Willa Bennett
Episode
51

The Evolution of Media: Insights from Willa Bennett

Show Notes

Summary

Willa Bennett, a trailblazing force in media, is the editor-in-chief of Highsnobiety, steering the publication to new heights of innovation and influence. A Forbes 30 Under 30 luminary, her journey began at Seventeen, pioneering its queer vertical before igniting social strategies at GQ, and championing diversity as Condé Nast's global co-chair. The American Society of Magazine Editors recognized her for social media excellence and video programming, and her leadership at Highsnobiety garnered recognition in the Digiday and Muse Awards. Highlighting the importance of authentic narratives in connecting with young audiences, what she sees as contemporary now is pushing the boundaries and shaping the future of media—even if that means tuning out the background noise and tapping into real community.

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Episode Highlights
  • Bennett grew up in LA, balancing two passions: masculine menswear magazines and hyper-feminine ballet practice.
  • Talking about her early passion for vintage finds and retro styles, Bennett says experimenting with styling became another medium for her, “like writing.”
  • She grew up reading publications like Teen Vogue, Seventeen, Nylon, and Dazed—publications she says understood young consumers and which she still keeps a few print copies.
  • Bennett moved up through various roles in the industry at a time when social media marketing was in its more raw, early stage.
  • Her role at Highsnobiety gives her creative freedom in that it moves with the youth culture and its fast-paced, creative, adaptive, and reactive workplace environment.
  • Bennett is ahead of the curve, balancing personal perspective with editorial consideration and curation.
  • Her team at Highsnobiety pushes a particular and intentional editorial vision, championing designers and talent that they want to carve out a space for.
  • Some of Bennett’s favorite cover stars have been Billie Eilish, Andre 3000, and Pamela Anderson, though she felt strongly about the Dries Van Noten cover.
  • Bennett has spoken about forming real connections as a priority over solely professional relationships, despite how “transactional” the industry can be.
  • Under Bennett’s eye, Highsnobiety’s niche is to move in tandem with the zeitgeist instead of against it, never telling readers what to do or who to wear.
  • Bennett considers real-life events crucial to foundational community building, saying, “that to me is a way bigger metric of success than like any influencer with 16 million followers posting one slide that everyone’s going to skip over anyway.”
  • She’s published poetry collections benefitting The Audre Lorde Project for queer youth.  
  • For Bennett, deleting social media is what’s contemporary now, surprisingly.

Notable Quotes:

  • “I still remember buying blazers and going home and unraveling them and figuring out like, ‘Oh, you could take the elbow pads out, you could take the shoulder pads out,’ and it just became almost another medium of writing in a lot of ways. It was really cool. I wish I could sometimes replicate that feeling of finding a—like discovering a blazer for the first time and realizing that you could deconstruct it.” —Willa Bennett
  • “I have just always been such a fan of all these publications. I feel like when you’re a fan of something, you reallyunderstand it on a new level. There is a sense of love that kind of gets deeper and deeper. Just devouring these publications as I was younger kind of gave me this intimate understanding.” —Willa Bennett
  • “I think for me, it’s never really been about, ‘It has to be a magazine. It has to be a product.’ It was more about the storytelling. I just want to tell stories where young people actually are.” —Willa Bennett
  • “At the end of the day, I really am a writer—the way I see the world is just through writing.” —Willa Bennett
  • “I love packaging stories in a way where young people can actually understand them.”  —Willa Bennett
  • “I also came from publications where, like I was the young person in the room, they’d be like, ‘We need a young voice. Willow, what do you think?’ And I’d always be like, ‘I can’t speak on behalf of a whole generation.’ I always thought that was so silly. So to be here and be one of the many voices that are pushing, that want to push culture forward, I think, is so exciting. And I just appreciate that so much about my staff here and the editorial team. We all are in this together.”  —Willa Bennett
  • “So much of my social life was happening online… I just saw that this internet was booming really quickly. And I wanted the magazines that I love to come with me in that evolution.” —Willa Bennett
  • “You believe in a story, but you never really know how anything’s going to hit. I’ve learned this in all my years of putting covers out on the internet.” —Willa Bennett
  • “There’s no one secret to marketing to this younger audience. But I felt like a question we were getting a lot as like these tokens to young people who had done things differently, it was just like, be honestly yourself, and be real about it.” —Willa Bennett
  • “I don’t really see a lot of people championing like this energy from the zeitgeist, this young energy, this ‘I wake up in the morning and have to talk about the new Rick Owens collection or else I’ll explode’ same ambitious way that we are, while also championing personal style and not shoving it down your throat. I think that is something that we’ve really carved out.” —Willa Bennett
  • “Tell the stories that you don’t see out there. Don’t try to do what everyone else is doing.” —Willa Bennett
  • “It’s about influence and not reach anymore. And I think that’s something that’s really cool. That’s happened recently. Like it was about going viral at one point in time, it was about having a bunch of followers. And I think it’s just too much now. It’s about having the right followers. It’s about archiving all your posts on feed. It’s about getting it right and building a real community. And I think that’s it, it’s contemporary now.” —Willa Bennett
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