The Industry’s Little Sister
A conversation with Willa Bennett (Editor: Highsnobiety, GQ, Seventeen, more).
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THIS EPISODE IS A SPECIAL COLLABORATION WITH OUR FRIENDS AT THE SPREAD AND IS MADE POSSIBLE BY MOUNTAIN GAZETTE, COMMERCIAL TYPE, AND LANE PRESS
Ed: You’ve loved our collaborations with The Spread—their Ep21 interview with former Cosmo editor-in-chief Joanna Coles, as well as recent chats with Stella Bugbee (Ep30) and Linda Wells (Ep39), are among our most-downloaded shows. Now, Rachel Baker and Maggie Bullock are back again, this time with ASME-winning wunderkind Willa Bennett, the disruptor-in-chief of e-com/magazine hybrid HighSnobiety.
You can find The Spread every week on Substack, where Rachel and Maggie round up juicy gossip—from The New York Times to The Drift, and everywhere in between—big ideas, and deeply personal examinations of women’s lives to create their idea of the perfect “women’s magazine.”
In early April, what’s left of the magazine industry gathered at Terminal 5 to see who would win this year’s National Magazine Awards—the ASMEs. Throughout the evening, the usual suspects stepped up to accept their Alexander Calder brass elephants—the ‘Ellies’—on behalf of their teams at The Atlantic, New York, and The New York Times Magazine.
Then came the award for General Excellence, Service and Lifestyle—a category that covers every food, fashion, and fitness magazine in the business.
And the Ellie went to… content juggernaut Highsnobiety—a sneaker blog-turned-cool kid media amalgam that encompasses a twice-annual $20-per-issue print magazine, plus a flood of social media, a website that is also an e-commerce platform, and a creative agency that does 360-degree marketing and storytelling for brands.
Before the crowd could start scratching their graying heads, a Billie Eilish lookalike in a gray Thom Brown skirt-and-pant suit took to the dais. There were plenty of people in that room who had never given Highsnobiety much, if any, thought.
But in that moment, this woman, Willa Bennett, Highsnobiety’s 30-year-old editor-in-chief, had officially become a force to be reckoned with. Not only that, but Highsnobiety’s business model, which bends rules that had long been sacrosanct in magazine journalism, suddenly appeared to have won the seal of approval from the oldest of the old guard.
The post at Highsnobiety was a major leap for Bennett. Just two years ago, she was the social media manager at GQ. Our friends who worked with her there tell us they thought of her as “the industry’s little sister”—hungry, passionate, and looking to translate the magic of magazines to a new generation. They said that even though she’s disrupting the magazine as we once knew it, at heart Bennett is a “a magazine junkie who really venerates the old ways.”
And now the surprise win has put her in the spotlight of the establishment media, with The New York Times Styles running a portrait of Bennett in her signature suit-and-tie look on its cover. The win inspired a segment on the Slate Culture Gabfest in which the hosts pondered, “What Is a Magazine Now?”
Over in Spreadlandia, we thought, Why not turn that question directly to Willa Bennett herself? In the end, this conversation left us feeling more optimistic than usual about the future of media. It also made us feel old as shit. We hope you enjoy it as much as we did.
Rachel Baker: Willa, thanks so much for being here. We’re so glad you’re here today. We’re especially excited because last month your magazine, Highsnobiety, won the National Magazine Award for General Excellence—which is a huge deal! Can you describe ASME night for us? We’re both ASME geeks. And we weren’t in the room, but we had some spies texting us throughout. Describe it from your perspective for your big night.
Willa Bennett: Thank you for having me. I love the pod. I love the conversations you guys have. So excited to be here. Yeah, ASMEs are really surreal, to be honest. I had never been before. I’ve been nominated a couple of times but I’ve never made it in that room. And it was pretty wild to look around and just see so many people, like my old bosses, or people who had edited me, people I’ve crossed paths with, people I just admired online.
And to be sitting there really felt so special. It was one of those moments in my career where I honestly was like, “Wow, I’m in this room!” It was really cool. It’s funny. Like the vibe inside, people were like, “Oh, this is Terminal 5.” And I was like, “No, this is so special.” To me, it felt so surreal.
And, yeah, I was truly not expecting at all to win. Especially General Excellence. I thought maybe our visuals would have potentially won something. I saw a path that way. I thought maybe like our social media platforms. But General Excellence really has always felt so unattainable. So I was really surprised.
Rachel Baker: Who were you starstruck by in the room? That feeling of being in the ASMEs if you’re a magazine geek is so much fun. And I feel like it’s like the biggest celebrities—if you’re into that kind of thing. Who were you excited to see?
Willa Bennett: There were a couple different young writers. Honestly, the 30 Under 30 journalists. There’s a visuals editor at New York mag I thought was really cool to meet. Obviously, Anna [Wintour] was there, gave her a hug. But David Haskell, Will Welch, Lindsay Peoples [Wagner], they were the ones that were really there for me when I was coming up in this industry.
