversation and careful analysis, this episode invites listeners to move beyond assumptions and toward deeper understanding.

Sherwin unpacks the long and often hidden history of Black literacy suppression—from anti-literacy laws in the slavery era to modern disparities in school funding and access. He explores how the ability to read has always been tied to power, autonomy, and freedom, and why efforts to restrict literacy became a central tool of oppression. A revealing conversation connecting past strategies to present-day challenges.

Sherwin explores the practical steps communities can take to stay safe, stay informed, and stay united. From strengthening neighborhood networks and fostering mental well-being to building economic resilience and cultivating a culture of mutual care, Sherwin breaks down what it truly means to look out for one another.

Sherwin takes a deep dive into the rise, evolution, and staying power of Trump-ism—the political, cultural, and emotional movement surrounding former President Donald Trump. Rather than focusing solely on the man himself, Sherwin unpacks the forces that shaped the movement: economic frustration, identity politics, media ecosystems, and the shifting definitions of conservatism in America.