Remembering the Early Days of Jezebel with Anna Holmes

by Jen Doll

The Book of Jezebel is “An Illustrated Encyclopedia of Lady Things” edited by Jezebel creator and former editor Anna Holmes that includes funny-to-serious entries ranging from giggle (Tee-hee) to Wolf, Naomi. Published in October, it’s a work of art, a humor book, a compendium of writing from an array of notable names, and an excellent guide to important topics of our time.

It’s also a book that came from a blog, and not just any blog, but the blog that set the stage for sites like The Hairpin to emerge and implement and experiment with their own styles, voices, and content. Jezebel was the first to dedicate itself to breaking new ground in writing for women, to cultivate a female commenter culture, to do something that was at the time rather unheard of. Now, there’s a range of great sites to pick and choose from, but in the early days of “Girly Gawker,” the Internet was a very different place. In honor of the book’s release, Anna and I reminisced.

Jen: Let’s go back to very beginning of the site. When did it start?

Anna: It launched in May 2007, six and a half years ago.

Forever ago, in internet years. How did you get involved?

I had a friend named Geraldine who was friends with Nick Denton, and he asked her if she wanted to start a “Girly Gawker.” She asked if I wanted to do it with her, and I said no. The internet was scary. I didn’t know anybody who was going over to the Web. I thought it was too risky, but she and I kept talking about it. Then Nick’s deputy, Lockhart Steele, said he’d match my salary at InStyle, where I was working at the time. That was a surprise. I said OK, maybe. But after I agreed, my friend decided she didn’t want to do it anymore. I was informed that I’d be starting the site on my own — that was terrifying — and my name would be at the top of the thing.

That was probably January of 2007. I spent the next couple of months thinking about what this would be, what features it would have. I started getting some resumes from writers, and I met with a couple of people. One of them was Moe [Tkacik]. She was very funny, we got along very well, and she was totally into it. I hired her, and then I hired Jennifer Gerson. I interviewed Tracie [Egan, then known as “Slut Machine”] and Dodai [Stewart], but I didn’t have the budget to hire four people at once.

We just sat around brainstorming ideas, and then we started test-blogging. I had to learn a CMS, I had to learn html. We talked about the name and what would it look like. I didn’t really like the name.

What were the other options?

I don’t remember — I didn’t love any of them, and I didn’t really like Jezebel, either. But we were so far into it. I had to believe the name would work out, that it would resonate with people. At some point, we had to throw it out into the world and see what would happen.

In a month, I had enough of a budget that I could hire someone else. Tracie was already writing for the site but she wasn’t on staff. I hired Dodai, and then I hired Tracie, and then after that I think it was Jessica Grose. There were also contributors who were freelancers who I ended up hiring later on.

What was the immediate reaction, and how did things progress from that? I’ve heard you mention burnout.

It was successful pretty much in the beginning. It got bigger and bigger, and I got really burnt out and I quit. My last day was June 30 of 2010. I think I gave notice a month or two before, and I’d hired Jessica Coen earlier in 2010, with the idea that she’d run the site: she also has a broader, more commercial sensibility than I did. Also, I was getting a little bit irritated with Nick. It was becoming a big site, and he was suggesting I do things I didn’t really want to do.

Like what?

Nick wanted stuff about makeup. I didn’t want to do makeup; there were plenty of sites that talk about makeup. I mean, I wear makeup, but I couldn’t figure out a way to do it in the spirit of the site. He’d complain that we had too many posts about politics. I felt like he maybe wanted the site to change, but he wasn’t explicitly saying that, and I thought, if that’s what he wants — to turn the site into the very thing we’d been making fun of for years — he needed to get someone else to do that.

Reasonably so. How did it feel to leave this thing that you’d created and developed into a significant media entity?

I was very addicted and proprietary about the site. I knew that it was unsustainable and not the healthiest job in the world, but there was this adrenaline rush that came with it. I think I cried all day on my last day. I think I left at the right time, but in the weeks following I felt a little bit lost. Even though I’d agreed to help them do Jezebel-related projects (like a book!), I just couldn’t run the site anymore.