And so to be sitting alongside those three specifically, it felt really meaningful. But the General Excellence award was right after the 30 Under 30. “ASME Next” it was called. And I found that really cool. I was cheering for them so loudly. I felt just like they’re the future of this. I hope they’re all winning the General Excellence in the next couple of years.
Maggie Bullock: So you name-checked some of those people. Our spies, as we said, who were in the room, were touched when you got up because, you were the “young disruptor,” but when you got up, they said, we were told that you acknowledged some of your predecessors and gave it up for the “oldsters” in the room But what did you want to say and who did you give that tribute to?
Rachel Baker: And how did you plan it? Did you practice?
Willa Bennett: It was pretty much like the night before, the PR team at Highsnob was like, “Hey, you should prepare something because if you win, you’re going to walk up.” And I responded via text. Literally, I said, “LOL.”
And then when I couldn’t sleep, I was like, “All right, I’ve just got to be prepared. I’m so unexpected to win. And I’m so unexpected even to be in that room. Let me just jot down some notes.” And what I wrote was, “Everyone in this room, your job matters. We need journalism. And print matters. We need to inspire young journalists to still want to dream of this.” That was basically the gist of it.
And why I said that was—and I’ve said this in a couple of panels before—I really do feel this responsibility to make young people feel excited about journalism. And I feel like every time I go to a school—I just spoke at FIT, I do an NYU seminar every once in a while—everyone is feeling so disillusioned by what’s possible. And I feel, as the young person in the room, as this unexpected winner of the ASMEs, but even a nomination, honestly—it was the first time we’ve ever been nominated. I feel this responsibility to young people. And I feel very close to young people.
But the reason I thanked those specific people is they just stood out as people throughout my career that had really given me space to have my own voice. Lindsay Peoples, really was crucial in publishing my first piece for Teen Vogue. Welch, obviously I learned so much from him. And he was my most recent boss. And I still feel like a lot of my leadership skills came from him.
And then David Haskell. We’ve just gotten coffee at different points of my career and I felt like he’s really inspired me on what an EIC can be, what reporting is. And, I think there’s a lot I can learn from him and I have learned from him.
Maggie Bullock: So that night, The New Yorker got completely stiffed. Vogue always gets stiffed at the ASMEs. So it was big news that you won in general, but also the contrast of that was big news. And I think some people were really shook that Highsnobiety was winning General Excellence. Did you perceive that at the time? What was the energy like around that for you?
Willa Bennett: I was so shocked. It really is unprecedented what happened. The ASMEs, to me—and I’ve judged before—it really is as old school as it gets. You’re really sitting there looking sentence by sentence, photo by photo. And I believe in it so deeply.
I studied journalism. I really believe in the ASMEs and I see the power in them. And I was honestly really surprised. And I think what it means, to answer the second part of your question, what it means for journalism is I think there is space to innovate. And I think it was really amazing that the judges on that category did select us. I think it was not expected, and I think in a lot of ways we’re not traditional journalism with a capital J.
Maggie Bullock: This would probably be a good moment for you to tell us what “it” is. And a lot of the people listening to this, because we cannot put it into a one-sentence description. So what is “it”—this whole organism? How do you describe it?
Willa Bennett: Highsnobiety started off in 2005 as a sneaker blog. Incredible. Our co-founder, who is now my boss, the CEO, was sitting in his dorm room and was really passionate about the emergence of streetwear and fashion. And then I think with previous EICs, it has really evolved into a magazine closer to fashion, with a capital F, evolved into the thought leadership.
And I think my journey here, and where my POV comes in is, I’ve really pushed it into a youth culture platform. So it is this ecosystem, this universe that is very unique to young people, to looking at, not what people are wearing, but why they’re wearing it. And storytelling from different unique angles.
Rachel Baker: Can you describe all of the different tentacles of the beast? There’s the print magazine…
Maggie Bullock: … Wow, it went from an organism—now it’s a beast!
Willa Bennett: I think that’s all a compliment, by the way.
Rachel Baker: We’re just poets over here at Print Is Dead.
Willa Bennett: That’s cool. I’m a poet too. So the different tentacles. Nichelle Sanders said it beautifully, she’s the GM here. She said, “It’s not church and state between editorial and sales. Editorial is God and everything else is sales.” So there’s the agency side, there’s the editorial under me is website, social media platforms.
And then we have the agency side, and then we have e-commerce. I credit Highsnob—look, they were first. I think a lot of people in the pandemic were trying to catch up to what Highsnob had been doing. They’re really great at it. The curation is amazing in the shop. It’s not your typical e-commerce site.
But yes, those three exist cohesively. And I think the diverse revenue stream is part of what gives me the freedom to be a true editor in the sense of really writing stories that are true.
Rachel Baker: And so what is your role? Do you touch the agency stuff or do you touch e-commerce?
