When Libby Callaway realized that good fashion PR revolved around engaging story telling, much like her previous job as the fashion editor of the New York Post, her newest career took off. Today, her Nashville-based communications company, The Callaway, is busy bringing luxury brand experiences from companies such as Hermès and Cartier to Tennessee, taking a taste of Nashville to NYC (she just finished a pop up “Greetings from Nashville” at the Wythe Hotel in Brooklyn), and working with other brands based around the globe including skincare brand Erno Laszlo and Toronto-based ethically sourced cotton basics company, Kotn, which just opened a store in Soho. I love Libby’s quirky style and her warm, Southern, demeanor. It’s also inspiring to see women you knew years ago reinvent themselves so successfully. Here, Libby shares her career path, how it’s not where you’re located but what you do that matters, and the 97 cent purchases that led to a collection she’s now known for.
Tell us a little about who you are and what you do: I always like to start by saying I’m a native Tennesseean. I grew up wanting to be in New York, because I was a writer. After college I applied to grad school and got into NYU journalism school, so I moved to New York in 1995 and didn’t know a soul. I’d heard of the New York Post, but I didn’t have any idea about the tabloid wars or the history that it had. I started as an assistant there I guess, 96 or 97 and was there for my entire career up in NYC.
They didn’t have a fashion editor at the time. I told them they needed one and made them send me to shows and created this amazing job for myself which really became a really kind of singular job at the paper. I just kept on giving them ideas and they kept on saying yes. We started a fashion supplement and we did bigger photoshoots. They covered the European shows for the first time in a decade. I pushed the envelope a lot, I suppose, and got to have a really good time.
I left in 2004. I was just exhausted. I had a really good ride. I got to a really wonderful place in fashion and the only job I wanted was the job I had, but I didn’t want it anymore. I literally had a revelation one Friday night after coming home from closing an issue. It was 9:30 and I was washing my face and I was like, “Oh my god. I don’t want to be here,” and I left. I was gone in three months.
Wow. That was very decisive. It was like a lightning bolt. Well, something that did happen, about a year after I got back to Tennessee, I got sober. If you subscribe to the whole idea of divine intervention, I think hitting bottom in New York would’ve been a lot uglier than it was in Tennessee. It wasn’t a bad bottom at all. And there was more room to build myself back up after kind of dropping down.
I worked in newspapers for a while, but then left and worked as a stylist in Nashville with music row people. I costumed a movie. I sold vintage clothes. I had a great vintage clothing side business that was really popular.
Then in about 2010, I started doing content creation for a denim company here, Imogene & Willy. At the same time, I was calling my friends in NYC and telling them I was working for a really great denim company that they needed to know about. The whole Americana movement was happening and heritage was a big story, so I was getting them coverage. They said, “Well, why don’t you do our PR?” I was like, “Because I’m a journalist. I don’t do PR.” Very self-righteous.
But then I started thinking about it and what it is–at least what I think I’m doing, is just telling a story in a different way. These days it is almost a more creative place to be on the marketing side because I feel like there are more opportunities.
After that, I started consulting for Billy Reid who’s based in Alabama. So I moved back up to New York and opened an office for Billy. It was open for only about a year, when I moved back to Nashville and started The Callaway. We do some very straightforward PR for some brands in fashion, beauty, lifestyle, hospitality, retail, but we also do a lot of events. Our first big one was this Hermès last fall, we helped them with the Hermèsmatic project in Nashville. Then it was Restoration Hardware. Then KCD subcontracted to us to do an event with Cartier. We’re becoming this luxury go-to company in the Nashville region and that’s been really fun and something I didn’t see coming.
I think the most important thing that we do is we teach other people about what’s happening in Nashville’s creative community. Probably less than 40% of our clients are Nashville clients. We’ve got two brands out of Toronto. Our events usually come in from New York or LA, so they’re not really localized. But we still sell the idea of Nashville as this vibrant community that people are interested in. We try to represent Nashville and help brands from the outside integrate themselves into the community in way that’s organic. Nobody here cares that you’re from LA and the quickest way to get somebody to not want to work with you is to brag. Teaching other companies how to speak the language has become something that we do. I call it local culture Sherpa-ing.
Typically you think that a PR firm would have to be in a big city. Not that Nashville’s not a big city, but that you can be in Nashville and have clients like Hermès and clients that you represent in places like Toronto. Erno Lazslo is one of our clients and their CEO lives in Shanghai.
