AI Matchmaking & The Future of Dating Apps (Sitch Founder + M13 Investor)

Why was it that when it came to our love life, which is fundamentally the most important decision that you make in your life, there was no resources? So I love the idea of matchmaking. Not even from like, of course, like there's a cultural connection. Like I've seen how it works. I introduced couples who got married.

AI is the perfect mechanism for doing this. Where matchmaking used to be a very premium service only available to the top 1% and AI is able to do it at scale. So now the service that was only available to the top 1% is. Can be brought to the masses in a really unique way.

Welcome to the venture capital podcast. Today our guests are Deenie Milaji and Whitney Hazard. Deie is the co founder of Sitch, a next gen dating app using AI not to replace chemistry, but to engineer it. Before Stitch, she built another company in the dating space and worked on the venture side as a scout with a 16Z speedrun program. She's seen this world from both sides and she's doubling down on one of the tech's hard, hardest, most human problems, helping people truly connect. Whitney Hazard is an investor at M13 and one of Danny's earliest backers. She's built a career investing in AI applications that change how businesses work and how consumers live. She looks for founders and products with the potential to shape how we experience the world and engage with one another. She's not just bettering the future of AI, she's helping to fund it. So welcome and we're glad to have you both on the podcast for.

Excited to be here.

Yeah.

This should be fun, super exciting and do you want to tell your story, Dini, before as we get started?

Yeah. So I grew up in Bombay, India and my grandmother's a matchmaker. So I grew up around a culture where everyone was involved in this life changing decision of who you marry. Right. And I would just set my friends up for fun. Ever since the eighth grade school dance, as people have reminded me of late. So I've been doing this a really long time, but I never thought I would do it as a career. You know, I did the classic McKinsey VC early stage startup business school sort of did like the whole journey of like everything before figuring out that I wanted to build in consumer, I wanted to build in whatever the frontier technology of the time was and I wanted to solve a problem that felt incredibly meaningful to me and the people closest to me. So while I was at business school at gsb, which is also where Whitney went, we I, you know, was talking to all my friends about what was the thing that was most just top of mind. And my friends were all like, interesting, smart, successful, gorgeous. We're all so stressed about going back on dating apps. So it felt like the most obvious answer was, how do I solve this problem of how to deeper meet, fall in love and stay in love? So built a different dating app in 2023 after I graduated, bootstrapped it, launched it in New York. We were doing about like 30k a month in revenue. But it was the wrong idea. It just wasn't frontier technology enough. And it was the wrong co founder, which as many founders and VCs will know, is really the thing that makes sure that your business survives in the long run. So as LLMs came about and I saw that there was this opportunity to sort of expand what dating could look and feel like, move from swiping to actually a more concierge, matchmaker type approach, I was actually introduced to my co founder, Chad, and it was obvious within the first 20 minutes of meeting that this was why I needed to build this with. And we were both very missionary on the idea that everyone needed a matchmaker. So in a funny twist of faith, you know, what my grandmother has done for decades, I now get to do on a daily basis, but I get to do it at scale and with technology.

Awesome. That's a great story. And my wife and I met on both. So I love the dating apps. They're fun.

Yeah, when they work, they really work. The problem is that they no longer work and it's time for a platform shift. But people have always needed tools and people and ways and means to connect and meet because this is a really important decision and you shouldn't be just left to luck to figure it out.

Whitney, do you want to take a moment before we begin and talk about why you invested in Cish and Deanie?

Yeah, absolutely. So I'm Whitney. I'm an investor at M13, which is an early stage venture capital firm. We invest in seed and Series A companies. I spend my time primarily investing in AI applications, both for businesses and consumers. And as soon as I met Deni and her co founder, Chad, I knew I had to invest in Stitch. There are a myriad of reasons I could go on for for a while, but first and foremost, just as a team, they are so complimentary, amazing skill sets and just a clear vision to solve this market. And with Stitch in particular, like I've always said, I love love and we want to bring people together. And what Stitch is doing is bringing the best of to completely reimagine dating apps for the future and to actually focus on what matters, which is helping people find the loves of their lives. And so there are a whole bunch of reasons we'll go in through in the episode, but it was an easy decision as soon as we got to know Chad and Deanie and heard their vision for Sitch.

Did you guys meet on Sitch?

Sorry, we did not. We did not. But we actually met. There are so many, like overlapping points of connection. So Deanie and I, as she mentioned, both went to Stanford's business school called the gsb. We were different years, but, you know, had had similar communities and ties there. And then Anna, my partner at M13, and Chad, Deanie's co founder, were both like longtime LA tech ecosystem natives. And so they had crossed paths many times over. And the kind of dual synergies of those relationships just made it a really natural fit.

Awesome.

Dini, do you want to talk more about why you chose. Why you chose to make this pivot into the matchmaking side?

