In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Nandini Mullaji, co-founder of Sitch and the personality behind Dini in a Bottle. From her Bombay roots (with a matchmaker grandmother) to Georgetown → McKinsey → VC → Stanford GSB, Nandini shares how she shut down her first dating app, found the right co-founder, and built an AI-powered matchmaking service that people actually pay for.

We explore why dating apps miss the mark and what AI matchmaking does differently, the moment she pivoted from a Big Tech career path to founder life, and the lessons she learned from shutting down her first startup. Nandini also breaks down how Sitch blends AI and human judgment, why people overshare with bots (and how that becomes a moat), and the onboarding + verification process behind their pay-per-date model.

Along the way, she talks about data points that don’t actually predict long-term compatibility, the challenges (and strengths) of being a woman founder in this space, and the zero-to-one lessons that apply equally to building love and startups.

Whether you’re single, curious about the future of dating, or thinking about starting something of your own, this conversation is packed with insights on technology, relationships, and the art of building connection.