Conversations with Jeff

Years ago, a few months after my son was born, a friend asked me to go to the movies with him. I was a single dad with an infant at the time, and just thinking through the infrastructure required to leave the house exhausted me. “You have no idea how hard this is,” I said, with a hand on my hip and swaddled baby on my shoulder, looking like Mr. Mom of Logan Circle. This was a friend who’d lost bot...

We may be on the cusp of a neo-Enlightenment. That was my biggest takeaway from this conversation with Hollis Robbins . Hollis is one of the world’s most visionary thinkers on how universities should evolve in the AI age. She was previously Dean of Humanities at the University of Utah and is currently a fellow at Harvard. She also writes a publication on Substack called Anecdotal Value , which is...

After Trump’s tariffs took effect, I was eager to catch up with my friend Richard Hanania . I wanted to ask: Would he still vote for Trump? Richard is one of the most influential political essayists of the moment. He’s wicked smart, relentlessly honest, and kind of quirky. His book, The Origins of Woke , is credited with seeding Trump’s anti-DEI executive order. We had an impromptu, off-the-cuff c...

I was delighted to speak with TracingWoodgrains about Wikipedia corruption, cultural renewal, Mormonism, furries, generational issues, and more. It all makes sense if you listen! I apologize: The audio quality isn’t great due to connectivity issues — but the quality of Tracing’s remarks more than makes up for it. “Trace,” as many call him, is one of the most interesting thinkers I’ve met in recent...

On today’s episode, I talk with Rajeev Ram about his life in rural Tennessee, where he practices MMA with the bros on the one hand and works with a gay matchmaker to find a partner on the other. Quite the combo, right? We talk about navigating male spaces as a gay guy, fellowship and mentorship, intergenerational dynamics, and building a life in a rural area as a well-educated, 29-year-old man of...

Welcome to the second episode of “Conversations with Jeff,” a podcast where I talk to interesting people and explore topics at the forefront of politics, work, culture, and personal development. How do you find your place in the world as a shapeshifter? What is it like going from being an MIT-educated software engineer who worked at Substack to embracing a new identity as a coach and artist? Find...

Welcome to the inaugural episode of “Conversations with Jeff,” a podcast where I talk to interesting people and explore topics at the forefront of politics, culture, and life. Have you ever noticed how people in their 20s and early 30s are redesigning their relationship with work? How some are ditching coastal tech jobs in pursuit of a different kind of American dream in rural America? After writi...