Does that surprise you? Yes, it does surprise me, but it only surprises me because it was unexpected. But it doesn’t surprise me that we’re able to do great work. That’s because of the team that works with me and their expertise and their insistence on excellence and working hard. And it’s all the things that I believe in–being kind, helpful and loyal. That’s why I think they come to us.
What do you love most about being in Nashville? I love having space. I like the accessibility that’s here and I also really appreciate the fact that it’s an industry town–the entertainment industry is so prominent, and I think that’s the reason I’ve been able to be here and have the career that I’ve had. The music culture begat the creative culture that’s here now, which is about food, fashion, design, art and dance and it’s a really wonderful place to be. The support people in different creative industries give to each other is really inspiring and different, it’s not forced.
What did you apply from being a journalist to what you do now? I think storytelling. Just knowing what a good story is and having been pitched so many unprepared, unexcited, and uninspired PRs in the past, I’m able to come at it from a totally different angle because I don’t want us to ever sound like we’re not excited about a client. There’s a level of sophistication that I became accustomed to in New York that I think that we’re able to execute on a level that potentially other people don’t.
When you started The Callaway, what was easiest for you and what was the hardest? I think the easiest thing was how natural it felt. The whole idea of, it’s just a different kind of storytelling, made it feel so natural to move into that other side.
I think the hardest thing was when I started, I thought I was going to concentrate on local clients. I thought I was going to represent all Nashville brands and just realizing that the market’s not mature enough. These people and small brands that I really believed in, I can’t do everything pro bono. We’ve only been able to grow the company by having outside clients. But there are still projects we work on because we believe in our community.
One of your attributes that helped you succeed: The thing that’s always got me through and I think I had a reputation for in New York, is being nice and fair and doing what I say I’m going to do. There’s nothing that makes me more angry than somebody telling me they’re going to do something and then dropping the ball, just because they don’t care enough or they’re sloppy. I don’t like people who don’t hold up their end of the bargain. That’s something I think that we always do at The Callaway. We do what we say we’re going to do and we always try to exceed expectations.
Best career advice you’ve received? I don’t really have any. I’ve gotten a lot of good advice, but honestly, this is something I thought of about myself … I haven’t sought out role models or mentors like I wish I would have through my career. It had something to do with being an introvert, not wanting to inconvenience anybody or be presumptuous that they would want to spend time helping me. As I’ve gotten older, I have gotten a lot better about it. But I do wish that I would have taken advantage of some of the mentorships that were available to me as a young journalist. They were right there and I just didn’t.
We’re all our own worst critics. That’s something especially with young women who want to be in media or interested in fashion, I try to have as many coffees as I can. I try to pay it forward.
What motivates you? I’ve never been motivated by money, creativity motivates me, beauty, and growth opportunity. But I will say that the Callaway is my retirement plan. Period. I’ve got a 401K, but growing this company and making it into something that I can have my incredible, loyal, dedicated, I-hope-they-stay-with-me-forever team take over someday is what I want to do.
So I am motivated by growth right now, just figuring out how to grow this company and how to get to where I can retire and travel the world and call myself an interior decorator and have a string of lovers at every port!
To date, what has been your biggest success? I love these questions so much. My biggest success, I think, is starting The Callaway. My team has grown 300% in the last year. I think everything I’ve done in my life up until this point has been preparing me to start this company. I love what I do and since I’ve started The Callaway, I have never woken up and been like, “Fuck, I’ve got to work today.” It’s always fun and different and exciting.
What has been your biggest failure and what did you take away from that? The biggest dud I mentioned is I costume designed a movie. It was six weeks of living hell and I failed on such epic proportions. One of my childhood friends is Janie Bryant, who was the costume designer for Mad Men and Deadwood. When I got this opportunity, I called Janie, and she said, “You should do it, but don’t do it unless your team knows how to do it and have done a movie before. You need people who have worked on a movie.” We hired all these people with experience and then Miley Cyrus announces that she’s doing her movie and is going to pay much more, so I lose my entire team and basically starting filming this movie with no idea of what continuity was period. It humbled me a lot.
Three words that describe your company: Warm, creative, responsive.
Three words that describe you: Kind of the same. I want The Callaway to be a direct extension of me. That’s how I hire people, that’s how I choose clients. I have a ‘no assholes’ policy. They have to want to work as hard as I work, and me and my team work really hard.
Life goals: I want to travel more. I don’t want to let my brain get old, I want to just keep moving. I realized a couple of years ago that the key to not getting old is physical movement, is moving your body and having new experiences. I’m 48 years old. I’m not married and I don’t necessarily want to get married. I do want a partner and I’m finally to the point where I’m focusing on that right now.
