Before she was even 30 years old, Willa Bennett took over not one, but two of the most iconic magazines in media: Cosmopolitan and Seventeen. In this episode, I sit down with Willa to talk about what it actually takes to run a legacy magazine in 2026 — in a culture driven by viral discourse, instant backlash, and internet-speed opinions. In this conversation, we get into: What it felt like to take over Cosmopolitan at 29 What an Editor-in-Chief actually does day-to-day How she decides who and what gets visibility Why story matters more than star power The Sydney Sweeney cover and how she thinks about controversy Whether editorial “rage bait” is real How viral culture and engagement metrics shape modern media What Gen Z readers are actually curious about And why “taste” might be the most important skill in journalism right now Timestamps 01:30 Growing up with magazines & coming full circle 04:30 Getting the Cosmopolitan job — the emotional moment 07:30 Running a legacy brand in a digital-first industry 10:30 What an Editor-in-Chief actually does in 2026 15:30 Instinct vs analytics — how editorial decisions are made 20:00 AI, dating culture & what young readers want 23:30 Story over star power & viral visibility 27:30 The Sydney Sweeney cover & navigating backlash 32:00 Is editorial rage bait real? 35:00 Celebrity culture, controversy & documenting the moment 37:30 Are we still in the Gen Z era? 40:00 The future of media & why taste matters Follow Willa on Instagram https://www.instagram.com/willahbennett/?hl=en Thanks to Banana Republic for my favorite pieces from the spring collection.