In our long-running series, "How I'm Making It," we talk to people making a living in the fashion industry about how they broke in and found success.
Let's go back a few years. What did you study in school?
I transferred to Brown from Johns Hopkins. I was a public health major the first year [at Brown], and when it got to the part where I would have to take science classes, I quickly got out from the public health track and went to the Urban Studies track, which was much more humanities-based. But I would take writing workshops every semester to keep it fresh.
I went through [Brown] not even really knowing that being a writer could be a job that you could have, somehow. It’s probably because I was in my own little bubble, but in terms of career services, there were people who went into consulting and there were people who went into finance. I was lost when I graduated. I had come out of the closet between my junior and senior year of college, and when I came back my senior year, I was like, 'I love fashion!' I think it was because, being out of the closet, I could become more in touch with my style and not try to pass or whatever I might have been trying to do.
I did not grow up reading Vogue or tearing out ad campaigns or that sort of thing. I was more of a consumer of movies. I was obsessed with Liv Tyler and Alicia Silverstone and people like that. I had a subscription since I was 13 to Entertainment Weekly.
That’s thorough entertainment news.
Serious industry chatter. But that was where, if anything, my head was at. I think I fell into the fashion thing because I was really into it at the moment. When I was graduating, I didn’t really know what to do, but I — being the sort of neurotic, high achiever that I was — was obsessed with getting a job before I graduated. I had a friend whose mom was best friends with the SVP of communications and marketing at Ralph Lauren Home. I interviewed with her to be an administrative assistant.
I was an editorial person, even though I didn’t know what that word was. So I interviewed at Condé Nast in the HR department.
A position opened up at WWD: Bridget Foley was hiring a fashion assistant. She knew I was a writer, but she stuck me in the [fashion] closet because it was the position that was open. About four months after starting that job, I started writing.
How did you do that?
My key to managing the closet was that, if I hired at least one really smart intern, she could manage the other interns, and then I could have time to do my thing. And I will say, I only lost one garment the entire year and a half I was running the fashion closet. It would maybe freak some of the fashion editors out when they’d ask about something and I’d be like, 'I don’t know, let me ask my one really bright intern.' But the morals of the story is that, if you hire bright and really motivated support staff, they allow you to do your job better.
I found a niche within Womenswear, which was the music scene. Basically what I realized was that no one was covering musicians, but musicians have really great style. So I sort of discovered that if I found a really stylish, young female musician, we could do a fashion shoot with her, and then I could interview her, and I could get her on the cover of WWD. So I started pitching girls who I knew from Myspace, which dates me. Bridget was really, really supportive and encouraging of me and my ideas, and I pitched Katy Perry. This was 2007, before she even had a hit. So she was on the cover, and then I was the first one to do a fashion story on Ke$ha, and we were the first fashion publication to interview Santigold.
What was cool about WWD is that it’s an amazing training ground because you do a little bit of everything. I did everything from checking in samples to waiting outside the courthouse for verdicts to come in to attending a novelty sweater trade show and having to report seriously on it. When I was there — and a lot of the people I worked with are still there — the senior editorial staff was super encouraging of the rookie reporters. So when there was an opening, I moved from the fashion closet into a fashion features job. I was writing these musician profiles and I covered Coachella, which was my first business trip in 2007.
When there was a position open on the media desk — it’s one of the most-read parts of WWD and one of the best media columns in the industry — I jumped at the opportunity, and they gave it to me even though I had no media experience. I had never taken a reporting or a journalism class ever, so I was learning journalism from great teachers as I went along.
What was that like?
The media desk is really intense, reporting-wise, because you learn all about [terms like] 'on the record,' 'off the record,' 'on background,' and essentially you’re not doing your job unless you’re getting angry phone calls the next morning. That is a really challenging position to be in as a 25-year-old reporter. It’s a daily column, so you can only do so much reporting. A lot of stuff is on background because people aren’t naming names, and you can only [fact] check it to a certain extent, and then you have to print it.
I enjoyed it in that I got to meet a lot of amazing people. It was where I met Joanna Coles, who became a real supporter and an inspiration, and I met Cindi Leive. How else can you have lunch with Joanna Coles and just pop over to her office? So I really liked and appreciated it for the opportunity to sit with these people, write about them, sometimes piss them off. After about a year of that, I realized that I didn’t enjoy the pissing off aspect. The best stories were the ones that were the juiciest. I covered the whole divorce of WWD and W.
...While working at at WWD.
Condé owned WWD, but it was always made very clear to me that I was to treat every Condé Nast publication as though it was not the same company that I worked for, and I never once felt like I was being told not to write something.
