A group chat for bad texters
Letterloop is helping overwhelmed people stay connected
Embedded is your essential guide to what’s good on the internet, written by Kate Lindsay and edited by Nick Catucci.
Should we make an Embedded Letterloop? Haha jk unless… —Kate
When a meme star is beefing with a nepo baby, who wins?
I’m pleased to announce that I have not backtracked, compromised, or otherwise disintegrated since deleting Facebook and Twitter in January. As I later wrote, this is largely because they really weren’t that much of a loss when replaced by the smaller, more meaningful apps like Raverly and Letterboxd that require users to be doing something in order to use them.
While I didn’t really use Facebook for some time, I kept it around because it was ostensibly the best platform for planting some sort of “I exist” flag in the ground, where I could share all my big updates with friends and family. Without it, I really didn’t have an app that could facilitate the connection that (early) Facebook promised. Then came Letterloop.
New to me, Letterloop was founded in 2020 by Candace Wu, Jonathan Weinstein, and Bharat Kilaru. It came across my TikTok FYP as an alternative to the ad-driven, centralized social media platforms. It’s essentially an app that turns a group chat into a newsletter—just enter in the emails, set a cadence, and it will send prompts, collect the answers, and collate them into one dispatch.
I got on a Zoom call with Wu, who previously worked at Accenture and Weight Watchers before going solo in March 2020 to found Letterloop. Virtual connection became more necessary than ever, but the upkeep resulted in things like “Zoom fatigue.” Letterloop solved both problems. At first, Wu and co launched the app to a small beta group of users. Now, “some of our oldest users in our community have been on Letterloop for over four years,” she says.
Ahead, Wu and I talk about Letterloop’s emerging role in this new social media landscape, how it’s rewiring what we think of as connection, and if Facebook will ever truly fall.
It's interesting to me that Letterloop sprung out of a need during COVID. I joined it because it feels like so many of the platforms that we first joined with the purpose of connecting don't really do that anymore. Was that something you also had in mind?
Yeah. I think the main intention for Letterloop was helping people connect outside of Instagram and Facebook. I think our growth happened because of Covid as well. We had launched at a time where people were really sick of Zoom and they were sick of Instagram and Facebook. And there's no other space for intimate circles. And what we noticed too, really for me, was I wanted to start conversations with my family. I think oftentimes you get into these normal modes of communication, especially with—I have two sisters and my parents are immigrants and it's hard to ask them questions that I would ask on a phone call, versus if I asked them in writing, I get a different response. So there were a lot of use cases for us that we were personally interested in, but I think for me it was: tired of Instagram, wanted something where I can connect with my friends in a meaningful way, sucked at texting.
For those who are just learning about Letterloop, what does the app do?
Letterloop is a fun and easy way to create a group newsletter with family, friends, and teams. The teams aspect of our product is not publicized as much, but is a use case that we offer. And we have a lot of companies on Letterloop, so that's just a side note. The idea is that you can create a Letterloop in less than a minute. All you have to do is add everybody's emails, and the magic of Letterloop is you don't need to have an app downloaded. It's accessible via email and or any device. We just launched our iOS app earlier this year and our Android app is coming, but fundamentally the idea of Letterloop is accessible to anyone anywhere in the world. And so if you have a friend in Korea, if you have a friend in Europe, you guys can all stay in touch without needing to coordinate a call or needing someone to download an app that's only available in the US. All those barriers fall down.
We have over 600-plus questions that we continually update. So as you're creating your Letterloop every month, you get to pick questions that can spark new conversation, or ask your own. And then the idea is once you set your Letterloop going, we do all the work for you. There's light design elements, but you're not trying to design an actual newsletter because we take care of that for you. And we also send out reminders and everything it takes to collect the responses. And then you get a really beautiful newsletter with everybody's responses and you can comment and follow up with the people there.
You mentioned that families use it and that teams can use it. Are there any, just from what you've seen over these past four years, surprising or just particularly interesting ways that you've seen people use the app?
Outside of family and friends, and those are our core users and people in our community, I would say some surprising ways that people have used Letterloop is sometimes there's authors who wanna connect with their community in a very intimate way or who lead a community. We had someone, I think it was an author, who was creating these little groups as book clubs, and it was taking them through a story and they're moderating each Letterloop. So that was interesting. But I would say the main use cases are long distance friends, long distance families, remote teams who are looking to connect outside of work, or even we have also a large of chunk people who are no longer on Instagram and Facebook and this is their predominant way of staying in touch with the people in their lives.
Do you have any thoughts about why Letterloop is becoming an alternative to those platforms?