Three years is a long time to run a site (or work on a website, for that matter)!

It was a long time. There was an added insanity because it felt so much a part of me in a way I assume it wouldn’t have if I’d come around after it had started. I felt like failure was not an option. I worked myself to death and I worked the staffers hard. I gave them a lot of freedom — the best stuff they did was what they were interested in — and I gave them ideas and feedback and I told them they were great. I wasn’t the sort of boss who had them work their butts off when I just went and had lunch. I was online before they woke up, and I was there after they signed out for the day.

By 2010 when you left, what did Jezebel look like? How did it change in that period from just-born to three years old?

In the beginning it was very insidery. I felt like we could take more risks, see what worked and what didn’t. It was more self-referential, it was kind of wackier. As it got more attention, I felt like we were under scrutiny. There wasn’t as much of an opportunity to get a free pass if we fucked up. We were representative of something, and we couldn’t let people down.

So we fell into a groove, which is not a bad thing, and people on the outside were paying attention to us. Our writers were getting quoted; we were asked to go on TV. We were being legitimized. That was thrilling but scary. There were sites that popped up that were somewhat iterative. It felt like they were direct responses to or influenced by the site, although I was too busy to analyze this in any meaningful way.

Which other sites were coming into existence around then?

The Frisky popped up first. Then Slate started Double X, which is now The XX Factor. There was Lemondrop, which failed. I don’t remember when The Hairpin started [Ed. note: October 24, 2010]. I think there were at least five sites that were responses to Jezebel.

How did you see them differing? Did you feel they were all competing for the same space?

I think they had different voices. I think they all tried to use humor and maybe that’s how they were similar. To be honest, I didn’t really read The Frisky because I didn’t have time to, though I paid attention to what they were doing because I had to. The Hairpin, it felt very cool-girl, very sophisticated. With Double X, I remember feeling threatened at first. The first post they put up was attacking Jezebel. But then I was like, this probably isn’t going to last. It felt like it was geared toward white women aged 30 to 50, who had graduate degrees and lived on the East Coast and were upper middle class and probably were married and had kids. There aren’t that many women like that. It felt very demographically homogenous. Now, it still exists but as a different form — I don’t think it is as homogenous as it was. Everything evolves; you react to market forces and what readers are asking for.

In some ways these new sites emerging was exactly as it should be, giving more women opportunities and space to write about topics of interest.

I was not objective at the time. I was very competitive with anyone who was entering that space. I didn’t know if there was enough room for everyone, which sounds stupid now. I also felt competitive because Double X stole Jessica Grose away!

The Double X call-out came at a time before widespread social media — Twitter had just been founded in 2006; we weren’t using it like today. Did it have a role at all for you?

I didn’t use Twitter. The discussions were taking place on blogs; it wasn’t on Twitter. I love Twitter, but it’s a good thing it wasn’t around. It would have been harder to keep track of stuff.

Speaking of social media, I love the photos of people holding the Jezebel book up to their faces on Twitter and Facebook. How did that come about?

That wasn’t a strategic plan. It was more like, shit, what am I going to use as my Twitter avatar on the month the book comes out? It occurred to me to hold the book up to my face. I felt like it was corny but I didn’t care. I had my friend Lindsay come over and take a more professional picture; it’s hard to hold a book and a camera!

I wasn’t going to make the staffers of the site to do it, but if they wanted to, they could. I’ve been putting pictures on Facebook, and people have sent them in. We had the book party and Victor, the Gawker Media employee who planned the party, had this photo booth in the back. He’s a professional photographer, and he did really awesome ones. There were things I tried to strategize, but the book selfies, that was just me fucking around.

I noticed you don’t define the term “ladyblog” in the book. Was that on purpose?

I don’t know if that was done on purpose or not. I don’t know if I kept it out, or if it just didn’t feel like a very compelling entry. Maybe because I don’t like the term. I don’t hate it, but I don’t love it. But it’s also possible that I just forgot. There were some things we didn’t do simply because there wasn’t enough room.

What else did you forget, or leave out on purpose?