Yeah. The first dating app I built was honestly just a feature, not a product difference. We made sure that instead of people messaging, they were just getting set up on a date. That's a nice to have, that's not a need to have. Right. What people were really struggling with was figuring out who they were and what they wanted, figuring out how to pitch themselves to someone else and how to actually navigate like with the limited information that they were seeing on someone's profile.

Right.

These are all really tough things for someone to actually figure out. And it's exhausting. You know, it's exhausting to swipe through 80 profiles a day, have 20 conversations with strangers, and do that on three different apps. In our life, we've gotten used to now a more con edge based approach with practically everything. Right? Like you literally have a nutritionist, you have a therapist, you have a career coach, you have a trainer, you have all of these services that help you like, take away the decision burden and help you figure out how to navigate these other things. So why was it that when it came to our love life, which is fundamentally the most important decision that you make in your life, there was no resources. So I love the idea of matchmaking. Not even from like, of course, like there's a cultural connection. Like, I've seen how it works. I've introduced couples who've gotten married, but it's really thinking about like with relationships, where is the place you go? Where's for this entire, whether it's 5, 10, 15 year period that you're dating, where is someplace that you go to keep learning, reflecting, figuring out who you are, what you want and then getting guidance along that journey. So when we started envisioning what sitch really was, it wasn't about swipe to get to a date. It was how do you think of yourselves as this partner on the journey of finding love. Right. So we really wanted to do a like it was a mission shift in terms of what swipe based dating apps did. It was also a platform shift where instead of it being self serve swiping, it was now conversational AI that had memory and the ability to get to know you and build a relationship with you. Right. So it just felt like the perfect confluence of the timing had shifted so much in the market of what people wanted. And there was this incredible technological opportunity. Right. Of building in LLMs, but also building in a space that OpenAI or like anthropic was not going to enter. They're going to enter most things and people are going to raise hundreds of millions of dollars only to realize that actually is going to point that canon and like fired in that direction. But they're not getting into like setting people up, they're not getting into the social layer. So we also knew that we had this great opportunity of just like the cultural moment and the tech moment coming together. And then obviously for me it was like deeply like passion forward. Right. Like I do think this is what I'm meant to be doing. So it was an easy decision. Yeah.

And I'll just add one thing. I think AI is the perfect mechanism for doing this. Where matchmaking used to be a very premium service only available to the top 1% and AI is able to do it at scale. So now the service that was only available to the top 1% can be brought to the masses in a really unique way. And so it's also a perfect point in time moment to leverage the latest technology to do something that used to not be accessible to most of us.

I think that's great. Can you talk a little bit about what the user experience is like in such versus a traditional dating app?

So traditional dating apps ask you to do two things. They ask you to talk about yourself. So that's creating a profile, writing like prompts and choosing a few pictures. And the second thing is that they ask you to navigate and figure out whether or not you're interested in this person and whether you can like glean from their profile if they meet all of your non negotiables. Right. So it's very much self serve. It's very swipe based. It's like, it really is almost like surface level. With cish, what we wanted to do was actually mirror the experience you would have with a human matchmaker. So you with a human matchmaker, you have a conversation, right? The matchmaker is asking you a set of questions. They're getting to know you. Then they're not expecting you to pitch yourself to other people. They're doing the pitching for you, right? So on sitch, you have a conversation actually with the AI version of me. And there's like a 35 minute long onboarding where we really get to know you. We then sort of tell you what we think you're like non negotiables. Your nice to haves and your red flags and are which gives our customers a real sense of feeling seen and understood which is really missing everywhere else. We also are able to then gather way more data to understand like, okay, you actually want to move back to Minnesota because you have aging parents, like just things like that that you would never put on a hinge profile. Then your matchmaker sends you candidates and you give feedback on those candidates. So it's again like exactly like if I was trying to set Whitney up with someone, I would send her a person, give a little background and have a conversation about it. And then if both say yes, we introduce them on a group chat. For us, the biggest innovation has been like realizing that you don't want to create new habits. You know that this is the way people behave. We know that. Like for us it's like imessage is a really good counterpoint to how we want this to feel. The way you would interact with a friend who was setting you up, that is actually the exact experience we want you to have on sitch. So it feels very authentic, genuine, and allows you to really like, you know, have a conversation about what you want and why you want it or don't want it.

Yeah.

And I think what I really love in particular is like I used to feel so frustrated of how I make a profile actually capture the pieces of me that matter. And just feeling like six photos and three prompts is never going to get to the essence of who I am. But because during the stitch onboarding you have such an extensive conversation about who you are, what your values are, what your goals are in life, how you like to spend a Saturday. It captures this extension really rich information that gets to the essence of who you are, which it then keeps sort of below the fold. It's not you know directly on your profile in every case, but it remembers this about you and then uses that to match you really effectively. And so it's taking away the like perfect profile problem and helping just actually get to the heart of who you are.

