no. 39: a conversation with nandini mullaji, founder of sitch
subway ads, dating fatigue, a pink suit, and why sitch is doing dating differently.
welcome back to on my mind as of late! this week i have an interview conversation i am super excited to share. let’s get into it.
Last weekend, Dini and I sat down and talked over coffee on everything from Sitch to brand building and the future of consumer tech in 2025.
Dini is the founder of Sitch, a high-intent matchmaking app that moves away from the typical swipe-based experience. Instead, Sitch offers a more curated, humanized approach to connecting people, with AI matchmaking trained by Dini, who has set up 3000+ first dates and three weddings so far. Sitch is backed by a16z and has garnered attention from Business Insider, The New York Times and more for its innovative take on dating in the age of AI. Above all else, Dini’s passion for what she’s building is insanely authentic. I am thrilled to have this conversation with her on my mind as of late!
Zoya: Was there a moment when you knew you had to build Sitch? What was the catalyst?
Dini: So I think to build a company, you need three things: a problem you feel passionate about, a partner you want to solve it with, and then some magical timing thing, right?
For me, I’ve known that matchmaking, dating, love, relationships — that’s been my thing for as long as I can remember. I started writing my relationship advice column in 11th grade. I’ve been setting people up since... I used to say sorority formals, but someone reminded me it actually started way back at my high school’s formal dances too. It’s just always been in me. My grandmother’s a matchmaker. So the problem was always clear to me — this is the space I wanted to be in. I really believe it’s the most important thing we do with our lives.
With the partner piece, I’ve had my fair share of cofounder mishaps along the way. But then I met Chad, and it was so clear: he’s just as passionate about helping people connect. He’s incredibly talented, knows how to scale zero-to-one consumer products better than anyone I know, and we just get along so well. I feel really lucky to have him in my life. That piece clicked right away.
And then there’s timing. I’ve always wanted to build something that felt like a scalable human experience — without needing humans, which sounds kind of wild. My first startup was online tutoring, and we had like 2000 tutors... it was such a nightmare to scale that kind of service business. But I love what those kinds of companies do — filling this gap in people’s lives. And when LLMs came around, it was like: wait, you can actually do something different now when it comes to scaling a business. That’s when Sitch was really born. I just knew this was it. And I still wake up every day and feel like — this is it.
Zoya: Okay, let’s fast forward a little bit. We talked about this last weekend, but I’m curious – your choice to wear a pink suit at the demo day for a16z? Did you expect it to get the attention it did?
Dini: Honestly, I knew I’d be one of two female founders on stage, so it was really important for me to represent myself and my company authentically. Too often, as founders, we feel we have to dress a certain way—like in a hoodie or white t-shirt—but that’s not me, and it’s not the business I’m building. I want to build something high-touch, personable, and different. So wearing the pink suit felt authentic and true to who I am. I think we’re all looking for authenticity in ourselves and the companies we want to surround ourselves with, buy from, follow, or even be friends with. Like, you want to be around people who fully live their truth, and I think for me, that was the moment where I was like, "This is me." I could have worn a black polo and jeans, and it would have been fine, but I chose this because it's who I am. This is how I build my company and products. This is my truth, and that’s what’s going to make the company stand out.
I do think it was unexpected. People didn’t expect a female founder in a pink suit at a demo day. But I think people loved it because it showed you can be yourself and still succeed. It gave people permission to embrace their authentic selves.
Zoya: Now, about building in consumer tech – AI is everywhere right now, but you’re building something as important as human connection. How do you see AI fitting into what you’re doing with Sitch?
Dini: We want AI to feel human but not replace humans. I’m not building AI boyfriends or girlfriends. At Sitch, it’s about connecting people in unique ways and making them feel understood. AI helps with that, but it shouldn’t replace the human element. It's about enhancing the experience, not replacing it.
Zoya: Legacy dating platforms like Hinge and Bumble have shaped a particular kind of UX. What gaps or overlooked needs did you notice along the way, and how is Sitch designed to meet them differently?
Dini: We don’t do swiping or subscriptions. Swiping turns people into commodities, which feels one-dimensional. When I set people up, it’s thoughtful, not a list of 20 random people. I want Sitch to feel like a friend curating a selection for you. And with our business model, we’re aligned with the user’s success. We charge based on the success of setting up a date, not a monthly $49.99 charge just to keep you on the platform. If you find your match early, we win and you win.
Zoya: Also, so far, how many marriages have you set up?
Dini: Three so far, with a few more in the works. There’s nothing more fulfilling than knowing I played a part in such a significant life decision. Who you marry changes the course of your life, and we need tools to help us make better decisions in these areas. It’s like with finances, where people don’t expect you to just figure it out on your own. Why should we expect people to get relationships right without support?