Willa Bennett: Depends on where you’re looking at it from. No, I am really passionate about brands. So sometimes I’ll tap in if I’m excited about a project. Sometimes I’ll just give some opinions on the side. But not in a formal capacity. And it’s really like for me, choose your own adventure.
It’s not mandatory. It’s not something I’m forced to do. I am just really fascinated by brands. And so I think that’s the exciting part of having an agency over there. As for e-commerce, I definitely weigh into some of the storytelling. But they are separate teams.
But of course Highsnobiety is 290 people. There are so many cool creatives. And so I look at it as, wow, we have so many different ways to tell stories that maybe isn’t just a magazine. The magazine is just part of it.
“Everyone is feeling so disillusioned by what’s possible.”
Maggie Bullock: So you’re talking to us from your office in New York, but there’s also Berlin, am I right? Where are these 290 people? So we’re magazine dinosaurs and we live in a world of shrinking stuff. So literally, we looked it up on LinkedIn and we were like, “What? Where are all these people?” How does that piece of it work?
Willa Bennett: Our biggest office is Berlin. That’s where our headquarters are. And then New York is the second biggest. We have London, we have Paris, we have Amsterdam. I have a few editors in LA now. To me, I think if anything, the pandemic has taught us different ways of working. We really do hire for the talent. But I do think you can tell in our content, our roots are in Berlin.
And that’s something that we do not shy away from. I see it as such a luxury, even. On Wednesday mornings, we have this meeting called “Office Hours” where everyone can tell crazy ideas, respond to things happening in the news. And I think it’s such a luxury that we have young people calling in from a lot of the big cities where our audience is.
But I agree. I come from a small editorial, legacy background. And I’ve never been used to having such a big team. And that’s something I've really thought about in terms of management. Managing a global team, there are some people that I've only met once or twice. And so how do you keep them inspired? How do you keep them in-the-know about what your vision is? And how do you actually make change and tell stories when it's just not as easy as walking into an office?
Rachel Baker: How do you do that?
Willa Bennett: The Office Hours has been really helpful. It’s like a Wednesday brainstorm that we have every single week. We all Zoom in and we all run through ideas. I think what’s also cool about it is I’ve set up this anonymous Google form where people can also submit ideas. So if they have an idea, but they don’t necessarily feel they can share it, I’ll just read through the ideas and we discuss them all objectively.
Some people are like, “I wrote that. This is what I wanted to say.” And I’m just like, as long as the ideas are coming out, I think it does help us stay connected as a team. But honestly, I haven’t really spoken about this to anyone yet, but I read a lot of parenting books.
Maggie Bullock: What? Incredible! Oh my god, say more. We need to know about this.
Willa Bennett: I was like, “I don’t know how this is going to land.”
Maggie Bullock: No, you’ve come to the right place.
Willa Bennett: Honestly, it’s like the most helpful thing with leadership, I think. I’ve tried to read a lot of leadership books and haven’t really felt them to be really effective. A lot of them are just like, “Listen.” “Take a walk.” But parenting books, I feel like actually teach you how to lead and really execute on something you’re trying to get done in a way that has been really helpful for me.
Especially with just staying connected. A lot of people it’s their first or second job. And so I do feel like I am setting the stage for their career. And so I feel like having hard conversations in the right way. It is important to model that.
Maggie Bullock: I’m just laughing internally because you’re, Rachel has two toddlers. So she fully understands the mental jujitsu of managing unwieldy stuff.
Rachel Baker: Right now I’m taking a nonviolent communication class, and I think a lot about how it would be great for managing a team. Unfortunately, I’m not managing people professionally right now. I just manage my family. But it’s a lot of, “I observe this.” “I am feeling…” “This is my request.” I think it’s pretty great no matter what the age.
Willa Bennett: And even like what you just said, “This is my request.” Like really articulating that. Like, “This is a change in strategy, we’re pivoting to this.” Really being able to articulate that is something parenting books really harp on. And they really teach you how to listen. And I think that’s, honestly, been helpful, in all places of my life.
Maggie Bullock: I think you just dropped something. We’ll have to come back to that at some point. Rachel and I will probably meditate on that for a long time. Now this feels like a little bit of a non sequitur, but I feel like now that you’ve told the listener what this organism is, it gives us more context to just touch on the message of ASME. I think that what happened is it opened up this conversation—again, not for the first time—but what even is a magazine? And what is ASME trying to tell us we need to do for survival? I think people were parsing that after the fact, which is an interesting thing to reevaluate. What do you think about that conversation?
Willa Bennett: I think that we owe it to the industry to just always be open to what a magazine is. I think a lot about book publishing. I’m very passionate about writing and I would love to write books one day. I haven’t written a book, but what I see from afar is they have found a way to sell physical copies of stories in a way that we maybe haven’t cracked. And I think that’s interesting. Like just what #BookTok has done for authors. Authors are selling more copies than they ever have historically. And ones that aren’t published.
