People are hungry for truth
Podcaster and strategist Alyssa Vingan on unlearning the grindset, tweeting through her divorce, avoiding TikTok, and putting yourself first
Alyssa Vingan is trying to unlearn some things.
She tells me as much maybe 10 minutes into our conversation. It’s Monday morning and she’s sitting on the couch in her New York City apartment. Her white Havanese, named Leche sits beside her, listening attentively.
From the outside, you could forgive someone for thinking Alyssa has it all figured out. A fifteen-year veteran of fashion media, she started in the trenches, covering fashion news as an intern for the now-defunct Lucky Magazine, but soon managed to secure more gainful employment. For much of the 2010s, she flitted between new and old publications. Paper Magazine, Marie Claire, Fashionista.com.
In 2019, she dropped a major bomb, announcing she had been hired as NYLON’s new editor-in-chief. The following year, she helped relaunch the brand, drawing more than a little inspiration from her own Y2K nostalgia, and eventually scoring interviews with Pete Wentz, Vanessa Hudgens, and Travis Barker.
Amid shrinking revenues, and shuttered publications, it’s rare to see a millennial on the masthead of an established brand. It’s rarer still to see anyone — in media or outside of it — so willing to challenge their own recipe for success.
And so I want to know more. About her layoff from NYLON, about her new podcast and Substack, The New Garde, which offers advice and commentary for emerging fashion gorlies (and guys).
But mostly I want to know more about her and her view on life.
Our conversation, which has been edited and condensed, touches on all of that, as well as her friendship with Brynn Wallner, her successful fight against cancer, finding herself after her divorce, learning to break the rules, loving TRL, and which emo legend she still needs to interview.
ES: Happy Monday — how are you?
AV: Happy Monday! Every day feels kind of the same for me now.
ES: How so?
AV: I was so used to having a full-time job, and now I’m doing my own thing, and it’s still hard for me… Not in a bad way. I’m just unlearning a decade-plus worth of being on somebody else’s time.
ES: Well let’s follow this feeling. How has your life changed post-Nylon?
AV: Good question. Truthfully, I never saw myself as being my own boss. I always thought: go to college, graduate, get the internship, get the job, climb the corporate ladder. Nobody in my immediate sphere did anything different than that. Sometime in the past six years, I realized that that plan was more precarious than anticipated. So it’s shocking to wake up on a Monday and be in control of my own destiny… For more than a decade, my routine has been to wake up, log on, do the job, and then do work-related activities in the evening, be it drinks with a publicist or with a freelance writer, whatever the case may be…
Now, with the podcast and my freelance consulting career, I wake up every morning with my dog. We go out for a walk, I try to get some time away from my phone and my computer. It’s so nice to be able to choose who I spend my time on, and where I put my energy. But the days when I record take a lot out of me because I feel very vulnerable. It feels like I’m laying it all out on the table. Anyone who knows me would probably tell you I’m normally a behind-the-scenes girlie. I am extremely out of my comfort zone right now. I was texting with my friend Brynn Wallner, who you interviewed, and I was like “Is it normal to cry every day?” She was like “Yeah girl.” I know this is not necessarily a unique experience, but it’s new to me, and I’m just really trying to feel my through it because I’m never going to just rest on my laurels. I want to do better things than what I’ve done before, but that means taking risks and unlearning a lot of behaviours.
ES: You’ve gone from being a caged bird to being able to fly anywhere you want. That’s a big, scary change.
AV: Yeah. And also it wasn’t my choice, to be completely frank. I was putting plans in place to leave my previous job because I didn’t want to be a caged bird anymore. My career had changed so drastically and it was weighing on me spiritually. You can only put on the smiley face for so long before it starts to feel like you’re lying to yourself and everybody else. I had a one-year plan to pivot to something more me. I wasn’t sure what that was. I didn’t quite get there before I was laid off…
It took me a couple of months after being laid off to get in touch with myself and my desires. What did I love about the job that I stopped getting to do for whatever reason? And the answer is something similar to what we’re doing right now. I love interviewing people. I love just making people feel seen and heard authentically. And I also love pop culture. I feel like in some small way my podcast is a way for me to get back in touch with that.
ES: And it’s just you, right? There’s no team behind the scenes?
AV: It’s just me. I would love to eventually bring on an intern, or a student assistant level person to help me get on YouTube and TikTok. When I was fresh out of college I interned at Fashionista.com, it was one of the most special experiences of my life. I was thrown into the fire. My editors at the time, Britt and Abby, showed me the ropes and gave me opportunities. I will never forget them for that… I would love to be that for somebody. But if I’m being honest, part of me feels that I don’t want to learn how to make a TikTok, you know? I would prefer to have someone who knows that platform do it for me, and show me how to do it authentically. I’m trying to get off my phone, not be on it more.