Off the top of of my head: Althea Gibson, Susan Brownmiller. Another one we forgot was “scrunchie.” Then, there were things that got to us too late. With Wendy Davis, the book was already done. Someone wrote in very angrily, how could you not put Taylor Swift in there?, but a lot of the book is just my and the other writers’ points of interest, and Taylor Swift is just not on my radar, but someone like Debbie Gibson might be [Ed: she’s not in the book, though “Gibson girl” is].

I like that there’s an entry in the book for the name Jennifer.

Anna North did that feature for the site, a series about female names, addressing the idea that we have preconceptions about Jennifers, Kirstens, Emilys, or what have you. Same for guys. We think of the name Paul, and we think, he’s a nice guy. Chad, he’s a doofus.

Chad was my first boyfriend! Can you share some of the wackiest Jezebel moments you experienced?

We had a big fight with Scott Baio. It was totally fun. He and his wife were making it worse for themselves and being more bananas, and the readers loved it, and we did too.

Did you ever make up?


Moe and I would argue quite a bit, mostly over IMs. I think of that fondly; I think we’d laugh about that today. The public-facing things that were bananas: the Daily Show piece that Irin wrote and then Jon Stewart responded to. After I left, there was a parody of the site on 30 Rock.

One thing that was fun, in August of 2007, for Fashion Week, I had barf bags emblazoned with the name of the site. We put a tongue depressor and a mint in them. The idea was that the industry of fashion was vomit-inducing; you could vomit because the spectacle was so gross. We had them delivered to fashion editors at magazines that week, which I’m sure they didn’t appreciate. That was a fun stunt. It wasn’t about fashion; it was about the preciousness, the consumption, the lack of diversity.

That’s awesome. I feel like there were more stunts back then.

Yeah, totally. Depending on whether Nick wanted to finance them! I probably have 200 of those barf bags somewhere. I’m very fond of them.

Anything else you remember off-hand about the early days of Jezebel?

I kind of do miss the era when Tracie was anonymous and wrote about her sex life, she was so balls out. I remember being in awe of whatever she was going to say. She was totally unapologetic about it, and she wasn’t reminiscing, it had just happened: “I went to the bathroom of a bar in Williamsburg and had sex with this guy.”

Also, once they tried that thing, the Shenis, to pee standing up.

The what???

It’s for women who are camping, these large dildo things. They drank a lot of water and tried to pee standing up using them. That’s not something I would have done in 2010. It was too wacky.

How much of that old feeling remains, do you think?

The site still retains some of its original DNA; Tracie and Dodai have been there since the beginning. But everything evolves.

How does the book channel the spirit of Jezebel?

I got everyone who used to write for the site together, to do things in their voice just the way they did when they wrote for the site. I don’t think the book is wacky in any way that resembles the site the first year. But it’s a book; it has to be grown-up!

The Shenis, and Other Memories from The Early Staffers

Jessica Grose

Man, I loved being there at the beginning. I was 25 when I started working at Jezebel and I really do think it was magical in many ways. People complain about working at Gawker Media, but for me it was a total bootcamp. I learned how to be a person on the internet, how to be a professional, how to have a thick skin, and also how to be more sensitive. The Shenis video was epic and I can’t believe it’s not online anymore — I remember filming that and laughing so hard. I remember caring so much about the 2008 elections and everything that was happening for women then. I wasn’t really a political person until I started working at Jezebel. It just felt like we were doing something really new and special. And Anna also taught me a whole lot about developing a voice and having honest conversations.

I remember getting really drunk on the roof at Gawker HQ (several times!). I remember going to interview Kate White, then EIC of Cosmo, at a Gray Rape panel they had convened after that controversial article came out, and having her refuse to talk to me (and Moe? I think Moe was there) when she realized we were from Jezebel. I remember Moe and I going to see Liz Phair do Exile in Guyville on a revival tour, I remember talking to Tracie (and Anna, I think) on IM about pooping. Just like, in general, every day, about our coffee intake and poop outtake. I remember New Year’s Eve at Tracie’s. I remember Dodai’s really awesome silver sparkle platforms at that New Year’s party.