But with magazines, I think we give so much of it away on social media. Billie Eilish is on our cover. Her fans can see everything online. I think we owe it to ourselves to be open to that conversation and I’ve personally not been pushing subscriptions here because I think someone buying our merch and someone buying our clothes is our version of that.
I look at time spent more than I look at uniques onsite. I try to read a lot of the Instagram comments because sometimes I think that’s more valuable feedback. But to me, this takeaway was like, We all need to be open to different ways of working. And I think other industries have done it.
And I don’t think the takeaway is that you have to have a unique business model to be a successful magazine. I don’t think so at all. I think more of the takeaway is how else can we get young people inspired and excited about print.
Maggie Bullock: It’s so interesting because what you just described is like the reverse of a conversation that—we worked together at Elle for many years, and that’s where we fell in love—but we watched that pendulum go back and forth about how much to give away, the print, before it comes out when it comes out. We’ve literally seen every degree of “We don’t give it away at all.” Or, “We wait a week after the print issue drops before we release anything.”
Rachel Baker: Everybody’s already had the conversation and we’re late to it!
Maggie Bullock: That is something that people have always toyed with. What perhaps works better about it in your beast or organism is that the issues are more rare, they come out twice a year. And that also, perhaps, you’re producing so much other content on these other platforms that it’s not like all of the energy goes into producing that print. And therefore, that’s what you have to share with people. Does that make sense?
Willa Bennett: Yeah, I think The New York Times headline was really effective in the same sense of like print just being part of the picture was the headline. And I thought that was real. We are doing so much other stuff. It’s part of the picture. Our traffic is not reliant on one thing. Our uniques aren’t really reliant on one thing.
We have digital covers, we have print covers. There’s just more so that the pressure is off. And I think having an agency side that is responsible for most of the revenue does give the magazine the space to just be the best magazine.
Rachel Baker: It’s interesting thinking about how all that you’re saying is so new and there’s nothing new under the sun. Maggie and I started talking yesterday like, “Maybe this is in some way like a reframe of the same thing magazines have always been doing, but just way more honest.” We worked at magazines for many years when it was like there’s this idea of church and state, but of course your big advertisers just ended up on the cover. That has always been part of the stew of the magazine, the wider magazine organism. What do you think about that?
Willa Bennett: Yeah. You cannot buy a magazine cover. Full stop. That would be wild. Editorial integrity is something, especially from my journalism background, I take very seriously. But at the same time, there is a world in which—Champion is a great example. They’re a client of ours. We did these amazing raves and we were excited about them editorially.
So my team wanted to write about it. And I was like, “Of course.” So the goal is to make the branded content so amazing that we’ve covered it organically. Sometimes it doesn't work. Brands are brands. But sometimes it does, in the case of Champion.
And I do give my CEO a lot of credit for letting me say “no” to things. I think that’s also really helpful. He’s very open to feedback if there’s a brand that comes in that is just not a good fit for our organism universe. We can say “no.” And I think the flexibility of having a commerce agency and editorial really allows for that.
In Highsnobiety’s new world of print, the lines are blurry: “Our Dries Van Noten print cover—that was completely editorial,” says Bennett. “Is it the journalism I studied at Sarah Lawrence? No. My journalism teacher would roll her eyes.”
“You cannot buy a magazine cover. Full stop. That would be wild.”
Rachel Baker: Going back to what you were saying earlier about part of your purpose being to sell the idea of journalism to the next generation. I’m curious how you define journalism. And with all of these different outlets that you have within the brand, do you feel like they’re all journalism? Or do you think of them in different ways? Can e-commerce be journalism? Is that like when you say “stretching the bounds” of that word, how far do you think we can stretch it?
Willa Bennett: I think it’s storytelling in the way of the shop. The Highsnobiety shop is so carefully curated. That to me is a form of storytelling. And then the way we cover it online. If the team is really excited about our Dries Van Noten print cover, that was completely editorial. We were so passionate about that story. We pursued it.
The way it was curated on TikTok, for example, was a video of Dries receiving the issue before his last show. And then on Instagram we posted the cover. And then like we have a shop account and we did, like, a curation of all the Dries in the shop. And to me that is journalism. It was a story we wanted to tell and we expressed it through different mediums. Is it the journalism I studied at Sarah Lawrence? No. My journalism teacher would roll her eyes.
But what I was being taught at Sarah Lawrence, which was very valuable, but it was like, “Go to the city, talk to this visual artist, and write 10,000 words.” And I would do it. and I loved it. and I dreamed of that. But there was this disconnect that I already saw happening before I graduated that I was like, “It is more than that.”
And I think to tell the 10,000 words, you have to understand how young people are consuming journalism and what they’re thinking of journalism. And I’ve never thought you should fight against your audience. You should find a way to be closer to them. And so to me, commerce, brand partnerships—it all is a means to do that.