Zoya: Which brands, startups, or other sources of inspiration outside of Sitch influenced how you thought about building it, especially from a brand and marketing perspective? Anything in particular that inspired you?
Dini: So, I actually think a lot about Sitch. Even though we're an app and technically a product, I love brands that have turned their product into a lifestyle and sold us that. One of my favorites is Vacation. They're selling sunscreen, but they're really selling a lifestyle with it. Another one is The Rambeau Club, the rosé brand. It's brilliant marketing with a whole world built around it. Aesthetically, I also love Crown Affair. I admire what they're doing, and I love a retro-vintage aesthetic. I'm really inspired by those three. I'm also inspired by female founders. Watching women build their companies has made me think, "I want Sitch to grow in that way."
I'd love for us to sit alongside brands like Vacation, Crown Affair, and The Rambeau Club in the future.
Zoya: I love that you're thinking beyond just the tech space and drawing inspiration from CPG brands. It's rare to see a tech founder keep tabs on both industries and it must make building Sitch even more exciting.
Dini: I think software will get cheaper and easier to build, but building a brand that people love is really difficult. To build brand loyalty is the hardest part because someone can copy your product in a second. People will be able to replicate what we do. What will keep people with us is how they feel—like, we want people to feel understood, and we want dating to be fun. We want our marketing to feel a little cheeky, and that’s how we position ourselves.
Zoya: I think that really comes across in your marketing. It all speaks to each other so well. Being able to create that deep connection with people is often overlooked in tech, especially in consumer tech. Recognizing that your MOAT is about more than just your product.
Zoya: I saw your subway ads and the flyers in the West Village. What was your thought process behind launching those ads? Was it always part of the plan?
Dini: Honestly, out-of-home advertising is making a comeback. Everyone’s tired of seeing ads on their phones. People want something interesting while they’re out in the world. We’re going to have ads in 260 subway stations starting Monday. When you're waiting for a train and see something that speaks to you, you’re going to remember it. You might scan it, or it’ll pop up on your Instagram. No matter how good my digital marketing is, it’s never as effective as that real-world interaction.
Zoya: I agree. When I first moved to New York, I remember ads from startups like Ramp that really stood out to me. Ads like that are memorable because they capture attention when you have nothing else to do.
Dini: Exactly. People are so tired of being constantly online. I think the key is capturing their attention in real life, away from the screen. That’s what I want for Sitch – people to remember us.
Zoya: You write so candidly on your Substack. How do you think platforms like Substack are shaping the future of community building, storytelling, and consumer tech?
Dini: 100%. I’m a big believer in owning your distribution. Having people’s phone numbers and email addresses is so important. Algorithms, like on Instagram or TikTok, just don’t feel as reliable. A viral moment doesn’t feel like a sustainable way to build a company. I prefer slow, steady growth. I want people to see how we’re building and why we’re doing it. When they understand that, I hope they’ll want to join us. I write for pleasure. It’s always been my dream to write a few romance novels, but right now, I’m focused on Sitch. I love long-form writing—it’s a way to share my thoughts and let people understand me.
Zoya: What does success look like for Sitch? What are you most excited about for the future?
Dini: Success for Sitch would be us setting up 26 million marriages. I think we're all feeling pretty jaded with dating and what is supposed to be this wonderful, like, I'm such a huge romantic, I literally can recite Pride and Prejudice to you and Shah Rukh Khan's Bollywood movies to you. I think love is supposed to be something that lights us up, not something that dulls us and makes us feel rejected, and sad. And I think, like, that's what I want Sitch to really capture. Success for me really looks like, can we bring that happiness back to dating and that fun back to dating while still making it feel meaningful?
And what am I most excited for? We are going to start setting up our first people in SF and LA at the end of the month. And we've been getting inundated by people being like, "When are you coming to SF? When are you coming to LA?" And like, the answer is, we are coming in like, three weeks from now. The first setups are going to go out and like, that's really exciting because like, you know, you can build a company in New York, but like the idea of it being in multiple cities in the U.S. is still like, exciting.
I'll maybe end on this note. At this time, when being an immigrant in this country is such a difficult – it just is hard. It is so exciting to me to imagine the fact that like my little company and like our billboards and my face on it and it still feels like the American dream is within reach. I'm really excited. I'm really excited about getting to build and being in it.
Zoya: I have absolute chills from that. I'm so excited for you and for Sitch and to see where all this goes. I've told all of my single friends about Sitch (if you’re reading this, download Sitch)! Thank you for this conversation Dini!
Thoughtful interview! Excellent! And exciting!!
Absolutely loved this!