Sherwin is back with part two of his deep dive into Wisconsin’s political future. This time, he’s zeroing in on one name in particular: Milwaukee County Executive David Crowley. Could he be the fresh, unifying force Wisconsin needs? Sherwin lays out the case for Crowley as a potential gubernatorial contender—his leadership style, policy wins, and the energy he brings to the table. Plus, Sherwin unpacks the broader field of possible candidates and how Crowley might stand out in a crowded race. It's a passionate, thoughtful take you won’t want to miss.

In this unexpected detour from politics, Sherwin shares that he’s been summoned for jury duty—and he's not sure how he feels about it. Is it a civic duty, a pointless chore, or maybe a secret opportunity to see justice in action? Sherwin talks through the pros, the cons, and the excuses (real and imagined) running through his head. Tune in for a funny, honest reflection on responsibility, the justice system, and the universal feeling of getting that dreaded envelope in the mail.

In this thought-provoking episode, Sherwin dives deep into the complex intersection of wealth and marriage. From financial compatibility and shared goals to the silent pressures money can place on a relationship, Sherwin unpacks how couples can build not just love—but legacy. Whether you're dating, engaged, or decades into a partnership, this conversation explores how money influences trust, roles, expectations, and long-term success. Tune in for honest stories, hard-won insights, and strategies for building both wealth and a resilient marriage.

In this special and somber episode, Sherwin shares the heartbreaking news of the sudden passing of wrestling legend Hulk Hogan. With reverence and reflection, Sherwin looks back on Hogan’s towering legacy in the world of sports entertainment, his cultural impact, and the unforgettable moments that made him a global icon. This episode honors the man behind the persona—his triumphs, his struggles, and the millions he inspired. Join Sherwin for a moment of remembrance, gratitude, and tribute to one of wrestling's most iconic figures.

In this fiery and unapologetic episode, Sherwin doesn’t hold back. First, he dives into exactly why he can’t stand Roland Martin—from media antics to political grandstanding—and gives his unfiltered take on what’s wrong with the commentary culture Martin represents. Then, Sherwin shifts gears but keeps the passion high as he continues reflecting on the shocking loss of Hulk Hogan, honoring the wrestling icon’s lasting impact while examining the complexities of his persona. It’s part critique, part tribute—100% Sherwin.

In this episode, Sherwin dives deep into the candidates vying to lead Milwaukee's newly formed Office of Community Wellness and Safety. As the city reimagines public safety beyond traditional policing, Sherwin breaks down who’s in the running, their backgrounds, community ties, and visions for a safer, healthier Milwaukee.

Sherwin takes a tough look at how DEI efforts in predominantly white-led companies have often fallen short—turning into symbolic gestures with little substance. In this episode, he critiques the rise and rapid retreat of diversity programs across corporations

In this episode, Sherwin takes a deep dive into the evolving landscape of national welfare reform—breaking down what’s being promised, what’s being cut, and who’s being left behind.

In this gripping episode, Sherwin dives deep into the teen influencer event that spiraled into chaos—what was supposed to be a glamorous gathering of rising social media stars turned into a logistical nightmare, with frustrated fans, overwhelmed security, and some influencers fleeing the scene. Then, in a heartfelt and reflective segment, Sherwin discusses the unexpected and tragic passing of Malcolm-Jamal Warner, the beloved actor who portrayed Theo Huxtable on The Cosby Show. With personal insights and cultural context, Sherwin pays tribute to Warner’s legacy, impact on Black television, and the role he played in shaping a generation.

In this powerful episode, Sherwin unpacks the journey of LGBTQ+ identity—specifically the culture of being gay—and how it has evolved over the decades. From silence and stigma to celebration and visibility, Sherwin explores the milestones, the struggles, and the breakthroughs that have shaped how the world views and accepts gay individuals in 2025.