But, again, like Dries van Noten couldn’t have paid for that cover. We pursued it. And I think that’s the detail that keeps the magazine special and not branded.
Maggie Bullock: So what was the disconnect that you were referring to there with the idea of going and just reporting a straight feature? Where did you see that as a disconnect?
Willa Bennett: Yeah, the journalism school at Sarah Lawrence is very, it’s, “We’re going to teach you how to write profiles.” Which I love writing. Personal essays and profiles are my favorite thing to write. If I had more time that’s what I would 100 percent want to do. And I love both of those. We studied it very formally. My journalism teacher would bring in stacks and stacks of magazines. We’d literally just write profiles, critique them, go back and forth.
And then, as assignments, we would be sent to the city. And we talked to different types of people, go over why we were asking questions. It was really immersive and exciting. And Sarah Lawrence is so close to the city, so that was really helpful. But I would just be writing, writing, writing. And then I would buy the magazines that I was dreaming of working at and it just wouldn’t exist.
I would go and buy a Cosmo and it would be like a three-paragraph story. And so I’d be like, “Where is this 10,000 words on a visual artist that doesn’t have Instagram?” I just already was like, “Where do those go?” Maybe The Paris Review or, like, Harper’s. But as a college student, you can’t dream of something that far away.
I looked at Seventeen, where I ended up getting my first job, and even once I got there, I remember writing news posts and I was like, “There’s just no space for the type of journalism I studied.” And that’s really what sparked my career. I was at Seventeen magazine, and I was like one of the first people to be like, “Hey, Troye Sivan’s on the cover. Can we post on Instagram?” And they were like, “Sure, try it.” This is like before social really blew up. I think, now it’s pretty normal that if you have a big cover story, you’re going to post it on Instagram.
Pretty much all mastheads have some sort of social director and a team under them, which is really wild. I still can’t believe that we moved there so quickly. And it’s cool to me when we take that experience and we really bring journalism out of it. So an example I always give is, Valentine’s Day we were all in this brainstorm Office Hours and we were talking about how all these publications were publishing these studies about young people not having sex.
And my team was heated about it. They were like, “That’s not true. We are having sex, we just literally missed a couple years from COVID.” And my response was like, “Okay, so what is happening romantically? Let’s do some studies.” We had the insights team pull data from our readers and we did a massive study. We had reporters on it.
And it basically came back that it wasn’t that they weren’t having sex. It was that they were disillusioned from romantic partnerships. And they really were just used to connecting over their phones on creativity. And, like, collaboration to them and friendships were just more important.
And so we photographed three creative duos and we published this study that was like “Creative Collaboration Is the New Sex.” And to me, it’s a perfect example of responding to the audience and saying something new. But also, it is something that actually resonated and it did pretty well.
Maggie Bullock: While you were talking about the audience, I realized we didn’t ask—do you view it as a men’s publication? Who’s the audience? What are the demographics? And what does it mean to be a High Snob?
Willa Bennett: So what I inherited was I think it was 70/30 male/female. It’s 50/50 now. And I feel like I keep getting asked questions about that. And I feel like my answer is I think we’ve just expanded storytelling. In some ways we’ve become more niche, I think. Like in terms of really becoming a voice in men’s fashion, a hundred percent. We really doubled down on our coverage there. And I have social editors pretty much at all big men’s shows.
I really worked with the team to have a POV and not just have ambient content. But I think we’ve really been establishing ourselves in men’s fashion. But the other swing is we have really great reporting about youth culture. And that’s something I think that has really opened up the demographics and really helped us become more of a youth culture platform.
An example is like we did a piece on how young people were statistically addicted to nicotine again. And that’s like a perfect example where that has nothing to do with men’s fashion, but something that we were noticing and something that the team was talking about. And I was like, “Let’s go report on this.”
Rachel Baker: You’ve talked a lot about loving men’s magazines—and magazines in general—cutting them up and putting them on your wall like we did. Which ones did you grow up loving, and why men’s magazines especially? Even if you’ve brought your brand closer to 50/50?
Willa Bennett: Yeah, I think, my favorites were by far GQ and Esquire. I was just so interested in them. I was so interested in the types of stories there. I thought the journalism was really rich. But that being said I loved i-D. I love Dazed. I loved Nylon. I always had a Vogue subscription. I still have the same one. I feel like I have never even renewed it. It’s like on auto-renew. I love what Chioma Nnadi is doing at British Vogue now.
But yeah, I think I was just always so fascinated in menswear. It was a natural inclination for me. I always wore men’s clothing more than women’s clothing. I think I just personally related to it. But I was such a big fan of magazines. I think also like in the time I was in high school, like everyone read magazines. Magazines were bibles.
I would look at a magazine before I would ask for advice from my older sister, who I talked to everything about. To me it was such a resource and like a companion growing up. And then I think I just saw myself more in men’s fashion magazines.