ES: That’s a SHE-E-O mindset right there. “I don’t touch the phone, you touch the phone.” But speaking of the pod, I wanted to congratulate you. I’ve listened to a couple of episodes now, including the one with Brynn, and it’s cool.
AV: Thank you. It’s very me. I had a podcast when I was at Fashionista.com, and it was really fun. It’s a nice way to get off of the screen. At that time, we would blog all day long. I was writing three to five articles every day. And so I enjoyed just talking things through and not having this laser-focused goal. We’d have a topic, obviously, but I liked how the conversations meandered. My dream job growing up was to be an MTV VJ. That was how I learned about music, about culture. I was a tween when TRL started and I was a child when I was watching Cindy Crawford on House of Style. I was obsessed. Interestingly, now I feel like everybody is a VJ. You see them on TikTok with their tiny little branded microphones. Everyone is doing it in some capacity, so why not me? Why don’t I give it a shot? I love writing, but there are so many better writers out there. I’d rather write something when I know I can knock the assignment out of the park. I don’t want to force it.
Imperfections are what makes for an interesting conversation.
ES: You want to talk about unlearning? It probably took me a year after I started this newsletter… There’s no time for style in news, they don’t expect that. But the result is that personal writing suddenly seems way more vulnerable. You open yourself to criticism because people can easily say “Who the fuck is this guy?”
AV: I talked about this a little bit in my episode with Chrissy Rutherford, but I’m 37, and it was only a couple of years ago that I felt comfortable being myself. I know exactly who I am. I had to go through some shit to get here. I’m a breast cancer survivor. I’m divorced. I’ve been through some things in my life and I made it out on the other side, and I feel confident in what I have to say. I will defend it. That wasn’t always the case. In my early 20s, I was putting stuff out there on the internet that I didn’t necessarily stand by. Thank God some of those websites are gone. Laughs. I don’t even want to think about some of the stuff I was forced to put out there just for clicks. I don’t want to do that anymore.
ES: How does that freedom from clickbait factor into the podcast? Because it’s so tempting to book a provocative interview, to chase something flashy rather than something substantive.
AV: That’s an interesting question. Hate clicks are definitely real. People love to tear apart an incendiary guest. And I think we all have to play the game to some extent. I wouldn’t shy away from interviewing a guest who’s been called out for their past behaviour, or who is known for stirring up controversy… The thing I’m being strict about, though, is, whether the person is willing to take a hardball question. I’m still in the very early stages of podcasting, I’m not dealing with anyone’s publicist or agent or manager… But I hope that, if and when I am dealing with those people, I will be able to communicate to them that they should expect me to ask serious questions. I’m not in the business of gotcha journalism but I’m an honest person. I know I’m not perfect, and if you want to turn the question around on me, great, I will address it to the best of my ability. But I hope they will be comfortable doing so as well. Like I said, I’ve written some stuff in my career that’s really gross and embarrassing. Stuff about people being too thin or this or that. I don’t want to go back there, but no one’s perfect… I think that our imperfections are what makes for an interesting conversation.
ES: We don’t need to talk about your divorce if you don’t want to, but it feels like a turning point in some ways. That was when I became aware of you at least, and it felt like a real “Phoenix rising from the ashes” moment.
AV: So a funny thing about my divorce is… I tweeted through it because I needed a way to process it that felt true. In a lot of ways, I felt extremely gaslit in that relationship. I was questioning my reality of what was actually going on in my relationship, and I had one outlet that was not my parents, my therapist, or my lawyer, and that was Twitter. I have never had more engagement on my tweets than when I was in the middle of my divorce. It was healing, and I made friends with people who would DM me saying they were going through something similar. For whatever reason, I think divorce still comes with a lot of shame.
ES: It has to be pretty alienating, right?
AV: It was an interesting time too, because Mary-Kate Olsen was going through a messy divorce, and Kacey Musgraves, and I think Kim and Kanye divorced around then too. A lot of celebrities had some messy pandemic divorces. My divorce was not not that. We didn’t have kids, we didn’t own a home. I just had to get out, and I did. It was one of the moments in my life when I felt like I woke up. Like I said before, I was playing by the rules, doing what I was “supposed to do.” I did the thing, I got married. I was listening to what my husband at the time thought I should do. And it became very clear to me that I was in a bad situation. When I freed myself of it, it was like “Oh, you don’t have to play by these fake rules that are not real.”
I’ve said this before, so I don’t feel that I’m being ugly, saying it, but this person stayed with me when I had breast cancer. Society tells you you’re supposed to find someone who stays with you in sickness and in health. I found that. But your whole marriage can’t ride on that. Like “Oh, I stayed with you when you had cancer” you know?
