Investment Memo #1: Investing in the Future of Dating

The Fourplay Social Investment Thesis 

As someone who just celebrated her one-year wedding anniversary, it probably seems strange that my first angel investment was in a social app for singles. But when I met co-founders Julie and Danielle and learned what they were building, what I ultimately decided to invest in was their larger mission to improve the way we connect with one another online and make the internet a kinder place to form relationships. With the ever-increasing hype this year about web3 and living in the metaverse, I want to be part of crafting a world—both virtually and in reality—that is better for our mental health and improves our ability to meaningfully interact with one another in a variety of ways. I believe that Fourplay Social will be a part of what moves us closer to that type of future, and I’m excited to be on that journey with them. 

Fourplay Social (Fourplay) is a app where single friends pair up to match with other duos (kinky, right? Just kidding, it doesn’t have to be.) Founded by two best friends and headquartered in New York, Fourplay is building a healthier and more enjoyable experience for singles where first dates are more social and less stressful. 

I invested in the company via a SAFE (simple agreement for future equity) on Wefunder, an equity crowdfunding platform where anyone (including non-accredited investors) can support startups and get access to equity. Depending on when you read this, their raise might still be open for investment if you want to join in on the deal! 

The Current State of Online Dating 

With an endless number of apps in the market already covering everything from quick hook-ups to dating for farmers (I mean seriously, check some of these out) it’s easy to dismiss the industry as over-saturated and, to be fair, it’s not easy building something new in an already crowded market. But major dating apps have one of the worst net promoter scores (NPS) of any industry, with a ridiculously low likelihood of being recommended to a friend by their users. Dating apps are less popular than airlines, wireless carriers, healthcare plans, and TV services, meaning people are more likely to recommend their phone plan than their dating app, which is just a ridiculously low bar for improvement. Additionally, in a recent survey by NEA, 80% of respondents reported being somewhat or very open to trying a new dating platform, “confirming the opportunity for a new entrant.” 

While I’ve never swiped for a romantic date, I did sign up for Bumble BFF in 2021 to make friends in a new city during the pandemic. I was an active member for only three months before I deleted the app. 

All the friends I met on the site seemed nice, but I didn’t truly hit it off with any of them and we didn’t stay in touch. It became clear that, for me, the effort of scrolling, swiping, small talking, coordinating, and repeating wasn’t actually worth the outcome, so I deleted the app. This was a relatively easy decision since I had enough existing friendships to sustain my need to socialize and I knew it was just a matter of time before I made more friends the “old fashioned way” instead of spending all my time on an app. But I can see how this would feel different if what I was looking for wasn’t a buddy for yoga class, but a life partner. So many people in my age group feel increasingly desperate to find ways to genuinely engage with each other, which keeps them tethered to a dating app or online experience that irritates them at best or damages their own self-image and mental health at worst. 

This is the problem Fourplay is trying to solve, and it’s got a vast market to operate inside of. By 2026 it’s predicted that over 300 million people are expected to be paying for online dating worldwide, and nearly 10 million of those users will be in the United States (Tinder alone currently has 8 million monthly active users). The largest player in online dating is the conglomerate Match Group, born out of Match.com, with a $15B market cap and nearly $3B in annual revenue. Match Group has gobbled up most players in the online dating space, each with a different value proposition but none that match the process Fourplay has created, making the company a solid acquisition option for the future at what would be a lucrative exit if Fourplay can grow and retain enough users (Tinder was acquired in 2021 for $1.7b) to be an attractive option. 

Introducing A New Way to Double Date

A growing percentage of people have swiped their way to success. I know plenty of couples who first met online, although it’s always interesting to me to hear what they tell strangers or distant connections (like coworkers, for example) about how they first met. Many couples who met through a dating app lie, especially if they are talking to older or already married people. The stigma of online dating remains strong even as 3 in 10 Americans say they’ve used online dating apps and 12% of them have married or been in a committed relationship with someone they met online. So much of the online dating experience feels isolating which is an ironic conundrum for an event that by definition is supposed to take place with another person. Instead, it’s more common these days for a single person’s dating life to exist primarily behind the confines of a screen, with hours of alone time racked up before hearing another person’s voice or meeting someone in person. 

Fourplay has built a product where users can team up with a friend, create a shared profile, and match with other pairs of single friends. The product is focused on singles age 18-34 and initially launched in New York City, where 13,000 people are already using it (and the waitlist across the U.S. is another 12,000 long). Over 40,000 matches have been made so far in NYC and that early traction has led to the founders being featured on LIVE with Kelly and Ryan, CNBC, and multiple other sites (see here and here for starters). 