Yeah, I think it's great. So I read a report recently and this was Utah where I'm based on, and they were, they were saying that it's basically like 50% of single Utahns were using AI in some way, shape or form in their relationships. So it could be that they had a relationship with the AI. But also I think more common was that they were using AI to formulate answers and.

Yep.

Dialoguing back and forth with potential dates. And the, the big question was like, does that just like result in more disappointment? Right. Because it's like if both sides are just using AI to talk to each other, when you actually meet up, how do you maintain or how do you ensure that like, who you are as an individual gets communicated through and doesn't, you know, go through like an AI slop process and translation? Does that make sense?

Yeah, that's exactly like the principles on which this, the opposite of which stitch is built. Right. Like, we don't. Firstly, we always say, like, we're never going to get into the AI girlfriend, AI boyfriend business. Super, super lucrative. Not so much anymore though, given that OpenAI is getting into adult erotica. So no longer going to be that exciting of a place to be. And. But we've also said that like this, I think it was like Winnie Wolf who went on like some. I think it was a New York Times interview where she said, oh yeah, like the future is your AI bot talks to someone else's AI bot. Fundamentally disagree with that. What we really believe is that all technology can be used and misused. Right. We want to use AI to make it so that the things that we know, like we struggle, like humans struggle to scale AI can help with that. We can't have a high quality matchmaker sit and do like a 45 minute long onboarding with each person, remember all of these details, be able to successfully be like, oh, these data points match with that. I know this. I've tried to do it. I've watched my grandmother do it. There is a limitation to human cognition and network and we're really using AI to help offset those things rather than actually removing the things that intrinsically make us human. Right. The AI is not helping you, like, come up with the lines to talk. The AI is not telling you, like, oh, this is what you should Say or what you shouldn't say, the AI is not planning your date for you because we've actually gotten this question a lot of like, oh, like is it going to tell you where and when to meet? I now fundamentally like don't believe that that's the approach because people want to feel like the other person put in some thought into where they were trying to take them out for a first date. So we really think about using AI to improve and scale up the human matchmaker rather than replace the human dating experience.

Interesting. Yeah, I think it's great. Are you familiar with this company Bord that's popped up recently?

Yeah, yeah, yeah, yeah.

Pretty similar in a different venue, right, than Boardy.

It's super interesting, right? Because actually Whitney, I'm so curious if your experience is. I get like probably once every two weeks an email from Bodie and I'm like, I don't really care. Why would I want to talk to this random person? What's in it for me? And why did. Why are you like, why would I spend my time and energy talking to this person who's clearly like not actually useful to me, but maybe I'm useful to them. The problem with all of this like friendship and networking stuff is that where is the proven use case of like people paying for it? Right? With such a. And with just dating in general, we have a. It's like not just like in the last 15 years, for the entirety of like human history, we have known people really spend time, energy and resources trying to find their partner. And we know that people are paying. Right. And we've seen this time and time again. So I think what really differentiates us and you know, people who are using this in other places is that there is an actual business model behind this. Right. It's not just about like a viral loops of like, oh, like this person's going to call me. You need to have a reason. People want to actually like respond and some sort of buy in into why they are on that platform. And finding a life partner is a really compelling reason for you to pay up and to participate. Like me getting introduced to like someone who wants to start a company or like wants to apply to the gsb. And I'm sure wouldn't you get a million of these, like way more than I do. It's like this is why. What is in it for me? So the. I think, I think it's really interesting because people stay away from dating. But then dating is actually the use case for this where people always are willing to Pay.

Yeah, I completely agree. And kind of bringing those two questions together, I have a strict, like, only invest in things that will do net good in the world. And I think helping people find their like real life human love of their life is, is so clearly one of those things. Like I don't believe in a world where, you know, we all have our AI companions and that's our romantic, our romantic partner. I really believe in a world where AI can help us find that human connection we so desperately crave. And to Dini's point, one of the things that I loved about Sitch is that they are constructing the business model to want to find success for you. They want you to find their partner. The unit economics are totally flipped on its head and the willingness to pay is there because this is one of the most important factors of your life. I think where previous dating apps have gotten stuck is that it's almost more an activity. Like you're swiping as a pastime time. Like the same way you'd use a mobile game. Right. But what Sitch is doing is you're paying a little bit more up front but to actually find your partner. Right. To really find someone who's a true match. And I think that's what, what's so compelling about it. And there totally is willingness to pay because people crave that human real life connection. And that's what we hope to see more of in the world.

Yeah, I love that. Can you talk a little bit about the business model? Yeah, that's always been a huge challenge for a lot of dating apps is right. You, you don't want them ultimately as a business to find that match because then they leave and they stop paying you.

Right?

