Jessica Grose: The newsletter decision had been made before I came onboard. When Lena was on her book tour, she met so many incredible young women who were engaged, passionate, and political, and she wanted a way to continue to speak to them more directly. Girls speak to girls and her personal writing speaks to those women, but this was a way to have some sort of publication beyond just her own voice and a fictional TV show — a way to entertain and inform these women on an ongoing basis.

She and Jenni [Konner], her co-producer on Girls and the co-creator of Lenny Letter, were talking about what kind of publication they had the bandwidth to really be involved in when they had a million other things to do. Jenni goes way back with David Plotz, who was my old boss at Slate, and he was consulting with them when they said they wanted to start some kind of publication. He suggested that maybe a newsletter was the best idea, because it’s manageable. Also, newsletters are such an intimate medium, and they hold your attention in a way that I think websites deliberately don’t. Websites are always trying to get you to click on this and reroute you to some other article. Obviously, we have a website that we would love for you to read, but we liked the idea of having a kind of cloistered, almost, mini-magazine. Plotz recommended me for the gig and I met Lenny’s CEO Ben Cooley at the beginning of May 2015, met Lena and Jenni sometime later in May, and started Lenny at the beginning of June.

Grose: Every Wednesday we have an edit meeting where everybody brings their ideas, we look at new pitches that have come in, and we decide as a team. The team includes Lena and Jenni; Laia Garcia, our associate editor in charge of the art and social media; Doreen St. Félix, our editor at large; and Dianca Potts, our assistant. We decide as a team what we’re going to pursue, and I commission whatever we’re going to commission. [All of Lenny Letter’s contributors are paid.] The articles come in to me and Laia, and I do the majority of editing. A lot of the writing also comes from our team: Laia writes, Doreen writes, Lena writes a ton. When a piece gets scheduled, Lena and Jenni take a look and provide any feedback they have. Then we call it a finished piece. So [Lena and Jenni] are intimately involved from the commission of pieces to the final read.

Grose: I think it’s going really well. I’m not a business person, but I think the model is pretty unique. Hearst does our ad sales for us, and that is a very close partnership. The Lenny Letter website is also managed through the Hearst CMS. But Hearst has no ownership of Lenny; when our contract is up, we can part ways. Lena and Jenni weigh in on any potential advertisers and the angles we might potentially take to sell whatever the advertising is. We’re really cautious about any advertising we’re going to have in Lenny. We want to make the difference between editorial and advertorial very clear, and we want to make sure we’re not selling our readers any product that is compromised in any way.

Grose: We have a posting delay for the website. For our Tuesday newsletter, our main product, we generally have a delay of 24 hours. Subscribers get the email in their inboxes on Tuesday morning, so the only way to read the content then is to subscribe. Typically, everything then goes online on Wednesday at 6 a.m. ET. But in certain scenarios, we do things differently. An example is Lena’s piece about Kesha, which we thought was really important and really newsy. We were so proud of it and it was such a bold statement that we wanted to be able to share it as widely aspossible, so we put it up with just a three-hour delay. Most of our stuff is more evergreen and not really tied to any breaking news, but this was.

Please read this. So powerful. So important. #LennyLetter https://t.co/aEfqBISfDc

— kerry washington (@kerrywashington) February 24, 2016

There’s always some kind of delay, though, and that’s because we want to incentivize people to subscribe. The newsletter is the main product. We think it’s really special and different to read it in the newsletter format. We spend a lot of time commissioning illustrations. We really want people to look at it in this kind of combined mini-magazine format, ideally. But we also want as many readers as possible, so we’re trying to have both sides a little bit.

Our Friday newsletter is just one piece of content, an interview, that goes up simultaneously on the web and in people’s inboxes.

On social media, we’ve started teasing the stuff that’s going to be in the Tuesday newsletter on Monday. We’ll say something like, “You can only get this content tomorrow, before anybody else, if you sign up.” But once anything goes online, we, of course, want it to be read, so we tweet it immediately. This also sometimes includes calls to action to subscribe to the newsletter.

Grose: They do. We have an inbox, and it is monitored. Our staff is two full-time people, that’s it, on the editorial side, and two part-time people, so we respond to our readers as best as we possibly can. I think we’re incredibly responsive on social media: When people ask questions in Instagram comments, on Twitter, etc., they generally get responess that same day. With email, we try to respond as much as we can, considering our limited bandwidth.

Grose: It was always baked into our mission. It starts with approaching a really diverse group of people to contribute, and it’s important to be continuously mindful of it: Not everybody you approach says yes or has ideas or has ideas that are a fit, so you have to make sure that not just the asks that you’re making and people you’re going out to are as diverse as possible, but that the actual pieces that come in are from as diverse a group of people as you can possibly get.

Having a diverse staff is imperative to the process. Of the editorial employees, I’m full-time, and I’m white, but the other full-time employee, Laia Garcia, is Puerto Rican. Our two part-time employees are both black. Everybody has a bit of a different perspective and a different group of people they read. Just their influences — what they’re bringing in, who they talk about at edit meetings — is different. Having all these voices in the room, when we are talking about what we’re going to assign, is really pivotal.

In honor of Black History Month, Doreen St.Félix has been highlighting amazing black women whose lives are under-recognized for our Out of Print feature. This week she introduces us to the Fultz sisters, who achieved brief fame as the first black quadruplets in history. Link in bio! #LennyLetter Illustration by Sirin Thada

A photo posted by Lenny (@lennyletter) on Feb 17, 2016 at 10:06am PST

It’s also just continued intentionality, looking at the mix of every newsletter we put out and trying to make sure that not just the writers but the illustrators are diverse. The writers obviously get more attention, but Laia has done an amazing job of making sure that we’re getting illustrations from a group of women who are not just diverse in terms of race but in terms of sexual orientation and even in terms of being international. Laia is fluent in Spanish and she grew up in Puerto Rico. We have illustrators who speak Spanish, not English, and Laia’s able to commission these illustrations and have the artistic discussion with them that I wouldn’t be able to have because I’m not fluent in Spanish.

It has to be baked into every step of the process. We can’t be like, well, we made sure our first issue was really diverse, and that’s enough. It has to be ongoing. I’m sure there will be times when we don’t live up to what we would like to see in our publication, but we are really trying our best.

Grose: We have an event in the works. We would like to do a podcast. As an editor, I would really like to start doing more ambitious editorial projects like reported longform.

Enterprise reporting takes a lot of money and a lot of time, both of which we don’t have endless amounts of, but that’s a goal of mine. And maybe a serialized story. In some ways, newsletters are a really old Internet form, but people kind of forgot about them for so long that it feels as if there’s a way we can be innovative and do different things that haven’t been done before. I mean, everything’s been done before — I don’t want to pretend that we’re reinventing the wheel — but I would like to experiment with the form a little bit.