Maggie Bullock: So let’s just breeze through your bio a little bit, which is late in the game for this interview. But you grew up in Silver Lake, California. We’ve already established that you went to Sarah Lawrence. So can you just fill us in on the sort of broad strokes of where Willa Bennett came from?
Willa Bennett: Yeah, I was a dancer, but I wanted to be a writer. I always wanted to write books. I self-published two books of poetry on the side. That’s always been my dream, always been my dream. Always been my dream to write books and be in magazines.
And I remember senior year going to my advisor, Lita Sizer and saying to her “Alright, I’ve taken all these classes, I want a job at magazines. I don’t see this work there.”
And she was like, “Well, find the answer.”
And I was like, “What do you mean?”
And she’s, “Find the answer!”
So I basically pitched to her that I’d go to a middle school for a month and hang out with seventh and eighth graders. And just observe how they are consuming media. And I did it.
And basically the answer was like Instagram, Houseparty no longer exists, but Houseparty and Musical.ly, now TikTok, were the three things that they were really obsessed on. And so I wrote this paper on how you package content there, what’s there, and the magazines that had adapted.
Through that project I spoke to editors at both Teen Vogue and Seventeen, and I feel like that kind of opened up my career. My first job was at Seventeen, and then I ended up freelance writing for Teen Vogue. Those two publications are still near and dear to my heart. And then from there, I think I’ve just gone where I’ve seen an opportunity.
I was at Bustle Digital Group at a time of tremendous growth then, around the time that Will took over at GQ, I got moved over there and I really helped him re-envision social on this global scale. And really, famously he says, “Instagram is the face of the magazine.” And I feel like I really related to that and was excited about that chance. And then, yeah, Highsnob.
“I think that we owe it to the industry to just always be open to what a magazine is.”
Rachel Baker: What inspired you to apply for this job at Highsnob? To lead a brand that was a little bit more of a men’s magazine, and you’re a 28-year-old woman at the time. That takes some chutzpah.
Willa Bennett: Honestly, they reached out to me. And there was no job title in the description or anything. It was just a conversation, and I, very confidently, was like, “This is what I would do if I was hired.” And they liked that. It was a really frank, honest conversation of, “This is what I think is missing from the landscape. This is what I see. This is my experience in digital and social.”
I was always that person at GQ that was like kicking and screaming at the print budgets. I’d be like, “You’re going to waste all that money on this story that two people are going to see?”
And they were like, “Yeah.” And then I would be up until midnight trying to figure out how to package it on social.
And then I come here and I’m like, “Oh, now I have to do magazines.” I loved it. I think it's such a gift to have a magazine and how cool that there is this resurgence in magazines. And there are stories that are just better in magazines. And I think being able to have that is something I’ve really learned to love.
Maggie Bullock: So we did wonder, actually, we were like, If there’s all these other revenue streams, does that mean you get a better print budget? Can you pay writers in the way that legacy publications are really struggling to do. Does that open you up to be more generous with creators for print?
Willa Bennett: Definitely. I think our managing editor, Jake Indiana, does a really great job of paying writers, being open about how much we could do, does this deadline work for you? Working with writers, she does a great job with that. But yes, we have a healthy print budget.
Maggie Bullock: You may be sitting in the only growth print sector that there is—back to that big ASME question—but who else is saying that right now? I know that, like, Nylon has relaunched print but they’re presumably not working with the same revenue stream.
Willa Bennett: Yeah, I think Nylon is owned by Bustle Digital Group, so there is safety there. Yeah, I think it’s specific, but I do also know that print budgets are still healthy. I buy all of them and I consume all of them and the photo shoots are still really fancy, in my opinion.
Maybe it’s not like a private jet and a horse for a one page spread, but I don’t know. Will said this recently on a panel and I thought it was really interesting. He was like, “How great is it that I’m leading a brand at a time where we can’t afford a private jet and a horse? Because if we could afford it, I would do it for every shoot.”
And I was like—that’s so real. I’ve never even known that life. So I don’t even miss it.” I’m more excited by the constrictions and so motivated to figure out a way to make it work on a small budget. And I think also coming from social, I’m not used to being able to go on a private jet.
Rachel Baker: You’ve said that you guys are social-first. But can you talk to a couple of print dinosaurs, what that really means to be social-first? Like how that works and how you build the other tentacles around it? Here I go with that my beast metaphor again.
Willa Bennett: Yeah. So some things, like the Dries Van Noten cover, for example, on Instagram it’s a cover reveal. But on TikTok, it’s just a video of him receiving the cover. And then on Twitter, it’s like the story tweeted out. So it’s like taking that and then putting real thought into how it fits on each platform.
But then there’s things like Valentine’s Day, for example, when we were coming out with a study and we were all really excited about it and felt really seen by it. And on TikTok, two days before the research came out, we did these man-on-the-street interviews about personal style and relationships and asking them similar questions.