Yeah, that's because of that. So that's because the business model has been, is broken. So actually something we told Whitney and Anna when we were talking to them about Sej, right, Was that you actually need three innovations. You need product innovation, you need business model innovation, and you need like distribution innovation. Right. So we've talked about like how different our product is. It's a fundamental shift from swiping to actually conversational AI. For us, the business model, I actually don't think you should ever have a subscription for a dating app. Right. Because that is actually when you're at odds with one another. I don't want. This is not your Netflix account. You don't want to be on this forever. You really want to think of it as value based service. And I really think people are going to move more and more towards this value based service model across all different points of like the spectrum. Right. We're used to thinking about it from like a fitness class perspective. You're not buying a subscription to Barry's, you're buying five classes and you know exactly what you're getting and why you're like using it. And so for us, even the traditional matchmaker doesn't really charge you a monthly retainer. Your matchmaker says, hey, I'm going to set you up with five people and it's going to cost you $10,000. So for us we charge you per setup. So you buy a pack of three, five or eight from us and that means we're both incentivized for the same thing. You can be as picky and as specific as you want because those like have a one year long like expiration and in that time we will find you someone who actually meets the specific criteria that you want. We are not incentivized to send you like people who you're not going to say yes to and waste your time because we want you to actually use those up as fast as possible. And once you build a business model where you're not trying to say, hey, how do I, you know, on month six, ensure that these people are still paying me and instead say, actually we recognize we've, we've gotten the revenue upfront where you bought this back. Now we're just trying to make sure that we can recognize that over the course of the year we're actually all on the same page and that changes the incentives. Like I, like I said like very missionary about this. I think dating apps per se, not only are they bad, but like subscription apps are not really like a good use of people's money, but they're also just like, they're kind of predatory. Right? Like it's like they like, like, oh, your, your swipes are done or do you want to meet this hot person now pay up. Like it's always constantly like, like male whales who like us basically funding these entire business versus on search is very much like you're buying a pack of setups.

Yeah, no, I think that's a really interesting business model and approach. I'm curious, how do you, how do you grow that though? And how do you think about go to market and scaling and getting more customers?

So SG needs superpower. She's the queen of that. So you've come to the right place.

So honestly, I think what central Secret Sauce has been is throw out the playbook of what everyone else is doing and focus on what makes us different, right? Everyone in the dating space does digital marketing ads. Everyone does these like, like the new, the up and coming people will do these boring things on like swiping is broken dating. You're lonely, like very fear driven. And you're like your existing like big players like Bumble will do these random campaigns like love is love, like, okay, what do I do about that, right? Like there's nothing that excites you. For us, our secret sauce has been in the branding side, just like making it feel like the thing, the conversations that you're already having with your friends. Our first campaign that was across 260 subway stops in New York was focused on this idea that like you've wasted $200 on a bad first date. Like you're entitled to compensation, right? It was in the style of like old lawyer personal injury ads. And that really like hit a particular point for people because people are like, oh wait, this is funny. This is relatable. This is stuff that I talk about and this is the way I talk to my friends about it. So you know, that's why people like immediately got excited and signed up. We also have been first to the market, right? Like we've been talking about building an AI matchmaker and having an AI matchmaker before it became cool and before it became a thing that like a lot of investors, and this is why we love M13 is like they believed in us really early versus now. Everyone who's coming to us for a series A is like, oh yeah, we know that this has to exist. So there's like an inevitability about it, but sort of going back to like the hardest this drove. You can't grow through digital ads. You have to grow through actually referrals. And for us, 30% of our users come through their friends telling them about it. If you have a positive experience on a dating app, you are definitely telling your friends. You go on a great date, you're telling your friends. And if you can keep building that viral loop, that's what makes the difference. We're not going for like rocket ship virality. We're actually going for this more slow and steady growth which can be built through you telling your friends you having successes versus a viral video that actually doesn't get you any downloads or actually customers who will pay and stay.

No, I love it. And that ad ad campaign is brilliant. I've seen some of the ads, so.

Oh yeah, we have a, we, we have a new one that's going live today, which is me with in a Santa Claus hat, talking about how you can't buy love, but you can gift a setup. So we, we really lean into out of home. We really lean into humor. And I think those are really, like, really what makes such a difference.

And I, I was a marketer for many years before moving into investing. And this was so clear to me as soon as I met Deni. She is a marketer through and through, and she has sort of reinvented the monotony that is traditional marketing of doing the same things in the same tone and the same channels, and has really focused on the key meeting the customer where they are understanding who they are, like joking with them and bringing all this personality. And I think that's really what's resonated in the market because people don't want the same thing they've seen a hundred times over. They want, like, such is such a different experience. And so the marketing reflects that. It reflects how, like, unique and character based it is that comes through.

Yeah, no, I can definitely tell. Have you seen the. The movie the Materialist?

