Navigating A New Era of Virality, Rage Bait, and Gen Z Content with Cosmopolitan's Editor-in-Chief — Let's Get Dressed

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. Shop their new arrivals at www.bananarepublic.com #BananaRepublicPartner

Let’s Get Dressed

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