And so I think for me, it just means making high-quality content per platform. And then from a resource perspective we do have one person per platform, which is a bigger social team than I’ve ever led in my experience.
Maggie Bullock: Okay. Can you list off those platforms for us? What is the count?
Rachel Baker: We’re taking notes.
Maggie Bullock: Because we were like, “Wait, they have six Instagram feeds alone!” So what are the relevant platforms where you have to be right now?
Willa Bennett: Instagram, still really important. Most people are on it. Our audience is really loyal. We have 5.5 million followers. Twitter, really voicey for us, really exciting. I think for us it’s just keeping up with fashion news. TikTok, obviously huge. We’re about to hit 1 million. We just hit 900k after our Met Gala coverage.
Those are the three big ones I would say. But of course we have the shop account, we have some sub accounts. And then Facebook, still, for traffic. I think that one’s pretty much just like we keep it populated for traffic. But I’m feeling like we could probably exit at any moment.
Maggie Bullock: So when you say it’s social-first, do you think of that as like you start your coverage with the immediate bouncing of everything that you’re seeing onto social and then what people react to you build more coverage around? Or maybe it’s not that specific.
Rachel Baker: Because when you mentioned the Dries thing, it’s like it’s still bouncing out the print cover. I’m like, Oh, I can identify with that.
Willa Bennett: It’s still about the story. I think there's this misconception about people who come from social where, like, They are just going to be content creators. We don’t see it that way. We’re more like, Our rollout is just as important as our production of the magazine. I think that’s more what I’m trying to get across.
It’s not that we can just never post on the website again. I was talking to someone recently about their brand, and they were like, “Do we even need a website?”
And I was like, “Yes, everyone still needs a website.” I don’t believe that. I think that is not the answer.
Rachel Baker: They were thinking you could just do social?
Willa Bennett: They were like, “I wonder if her brand could just be social.” And I don’t think that. I think our website is very important. But what I appreciate about this person is they were thinking of how to tell stories in unique ways on social. And I was curious about that.
I think there is a world in which we’re like—this morning we wrote a review on the Gucci show and I wanted the headline to be on the social video when we put it out because I thought it really elevated the social content. And that was something we did. But I think you need all of it.
Rachel Baker: I’m surprised that you guys are so into Twitter.
Maggie Bullock: Which you’re not calling X.
Rachel Baker: You’re not calling it X.
Willa Bennett: X is interesting. I’m ready to ditch it. But we do have a loyal following there and we can be voice-y there. And Corinne Bickel, who just graduated from FIT, I hired her from Twitter, actually—from X—and I think she’s so brilliant at it and she’s doing such a great job. I would check it out.
Maggie Bullock: Definitely. So you made this huge leap in career, from being a social media manager to being editor-in-chief of the beast, the organism. So can you talk about what that meant for you personally? What does that look like for you? Yes, we would love for you to tell us how much money you’re making, but you don’t have to. But what does that look like on your side—again you are in the only growth print sector—what does that look like for you?
Rachel Baker: In terms of, like, perks. And, you know, you’re definitely in a more visible, prestige job, but also your life has to be materially different. Like, I know you have an assistant…
Willa Bennett: Wow! A Shay shout out! Yeah, Shay’s amazing.
Maggie Bullock: Hey, Shay!
Willa Bennett: Yes, I have an assistant. I did not have an assistant before. I still live in the same apartment. Honestly, the biggest change is that I got a gym membership.
Maggie Bullock: Oh my god, no! That cannot be the biggest change.
Rachel Baker: I hope it’s a really nice gym.
Willa Bennett: It is, unfortunately, Equinox. But I did get an Equinox—what’s it called? A membership? I was going to say a “prescription.” Yeah, I don’t know. I really discovered working out in this role. I think it's such a boring answer, but I really want to keep writing and I feel like I haven’t had as much time as I wish just to do personal writing.
Before this job, I self published some things. I really was excited about that. And I just truly don’t have time. And I think that is the luxury thing. I’m just like, “It’s worth it.” I try to go most days but it is expensive, honestly. It’s not cheap.
Rachel Baker: I’m glad you did that for yourself.
Maggie Bullock: I feel like, if the Equinox publicist is listening, an editor-in-chief does not have to pay. Come on!
Rachel Baker: ASME-winning…
Maggie Bullock: … an ASME-winning editor-in-chief here. Get on it!
Willa Bennett: I literally could not agree more.
“I would look at a magazine before I would ask for advice from my older sister.”
Rachel Baker: And what do you do when you work out? Do you listen to podcasts? Are you on your phone? Like I’m sitting here now wondering how much time do you spend on your phone a day?
Willa Bennett: What it honestly is, is it’s time without my phone. That is the gift that the gym has given me. I listen to podcasts pretty much exclusively. Sometimes I’ll listen to an album if I’m like, “Oh, should we cover this person?” I’ll really study their music. But I try to not look at my phone because it’s really the only time.
