Michael Sebastian is the Editor-in-Chief of Esquire, where he has redefined what it means to speak to—and about—modern men. Since taking the helm in 2019, he’s led the magazine to critical acclaim, including a Pulitzer Prize in 2025 and a National Magazine Award for General Excellence. Under his leadership, Esquire has evolved into a publication that pairs sharp cultural commentary with emotional intelligence, bridging the space between masculinity and vulnerability.

In this episode, we talk about nostalgia, ambition, and what it means to lead with empathy in a world that prizes performance. Michael embodies a rare balance—deeply masculine yet reflective, confident yet curious. Our conversation traces his roots in John Hughes country, the power of memory, and the art of being both nostalgic and forward-thinking at once.

xx William