The company was founded by Julie and Danielle, two best friends who have backgrounds in healthcare and were frontline workers during the pandemic, so it really doesn’t get more badass than these ladies. Clearly they understand dedication, commitment, and hard work, which are all characteristics that I believe are critical to becoming a successful founder and can’t be taught overtime the way financial or operating skills can. Neither of them are “traditional” entrepreneurs – they didn’t go to business school or spend time at consulting firms, and while most people see this as increased risk, I know from personal experience how much being an outside can help when building something new. Having spent time with them I also know they are smart and driven enough to quickly learn what they don’t know, and that their unique perspectives will help them build a product that’s more accessible and desirable, not something that any MBA student could cook up. Statistically speaking, underrepresented founders outperform white men over time, so it’s even more practical to support a fully female founding team.

The MVP that first launched in New York gained solid traction and positive reviews on the App Store, even with some clunky UI/UX. The team used their first raise to bring on a technical co-lead to help rebuild the app with a new and improved flow and feel that is currently being tested in beta before being rolled out to new markets. 

Why I Decided to Invest 

As we continue to push more and more of our lives online, dating apps will expand and evolve, offering market share potential that can be captured by creating a community that is safe and less stressful than what’s currently available. 

At a friend’s party in Brooklyn earlier this summer the topic of dating came up in conversation, and every single person in the group had a horror story from their experience with a dating app. Some were amusing in hindsight, like one story about a girl who refused to leave the restaurant because it was raining (even after she was offered an umbrella) so forty-five minutes of drinks turned into nearly four hours of awkward small talk. Some were creepy, like one guy who repeatedly asked for more pictures of my friend and, when she refused, said he was going to find her and kill her cat. Some were mundane, like being ghosted or showing up to see that the person you’d agreed to go bowling with looks nothing like their pictures. Honestly, I’m sure there were stories that went unsaid and were even worse. A Pew Research report shows that 60% of female users ages 18 to 34 have had someone on a dating app continue to contact them after they said they were not interested, while a similar share (57%) report being sent a sexually explicit message or image they didn’t ask for. 

When I mentioned to the group at the party that I’ve never used a dating app, most people were shocked, and more than a little bitter. Not one person had anything positive to say about their online dating experience. 

In the 2022 NEA study cited above, nearly 80% of respondents said they would be “very open” to trying a new dating app, and yet Tinder, Bumble and Hinge continue to grow their user bases. It’s apparent that the time has come for a new way of not just matchmaking online, but actually dating online, because dating shouldn’t be something people dread doing. And Fourplay is not just Bumble for double dates. It’s building a unique interface and system for GenZennials (people 18-34) to be social online. To me, this is a way more exciting way to build the metaverse than through online gaming or social media. Fourplay is designed to foster relationships that can exist within the boundaries of our digital lives or move into the real world if we choose, without the fear of negative interactions or the pain of awkward encounters, because users are going through the journey with their close friends.

The user strategy of dating as a team produces a flywheel that will beat the existing customer acquisition and retention problems plaguing other prominent dating apps. 

One of the hardest parts of building a dating app is the fact that if you’re successful, your customers eventually leave. As Hinge says in its marketing, the app is “designed to be deleted.” This leads to a high level of churn (having to replace users who leave) and can decrease growth. If the goal of a dating app is for users to meet their special someone and stop dating, eventually users will either actually do that and delete the app or will get tired of all the failed dates and switch to a different dating source. 

Fourplay combats this problem with its process of double dating, expanding their user base by requiring each person who joins the app brings a friend. If a double date is successful for one of the friend pair, the other can team up with someone else and keep dating, continuing to bring new people onto the app and building up a defensible moat against other apps that try to copy their style because if people are already double dating on Fourplay, they won’t switch to a different app if they’re friends aren’t there. This is also a great way to save money on paid acquisition channels that most dating apps use to find customers like Facebook and Google ads, for example, which can be extremely pricey. 

Early traction and super-fan feedback validates this idea, and having two diversified revenue streams will help the app reach scale.

Seeing the waitlist for the app continue to grow, as well as the number of connections made in New York, makes me excited to be an investor in this company. The app has received worldwide attention and has over 100 positive reviews on the App Store (4.5 stars) after launching earlier this year. Fourplay Social definitely has what I call “proof of life” data: it has shown that its building something people want, and are willing to pay for. Now they have to put the rest of the pieces in place to scale that idea into a thriving business that can serve more people and continue to iterate based on their users wants and needs. 

The company makes money through a typical SaaS subscription and ad model where users pay a monthly fee to use the app and the app runs ads. Both revenue streams are proven out and sustainable, as long as the app reaches a high enough number of users with a minimal amount of churn to cover expenses and continue to grow. 

The Risks 

Expanding a marketplace from city to city is an action that doesn’t scale and could break early success if it’s not done strategically.

