Her weekly newsletter champions self-care and mental health, while being the heart of a thriving tech company. Alisha talks about how investing $20,000 in herself led to building a massive online community that brings people together in real life.
Follow Alisha Ramos on Instagram @alisharamos or @girlsnightinclub. If you loved this episode, listen to How Aimee Garcia Took Charge of Her Hollywood Career and Why Pioneering Journalist Maria Hinojosa Put Herself in the Story. Show your love and become a Latina to Latina Patreon supporter!
Alisha Ramos founded Girls’ Night In in 2017 as a club for women who’d rather stay in tonight, and quickly found that lots of us would rather curl up on the couch with our best friend then do, well, pretty much anything else. Alisha started a weekly email newsletter that has quickly ballooned into a media brand and community. Today, we talk about steering her business through a time when staying in is as much a necessity as a choice.
Alisha, I’m so happy we found the time to do this.
Alisha Ramos: Thank you so much for having me. I’m so excited to be here and just such an honor.
Menendez: Well, about a year ago I asked you a question that I have to ask when an internet search is inconclusive, which was are you Latina? Do you identify as Latina? And you wrote back with a resounding yes and a dot, dot, dot, it’s also complicated.
Ramos: Yes. Definitely very complicated. My dad is Dominican. He immigrated to the U.S. in the ‘70s, and then my mother is Korean. She immigrated from South Korea roughly around the same time. And it’s complicated because I grew up with both parents, but my dad was in the army and was deployed for a lot of my childhood. And then I actually grew up in Seoul, South Korea, from age zero to age seven, so a lot of those formative years were spent in Korea. My dad was pretty much always away except every other weekend he would be home. I was speaking Korean. My whole Korean family, that was my world.
So, yeah, I think growing up I had a very Korean identity, and it wasn’t until I got to college really that I began exploring, “Well, there’s this whole other side of me, this amazing side of me that I never really got to connect with or explore.” And in college, I kind of shifted my identity mindset into being multiracial and mixed race, which was an identity that I had never really identified with up until that moment. I always felt very Korean, actually, up until college. And then I get to college and it’s like you’re in college, you’re trying to explore your identity and figure out who you are, and I tried to join a bunch of Latina groups and felt like I didn’t belong there, either.
On the flip side, I also tried to join the Korean student associations. There were several of them and I didn’t fit in there, either, for the very similar reason. Even though I am fluent in Korean, one look at me and everyone would say, “What is she doing here? She does not belong here.”
Menendez: Well, it’s so funny that you bring that up, because you in 2015 took part in this hashtag that went viral, #ILookLikeAnEngineer. And I don’t even know if you know this, but there’s a Reddit thread where people have a photo of you and are talking about it, and most of the comments are like, “She looks 100% Korean.” Because you say in the tweet, “I’m Dominican, I’m Korean, and I’m Spanish.” And people are sitting there talking about how they would code you.
Ramos: Yeah. I get it, like it’s natural to look at someone physically and try to identify them and put them in a box that you feel comfortable with.
Menendez: So, how did you finally latch on to that sense of identity, of being either Dominican or being Latina?
Ramos: I think a lot of it has to do with the relationship I had with my dad and how closer we’ve become now that he’s been retired for well over two decades, so he’s home all the time now, which is great, and he’s close by. And also, I think when you have aging parents, as well, that plays a whole factor into wanting to understand more of their story and by extension, your own history.
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Menendez: You say you loved coding and learning HTML. What did you love about it and where did that love come from?
Ramos: The love of coding came from just being an indoor kid all my childhood. Yeah, you’re raising your hand. Yeah. I would say by choice, but also I think my mom was pretty… wanted to keep me very sheltered and secure, so I was home all the time with my computer and AOL, so that was it. That was my social interaction, my world, and from a very early age I learned the power and the beauty of online community. I remember coding websites for Neopets, which I don’t know if you were of that era, but it was a virtual… It’s so silly. It was a virtual game where you took care of these little mythical creatures and there was a whole community around it of kids who loved that same game, and we would all make websites, and guilds, and share, and chat with one another about Neopets.
So, very early on I had that experience. It was just a really important channel for self-expression, for connecting with other people, because like I said, I was very sheltered. Not really allowed to go on sleepovers, and my mom had a very tight grip on how I spent my social life, so that was my social life.