Of course, of course, of course. I have not only seen it, I have made. I think at this point, I've made as many videos about the Materialist as they've made promo videos. And I did find out very recently, actually, from the person who does the marketing at a 24, that Celine song was sending around videos being like, wait, why didn't we pair up with these people? So I feel very excited about that.

I love it. I'm curious, since you, since you obviously have seen it and feel strongly about it, what are some of your big takeaways from it? What did you like? I mean, just give me the quick snapshot.

I think that what I loved was that it brought matchmaking into the popular conversation and that it saved me a lot of digital marketing dollars since they were literally, you could not be on Instagram or TikTok without getting an ad for the Materialist. Right. So great. When you capture a cultural moment where everyone's talking about it. I think a lot of the first half of the movie where she's actually being a matchmaker and talking to her clients is quite in line with how people look at marriage and partnerships and relationships. Like, it isn't just about chemistry. It is not just about love. It is about other things. Now, those other things may be money for some people, it may be power, it may be family values, it may be religion. It may be a range of different things. And, you know, at sitch, we're not here to to judge. We're here to listen and make sure that we can set you up with someone who actually matches those things. So again, very similar. What we saw is that the crazy things that people say to her, they say crazier stuff to the AI because they know that they can be 100% honest and not judged versus when you talk to a person, you still actually have some semblance of. Let me not say this absolutely crazy thing. So I think that is definitely like there's a lot of grains of truth. And I think that, you know, where it goes wrong is that they made it seem like the people who get use matchmakers are people who are honestly not like mainstream people. You know, they're like struggling to find love. They're like older, they're like richer, but they're like, you know, there's something wrong with them and that's why they're using a matchmaker. And I fundamentally disagree with that. Take this is the most important decision. And if you're spending money on literally an aesthetician, spend money on a matchmaker because that is going to give you so many times of that return. So yeah. Enjoyed the movie in the sense like I love a good rom com. Do I agree with Dakota Johnson's decisions in the movie? Absolutely not. But yeah.

Yeah. How do you go ahead, John.

How do you approach the problem of everyone's trying to date like the same 1%?

They're not. That's actually like the fundamental lie, right? Like the like just because TikTok tells you that you're dating, that everyone's trying to date a 65 guy with blue eyes, I can tell you that that's wrong because I have the data and the data says that women in New York, SF and la, the number one non negotiable for them is actually political beliefs. It's not height. So yes, there's always these popular narratives that exist, exist but the data says a different story. What you're really looking for and like why I think like I'm so fascinated by what we're doing at SIJ is if you could have a perfect data set about everyone in the world, you probably. I'm not going to say we can find you your soulmate because I also don't think you have one person who's your soulmate. You have a potential of like five to seven people who probably like really match what you are specifically looking for. We're just trying to make it a much more simplified process finding that. And I see this in the office every day where it's like, you know, like we have a team of actually everyone who's in the office is our growth team. So it's a lot of women and people don't have the same preferences, whether it is what someone looks like, what they do, what their values are, what's important. So it's, it's not that like it just, it isn't fundamentally around going after that 1% of people. But we like to make it seem like that because it's clickbaity.

What other things like that? I love that insight. What other insights like that have you discovered?

So we do a lot of this like data stuff because I think it's more just like I find it very fascinating because we don't have good sources of truth and information. Especially like when you think about like Pew and Gallup polls, they don't do a very good job or they do this sort of longitudinal thing across people in a variety of contexts. Sitch is like all major cities, it's single people, it sort of like touches that like 25 to 55 year old, like well educated person, right. And we know what their like preferences and beliefs are. I think it's like, it's interesting because men do tend to have a lot of preferences that one would think so, right? Like where age, fitness level, those become like really big criteria points for men when they're thinking about partners. When you look at age ranges, right, like the AB, like if you're a 40 year old woman on average, like the lowest age range that you will set is 40, right. If you're a 40 year old man on average, your age range on Its lowest is 26. So you know, again I'm not here to say that's right or wrong, but there are like a lot of the times there are certain stereotypes that exist because that's what the data sets and either I can set and you know, we talk about this a lot at our board meetings. It's like we are not here to make society in the image of what any of us at SIJ believe. What we're really here to do is listen. We're here to understand. If you're looking for abc, let us find you someone who has A, B and C. Let us not try to waste your time trying to show you someone with X, Y and Z and saying, hey, you know what, actually if you've decided you want to have five kids, let me introduce you to someone who's sure that they want to have one or maybe none and like force you guys to like reconcile like that's just, it doesn't make sense. So it's been really cool to sort of go through that experience of making sure that we don't have our own biases in our. The way we matchmake.

