Willa Bennett is pro discourse and in-person meetings.
She’s also pro Sant Ambroeus and Bowery Hotel.
Hello everyone.
Today’s letter includes: an interview with Willa Bennett, Post Malone’s new job as a Skims model, the building signaling return-to-office in New York, and my thoughts on what Substack hasn’t yet been able to replicate from magazines.
Guest Lecture: Willa Bennett
This interview is part of a Feed Me feature called Guest Lecture. In this series, I introduce you all to an expert who I’m curious about, and give paid readers an opportunity to ask them anything they want. Past guests have included Nikki Ogunnaike, Audrey Gelman, and Jake Sherman.
This week’s interview is with Willa Bennett, the Editor-in-chief of Cosmopolitan & Seventeen. She answered your questions about taking time off of work, returning to the office, and the state of girlhood in 2025.
Today’s letter is free thanks to Engine, a travel-booking platform focused on making group and business trips easier for everyone involved. Last week, while I was on a trip with Engine to learn more about how the platform works, Willa and I spoke about how we run our own media brands, and what role travel and vacation play in our very online work.
“How does Seventeen view the state of girlhood in 2025? Does the magazine keep a running, historical narrative on what being a teen is like over the decades? I am so curious how the magazine approaches establishing the referent identity of what it means to be a teen girl — what they’re thinking about, consuming, desiring, worrying about, etc.?” — Major
Thank you so much for asking this! I love Seventeen. I actually started off my career as an intern there and I still have all the magazines that have my name on the masthead. Magazines are an archive of that time, and right now the brand Seventeen is focused on adolescence today. Our tagline is “it all starts at 17.”
To answer this question literally — yes, there's an archive, you can go in there in the office. I always look at the market pages from past issues because they show what brands were hot then, which is so fascinating to see. You’ll see ads for Abercrombie & Fitch, Claire’s and Hot Topic. But then if you look at the brands actress Emma Myers is wearing in our recent cover story, you’ll see how girlhood continues to change today. We have her in Kiko Kostadinov, we have her in Dior, but also vintage. Young people are shopping differently today — they’re mixing traditional menswear with womenswear, wearing vintage from Depop and eBay, and exploring cheaper, non-vintage options from popular websites like Edikted, Princess Polly, and Brandy Melville.
If you think about it, social media is one big archive. If you go to Emma Myers’ Instagram right now, you’ll see her Seventeen cover, but you also see quite literally every single outfit she’s worn on her press tour. It’s an archive of her life.
“You mentioned your obsession with playlists in an interview once, who are you listening to right now and what’s the title of your most recently made playlist?” — Tatayana
I always make the titles of my playlists the date that I made them. Unfortunately, they’re not public.
I’m very lyric-first. One of the first pieces of writing that I read of yours [Emily’s] actually was on Gracie Abrams, and you were very early to her. I love Gracie. I pitched her in 2020 to GQ and I wrote a profile on her. It was during the time in the pandemic where you had to get a login to her bedroom shows. She is such a brilliant writer. I always tell her she’d make such a great journalist.
Audrey Hobert is great. “Sue Me” is the song of the summer. Chappell Roan is a star. I'm very curious about Sabrina Carpenter’s new album, and about Taylor's new album and her press strategy. Sombr is interesting. I love the new Dijon record. Mk.gee. I just spent the day listening to Ethel Cain’s new album on the beach in Palm Heights because I just watched her opening up to Jon Caramanica on Popcast. I get streams ahead of time — which I love to enjoy and is of course a sexy part of my job — but I make a habit to revisit albums, movies, and plays when an artist is in their press cycle so I can consume it all in real-time with the fans too.
“Unplugging is truly reading books, talking to my friends. I'm on vacation right now with two of my best friends that don't work in media. Even having them talk about where they are in their lives and their dating lives is so refreshing and exciting.”
“I want to know how you choose between taking meetings in person with people or on the phone and Zoom, and when you do meet in person, where do you go for drinks or coffee?” — Emily
I love in-person meetings. I am in the office five days a week. Ideas are always better in person. Photo selects are better in person. Social ideas come more naturally in person. Magazines are more fun to edit in person. Partnerships are more wild to dream about in person. It's important to get outside of your apartment. Plus, the Cosmo office is so romantic — I look out my window into Central Park and I have two vintage Cosmo covers and one Seventeen cover framed on the wall behind me.
I prefer getting coffee over drinking. I love a 30 minute coffee. Cafe Cluny and The Odeon are my favorite dinner spots. Partners for coffee in the West Village. I’ve been into Sant Ambroeus recently. I like that it’s quiet and you can actually talk. Bowery Hotel for a drink after work.
“How do you balance editorial quality with business objectives, like traffic views and page views? Do you find that business demands ever compromise editorial integrity? And if so, how do you navigate that tension beyond traffic. What other benchmarks or indicators do you use to measure the success of a story?” — Samantha
This is a lot of the job. I'm most excited when we're working with a partner that fits our brand mission. Cosmo Sports, for example, is something we all wanted to do. We all rallied behind it, and then Coach came in to amplify. Coach is a partner that makes perfect sense for Cosmo and Seventeen.
Engagement and time spent are important metrics. I look at overall traffic compared to previous benchmarks. I check Instagram comments. I check Tweets. I check TikTok discourse. I check newsletters like Feed Me. But I love our readers and their feedback the most. I recently launched a newsletter called Love Willa, and the most meaningful metric has been when readers reach out to me through that: askwilla@cosmopolitan.com. At the end of the day, everything we do is for our audience.