Oh also, I remember feeling agitated a lot. Which is funny to remember. I remember just feeling this deep sense of urgency all the time, and feeling SO upset when the commenters would get mad at us, and actually losing sleep over it. I don’t think I would feel so intense about anything that happened on the Internet again at this point.

Tracie Egan Morrissey

Having been at Jezebel the whole time, the thing I can say that’s changed the most is that I’m a lot healthier and cleaner than I was in those first few years. I used to just eat, sleep, and shit that blog every day, and my laptop was with me in bed, on the couch, on the toilet, etc. I would go days without showering, just sitting in my living room, chain smoking and working in a muumuu with no bra. I used to be so into my work that I developed hemorrhoids from sitting too much. There was a point where at least three of us had ‘rhoids at the same time. With a larger staff and more writers, the relentless churning out of content that we had to do before isn’t as necessary. Now I exercise and get dressed every day. It’s better mentally as well as physically. I still do part of my morning post while I poop, though. Old habits die hard I guess.

It was really exciting. It was as exciting as a job could be where you’re alone all fucking day long. (It’s different now: we work around a table and hang out together.) It was exciting to be doing something that was what we wanted to do, and people gave a shit, and we were saying these things that clicked with people. It was a huge validation. I didn’t ever want to be a part of the women’s magazine business because I never felt they spoke to me. They made me feel fat, and poor, and I felt they talked down to women. At Jezebel, we could tap into millions of people, and that audience that we wanted wasn’t a niche audience after all. Men were reading it, younger girls were reading it.

When I first started I was a 27-year-old party girl; now I’m 34 and married and have a kid and a 401(k) plan. My life is super different, and the way we work is different, but what we do hasn’t changed as much. We don’t go after women’s magazines as much because they’re catching up. You know what else I think is really great? When the first women’s site after us started, we were a little nervous, but as more and more started popping up, I thought it was cool. It just proves women are interested in so many different things and want a place where they can see these conversations happening, and that there’s a need for that. It can only help to have more of that. And that this is a viable career — you can grow up and say, I want to write about women’s issues — that to me is super-cool.

Dodai Stewart

OK, peeing on the roof using the Shenis was pretty amazing. We drank a bunch of beer beforehand, so even as we were setting up and the camera was being put into position, I already had to pee. In fact, I am the one who pees first in that clip. My claim to fame. Sadly, that video is lost in the bowels of the internet. WON’T SOMEONE PLEASE RESCUE OUR PISSING CONTEST?

Back in those days we didn’t work in the office. We were each at home in our underwear writing as much and as quickly as we could. If you could picture me in a tiny dark hovel of a 200-square-foot apartment crammed with junk, tearing pages out of Vogue and cackling, you would understand. I would meet Moe after work for drinks sometimes and we’d both be so happy to see another human. My favorite posts from the early days were my weird catalog and magazine posts. It was fun to do LOL Vogue (here’s another), also, but the catalogs! There was the time I turned Anthropologie into a Southern Gothic Novella. And OMG the 1986 International Male catalog, and food porn, and Urban Outfitters — so much fun.

Moe Tkacik

It was a really fun time of my life. Everything was quintessential in the beginning: The first time I met Tracie at Angel’s Share and we got drunk and realized that we’d had sex with certain people in common. Or the Shenis thing, we were all up on Tracie’s roof pissing out of these giant 12-inch schlongs, trying to see whose piss would go the furthest. I was always pretty serious about politics and had never been involved with anything that was that much fun before. Dodai lived in this tiny studio in this old-school tenement on the Lower East Side, and I lived at Rivington and Allen, and we got into so much crazy shit. (The place that sort of sums up that time is Dodai’s old apartment; it was covered in toys and girlie shit and teen heartthrob posters; I spent so much time there.) We were all funny, smart girls, and we were working so much and it was just so much fun. We were all probably just a little bit high from how much fun we were having; it was a very special time.

The Book of Jezebel is in stores now.

Jen Doll is a regular contributor to The Hairpin.