Menendez: In some ways, it’s like you had a Latina mother, even though you did not.
Menendez: What was the initial inspiration for Girls’ Night In?
Ramos: So, the origin story is really I went back home one day, or like for a week, and I sat down at my parents’ dining table and just started brainstorming all the things that I was passionate about, or all these different ideas, and I still have the notepad, actually, where I wrote down all the ideas, and I can share it with you, but they were things like board games for twentysomething women. Like floristry classes for millennial women, or like paint and wine night, and bringing that into the home instead of going to wine and paint studios. And so, you can kind of see they were all very similar ideas of creation, creativity, being in the home, the audience was like me, basically. Millennial women who were introverted and loved staying home.
And so, I had all these very jumbled ideas, and I didn’t really know how to launch this eCom business. I didn’t have any money to do that. So, I said, “Okay. Well, I know how to write, and writing a newsletter is free, so I’ll just call this thing Girls’ Night In, because I think that’s the general idea of this feeling that I’m trying to capture, and I’ll start with a newsletter and see if anybody even resonates with this message at all.” And it went out to like 300 people in February of 2017, and then it just started taking off from there.
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Menendez: Part of what was so smart too about the newsletter that I had not considered is lots of people are now creating on platforms that they do not own. So, they’re creating on Instagram, on TikTok, and the challenge there is that if Instagram goes away, all of your content goes away. So, you were taking your content and making sure it landed directly in the inbox of your consumer.
Ramos: Yes. In hindsight, that was a great strategy and I wish I could sit here and tell you that was the plan the whole time, but it really wasn’t. But absolutely, I mean, I think work at Vox was a really amazing primer to being in the media landscape. I got to see that landscape change so much. I remember when all the publishers were pivoting to video, pivoting to Facebook, whatever that meant. That kind of means that yeah, exactly, you don’t own your audience. You’re now at the behest of Facebook, or Instagram, or whatever other platform, and you can’t really control your destiny.
So, if anybody out there is listening to this and wants to start your own thing, that would be my number one piece of advice, own your audience. Or if you’re not owning your audience and you decide to start on something like Instagram, at least create a roadmap or a pathway to getting off that platform and figuring out a way to capture your audience’s attention where they won’t be able to escape it, essentially.
Menendez: What let you know that Girls’ Night In had potential?
Ramos: Yeah. A couple of things. I think the number one indicator was that it was growing by itself, essentially. Like yes, I shared it with my personal network, but that was only a few hundred people. And then it took on a life of its own. My friends were sharing it with their friends, and then I think once it escaped that outer layer of sharing, where it then becomes people you don’t know, complete strangers sharing it with their friends, that was the number one indicator.
Menendez: You had $20,000. Your life savings. Walk me through the steps and thinking that ended in you leaving your job to build Girls’ Night In.
Ramos: That was very… It was really scary. But as you mentioned, I did have this savings, a safety net, essentially, of $20,000 that I had saved since I started working, out of college. And that felt like enough for me to take the leap, and I gave myself a deadline. I said, “You know, six months. If I can’t make revenue at six months to sustain myself, meaning I can pay my rent and I can pay my basic bills, and I can pay for groceries. If I can’t do that, then I’ll just go back to-“
Menendez: That’s a tight timeline.
Ramos: I don’t know how I got to that timeline, but I think the 20K, I kind of walked backwards of like if I basically deplete that by the end of six months or close to depleting it, then I’ll have to find something else. Leaving was very hard, but I knew I had to do it because I got to the point where I was thinking about GNI at work and it didn’t feel fair to my employer.
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Menendez: What did you do in those first six months?
Ramos: The first six months, I remember one very practical thing I did was more on the legal side. I asked my founder friend for his lawyer’s contact, because I knew I wanted to create an LLC, create some sort of legal entity, have contracts and templates in place, because we were getting advertiser interest, so I just wanted to make sure, is this the right way to do business with other businesses? So, I invested a lot of upfront capital into legal fees, which are not cheap, but it worked out. So, I got the legal foundation into place and then from there, it was figuring out like how do I grow the audience?