I really believe that the reason why Facebook and all the social apps out there are no longer doing what it essentially set out to do, which is connecting people, is because fundamentally the incentives are not aligned. The way they make money is their ads. And so for them, when the focus is ads, it tailors their algorithms. So people are presented with ads. The way in which people interact with the platform is based on what they interact with, specifically ads. So the whole thing is not incentivized to the platform. Facebook and Meta, Snapchat, etc, they're focused on design that benefits advertisers and not the core consumer. Obviously there are things that are still designed so that the consumer's engaging, but ultimately it's so the platform can make money and generate revenue. And so the way that we've approached Letterloop has really been: we are a private social network and we stay ad free and we keep all your data private by creating a model that is a paid social network. Which is incredibly unusual in the space of social networking.
Do you think we’ll actually see a meaningful shift away from Facebook and Instagram?
I think that Facebook and the major social networks will continue to thrive and grow. They're always going to be there. But I do think people will find new tools. We think of Letterloop as a tool so they can get the connection that they want in their life. And different tools are for different people. Some people find Letterloop works for them, some people don't like typing and writing letters. It just depends. And so where I see things trending is the big networks stay there and then apps like Letterloop will continue to grow and find users who are looking for something like us and in a way that works for them.
I've also noticed a trend in not just our space, but more apps requiring a paid element. So a good one that comes to mind is Monarch, the finance app. Mint shut down and it was free, and I think that was the major finance app for everybody. And so there have been a few other competitors that have popped up into this space, but more or less all of them now are focused on building a sustainable business so the ad network is no longer the business plan. I think more people are realizing, hey, if you want something that is going to be sustainable in the marketplace for years to come, and is gonna be available for people for years to come, and it's a really, really good product that people really want, it's gonna cost money. I think that trend is where I see things going versus social always being free.
I'm seeing a lot of parallels with what you're saying with the journalism industry, where similarly for the past 10 years, ad-supported journalism has been the norm. And I think the issue is it got a lot of readers used to consuming these things for free. But now with tools like Substack, there is this shift back to paying for the media you want. It's going well and people are willing to pay, but I think there are also people for whom that concept is very unfamiliar. The hope I guess would be that as they see the enshittification of these other platforms, they realize the value of paying for the stuff that gives them the experience that they want.
A hundred percent agree. What has happened in the last decade is people have been trained to consume an overload of content, and some people are coming to realize that they are the product that's being sold. There's also the trend of digital minimalism, really wanting to curate what they see, what their apps on their phones are, what they're consuming.
I really like Letterloop for that reason, because it feels similar to the joy people still get from getting their disposable camera developed. There's something about the waiting. You'd think because we've moved past it, it would lose its charm, but those things have actually become more special. And I feel like it's similar to Letterloop. It goes against what you would think, but actually communicating with people more purposefully and meaningfully on a weekly or monthly basis, you actually get more excited about that. And also I think it's really great to figure out what connection is actually meaningful, because I do think also a big trend of the past few years is mistaking constant connection with real connection.
I think that one of the biggest fallacies in friendship is thinking that high frequency of time means intimacy. And that's kind of what I was sharing about connecting with my family in a new dimension. Just 'cause I see you and I talk to you and we have a group chat, it doesn't really mean I know you or you know me in a deep way, especially in adulthood where you start to have new interests and do your parents really know you about what you're doing in your free time anymore? Probably not. So I think a lot of what I love about Letterloop and what we've created is because we have a question bank and people get to ask each other these new things and can ask questions anonymously to each other too. It creates this element of, "Oh, I didn't ask that question. Letterloop asked you that question." And I can learn the thing about you as a result.
I think another big trend, as I quit my job, I was really thinking about, how can I slow down? And I think there's also been a rise in people moving to slow living. And I think part of what you were saying about the joy of waiting for the film camera to develop, all of that is part of this larger trend of Gen X and Gen Z and millennials feeling really burnt out by the speed of how the world is moving. And so everyone's ready to touch grass, right?
As you look towards the future, do you have any hopes for what's next for Letterloop?
We're continuing to build new features for the app, but all in service of helping people have deeper connections and not becoming a Facebook. And so the idea is to continue to build features, listen to our customers. We have a public roadmap, so that's where we really share what we are doing, based on customer feedback. And for us it's really about how we can continue to come up with features that help people. My hope is that everyone has a Letterloop with at least one group in their life, 'cause I really believe that there's always one group in your life that you would really benefit from them staying in touch in some kind of way. And we're just continuing to grow the product and build the app in a way that is exciting to us and also our users.
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What I’m consuming…
A letter written by Luigi Mangione in December 2024.
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