In my opinion this is the biggest unknown of this investment, and the biggest risk I’m taking in making this bet. For a marketplace to work there needs to be buy in on both the supply and demand side. So if I’m a woman looking to date men and there are only 3 men to choose from, I’m not going to have a great experience dating on Fourplay. Similarly, if I live in Ohio and I want to try dating on Fourplay, I won’t have a good experience if there’s only one other person in Ohio for me to match with. Bringing people onto a platform takes time and it takes money, usually in the form of doing things that don’t scale like hosting big events, running marketing campaigns, and paying influencers to be early users and to tell their fan bases about a new product. 

It’s important for founders to do things that don’t scale sometimes. It’s the little details and the extra effort that can make a product really sticky in a new market, but if you have to do it too much you don’t have a business and you’re just wasting money (see: Uber). This is where the network of advisors and advocates that Julie and Danielle are seeking advice and expertise from will be critical, because having mentors who have scaled successful startups and understand the details of customer acquisition and retention will help them launch past the cold start problem and get to their first dedicated users in new markets. I’ve already seen this in action through the team’s decision to launch in the collegiate space next, focusing on universities to reach critical threshold faster than would be possible in city markets more broadly. This strategic shift again reiterates the deep thinking and intelligent support system the founders have engaged to build their company correctly. 

Two non-technical first-time founders building an app will make iteration and future development difficult. 

While initial reviews of the app have been overwhelmingly positive, the main criticisms have to do with the app crashing unexpectedly and some issues with the onboarding flow. These are technical issues that require someone with coding and development capabilities to address. While the founders are not technical, their first hire is a VP of Engineering who has been brought in to address these issues as well as other bugs and continue to build out the platform. 

I’m impressed that despite these glitches most users continued using the app, and that the actual UI/UX has been reviewed positively. Again, I think this shows the level of deep thinking the two founders are capable of and the fact that they will continue to focus on their mission of creating a better online dating experience, which will embed itself into every decision that’s made. And while it’s obviously incredibly important to have the person actually building the thing to understand the nuts and bolts of app development, I don’t think it’s a requirement for founders. This is one of my core theses as an investor – I’m good with investing in excellent non-technical founders, and I think it’s important. Lots of engineers look, think, and act the same, and I don’t want that subset of people to be responsible for shaping every aspect of our future. Also, it takes a lot to run a successful startup, and it’s good to have a diverse set of skills on the team especially early on, which means not everyone needs to be in the code to move the business forward. 

What Will the World Look Like if This Works? 

Relationship building is increasingly becoming an online experience, and that experience right now isn’t a satisfying one. Facebook claims to be the epicenter of human connection and is going all in on its idea of a metaverse, but the problems around Facebook’s monetization strategies and the addictive qualities of social media more broadly are well documented and contradictory to the essence of what it means to connect with someone. Dating apps tote strong user metrics but no one speaks positively in real life about their online dating lives. There is so much room for improvement and I think what Fourplay is building, with its focus on a culture of safety, communication and connection fills a gap in the market. 

It will be critically important for the success of Fourplay that they don’t build a product that is just “Tinder for double dates” or any other incremental change to the existing big picture of online dating. Because the incumbents in the space are so large and well-resourced, it would be too easy for them to catch on to the success of a double dating feature and add it to their existing product, creating an overly competitive environment that a new app won’t be able to thrive within. 

But I believe what Fourplay is building is bigger than that. Everything about how online dating currently operates makes it difficult for anyone who takes it “too seriously,” and instead caters to a feeling of being “just for fun,” which in turn leads to a minimal level of commitment to doing the sometimes difficult work of building a relationship with a stranger. It starts to feel more like a game than a meaningful interaction, which opens the door for bad behavior and an overall sense of apathy. 

Fourplay isn’t an overly serious app, and it’s not just for people looking to meet the person they will spend the rest of their lives with. By using a double dating format, fun is embedded into the concept, as reflected in their marketing of “a night with your best friend is never a night wasted” even if the date itself is a bust. In addition to fun, the entire process is imbued with a sense of safety first (buddy system at its finest) and being a place for actually dating online, not just matchmaking. This gives Fourplay the potential to grow into other areas overtime. 

There are still plenty of logistical questions that the company (which is still in its early stages) will need to think through, and while they don’t have the answers yet, I’ve been extremely impressed with the level of strategic thinking Julie and Danielle have conveyed and am confident they’ll come up with compelling answers to these questions, like how to get enough men to join to sold the gender gap problem and how to provide a space where multiple relationship needs can be met. 

Beyond my support of the company itself, I invested because I want to see a world where more women get the venture backing needed at an early stage to build startups. I want to see more fully female founding teams. I want to see women with backgrounds in healthcare and education and fashion and non-profits moving into the tech ecosystem and being seen as credible and taken seriously. I want more women-run unicorns and more women as serial entrepreneurs. 

That’s why I invested in Fourplay Social.