So, I remember in the early days, doing a lot of brainstorming, trying out small experiments and growth hacks here and there, and I would be very meticulous about it, too. I would recommend this to anyone who’s running a new thing. Create a monthly plan of if you’re trying to grow, create a mini growth strategy. Try those things. And at the end of the month, just be kind of meticulous about understanding your metrics and understanding those numbers and is that working, what do you have to shift? I did that every single month.
Menendez: Where were you getting the ideas for these growth strategies?
Ramos: I have to give a lot of credit to other folks in the newsletter space. Ann Friedman comes to mind.
Menendez: Ann Friedman has one of the best newsletters. Yes.
Ramos: She has the best newsletter. I will say it here. She still has the best newsletter. But I remember, just to give you a very concrete example, one thing she did… Well, two things she did actually, that I stole, slash… By the way, she’s a good mentor figure to me and she actually had a mentorship call with me very, very early on, so shout out to Ann Friedman. Two things, so one was classifieds. She had this amazingly brilliant, I think, way to monetize her newsletter, where she would have a classified section like you would see in a print newspaper selling ad spots to smaller businesses and individuals. So, that was our first revenue stream, and it was a lot of work. Yeah.
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Menendez: Explain what you mean by a lot of work, because I think that it’s easy to hear the story and say, “Okay, you’re in your pajamas, you’re in your apartment, you have six months, you’re telling me the newsletter only takes you 30 minutes to write. What’s happening in the other hours of the day?”
Ramos: Right. A couple of things. Well, the other big thing that I forgot to mention is that I had the intention to fundraise after I quit. At first, the plan was not to. I thought, “Hey, I can do this on my own,” and I did do it on my own for about a year, and then after that, I started the fundraising process, which is incredibly time consuming, time intensive, very, very stressful. But yes, the newsletter took me a really short time to write. What took a lot of time was I would say the infrastructure and really partnerships. Partnerships were a lot of work. A lot of my mental energy was going into that. And then eventually I brought on someone part time to help me manage that workflow, but even then it’s a lot of work, because you want to be involved in those early conversations with larger partners.
Back then, I remember hitting our first partner where, or locking in our first partner who paid a little over $1,000, and that was huge for me at the time, because that was like a whole month’s worth of revenue back then. So, figuring out how to scale revenue took a lot of my time, and then aside from that was the fundraising process, which I’m happy to talk about, but that was a whole other time suck.
Menendez: When you say fundraising, did you start with friends and family?
Ramos: No, so I started bootstrapped with that 20K and that lasted me about a year. And then I raised a pre-seed round, which the size of it I guess people would say is friends and family. I raised half a million, so it was a very modest pre-seed round, and that’s the only round of funding that we’ve raised to date.
Menendez: And what did that look like? Like who were you going to for that?
Ramos: Yeah. I was going to everyone that I knew. It ended up being we have three VC firms involved, and then the rest are angels, so individuals, wealthy individuals who are from my personal network. I had about… I want to say like 50 conversations with both VC firms and individual investors. Most of them said no, of course, and the ones who ended up committing were people who were from my network.
Menendez: So, part of why I really wanted to talk to you, Alisha, is we’ve of course had a ton of entrepreneurs on, and I would say most of them went to business school, or at least a lot of them went to business school. And more to the point, there is a certain personality type that I see again and again, right? Which is a very extroverted, very forceful person, and that… Every article I’ve read about you notes how soft-spoken you are. And I think that that is part of what makes your story so interesting, is that in some ways you are going against type and you are still making it work.
Ramos: Yeah. It took a lot of energy and just determination to go down that path. I hated fundraising. I will say it. I’ll just be very honest. It was because I felt like I was playing this character that I wasn’t, and when you’re having so many conversations with VCs in particular, I felt like I was putting on a different hat during each conversation. But at the end of the day, the people who committed were people who really deeply understood me, my story, what I’m trying to achieve, my vision, and so looking back, I’m like, “Why did I spend so much energy trying to be somebody that I’m not?” I was trying to fit this mold of what an entrepreneur should be, should act like, should look like.
At the end of the day, it’s your life, it’s your business. You need to be true to who you are.
Menendez: What you are talking about reminds me of something that Natalia Oberti Noguera said in one of our interviews with her, which is we say a lot, “Don’t take no for an answer,” when really what we’re saying is, “Get to the right yes. Find someone who will give you the right type of yes. Find someone who’s aligned, and gets it, and sees you, and search out those yeses and forget about the people who don’t get it.”