ES: Totally.
AV: In hindsight, you know who got me through cancer? Me and my mom and my dad, who picked me up and dropped me off from chemo and cleaned up my vomit in the middle of the night. My husband was there as a comfort for sure, but I did that. I got through cancer and I kept a level head… God forbid, if I got cancer again tomorrow, could I do it without him? Yes.
Sometimes it takes you getting thrown under the bus or stabbed in the back to stop and ask “Why do I keep doing this?”
ES: Do you feel like in the past few years you have learned to be the center of your own life? Does that make sense?
AV: Yes, and the answer is yes. I know I seem like a confident, can-do person. But for whatever reason, I have struggled with that. I was always very sheepish and shy and tentative about many things. I think that’s why I was so good at following rules all the time… I think it took my being put through the wringer a few times, to be like “Maybe not everybody has your best interests in mind.” I’ve had some shitty toxic bosses and some shitty toxic friends and some shitty toxic boyfriends who took advantage of how kind and generous and good I can be. I think this is the first time where I am looking out for number one… It feels like society, generally, is always talking about breaking the cycle, and figuring out what our toxic patterns are. My toxic pattern is people-pleasing, baby. I am a recovering people pleaser, and I’m trying to break out of that. Sometimes it takes you getting thrown under the bus or stabbed in the back to stop and ask “Why do I keep doing this? Why do I keep putting myself in this position?” … I’ve missed so many red flags throughout my life and now I just run in the other direction. Even if someone is trying too hard to be my friend. It’s like “What’s your angle?”
ES: Speaking of red flags… Do you regret riding so hard for Machine Gun Kelly?
AV: Oh, I’m tuned out on Machine Gun Kelly, but I still standby Tickets To My Downfall. Great album. I’ve also lost the plot on Kourtney and Travis, too. I feel like they’re just playing house, which is cute. Good for them.
But yeah, I will say that while I think my trust issues are well-earned, I’m trying to unlearn them because I’ve had people come into my life in the past couple of years who are angels. I’m suspicious of people, but I also realize that maybe they see me as sweet and nice and they want to get to know me better.
ES: We’ve talked a lot about rules today, and the idea of breaking rules. What is one fashion media rule that you would like to break? For example, my interviews are often stupidly long because I think they’re for a special, highly curious form of reader, that the industry pretends doesn’t exist.
AV: My thing is: I don’t think you should base your subject matter on follower count. There are so many people who I thought would be a good fit for coverage at my past employers, but the powers that be would tell me “We can’t put the resources into this because the person is too niche, no one’s going to read it.” At the risk of getting a little tinfoil hat, you can’t tell which followers are real just by looking at the count. I’ve had experiences where you pick someone based on that number and they get zero engagement. No one reads the story. And it becomes clear that either those followers are paid for or they’re bots.
Maybe this is just me being an idealist, but I think people are hungry for truth. We are being fed algorithm-based crap for so much of our lives now. I don’t know how anyone feels about anything, about life itself, about the song that we’re being fed on Spotify. It’s another reason why I wanted to start The New Garde. I know so many people have feelings about what’s going on in the fashion and beauty business, and there’s nowhere to talk about it because the fashion publications that exist are worried about blowback. If you really want to write something critical, you might get a GChat from the publishing side telling you “Maybe reel that in about Miu Miu because Prada might want to advertise with us one day.” Like, no they won’t!
ES: It feels like brands and the people who run them are scared to do anything outside the sandbox. It’s almost like analysis paralysis.
AV: Yeah, and I’m not saying I won’t ever have advertisers or have to consider things like that. But I’m not trying to be a giant media conglomeration. I am okay with making a living for myself and being comfortable. I don’t need to be some person hoarding wealth. I feel like that gives me the freedom to say what I want. I’m not trying to be everything to everyone.
ES: I don’t want to take up too much more of your time, but I’ve alluded to your love of pop-punk. Who would you love to interview from that 2000s era that you haven’t already?
AV: I’m trying to think of people who have veered out of pop-punk into doing other things… Maybe someone like Hayley Williams. She’s obviously an icon, but she also has that Good Dye Young hair dye brand and she opened a salon in Nashville. I would love to go deep with her. I feel like she’s been very forthcoming about the challenges of being a young woman in the music scene.
I’d also like to sit down with Mark Hoppus from blink-182. I’ve interviewed Travis before. My king. But I saw blink-182 with my dad two years ago, and I fully cried because he had just gone through cancer treatment and he was back on the road. It was just like a very humanizing moment. I really love to talk to people who have been through life-altering shit.
