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.

In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Nizzy, cofounder of Mail0 and one of the internet’s most popular coding educators turned founder. From making fun, beginner-friendly YouTube tutorials to building an AI-native email client backed by YC, Nizzy’s journey shows how consistency and community can transform side projects into startups.

We explore how teaching as a beginner made him a better developer, why “there are no moats anymore” in tech, and how distribution — not just features — is Mail0’s real edge against giants like Gmail. Nizzy also shares how Twitter/X acts as a funnel for YouTube and product growth, why open source has been core to building Mail0, and how remote team rituals like Demo Days keep morale high.

Whether you’re an aspiring creator, a developer wondering how to stand out, or a founder curious about taking on incumbents — this episode is packed with lessons on consistency, distribution, and building community-first products.

In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Soundarya Balasubramani — author, entrepreneur, and founder of Unshackled, a community for immigrants in the U.S.

We explore the harsh realities international students face navigating U.S. immigration, from the uncertainty of job hunts to the broken pathways of the O-1 visa. Soundarya opens up about her own journey. Going from an O-1 denial, to finally securing approval, and the strategies she used to build a strong case.

She also shares why she started Unshackled, the impact of her books (Admitted, Unshackled, A Thousand Days of Love), and how she manages to juggle writing, entrepreneurship, and advocacy while living through the struggles she writes about.

Whether you’re an international student, thinking about grad school, or curious about the visa system that shapes global talent in the U.S., this episode is packed with hard truths, practical advice, and stories you won’t hear anywhere else.