Alisha Ramos Knew It Was Time to Change Everything With Her Newsletter

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In the summer of 2023, Alisha Ramos did one of the boldest things I’ve ever seen a newsletter operator do.

Six years earlier, she had launched a newsletter called Girls’ Night that covered topics from books to self-care. It was a breakout hit among readers, turning from a side project into a widely-read weekly product. In 2019, having surpassed 100,000 readers, GNI raised $500,000 to build offline communities around their newsletter. Alisha used the funding to make her first hires, bringing seven people on full-time, plus a few part-time hires, to help her scale the business.

When the pandemic hit in 2020, GNI pivoted from the offline models to an online community called The Lounge. It kept growing. A newsletter all about staying in and being cozy turned out to be just what a lot of readers needed at that moment. With GNI’s list nearing 180,000 subscribers, it was bringing in close to $2 million in revenue per year. They had several significant revenue streams, including paid memberships, advertising, affiliate revenue, and profits from physical products. 

Then, Alisha made a series of big decisions. She decided to downsize her team, offering buyouts for staff and turning GNI back into a one-person operation. She took time off from the newsletter during maternity leave for her first child. 

After leave, Alisha announced she was re-launching the entire newsletter under a new name, Downtime, with a new membership offer. (Readers can pay $7 per month or $70 per year for access to premium content, like essays and recommendations.) The new newsletter still has elements of GNI at its core — plenty of writing about books, style, and recipes — but with deeper conversations about ambition and motherhood mixed in, reflecting where Alisha is in her life and career.

In the announcement about the pivot, Alisha wrote:

After six years of running and growing this newsletter, I wanted to decompress and figure out what was next for me; I was burned out from trying to grow a “big media business” (a pressure I placed on myself…). I handed over the keys to the talented Aliza Abarbanel, who’s done a top job as Executive Editor each week, and I had the full intention of stepping back indefinitely. 

My break (which I was grateful to take!) helped me realize that actually…I miss writing and creating and connecting with readers! It helped me realize that rather than stepping away completely, I could make a few changes to make things feel fun, fresh, and sustainable again.

I was still curious: Why make the pivot? Why change the name of the newsletter? How would readers respond to all these changes? We sat down on Zoom this past February to discuss Alisha’s journey, influences, and choices, from GNI to Downtime to today.

I’m grateful to Alisha for being open in sharing much of her story. She’s proof that growth is rarely linear, and the smartest newsletter operators are the ones willing to change to meet the current moment.

(This interview has been edited and condensed.)

Why did you start Girls’ Night In, and what were your expectations at the start?

I remember my first-ever newsletter very distinctly. I was in fifth grade. I made it with AOL. It was all about Britney Spears, *NSYNC, and Backstreet Boys. I sent it to my friends, and it was designed, you know, with different colors and Comic Sans. So, this is in my DNA, creating things via email. [laughs]

I had zero expectations. I was at Vox for a few years, and when I started GNI, I had recently started a new job at a government contractor, Nava. I was working on healthcare.gov, and in my first week, Donald Trump was elected; it unfortunately paused a lot of the work that we were doing across all of the social safety net programs. I felt like work was stalled. I wanted a side project, and I’ve always loved sharing recommendations. 

I started writing about things that I thought would make people happy during a time that was stressful and overwhelming. It took off by word-of-mouth, first with tech people in my sphere. It was something that people were looking for at that time, just a break from everything. I sent it out every Friday, and then it evolved — the mission and the idea behind it eventually evolved into Girls’ Night In is about sharing fun things, but it’s also about community and building offline community.

A lot of that was centered on our book club program. We had these awesome book club meet-ups in over 10 different cities across the U.S. and a few in Europe, just readers getting together, discussing books with new people, and making friends. Then I raised a small round of capital towards the end of 2018 to build upon this book club idea. How can we scale this online-to-offline community in a big way? Because people are looking for connection. People are lonely. Let’s figure this out. 

I hired a team, and we built that vision of scaling up our book club community into this self-organized community gathering platform called The Lounge. I would describe it as Airbnb for meeting with strangers in your city to talk about books or cookbooks, or having a meal together. That launched right before COVID. We piloted it in 2019, and it was a huge success. We had a couple of hundred paying subscribers through our pilot in Washington, D.C. 

Then COVID hit. 

We had to pivot to digital gatherings. We revamped the entire platform, making it into Zoom-first gatherings. We had a successful pivot, and we came out of the pilot program and launched it nationally. At the peak, we had about 1,700 members paying $10 a month. It was pretty successful.

So, The Lounge was bringing in $17,000 in monthly recurring revenue. That’s not an insignificant chunk of revenue from a membership.