And one of my favorite things that Sittch is doing on the data side is this idea of non negotiables. I think we all have been that person or have friends who are that person who have their list of a hundred different criteria points that they're looking for and they can't find their perfect person because no one is going to ever hit those hundred different points. What Stitch is doing is learning all of those things that you're looking for, but then also asking you, like, what's most important here? Is it political preference? Is it that you want to find someone else who wants to have children? Is it that you want to make sure your travel lifestyle is compatible? It really introduces the idea of the non negotiables and then works as hard as it can to match the other things. But actually, turns out we might be surprised by who we end up falling for. And so it's a bit of like a mix of, you know, strictly what you're looking for, but also being open minded to the perfect match.

Do you think there's an opportunity here for the AI to kind of take it another level? Because one level is for me to say, oh, this is my list. But there's another level which is like, understanding who I am as a person and identifying the right other person, even if I don't necessarily know that about myself. Does that make sense?

Yeah. The nice thing about Stitch is because it's conversational, it's very dynamic. Right? So it's like we send you someone and you're like, oh, I think they might be too old for me. And it's like, oh, well, actually, your age range did say that you were open to someone who was this strange. But do you want us to reduce it? Right, like. Or, like, let's talk about it some more. So a lot of what we do is actually the conversational element that, like, Hinge can never do, but a real matchmaker would, which is like, oh, you know, maybe, yeah, this person is like 5, 10, he's not 6ft, but he meets everything else. Why don't you at least, like, give him a chance? That is so much of the nuance, which you can't do if you're just like, like. And that's what your friend does, that's what a matchmaker does. Like, and I love this idea of the adjacent possible of rather than just showing you what you want or like, in some ways, like thinking about, like, how on Instagram or TikTok you're like, serve the same video. If you, like, look up one thing, you'll serve that video 100 different times for the next two months. Right? But if you're on Pinterest or Spotify, there's this whole idea of, like, it's not looking for the exact same thing. It's looking for things that are similar to and have, like, interesting core values that you might not have seen or like, are not able to be spotted by the untrained eye. And that's a lot of the discovery at such. Right? It's, it's this journey that you go on with the matchmaker that helps uncover these things about you and hopefully, like, leads you to a happy, happy ending. And I also think that's the stickiness of the product, right? Like, you build a relationship with the matchmaker in order to make sure that people stay on it. Right? Because you can't then just transfer all this data and learning to somewhere else. But you can very easily build a 6 prompt, 6 picture profile on any other platform.

I think that's great. So one of the things I think a lot about in this space is apps have made kind of democratize, but also like broadened access to lots and lots of people across lots of different areas, whether that's regions or social circles or income levels, et cetera, et cetera. But I wonder if kind of. And that's been great, right, because you're now able to connect with all kinds of people that you weren't able to connect with before. But I think, I wonder about kind of the more negative side of it, which is all of a sudden now you're switching costs effectively, right? Are a lot lower because if this doesn't work out well, I'll just go back onto sitch and have them serve up 10 more options for me.

And.

And I wonder if that, like, ends up creating like, more loneliness, more frustration on both sides. Does that make sense? Do you see that? Or is that just unhappiness?

And like in marriages, unhappiness in relationships, divorce has all existed well before dating apps did, right? Like, it is like, we're actually like, the idea of finding someone and who's you have chemistry with and who you're compatible with and then hoping that the rate of change across a lifetime is enough to keep you two together is a huge task. It is a massive and mammoth task. So, yes, in the age of like swiping, in the age of limited attention spans, sure, we can say it's gotten worse, but this has always been there, right? Like this like fundamentally human idea of like, am I in the right, Am I with the right person? Am I doing the right thing? Like we always. The only thing that you can't put doubt over is doubt itself. Like, Aristotle said that in like 2000 BC and I think we're grappling with that now. Of what does it look like and feel like to try and build a relationship? When we live longer than ever, we have more options than ever. And maybe that's why this is as critical a moment as ever to think of Sitch and like, it's full lifespan is not just how do you meet someone? But really, like, I often talk about how your aura, ring or whatever tool you're using as a wearable captures your fitness data for hopefully a lifetime and allows you to like, make smarter and better decisions. So if you think about your matchmaker and you think about sitch, it's not just like, how do you get a date? But really, how do you end up happy? How do you end up in a happy relationship? Then that helps this where it's like, okay, maybe you did go on like five dates with someone and you went back because you realized like you. Yeah, this wasn't what it was. There's no harm in it as long as there's like a journey and a learning and a reflection process. We found that stitch attracts a high intent data. I think it's like a 35 minute onboarding. It's an older crowd, it's all paid, so you see less of like the swiping hinge type behavior. But I think the idea of questioning is healthy, is really healthy as long as you have a place to question and reflect.

Yeah. Do you, do you see an opportunity to continue in these relationships over time? Because the AI should have like really interesting insights into both, both parties and can be a resource for them to resolve issues that arise. Right. Like part of being in a relationship. I think, as we all know, is like, what do you do when things are hard? And do you have frameworks to work through them? Right. And those tend to be the things that really determine whether or not you are happy and you stay together or not, rather than a lot of the other things that get Talked about on TikTok. Right.

