Jane Coaston, host of Crooked Media’s What a Day podcast, is known for sharp political analysis that resists easy, black-and-white partisan divides. After crossing intellectual paths for years, it was a real pleasure to finally sit down for a one-on-one Conversation. Jane has a fascinating political journey that we delved into. For years, she identified as a libertarian, but it’s a definition she no longer feels attached to. We talked about the appeal of libertarianism, how libertarian ideas have shaped American political life, and where she found the philosophy breaking down. In her work at Crooked Media, and her contributions at The New York Times and CNN, Jane has spent years covering politics—especially the conservative movement—for a largely liberal audience. She thinks political debates too often collapse into left-versus-right talking points, leaving little space for the complexity of real people’s views. I asked her about the state of conservative politics today, including why the Republican Party has seen modest but real gains with black Americans, and how narratives around race and politics are frequently flattened in media coverage and social media. Jane’s perspective reveals both the frustrations and the possibilities of doing political journalism in an era when nuance is often in short supply.