No, not at all. We went back and forth a lot on pricing. Using my background in tech, we did a lot of A/B testing, showing people different sign-up pages with different price points. There was much upfront user research before we even built a single page or wrote a single line of code, which could be a good piece of advice for anyone building anything. Talk to your users, talk to your community, have 1-on-1 Zoom conversations with people who are actually in your community and get feedback early and often before you waste a ton of time and resources. That was a big part of our success — we did a lot of the work upfront in doing research and in talking to real people. We would have Zoom meetings where we would show them sketches or wireframes and say, “Okay, tell me what you’re seeing. What is speaking to you? Does anything look not cool? What’s most exciting?” Getting all the information that you can is valuable upfront.

Was audience feedback — whether it was surveys, whether it was 1-on-1 conversations with your audience — always part of the GNI ethos? 

Absolutely yes. Even in my early days of writing the newsletter, if someone replied to an email, I would always respond, even with a quick thank you. That 1-on-1 contact, especially in the early days when you’re starting something, means so much. There’s much focus on growth, growth, growth, but when you’re starting, the first couple of superfans will be the people who drive your growth and send the newsletter to their friends. That investment early on will pay dividends. 

To give you an example, I do these monthly giveaways with Downtime. The person who won this month has been reading GNI since it started. People will stick around if you respect them, respect their time, and show them that you care. Community building is careful listening and also soliciting feedback whenever you can. In those early emails, I would ask things like, “How did you find the newsletter? Do you have any feedback? I would love to hear it.” I’m sure you’ve seen this, too — people are surprised when they see that Alisha or Dan or whoever writes the newsletter has responded to them. They expect their email to go off into the void. When you do get a response, it feels special.

At least once a week, I get an email from someone who says, “I know you’re not going to read this.” Then I do write back, and they go, “You actually read these?” Those people are the ones who share the newsletter with their colleagues, who engage on social media, who often become clients. 

A piece of advice, maybe for someone who is getting started is, even if you’re not getting a ton of responses, if you, 1.) Respect the reader, but also 2.) Model and show that respect in whatever you publish.

Right now, with Downtime, the audience size is at the point where it has become difficult to respond to every single comment and email, and chat thread. But I set aside time for each week to skim through everything and choose the best comments, the funniest comments, the wisest pieces of advice. I will publish that in the Friday newsletter. As a reader, when you see that, you think, “Oh, there is someone who is actually paying attention, and if I write a comment, it’s not gonna just go off into the ether. There’s value in engaging in this community.” I keep coming back to respect — it is about respecting the reader and their time, and the investment that they’re putting into your work and your community.

When you lean into the ability to engage with the audience and make space for them, it opens up a whole new level of newslettering.

I subscribe to a lot of newsletters, out of curiosity, because it’s cool that more people are into newsletters now. But I do read a lot of newsletters that are very much focused on the writer, and there is a time and place for that, but nine times out of 10, a reader is not wondering what you had for breakfast. They are wondering, “What is in this for me? What value am I getting out of this?” Something that I actually have this written down on my newsletter checklist that I gut check myself on every time I write a newsletter, one of the questions is, “Is this too ’me’ centered? How can I recenter the reader? What are they getting out of it?” That’s helped me in my editing process, because it is hard when you’re writing by yourself to self-edit. Having guidelines like that in place is valuable.

When did you realize that GNI was working, by which I mean it was growing, it was monetizable, it was bigger than just a side project? You had tapped into something real.

There were a couple of mini-moments that made me realize, okay, this is bigger than what I thought it was. One was sponsor interest — people wondering, “How can I get in front of your audience?” Getting those emails was interesting to me. 

There was the early press traction I got. There was one article in the Washingtonian that helped the newsletter grow, especially locally. [Editor’s note: Alisha is based near Washington, D.C.] Of course, that made me feel like people were catching on to this. 

There was one conversation with my now-brother-in-law, who had gone on a trip to California. This was early on with GNI, and he was just in casual conversation with someone and mentioned my name, and this person said, “Is this Alisha Ramos by chance? I read her newsletter!” This was just early, early on. I had no connection to this person. The fact that she found the newsletter and loved it so much — that was meaningful to me.

You raised a $500,000 round at GNI, at the start of 2019, when you had about 100,000 subscribers. What were your revenue streams at that point?

At the time, it was advertising. We had just started looking at or testing affiliate links for things that we were recommending. 

Had you hired anyone before you raised the round?

No. At that point, I had one person working part-time. She was incredibly helpful with sponsorships early on, just coordinating all the inbound interest. I also had a lawyer who helped me with all my stuff, maybe a designer with little things.

After you raised the round, what did the team grow to?

By the end, we had seven full-time employees. My first hire was on the editorial side. My second hire was on partnerships. My third was community, and then we grew the editorial team a little bit more after that. A lot of content and community, and partnerships.

How did the pandemic change GNI?