For me, I just wasn’t cut out for the morning phone calls. It didn’t excite me. It kind of terrified me. What I liked doing is when I wrote about André Leon Talley joining "America's Next Top Model." I was on that. I did a full-on interview with him, with Tyra. A really good story is what gets me off.
When did you start thinking about leaving?
I was at WWD from July 2007 and the recession happened [later that year]. Within months, this industry in which I was sort of starrily-eyed entering with these grand ambitions to be an editor-in-chief had come crumbling down. All of a sudden things were changing, people were freaking out, and I had to very quickly figure out how to realign my ambitions and my aspirations in an industry that’s just suffered an enormous blow. That’s when I started to think about what else was there. Obviously nobody goes into editorial for the money, especially after the recession, but I started to think about where the money was.
I went to Elle, and Anne Slowey hired me as a senior fashion news editor. I was covering the London collections and writing fashion profiles of Alexander Wang and Roberto Cavalli. The cool thing about working in fashion news is that you’re covering designers, and designers are personalities. You get to do amazing things. I went to the hometown of the designer of Akris and spent four days in the Alps. I went to Venice to interview Frida Giannini for Gucci and did all these trips, and it opened my eyes to traveling, which I had never really done, actually.
Working at a monthly fashion magazine was different from working at a newspaper. At newspapers — the New York Times, WWD — there’s a no-gift policy. If you’ve ever been around a fashion website or a fashion publication, there’s obviously not a no-gift policy. Magazines have a different business model. They’re meant to entertain and inform and excite people. They’re not hard news publications. I was learning how the push-pull of magazine publishing works. I know this from Into the Gloss, having been the editor and publisher of that: you have advertisers and they have certain expectations of credits and coverage, which is part of what they’re buying into. They’re buying into your audience but they’re also buying into your point of view, and part of that is your point of view on their stuff.
I never was told to write a positive piece about a designer, but it was me figuring out that, well, the money is obviously in advertising. The money is not in editorial. And Elle has rigorous editorial standards, but [I was] exploring meeting people on the advertising side, learning what were the best examples of fashion coverage that both excited readers and also excited advertisers. That put me in a really good position for co-founding Into the Gloss.
How did you feel about the editorial/advertising relationship as someone who was coming out of reporting, which is very strictly separate from advertising?
I felt fine. I think if you have integrity, which [Elle EIC] Robbie Meyers does coming out of her ears, you sort of figure out. You edit by omission. Nobody’s going to write a terrible article about a fashion collection; you just might not cover the collection.
So how did Into the Gloss come about?
I met Emily when we were both at WWD and W, when they were still linked. She was an assistant, I was an assistant, and we became very close friends. I remember having conversations with her when she was like, 'I’m thinking of starting a blog,' and I was like, 'Everyone’s doing a blog.' But then we would brainstorm all the time, and, as friends do, chat about things we were working on.
Talks intensified, and I came to her in the spring of 2012, two years into Into the Gloss, and said, 'Why don’t I just leave Elle, and I can be a force multiplier and we’ll do this together?' Emily at this point was publishing two to three times a week — beautiful posts — and she really had a lot of respect in the fashion world and a lot of fans and a small but very loyal following. And I said, 'Let’s blow this out of the water.' At that point a lot of opportunities were presenting themselves to her, and I said, 'Let’s hold off on any kind of outside opportunities.'
Opportunities like investors?
Like agents or managers, people who wanted to work with her and her brand. We came to Soho House and I met [Michael Harper], who was our third cofounder, and was immediately impressed with him. To this day, he is a gentleman and a genius and a good friend of mine. I essentially said to Emily and Mick, who coded and designed the site, 'I’ll leave Elle. Let’s do this. There’s a lot more potential here, in a lot of different directions.'
We grew it from around 100,000 visitors to almost a million. We grew, we hired and what I was successfully able to do was transition the site from something that was Emily’s to something that was a brand.
People like Molly Young and Edith Zimmerman — women whose writing I really admired and had friend crushes on — I brought on to inject their wit and wisdom into it. Editorially I always been obsessed with "This American Life" and storytelling, and I wanted Into the Gloss to be something that you could read if you weren’t particularly interested in beauty because it’s a good story.
What did your days look like during that period?
It’s a constant hustle, as anyone who works at a small company knows. You’re always on. At first I was a force multiplier. Increasingly, as the site became more popular, I was overseeing editorial and advertising partnerships, and Emily was overseeing things as we developed the product stuff [Glossier]. We created the brand book together, but she was quarterbacking the beauty products.
I was so excited to approach [Warby Parker] for a collaboration because I knew that working with a startup that was several big steps ahead of us would just be a fantastic learning experience. I did learn a lot from working with that company and seeing how they marketed things, how they approached collaborations, how they think about their brand and consumer touch points.
