Today’s The Daily Whatever Show had me flying solo with Lawrence Winnerman still off on his top-secret spy mission till Friday. The good news was that I got to spend the entire hour with my guest, Leo Caldwell from Trans Collective.
Leo’s not just a journalist but a fearless guide through the messy intersection of media, culture, and social commentary. We kicked off in the deep end, talking about guns, free speech, and the odd national dialogue that sometimes protects a legacy rather than the people it affects.
We also touched on his latest story about trans Americans leaving their home states to move to blue states or abroad.
Leo expressed how citizens shouldn’t be navigating daily life armed, and students need safe spaces to interrogate these ideas—he’s proud of the way his students are stepping into that role themselves.
From there, we waded into topics about feminism, power, and the paradoxes of visibility.
Leo reflected on his own evolution toward a more outspoken feminism in 2026, wrestling with what it means when society celebrates certain women like Erica Kirk for beauty or widowhood while silencing other voices.
He tied this to his work in journalism education, where he’s trying to reconcile the decline of traditional newsrooms with the rise of independent platforms like Substack, encouraging students to create their own opportunities while navigating real-world constraints such as health insurance and entry-level jobs.
Then came the part I loved, our discussion about his Kardashian class. On the surface, it was a playful nod to pop culture, but it became a brilliant portal into race, class, appropriation, and body image.
Leo described students debating Kendall Jenner’s Pepsi ad, arguing about appropriation versus appreciation, and even engaging in heated discussions after class. The debates didn’t have neat conclusions, but they were precisely the kind of critical thinking he’s trying to foster.
We also got his perspective on the Kardashians themselves—not just the beauty standards and consumerism, but the sheer scale of their influence. Leo pointed out that one-eighth of the world’s population follows them, and that’s a reality worth thinking about, whether you love them, hate them, or want to understand why.
Before wrapping up the show, we drifted into music and nostalgia with the question we always ask guests on their first visits: what’s the most GenX song of all time? Leo’s pick of “Hungry Like the Wolf” was perfection, and I couldn’t resist sharing my own memory about Duran Duran—when my friend group and I successfully championed for them to meet our friend Jenny George, a teenage cancer survivor whose love of Duran Duran helped her three years of chemotherapy.
I was so scared the band would be dismissive, but they bounded into the meet-and-greet asking, “Where’s the survivor??” It was truly a dream come true, and I’ll always love the band for making it come true for her.
You can read all about it on Medium: I Helped My Best Friend Meet Duran Duran.
Talented, handsome, and genuinely kind, Duran Duran showed up for someone who needed it, and that’s the part that sticks with me. Note to self: I should really move that story to Substack. It’s such a good one!
By the end of our great chat, Leo had managed to bring guns, journalism, the Kardashians, and Duran Duran into the same conversation, all while keeping it thoughtful, wry, and very human.
Lawrence will be back tomorrow, January 9th for Fucked-Up Friday with Zev Shalev.
Thank you Nick Paro, Stephanie G Wilson, PhD, NeuroDivergent Hodgepodge, Cat, Margaret Williams, MS, ACC, The Bathrobe Guy (Robes) 👘, Melissa Corrigan, she/her, JR Roessl, and many others for tuning in. Huge thanks to Karen Marie Shelton for helping us moderate the chat and write the recap. Yer a peach!
We love you all, mean it!
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