Honestly, I was thinking about this today. It’s the first thing I look at in the morning, the last thing I look at before I go to bed. Which is horrible for you. And sometimes even when I'm in the shower, my phone is next to me.
So it really is like the only time where I’m just completely unreachable and I’m really just thinking internally. And it does seem similar, it feels similar to writing to me where it’s like meditative and you’re like for a second get outside yourself. I have a lot of my best ideas at the gym
Rachel Baker: Maggie, should we start working out?
Maggie Bullock: Shut up, Rachel.
Willa Bennett: I was saying this to someone last night, I wonder if it’s going to stick. I don’t know, because I’m not a gym person. That’s the thing.
Maggie Bullock: Yeah, but your generation is wellness-oriented. I feel like, yes, you have to, right? You also have to eat weird grains and …
Rachel Baker: … our generation is more, like, wine-oriented.
Willa Bennett: I won’t spend money on wine. It’s weird. That’s not my thing. My partner always makes fun of me. They’re always like, “Why don’t you buy more clothes? Like, you work in fashion.”
I really have to love something to spend money on it. But the gym is the one thing I’m like, “No problem.”
Maggie Bullock: Okay while we have you here—this very esteemed and also captive audience—we wanted to ask you a question that is somewhat outside of your purview … maybe not. We make this newsletter, The Spread, which is really a love letter to women’s magazines. But even we are aware that the term “women’s magazines” conjures some “psychic trauma” for a lot of people. And we understand why. We’re on board with that. But we always loved the sort of clubhouse element of a magazine that speaks to a particular…
Rachel Baker: …community.
Maggie Bullock: Thank you, Rachel. So you’re this—you probably love this term—you’re a disruptor who’s always been drawn to men’s media. But I wondered—we’re living in this, or we’re headed towards what seems almost like a “post-gender” era. Do we need this clubhouse? What do you think about women’s media? And what is a possible future for women’s media in your mind?
Willa Bennett: That’s interesting. I think you need to just reach young people. Your gender identity can continue to shift and change. Those labels are really just for marketing people. Like if the story is good. The story is good. And that’s where journalism comes in. And my journalism background comes in. Because at the end of the day, good stories are why we do this all. So let’s focus on that and not, “Is it Marie Claire or is it Highsnobiety?” We actually could tell the same stories if we wanted. And they would just reach different people.
I also think brand IP is increasingly everything. I feel like I tell my news team this all the time where I’m like, “Influence over reach.” I’d rather have 20k great comments than a video that just goes viral and half of the comments are bots. To me that does nothing.
We were actually having this conversation in a post-mortem about the Met Gala, where it was like, so cool that we had exclusive access. But I was really challenging the team, “What makes this content ours?” And to me it was a story we wrote about one of the biggest social accounts in Brazil that actually pays its entire rent off of covering the Met Gala.
And to me, that was a Highsnob story. Instead of just a video going viral. It’s cool, but what does it actually mean? And so I would say the same thing about this, like women’s media, men’s media. It’s “What is your brand saying?” That is, I think, what’s most important.
Maggie Bullock: Do you think this term “women’s magazines” is too tainted at this point from, you know, generations of diet stories? Can it be reclaimed?
Willa Bennett: That’s interesting. Yeah. I wouldn’t say flat out “no.” When I’m at Casa Magazines, getting my magazines, I have never once thought, “Oh, I’m going to go pick out a women’s magazine. Now I’m going to pick out a men’s magazine.”
I go there and I’m like, “I want to see what Chioma is doing at British Vogue. I want to pick up the new Nylon because I’m curious. I want to pick up GQ because so many people I love still work there. I want to pick up … Gayletter is really interesting to me. Hommegirls I love. To me it’s just magazines I love and support. And I think it’s almost an afterthought.
Rachel Baker: It’s interesting hearing you say that you just feel like age and generation is like the great divide.
Willa Bennett: Someone recently said to me—and I really never thought of it this way, and I don’t have an answer—that when I was in middle school the magazines I was so obsessed with, the men’s magazines at the time, so GQ, Esquire, and maybe Playboy—but I would actually take Playboy out—had longer reporting than women’s magazines. Do you think that’s true and why? I have been thinking about that because maybe that’s part of the reason I was so obsessed.
Rachel Baker: Yeah, same. I was the same as you, Willa, in high school, college, and right out of college, I was just, like, this freak for GQ and Esquire. And it’s because of that. It’s because of the, and also the voice. They never talk down to you. They talk to you like you’re a badass.
Maggie Bullock: The women’s magazines could only give a certain amount of page space to features because those features did not make as much money. You couldn’t sell ads against them. Rachel, how many features have you published that were opposite like a tampon ad? It was just sheer economics. But I think the end result is that it read as if women’s magazines looked down on their readers and didn’t think they wanted big reads. This was always a dance that we were doing.
For more on Will Bennett, visit her website, or visit Highsnobiety and follow them on Instagram.
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