Newsletter Tips To Live By From Lena Dunham's Lenny Letter

Editor-in-Chief Jessica Grose talks with HuffPost about engaging readers in their inbox.

Lenny Letter -- the new newsletter by Lena Dunham and writing partner Jenni Konner -- has been a wild success since it launched on Sept. 29. From the beginning, Dunham and Konner have published fresh interviews, landing exclusives with Hillary Clinton on feminism and Jennifer Lawrence on making less than her male costars, as well as important essays on topics such as reproductive rights and domestic violence.  

Editor-in-chief Jessica Grose, 33, is the captain behind the ship. HuffPost talked with her for our own recently launched newsletter, Must Reads, which we kicked off last month to highlight stories we just couldn’t stop reading (sign up here). We reached out to Grose to hear about how it’s going in the infant days of Lenny Letter, and to get advice on what makes a successful newsletter.

This interview has been edited for clarity and length.


Jessica Grose

How did Lenny Letter come to be?

Lena met a lot of really incredible young women on her book tour for “Not That Kind of Girl.” She was so moved by how enthusiastic and engaged they were that she wanted a way to continue to speak to them. A newsletter is a way to talk to readers in an intimate way. And from a financial point of view, it makes the most sense. It doesn’t take a lot of bandwidth to put together.  


You come out twice a week. Any words of wisdom on what makes a newsletter a must read?

It’s that combination of great writers and personalities, and a fresh take. We’re lucky enough to be in a position where big names are willing to write for us. Ellen Pao, the former CEO of Reddit who made headlines for suing her former VC boss for gender discrimination, had had some very public experiences. Despite her experiences, she said things are actually getting better for women. That felt like a really interesting angle I hadn’t heard before.


Any advice on what not to do?

This goes for any kind of writing: Don’t write about something because you think it’s what the audience wants. It helps to be passionate about what you’re doing. In a newsletter, as opposed to the open web, when something feels perfunctory, it’s obvious. Not sure if that’s because of fewer distractions, but it can come across as more stark in the newsletter space.

Also, be sure the email is not going to spam folders!


How are you measuring success? Number of subscribers? Letters to the editor? Instagram followers? Trolls? Emojis sent your way?

Number of subscribers, open rates, how many times the email is being forwarded. Some of it is reader response and looking at Twitter and Facebook to see what people are saying.

The majority of our readers are what my old boss David Plotz would call “virtuous readers.” When you subscribe, you’ve entered your email somewhere. You’re not just lazily clicking away at the web. The people who are reading it are there because they want to be there, as opposed to the open web. This may sound cheesy and old-fashioned but when we read the issue before it goes out to the public, it is important that we feel proud of what’s in it, and that we believe in the quality of what’s going out there. That’s success to us.


What's surprised you so far?

Honestly, the overwhelmingly positive reception has been gratifying. We worked on it all summer and validated the shit out of each other. But the week before launch, I was like, “What if it’s terrible?” I’ve been happy to see it’s been so well received and that people seem to get what we are trying to do. I feel understood. So I wouldn’t call it surprising, but tremendously gratifying. It makes me really proud.


Where do you want Lenny Letter to be in a year?

Editorially, I hope that we get to a place where we can do more enterprise journalism. So far we’ve had great interviews and essays. I would love to see us do real on-the-ground reporting.


Anything else we haven't asked that you're dying to tell us about? ’Cause we need all the advice we can get on making Must Reads, well, a must-read.

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