“Hi, Willa. You mentioned in a How Long Gone episode that you visited a middle school for a month and based your college thesis on the future of magazines being dependent on social media. I'm so curious to hear more about what you observed during that time and if you feel like anything has changed since then.” — Nat
This was a project I did my senior year of college. I went to a high school for a month and talked to 11th and 12th graders about what magazines they were reading, how they were finding them, their approach to discovery.
House Party was something I wrote a lot about in 2016. They were all doing their homework with FaceTime. I thought that was so fascinating and that inspired me to really think about video content and the way that young people need to be communicating with each other constantly. Young people are never not swiping, streaming, and/or texting. I was in sooooo many group chats. I got sooo many Instagram DMs and Snapchats. And YouTube has only gotten bigger since. It’s wild how much I still think about YouTube. I recently launched Blind Date, which is this series where I am blindfolded and go on a blind date with a celebrity. E.L.F. is our partner on season 1 and 2.
“What media/content do you turn to to 'plug in'? And what do you turn to when you need to unplug?” — Paige
I try to read everything. I'm on vacation right now, but I’m excited because when I go home, all the September issues will be out. To unplug is the more interesting question. I can't say I'm the best at it, but I do think reading books and being off my screen are good for me. Currently I’m reading a book called See Friendship by Jeremy Gordon. He's an editor that I've worked with in the past. I'm on this trip with two of my best friends that don't work in media. Hearing them talk about where they are in their lives and their dating lives is good for creativity.
“Cosmo cover stories are some of my favorite articles to read. Would you say that the ever growing insanity of fan/fandom has changed the nature of interviewing and writing about celebrities, and if so how can a publication harness or utilize viral moments in online fandom?” — Lilly
We take our cover stories really seriously. Our goal is to recontextualize the celebrity through the lens of love and relationships. I love our footnotes. I love our Q&A format. And we always, always respect and research talent’s fandoms and personal style.
“What's the most exciting piece of print that you've read recently that more people should know about?” — Samara
One of my friends brought me a magazine from a student publication from University of Bristol. I’m obsessed with the layouts and writing. Always support student publications!
“How do you resource yourself to lead this large of a team?” — Camille
I have an amazing operations lead, Danielle. I trust her so deeply. We talk through all things operations and team management. Part of the magic of being an editor is bringing on creatives and giving them the room to do their best work. I love this part of running a brand. It's something I’ve also really admired about my previous bosses; creativity thrives with feedback and discourse, that's why we do what we do.
“How important is taking time off for you?” - Emily
It is something I need to work on. I see my friends, is my honest answer. That's the only time that I really am not working. It's really important for me to be present with them and always be an active member in the group chats. Most of them don't work in the media and literally don’t know what I’m talking about half the time. It’s important to have friends (and romantic relationships, obviously) who don’t just see you through your work. I need to get better at taking time off (hence us doing this interview literally on vacation) but hanging out with my friends and reading really good books works for now. The ocean is pretty sick too.
"It took me TOO long to be a paid subscriber after being a freeloader. For this, I apologize. Excited to get more of Feed Me!" - Mike, paid reader
It’s crazy that last fall everyone was wearing Realtree camo Kamala hats, and this fall everyone will be wearing Realtree camo Skims x Post Malone hoodies. Everyone in the latter case = me.
Mark Guiducci was right when he said “Cover stars, long lead ambitious investigations, sophisticated visuals — those are all things you can’t do on Substack.” September issues have been hitting my newsfeed all morning, and my reaction is something like muscle memory: the same feeling I had going through magazines on the floors of the library, and on top of the covers of my dorm room bed, or in the pedicure chair next to my mom on Long Island. Substack publications and new media startups like Puck and Punchbowl are great at constant commentary, and breaking news, and events. But there’s a key aesthetic part of magazines that has been forgotten (or abandoned) and I feel it most intensely when I see such incredible work going into fall fashion shoots.
Louis Vuitton’s beauty products finally have a launch date: August 29th. The lipstick is $160, and the eye palette is $250. Pat McGrath is the creative director behind the beauty line. Feed Me’s review will be thorough and penned by a special beauty contributor.
J.P. Morgan is moving employees into their enormous new office building later this month. Looking forward to seeing more people return to the office this fall. Feed Me is in the process of getting an office too.
The East Village location of Corner Bistro has almost the same menu. But there are a few additions: “This location has a kitchen, allowing [owner Elizabeth] McGrath to add menu items like meatloaf, chopped steak with onions, a mushroom burger, and a brunch service.”
Trump’s merch shop has candles. One of the most depressing product pages I’ve seen in a while.
Despite being in the “learning phase” of gambling, Livvy Dunne is the new face of Fanatics Sportsbook. The ad, which features Livvy lounging in a bathtub on a football field, seems to be a slight nod to the Margot Robbie bath scene in The Big Short. I’m surprised that this is the best commercial they came up with, but I guess people are talking about it. Reminder that I once co-hosted one of the best gambling podcasts of all time, Chips and Dip.
Alex Cooper’s Unwell events business continues to bring together young women who like to party with strangers. She’s hosting a two-day event in Vegas this fall, which includes DJs (Paris Hilton commented on the post, we can assume she’s attending), comedians, pool parties, and reality stars. Packages have two price points: $300 + tax and $350 + tax, depending on your seat selection for the Unwell Live show. Kind of a fun idea for a bachelorette party or a 21st birthday.
Seventeen magazine forever. I do what I do today because of Seventeen. I used to read it in the grocery store while my mom was in produce. I wasn’t allowed to buy it so I had to get through all of the pages while she shopped.
Major’s question about how Seventeen thinks about girlhood and identity and how it changes was amazing! I was bummed Willa only answered it with the lists of brands 😔