1/28/26 11AM: Why Poverty Has to Exist

In this hour, Sherwin pulls the curtain back on how poverty actually works in America—starting with a conversation about the Nobel Peace Prize that quickly turns into a raw breakdown of why capitalism requires poor people to function. Using a sports analogy that hits hard, he explains how extreme wealth and poverty grow side by side. The conversation shifts to Milwaukee’s housing crisis, where plenty of people are angry about landlord Joe Berrada—but few are stepping up to help the tenants caught in the middle. Then things take a serious turn when Tiffany Miller’s store is broken into again, raising questions about whether the crime was targeted and what self-protection really looks like for small business owners. This hour is uncomfortable, honest, and exactly the conversation a lot of people avoid—until now.