1/28/26 10AM: Love, Power, and Why Everyone’s Mad

Hour 2 starts light with Valentine’s Day plans before Sherwin veers into a brutally honest conversation about masculinity, dating, and what it means when men are raised primarily by women. From the viral “bear vs. man” debate to why grown men wearing jerseys might be doing too much, nothing is off-limits. The hour takes a sharp turn into deeper territory as Sherwin connects mating, marriage, and monogamy to capitalism itself—arguing that the system benefits from keeping people locked into lifelong arrangements. He then pivots to Milwaukee’s housing crisis, claiming Democrats talk tough about the rich but fail to help the poor because once people escape poverty, they often flip politically. The hour wraps with talk of neighborhood redevelopment, a tense call from Bob that ends abruptly, and a follow-up call that has Sherwin questioning his entire day job. This hour is unpredictable, provocative, and exactly why people keep listening.