Ramos: Absolutely. I think when you’re starting the fundraising process, it can be really easy to internalize all the noes. And that, a lot has to do with your personal internal work you do on yourself, too, like I will admit, I have a fear of rejection. I hate hearing no, because I internalize and I think, “Oh no, something is deeply, deeply wrong with me if this person isn’t taking me seriously, or doesn’t believe in my idea, and won’t give me a check.” You have to develop that thick skin, because at the end of the day, a lot of these noes are not really about you or about your business. A lot of the times, it’s about circumstance, too. You don’t know what’s going on at the firm. You don’t know how they’re constructing their portfolio. There’s a whole economic atmosphere you have to take into consideration. A lot of firms are shifting their strategies, even if externally they’re saying they’re not.
It rarely has to do with you and it really is about finding the right fit, and I’m so glad that I have the investors that I have right now, because we have chosen to take a very unconventional path, like we haven’t raised money since 2018, and I’ve been very clear with our investors. We’re trying to build a sustainable company and grow it in a sustainable fashion. We’re not following a crazy D2C playbook, or a media venture playbook.
Menendez: Say what D2C is for someone who doesn’t know.
Ramos: Oh, sorry. D2C means direct to consumer, so it’s things like Harry’s, or Warby Parker glasses, or Glossier, like those kinds of buzzy internet brands that you might have heard of. And I feel really grateful, because they all get it. They know. They’re in my corner. Never have they questioned or pressured me into going in a direction I’m uncomfortable with or growing at a pace that I’m not comfortable with.
Menendez: It's a good relationship for dating, it’s like you really apply that to pretty much anything and it works. Girls’ Night In makes money four ways now. Brand partnerships, affiliate marketing, a new subscription membership, The Lounge, and now a merchandise arm. Wild.
Ramos: Yes. It’s been an exciting ride to launch so many revenue streams back to back. It’s been really exciting. I think going to The Lounge and speaking specifically to that, The Lounge is our membership community. It’s a recurring revenue model, so you pay an annual or a monthly subscription to be a part of, and I think The Lounge gets to the very heart of the why of why Girls’ Night In started, which is to not only help people relax and recharge, but to build meaningful community, and I think now we’re almost seeing a resurgence of that. People are really looking for ways to create and foster new friendships especially.
You know, speaking personally, I’m now 30 and entering a new life stage. A lot of my friends have moved away from the city, or just like relationships are shifting, and I wanted to create a way for the GNI, Girls’ Night In community to find people specifically in their cities to connect with and become friends with, hopefully. We launched The Lounge in beta in October of last year and the idea behind it was actually in-person gatherings.
Ramos: Yeah, and it was going really well for a while. You know, we had literal strangers going over to other strangers’ homes for shared dinners, for watch parties, for like DIY craft nights, and it was really cool to see all that come to life. And then of course now we’re in a different spot with COVID. We had to shift everything to online only.
Menendez: Alisha, I’m so glad we got to do this. I’m glad I got to be in in a different capacity with you.
Ramos: Thank you.
Menendez: Thank you for coming to my closet.
Ramos: It’s a lovely closet.
Menendez: Thank you. Anything I missed that you want to make sure you get in?
Ramos: No. If you’re listening to this, definitely subscribe to the Girls’ Night In newsletter at GirlsNightIn.co. We have a new sister brand launching this fall called Whiled. W-H-I-L-E-D.co. And you can follow along there.
Menendez: Thanks for joining us. Latina to Latina is executive produced and owned by Juleyka Lantigua-Williams and me, Alicia Menendez. Virginia Lora is our managing producer. Cedric Wilson is our producer. Carolina Rodriguez mixed this episode. Manuela Bedoya is our social media editor. We love hearing from you. Email us at firstname.lastname@example.org and remember to subscribe or follow us on RadioPublic, Apple Podcasts, Google Podcasts, wherever you’re listening, and please, please leave a review. It is one of the fastest, easiest ways to help us grow as a community.
Menendez, Alicia, host. “How Girls Night In Founder Alisha Ramos Started a Stay-at-Home Movement.”Latina to Latina, Lantigua Williams & Co., November 9, 2020. LatinaToLatina.com