The Most

Woman in the World


Brandon Holley

CEO of Everywear, magazine industry veteran, decent surfer

The Most

Woman in the World

Growing up in Virginia, Brandon Holley dabbled in punk music, had a partly-shaved head, and aspired to open an art gallery. But when she published her first magazine story in the early ‘90s (about muscle cars, no less), she realized she’d found her medium. She cut her teeth at GQ and TimeOut, and later became the editor-in-chief at ElleGirl, Jane, and Lucky. Then, in 2013, she ditched magazines for tech; she’s now the CEO of Everywear, a software platform that helps women shop and dress more efficiently.

ON IDEAS: I was a good fit for magazines because I’ve always had ideas. While I loved sitting front row at fashion shows and all the other trappings of being an editor-in-chief, what hooked me was that you got to start over from scratch every month—it was an ideas factory. I’m not a great writer and I’m not a great editor, but coming up with ideas is my natural state.

ON CHAOS: I tried to run staff meetings like a writer’s room at a comedy show. Sometimes we’d crack up at how stupid we sounded, but the sillier we got, the better the results could be. Sure, you might go off on the wrong tangent and need to pull back, but in general, I’m not formulaic—I like a more chaotic approach.

ON INCLUSIVITY: I believe that people are more creative when they’re in a cool, safe environment, and I always wanted my staff to feel that way—no backstabbing. I hired people the same way you might pick a basketball team: by encouraging the players to play off each other. Jane and Lucky were not bitchy magazines, by nature; they weren’t about fashion you can’t afford and blue-blooded women who don’t have anything in common with you. They were more inclusive, and the staff had to be that way as well.

ON CLOTHES: Lucky was such a success because it showed “real” women in clothes, and it demystified fashion. After women read it, they felt empowered to go shopping, because they could actually see themselves wearing those outfits. That’s what inspired me to start Everywear. I thought that what we did for women at Lucky should happen in tech, as well.

MBW-Brandon-Holley-02

ON FASHION INTERVENTIONS: The seed for Everywear was first planted in Milan. I was there with Lucky’s fashion director Anne Keane, and I was about to buy this laser-cut corset belt by Azzedine Alaïa that I felt like I really needed and wouldn’t be complete without. She was like, “Brandon, don’t buy that. Buy these three V-necks in different colors. You can wear them with…” and she started to rattle off all these different things. And I was so glad she intervened and told me exactly what to do. Every time I put on one of those V-necks, I was grateful to her. With Everywear, we put that fashion editor into an algorithm. It’s software that says, “Wouldn’t you rather buy this shirt, because it goes with this other thing you have, and you can wear it to work, and out with your moto jacket on a Saturday night?” Women are always telling me that they buy all this stuff on sale and then they never wear it. Everywear is designed to prevent that.

I started experimenting with Everywear by styling friends on Skype at my kitchen counter. I looked at their clothes, and then I suggested adding one thing, and showed them how to pair it with what they already had. And my friends loved it. Then I brought in some tech folks to help me make it into a platform. They saw the emotions of the women who were part of it, and they said, “Oh my god, it’s crazy how women are reacting to this.” Then we trimmed it down to what it is currently—a software system.

I tried to run staff meetings like a writers room at a comedy show. Sometimes wed crack up at how stupid we sounded, but the sillier we got, the better the results could be. 

ON CONFIDENCE: When I was a teenager, I never thought I’d be in magazines. I played the drums and would go see shows at the 9:30 Club in Washington, D.C. My friend Wendy had every issue of Vogue, and I didn’t think it was interesting; I was a tomboy. I was also very into horseback riding, so even though I was an alternative, punk-rock-ish girl, I had a serious side. Competitive riding is an all-encompassing, almost militaristic sport. If your horse isn’t warmed up or you haven’t picked his hoof or given him the right food at the right time, then you’re in trouble. You’re taking a 1,200-pound animal over a 4.5-foot fence—you’ve got to be prepared, and you’d better be confident.

ON BEGINNINGS: After college, I started writing a book called A Girl’s Guide to Muscle Cars while I was bartending in the East Village. Paper magazine published a version of it, and when I saw my story in print, I was like, “Woah, I got paid for that! That’s so cool.” My parents wanted me to go to law school, and then I found this other thing that I loved. Before that, I had no idea I was interested in magazines. Then I fell into fashion by working at a trade magazine in the industry. I was never fashion-crazy; I wasn’t a super fan-girl. My take was, “Let’s see what these clothes can do for us.”

ON LEADERSHIP: I had some great bosses over the years. When I was working for Cyndi Stivers to launch TimeOut New York, I remember thinking, “If she cracks, this whole thing is going down.” And she never flinched. She was confident that we were going to get that thing out the door when none of us believed we could. I had another boss at a tiny magazine who would rip my writing to shreds, which taught me to not fuss over it—just keep going, keep going, keep going. She’d write in the margins, “This is bullshit.” That kind of strenuous editing makes you better.

ON STARTING FRESH: When I left Lucky, I had offers from other magazines, but I didn’t want to go back. I was done. I decided not to interview for any other jobs, and go full speed ahead with Everywear, so I started talking to people. I’m like a foghorn: When I have an idea, I put it out to everybody. I’d never asked for money before, and the tech world is very competitive with funding. I had to put my hand out and say, “I need money by Tuesday. Are you in or are you out?” It was very different from editorial. I had times when I was barely making payroll because the money wasn’t coming in fast enough. You have to call someone up and try to figure something out; sometimes I rent out my house on AirBnB to pay salaries.

ON DRIVE: It’s incredibly motivating when I’m pitching Everywear and all the women at the table say, “Oh my god, that’s me. I need that.” When you get this constant reassurance that you are solving a problem, it keeps you going even when the fuel tank is low. You don’t go on a road trip and wake up and decide to stop driving; you just keep going.

ON FEAR: It’s a weird thing: I’m not risk-averse. No matter what, I know I’ll land on my feet somehow. If I have to sell my house, I’ll sell my house. If that means I have to go camping for a while, so be it. There’s always a solution. I’ve been in plenty of situations where I’ve just tightened my belt, and it’s given me a good outlook. There’s just nothing to be afraid of. I’ve spent a lot of time on $20 a day.

ON HAPPINESS: I think the company is going to make it, and I’ve never been happier. I started surfing again. I’m divorced, and I’m enjoying meeting new people. When I was in magazines, I knew that it wasn’t going to last—I felt like the creative train was passing me by, and heading into tech. I’m so glad to have gone through that period of uncertainty to find out that there’s something on the other side. I talk to friends who are still at magazines and they’re worried about their next step; I’m relieved to not feel that way anymore. It’s a great time in my life.

I’m not risk-averse. No matter what, I know I’ll land on my feet somehow. If I have to sell my house, I’ll sell my house. If that means I have to go camping for a while, so be it. There’s always a solution. I’ve been in plenty of situations where I’ve just tightened my belt, and it’s given me a good outlook. There’s just nothing to be afraid of. 


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