Let's talk about following the money in the context of what you were doing at Into the Gloss.
The new normal, to borrow the term, is people making content and also making the advertising. I think that if it’s one cohesive vision and voice overseeing both sides of things, the two will be harmonious and readers will be as interested to read something that’s sponsored as they are to read something that’s not sponsored.
Do you really think so?
With one of our most successful collaborations, we got a comment that was like, 'Are there any more of these coming?' Like, has anyone in the history of sponsored content ever asked for another installment of it?
Who was that with?
Estée Lauder. It was for Modern Muse. We commissioned Stacy Nishimoto, who is a stylist out of L.A., to create these 'muse' profiles of people she was inspired by wearing Estée Lauder makeup. It was so seamless; she’s so fucking cool. People wanted more. That’s the goal with sponsored content.
With integrated advertising or integrated marketing, I think it’s about being seamless, which doesn’t mean sneaky. And we turned down deals that just didn’t fit with our vision and voice. We slowly rolled out integrated content and put as much energy into creating compelling sponsored content as we did in our editorial content.
We essentially acted as our own creative agency. With a lot of brands, they would just say, 'This is our launch,' and we would create a campaign. We’d create custom ad units and use their logo, or maybe not use their logo at all because they trusted that we would know how to communicate their brand to our audience. That trust I think was the most important thing. Both our readers’ trust and our brands’ trust that if we’re putting this on our site, it’s not crap. Brands that we worked with three times, four times, would trust us that we’re not going to mangle their brand or sully their brand name.
Tell me about the experience of raising your first round of venture capital funding.
It was not a world that I came from, it was not a world that Emily came from. Michael is a voracious reader of everything — tech, finance, beauty, fashion — he’s just a brilliant guy, so I think he had a lot of input and guidance in the day-to-day.
But if you take enough meetings and if you’re smart you can figure out what you need to do. You need to create a deck, which is what you present to potential investors, including what you want to raise, where the money will go, how much you’re spending.
You’re relying on a lot of favors, which is why, when anyone emails me who has a startup, I try to answer. All I was looking for when I was raising money was people who I could be stupid to. Like, 'If I say this, is that a bad number?'
So did you just email startup people you knew?
You never put it in an email. If we learned anything from the Sony hacks, it’s that you never put it in an email. But you call people up. You find people that you really trust and who believe in you and who won’t judge you for trying to make your way in the world that’s completely new to you. You use the information that you have, and then you have to operate.
So why did you decide to leave Into the Gloss?
I love brand building, but I think in terms of a women’s beauty product brand, Emily is obviously the most qualified person to head that organization. I felt like I had accomplished a lot, I had learned a ton, and it was time for me to figure out my next thing — to apply the knowledge I had gained to other companies, and also to take a step back. I will always be a co-founder of the company, and love the company and check the website.
Do you have equity in it?
When you left, did you know what you were going to do next?
No. I’m still freelance, part-time with Yahoo [Style], with Joe [Zee]. But I knew that I basically wanted to consult and take on projects, because I’m someone who really gets my hands dirty. I would want to take on a few very intense projects and see them from beginning to end.
The companies that you’re consulting on, have they launched?
It’s existing brands. It's media brands that are looking to pursue new verticals or just rethink how you approach Instagram. How do you approach video? What does editorial look like for this kind of thing? Everyone wants content, and a lot of conversations that I had with people were like, 'Don’t start a blog.' I think a lot of people get their content from editorial sites, and brands have different assets. So you don’t need to be all things to all people, and here’s what a brand could do in order to really connect with consumers.
With Yahoo, I created a video series called 'I Yahooed Myself,' where I basically sit with a celebrity and we look them up on the Internet and talk about the results, and it’s been really successful so far.
How you really create compelling video content is a thing that I stay up at night thinking about. You can’t engineer viral content, but you can engineer interesting content. I think that if you have a creative conceit, you can apply it, and what I think people like about the Yahoo series is that it’s a funny idea: celebrities looking at themselves on the Internet.
What advice would you give someone who wants to get into editorial?
This is, I think, my best piece of advice for interns: I never got a job interview without double or triple emailing someone. It seems simple, but people oftentimes feel like they’re bothersome by emailing someone. But when you email someone, always ask for five minutes. Everyone has five minutes. Don’t ask for an interview; not everyone has time to interview someone for a position that doesn’t exist.
I never got a response until the second or third time, because either they’re going to tell you to shut up and there are no job openings, or they’re going to open up your resume. You have to have a good resume to back it up, but beyond that, politely bringing your email to the person’s attention will at least get them to reply. And once you have them responding, you have them on the hook.
This interview has been condensed and edited for clarity.