It was weird for our team because it was a very anxiety-inducing, scary time. But on the business side of things, things were growing pretty quickly because our messaging, our branding, all of it was about being cozy, staying in, staying home. It became, weirdly, highly relevant in the culture.

We saw a lot of advertising growth at that time. We reached our peak revenue between 2020 and 2021, we were a little under $2 million in revenue per year.

But internally, it was tough. I was 20-something years old, managing a team, and suddenly you’re managing under crisis. I remember scrambling, for example, to apply for the PPP loans. Our last day in office, one of my employees came up to me and was, like, “This COVID thing is like taking off. Do you think we should maybe switch to working from home for a bit?” I was just in my head with all these other things. I was, like, “Yes, of course, that is the right thing to do.” That was the last time all of us were in an office together. It was just such a weird time to be managing a team internally through a crisis, pivoting the core of our business from an offline model to an online-only model, figuring out our revenue streams from there.

Was there a moment when you started to realize it wasn’t working for you anymore? 

COVID was the biggest catalyst. At that point, when you have such a small team and you can’t be in person together, that erodes a little bit of the specialness of having a small, start-up team. That was part of it. Having to do such an extreme pivot was difficult, too. The reason behind raising money to scale GNI was to power offline communities and interactions. Having that not taken away, but having that off the table for a bit, was difficult. 

I also had a rude awakening about how hard it is to manage a large online community that is always online. During COVID, our community members were all online. That was definitely a crash course in how much emotional and mental labor goes into community management. I have much more respect for anyone who works in community management today.

You’re a mom now. How much did your personal life and starting a family impact the decision to make the pivot from GNI to Downtime?

Almost 100%. At that time, it’s hard, as you know, to run a start-up, and then having gone through COVID, all these various crises, you do feel burnt out. We had been trying to conceive for a while — it wasn’t working for us. I knew that we had to go down the route of infertility treatment and eventually IVF. Knowing that, knowing the physical strain that that would have on me, physically and mentally, I knew I needed to make things a little bit simpler and easier for me and a little less stressful. I had those conversations with my investors, who were very understanding of the pivot of going from a full-time team down to just me for a little while.

My wife and I went through IVF, too. There’s the literal cost of doing it, the dollar amount. But then there’s also the emotions of all of it, the physical aspect. It takes over your life in a way. To try to do that and run a team and manage a business during a pandemic is maybe seven or eight things too many!

If I had a co-founder, that would be a different story, but being the person where the buck stops with you, it’s hard to be in that position.

What was it like telling your team that you were going to downsize and make the pivot back to being a one-person operation?

It was hard. It was one of the hardest things that I’ve had to do.

It happened in two phases. The first phase was a buyout phase, where I offered people the opportunity to leave, and then I made the decision to downsize, and at that point, you’re essentially letting people go. It was hard, but I also think at that point our team had endured quite a few challenges already. I don’t know if it was surprising to all of them. It probably felt natural, even though it sucks to not work for the company that you believed in for a while. There’s something special about early employees at a start-up. They are passionate about the mission behind what you’re doing. I will be forever grateful to everyone who joined in early with such little resources. The amount of work that went into GNI was just gargantuan. 

It’s like losing your family, in a sense. I know that’s an icky word, but you’re working with a small group of people for three, four years. It’s hard to say goodbye.

You were working with a small team during this moment of tumultuous change in the world, change for your organization. 

I made a lot of mistakes as the leader of the team, definitely a lot of hard lessons learned. Like one, I was pulling us in way too many directions for a team that was small. In the midst of all of this, we launched an e-commerce company called Whiled, from scratch. We manufactured puzzles. That was a huge lesson for me in understanding myself. I am a classic visionary founder with ADHD — like, I don’t know how to focus on things, and when I have a harebrained idea, I need to get it out into the world. But I’ve learned that if you have a team that is focused on other things that are already successful, maybe give your attention to that and focus on that.

I have this written on a note card on my desk: “Not everything has to happen all at once,” because that was the big mistake that I made with GNI. I felt an internal pressure to grow quickly. Part of it was internal. Part of it was being on this venture-backed path. You see other companies launching new products or launching new revenue streams and doing exciting things that it’s hard to put your blinders on and just focus on executing the one thing that you’re good at right now. That was a big mistake, and I guess this goes back to the team thing because they were feeling the pull of just being spread a little too thin. 

Tell me more about Downtime. Why did you decide to change the name? 

I still don’t know if it was the right decision, because there was much brand equity in the name when I made the decision. There were a couple of factors: One, I wanted to get away from the gender specificity of Girls’ Night In. The second was that I felt that in the media and in the industry, the business was not being respected because it was called Girls’ Night In. It sucks, but people hear the name and they don’t take you seriously. I wanted to get away from that feeling, which is more of a reflection of my own insecurities, of wanting to be taken seriously as a person, as a business owner. That was a big part of that as well. Then the third silly thing is that people would always misname Girls’ Night In as Girls’ Night Out, and it drove me crazy. Or they would send us emails like, “Hey, we love Girls’ Night Out!” No, that’s the exact opposite.