Daily goals: On the bad days, just making my bed is about it. I always make my bed. If you leave your bed unmade, to me, it says something about your state of mind. I also try to do something or say something nice to people every day to spread positivity. If I think somebody did a good job or looks nice or I look their purse, I’m going to tell them. I’m trying to not just think things, but actually say them out loud; somedays I’m more successful than others.
Favorite sites/people you follow: I am really obsessed with interior design. It was my mother’s family business growing up, so something I’ve always been motivated by is making a beautiful space. Going down rabbit holes on Instagram with the really out there sites, like Décor Hardcore is one of my favorite ones. It’s such a weird feed and I love it.
Daily rituals: Coffee and I get a physical copy of the New York Times and the Tennessean and I try to read them before I take a shower. And exercise, I try to exercise three or four times a week, more if I can. Right now I’m doing Pilates, but I’ve had points in my life where I’ve been really into yoga. Then I started working out with a trainer and got into weights; I feel like I need to go back to that because the endorphins that come from lifting weights are pretty phenomenal.
How do you unplug? Shopping. It sounds so shallow, but to me, it’s a sport. It’s like going out and playing ultimate Frisbee or something. That search is really fun. When I sold vintage clothes, I loved driving from thrift store to thrift store and finding things. One of the most exciting things is still going to a flea market or an antique mall.
But also being an introvert I need to be alone, so I like taking road trips by myself where I don’t have to talk to anybody for hours but I get to see new things and make my own schedule. I love that.
Hidden talents/hobbies: I like cook. I don’t know if I’m any good at it, but I enjoy it.
You don’t have to excel at your hobby, you just have to enjoy it. That’s true. I’ve stayed good friends with Kerry Diamond. I helped her out with her Cherry Bombe University this week. She’s terrific and has been so supportive and has come to Nashville and helped me on projects. I love what she’s doing. She’s inspiring.
Favorite charity: I’m on the board of the Sexual Assault Center in Nashville and it’s incredible. After the Kavanaugh hearings, call volume to the center went up 500%.
That’s so depressing.
It’s it’s really hard to process, honestly, because the center is doing good work, but now the people receiving the calls are totally overwhelmed and exhausted and so The Callaway is trying to find ways to be supportive of them. We’re getting our restaurant clients to take some meals and our beauty clients to give them special oils. So just finding ways to be helpful there. It’s such important work, especially right now.
Do you collect anything? I collect everything. I’ve got a really big clothing collection. But beyond that I collect lady paintings, which are paintings that are not professionally done, but are portraits of women. I started in 1993 right out of college and I found a collection of four at a thrift store for 97 cents each. I still have them. Now I have almost 80. People give them to me and sometimes that works and sometimes I’m like, “Thank you for this shitty picture.” They all have to be a little weird, but I have to dictate whether they’re weird. Sometimes they’re just bad. And I try not to pay over $20 for them.
Biggest splurge you don’t regret? It’s funny, it’s one of the first times I ever spent a lot of money on a pair of boots was at Bergdorf Goodman. They were a pair of Marc Jacobs boots that I bought probably in 2002. I still wear them. I’ve had them resoled 10 times.
Favorite small indulgence? Baked goods. I love getting a really good cookie.
Album currently on repeat: I’m so out of it when it comes to modern music, but I like the new Courtney Barnett album. I am still am stuck in my 70s rock and roll bands like Big Star and Bad Finger.
Scent that brings back memories: Joy by Jean Patou. My mom’s best friend who was like my second mom wore it. Her name was Gaye, she was glamorous and ended up being a very tragic figure, but she was a really wonderful, inspirational person to me growing up.
Lucky charm: My dad sometimes will send my sisters and I buckeyes. They’re a nut that falls off buckeye trees and they were something his dad gave him. Every once in awhile, he’ll mail us buckeyes with no explanation. I’ve got some on my table that he mailed me last year. Those are lucky for sure.
Favorite hour of the day: 6 AM. There’s nothing happening that I need to respond to quickly. I get to sit there and drink coffee and read the newspaper. I don’t have kids so I don’t know what it’s like to have somebody needing your attention all the time. I’m really spoiled that way.
Libby’s portrait and Hermesmatic photo: Emily Dorio; Wythe pop up image: Steven Visneau; Andra Eggleston: Heidi Ross; lady wall: Caroline Allison.