I mean, honestly, it's a. You're putting me in an interesting spot given that Whitney is on the call. But we believe that there is a Large enough business to be built from just matchmaking. But is Chad and my eventual goal only to build a really big business in matchmaking? No. We've always said that, like, Sitch feels like part of this larger universe. And if we think about the journey that one takes in, like their relationships, we would love to build products and tools that sit at each of those different juncture points. Like, maybe you're on set and then you find your person and then you move to Hitch. Right. And it will exist as a different, like, product line. But we'd love to be involved in that. You know, Chad found success on dating apps. I've been married for a while, but, like, the problems don't go away. Like, they don't go away and we should, like, create the tools and products that help with that. So we have a larger vision, but we also know that there's a very defensible large business to be built with, even just what we have right now.

I have a question for Whitney, or do you want to follow that, Peter? Whitney, how are you approaching this, like, with AI? Because in some scenarios, like we're looking at AI.

Is.

Is AI an additional feature or is this like a complete breakaway? And in the dating space, I think Bumble and Tinder could come through and say, hey, this is when it's the right time. This is a feature. How did you defend this to your partners as you made this investment?

Yeah, I mean, I think with any AI application, we're wanting to make sure that the AI is not just a feature, but is part of. It's one of the tools in a bigger system. Right. And that's something that Sitch does so well. They're building an end to end platform that includes both historical, you know, technology, ML, et cetera, but also leverages AI where it's most powerful. And so it's really about like the end to end platform, not just investing in AI for the sake of AI. I think in some cases it makes sense for AI to be a feature. In Stitch's case, AI is what completely unlocks this business because it brings a scale that an individual matchmaker couldn't have before. And so when I'm looking at new companies, I'm always trying to figure out, like, what is the role that AI is playing here? Is it unique enough or is it easily replicable? And how is a broader platform built around it so that it's less replaceable and really is like a more durable end to end experience? And I think Sitch is a perfect example of that, of their Leveraging AI and all the points where it's useful, but also building like a world class user experience and a world class brand and a world class team that will continue to evolve and iterate and bring on the latest technology as it must.

So just to double click on that a little bit, I'm curious what your response is to the question that I think every AI application company has to ask itself every day, which is how do you keep OpenAI at bay from just copying this?

Right.

Yeah, because they've, they've made, they've. There are rumors that they're, they're building and launching a LinkedIn competitor which is kind of one step away.

Right.

It's another type of networks and relationships and you know, they are like the number one consumer app for the most part. They know people intimately well. So, yeah, just, just curious how you think about that.

Yeah, actually my partner Anna wrote an amazing piece on this, so it's worth a longer read. But in short, I think you need to be very thoughtful about where OpenAI is playing, but realize that you can't live under the threat that they could turn something on tomorrow. And you need to make sure that what you're building is defensible. And I think there are some areas where you want to trust OpenAI and other areas where you don't. There are some where it's more a solo player mode, like me talking to ChatGPT and others where it's much more about the network, like me using sitch and who's on the other side of the application. And so I think there are various points that we look for in consumer apps to make sure they're not under like imminent threat from OpenAI. But there certainly is enough room to play and in these bespoke unique areas that have willingness to pay, where OpenAI isn't really incentivized or constructed in the way to make them the best fit to solve this. And I know it's something Dini has thought a lot about. So Dean, if you want to share more about like why, why you're so bullish here, I'd love to hear.

It's, this is a really personal thing, right? It's kind of like why everyone's always been like, Facebook dating has never worked because we are fundamentally different people on different platforms and we share different facets and parts of ourselves. Right. It's kind of like if you use ChatGPT as your therapist, you're kind of like, I don't want my therapist to be now setting me up up. You don't actually, like, I'm not a big believer that you're going to have these massive super apps that just do everything and then you trust them implicitly. I think this still continues to be a pretty personal experience and decision, but you know, from like, like forget the philosophy behind it. Right. Like, one of the things that OpenAI cares about is attention span and time spent on the platform. We fundamentally don't give them that. Right. Dating apps are offline businesses. They want to pull you off and you stop giving revenue because you move off the platform and you are no longer single. So on the like, if we imagine like a scale of like places they're going to go, yeah, actually they might eventually like come to into dating, but it's going to be so far down the line that hopefully by then we've already built an amazing business and if they want to buy us for like, you know, tens of billions of dollars, sure. Like, you know, Whitney, Anna, Chad and myself will have a conversation.

I love it. You know, one of the things that I've believed for a long time is that AI applications that have a really unique and exceptional user experience will be able to have some defensibility against OpenAI and other businesses like that. I think a lot about businesses like Canva, you know, phenomenal business that honestly, there's nothing that special about Canva. At the end of the day, you can do everything in Canva and PowerPoint for crying out loud. Right? But the user experience is like 10x what PowerPoint is.