Where did the name Downtime come from?

Just a lot of brainstorming. What feeling do I want to capture that evokes where Girls’ Night In eventually evolved into? Because Girls’ Night In started as a literal celebration of staying in with your friends and that cozy feeling, but it was a little too literal. I wanted a name that felt like we could imbue it with meaning. Downtime captures the quiet spaces between our busy lives.

How much of Downtime is a carryover from GNI, and how much is a new thing that you’ve brought to the new newsletter?

To me, it’s mostly the same. The main change has been that Girls’ Night In, when it started, was much about my own personal reflections and experiences, and recommendations. Now, it’s shifted in the way that my life has shifted — becoming a parent, transitioning into motherhood. That’s actually been nice as my audience has grown with me. Some of them write to me and say, “It’s been nice to go on this journey with you. I’m also expecting my first soon.” That feels special to have that community carry over in that way. 

I’m also trying to push the writing a little more editorially. I just launched a series called Bookmarked, which is a deeper dive with authors and very avid readers of books, trying to get back into where I first started with Girls’ Night In. They’re these very intimate conversations with other people. How are you slowing down? What are you reading? How are you taking care of yourself? Those meaningful conversations are what’s missing on social media, especially on Instagram. That’s an area that I want to push into — more longform, thoughtful, meaningful content.

You had a membership that went away when you shut down The Lounge. Now you have a new paid subscription offer through Substack. How have readers responded to that?

It’s been successful. I’m still trying to get my paid subscribership numbers up, but as soon as I launched paid, there was a huge influx of interest. It felt nice to know that people would still support me in that way. The benefits of a subscription or membership don’t include all the things that The Lounge did. This is also about gaining membership in a community of a different sort. It’s showing support for a writer or a creator that they’ve been reading and following for a long time. It’s been, overall, a positive change.

Is Downtime the right fit for where you are in terms of your career and your life?

Yes, 100%.

The no. 1 thing is flexibility. Right now, what I value most is flexibility in my time, and also flexibility in being able to explore my own creative curiosities. Whereas with Girls’ Night In, it felt very much like this is a product, this is what we are delivering. With the Downtime model, it feels very much like people are invested in you as a writer. I ask readers all the time, “What do you want to see?” I give a couple of options, and the answer is overwhelmingly, “All of it, any of it.” There’s freedom and flexibility. That’s what I need right now as a mom to a toddler who, you know, on certain days, needs to be taken out of daycare — maybe she has a fever. It just works well for my lifestyle.

I’ve never felt more creatively inspired than I do now — I almost have too many ideas that I want to explore creatively. I feel the most relaxed and least stressed than I ever have before. 

I look back on the time when I was running GNI, and I have a lot of empathy and compassion for that person, because she was under much stress and was carrying much unneeded burden on her shoulders, and now I feel like it’s lifted. a lot of it too, I have to say, is not managing a team. I don’t think I’m cut out to be a manager or a CEO. There’s much responsibility. I cared — I still care — a lot about people who worked for me, maybe too much. A good CEO, quite honestly, is able to emotionally cut off a little bit of that and focus on growing their business. That’s just not who I am. 

So that’s been great. I still do work. It’s nice too, because I still do work with other people. It’s just not people whose paychecks are reliant on you.

You do some side consulting with other folks.

I do a little. Last year, I did some consulting projects with other teams, which was awesome to be able to flex my skills. A big part of winding down Girls’ Night In was that I felt like, “Oh my gosh, I’m a failure, I’m not good at anything.” That was a big, emotional journey that I went through with winding down GNI. 

I’ve loved helping other teams get things done. I’m good at it, and having that confidence built back was amazing. 

What’s coming up that you’re excited about for Downtime in the next year?

The Bookmarked series is continuing, which I’m very excited about, with higher production quality. We have one kind-of celebrity author interview coming up, and we’re doing her photo shoot in her home. I’m very excited to dive deeper into this more immersive storytelling and increase the quality across the editorial products. I’m also reintroducing the book club later this year with the hopes of re-encouraging people to meet in-person, offline. To bring the book club back to Downtime, it feels like a full-circle moment. Right now, people are looking for community in a way that I haven’t seen since 2016 or 2017.

The positive change through all of this is that I have smaller goals. I wrote a piece about ambition for Downtime, and how I’m at this phase where I’m very content with where I’m at and what I have, and not having the drive or the desire to grow, grow, grow is actually nice. I have small, baby goals this year.