Right.

And so ultimately Canva wins because they have this incredible user experience. They have a lot of other great things too. But like, if you really boil it all away, like that was the thing that like caused them to be successful. And I think there are similar opportunities where it's like, yeah, everybody will have the AI, but the thing that will differentiate is like, like how people interact with that AI through the user experience and that you can create kind of interesting moats around that.

So something that our users have said and really commented is like, we don't believe in like kind of a bot that has no personality. Right. Like it's been really important and something we spend a lot of time and energy training match. Like we, we have, we kind of took a bet and we said that people don't want this like random amorphous like cloud shaped object talking to them. They don't want to choose from these like obviously fake AI people. They kind of want it to feel human. Like there is this like, honestly, like a suspension of reality. Like the Concept that you see in fiction. We're playing that into the way we're building this product. You aren't talking to me, you know, you're not talking to me, but it has my face, it has my likeness, it has my tone, it has a personality. It makes jokes about guys DJing and like vaping and like stand up comedy. It like, it has a perspective. And I do think that that's something that again from like the product lens is GPT doesn't have a personality. Right. And you maybe you sure will like, like version number 10 will be like, okay, train it so that it like acts the way you want, but like, you don't want your matchmaker to feel like this, like sort of like sims for you. You want it to feel like it's a real person with like some guidance, without experience. So there has been this personification of the bot has been really essential to like our brand building where people are like, oh, like, I know why I'm going here. And it's different from Chat GPT. In fact, in sf, we had a billboard that said, chatgpt can't find you a girlfriend, but I can with a picture of me. And there was this real, like we would. When I was in sf, I would just see people taking pictures of this billboard because it captures the. What Citch does, which is how do you make it feel so essentially human while still leveraging the power of AI to actually scale up humanity?

Well, as we kind of wrap up, what are some of the things that you're most excited about, you know, going forward in this business and opportunities that are ahead of you and then would love to hear your perspective, Whitney.

So I think for us it's, this has been a magical year. We are almost at one year of our first paid users, which is really exciting. What I'm really excited for is our first like such engagement. I think as soon as that happens, that makes you really like feel like thrilled about the impact you're having. We're launching V2 of our product actually in Austin in 10 days, which is again, something I'm really excited about because that's the future of like, how do you keep building a relationship between the product and that delightful user experience and your end user? And then we're really looking ahead to, we're in four cities right now, launching a fifth next week. But beyond that, how do we make sure that we do what we started out to do, which is we want to make sure everyone has access to this, your personal matchmaker in your pocket. So lots of scaling, lots of growing, lots of love, lots of setups.

I completely, completely agree. I think that moment when we have the first couple that has truly found everlasting love on such, that will be a moment to celebrate. I think I'm excited about such reaching more people. I think the people who have gotten to experience it and I've felt how special it is to be on a such first date with someone who just kind of gets you. I want more people to be able to experience that. And so that means reaching more cities, reaching more people in those cities, building a brand that everyone identifies with, and then getting that special moment that you tell all your friends about of what that first date was like, I think is going to be really great. I'm also really excited on the technology side. We didn't spend as much time, but Chad and Dini are really at the forefront of what they're doing with AI. It is super, super cool, and I'm excited to see that technology come in to play a bigger and bigger role, to drive more and more successful matches, to make people feel so seen by their matchmaker and understood. And so I think there's a lot of cool stuff going on under the hood on the technology side that I'm excited to see come to fruition, primarily because it serves that overall goal of driving more happy couples.

I love it. Yeah. I think one of the big unlocks of AI that maybe doesn't get as much attention as it should is that it just creates personality, like personalization at scale in a way that's never been possible before. And, like, this is, like, the perfect application of that in so many ways.

Totally.

Awesome. Well, what are the best ways to kind of follow both of you and keep in touch with what you all are working, working on?

If you're single, please download Setch. That would be, like, the best way for you to keep in touch with all of the cool things that we've talked about and what we're building. Code is Dini, literally my name, Di Ni, which will get you off our wait list really fast. If you want to follow along on the journey on Instagram, it's at Sitch, Matchmaking, and then my LinkedIn, if you want to hear the founder story behind what we're doing, how we're doing, and some of the crazy decisions we're making. So, yeah. And then obviously I'm also on Instagram, but I feel like the most exciting content is definitely on LinkedIn.

Awesome.

Totally. And for me, I'm on LinkedIn. Whitney Hazard 13, actively investing in seed and Series A companies. I also write on Substack if you want to hear all my musings. So find me on either.

Awesome. Well, Vinny and Dean, it's been such a pleasure having both of you on the show today. Thank you so much for taking the time and sharing all of your insights about sitch and dating and the world that we live in with AI. So thank you so much.

Thanks for having us. This was super fun and what a great conversation and such great questions.

Thank you so much.