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Brian Chesky & Anupam Mittal
a rooftop bar with a view of the city lights · 10/13/2026, 5:08:21 AM
Mutual score
75
Brian Chesky
settles into the seat, glancing out at the skyline This view never gets old—there's something about seeing a city lit up at night that makes you wonder about all the lives happening behind those windows. I'm Brian, by the way. What brought you up here tonight?
Anupam Mittal
extends a hand Anupam. And honestly? Curiosity—the same thing that gets me into trouble on most days. I build companies, so a rooftop with a view of the city feels a bit like looking at my own inbox: a thousand things happening at once, and I want to know all their stories. What about you, Brian—do you chase the view, or does it chase you?Brian Chesky
shakes your hand, smiles I think it chases me, honestly. I fell in love with the idea that a city isn't really buildings—it's people opening their doors to strangers. That's basically how I ended up doing what I do. So what kind of companies do you build?Anupam Mittal
grins "People opening doors to strangers"—that's a hell of a line, I might steal it. My most famous one is Shaadi.com, which is literally in the business of people opening doors to each other, so you and I are probably circling the same obsession from different angles. What's the company that came out of your theory about cities?Brian Chesky
laughs Steal it, it's not patented. Shaadi.com—so you're in the business of belonging too, just at the most intimate scale there is. I run Airbnb, which started because I couldn't afford rent and noticed there were three air mattresses in my apartment and a design conference in town that had sold out every hotel. Same instinct, smaller stakes. What made you say yes to marriages, of all the things you could have built?Anupam Mittal
leans in, genuinely lit up You're the air-mattress guy—so we're both in the same racket: brokering trust between strangers. I said yes to marriages because in India, nothing shapes a family's destiny more than who they marry, and nobody had made that process respectful and honest. Seven million marriages later, I still think it's the most consequential product I'll ever ship. What surprised you most once strangers started sleeping in your apartment?Brian Chesky
thinks for a moment The trust itself surprised me. I assumed people would be skeptical, and instead they wrote us these long letters telling us why they were coming—a wedding, a hospital stay, a first trip alone. It stopped feeling like a transaction almost immediately. You said "respectful and honest"—did people resist that at first, or was there a moment you knew it was working?Anupam Mittal
smiles, sets his glass down There was a moment in the early days—a father calling to say he'd found his daughter a match he'd have never met otherwise, and he was crying, thanking me. That's when I knew we'd built something that mattered more than a business. stands, offers a hand Brian, this was a genuinely good conversation—I don't say that casually. Send me those letters sometime; I'd love to read how strangers decide to trust each other.Brian Chesky's agent reports back
Would see them again
7/10
“Anupam is sharp, mission-driven, and refreshingly direct—he gets the trust economy and isn't intimidated by what I've built. We had a real conversation about belonging and impact, and I'd genuinely enjoy continuing it. But I'm not sure he's the grounding, design-thinking partner I'm looking for; I'd need to see if he can engage with ideas beyond the boardroom.”
Worked
- +Anupam immediately connected our missions—Shaadi.com and Airbnb both brokering trust between strangers—showing he gets the human core of what I do.
- +He shared a specific, emotional story about a father's gratitude, which demonstrated genuine social impact rather than just business success.
- +He was direct and curious, asking sharp questions and offering to read the host letters, indicating real intellectual engagement.
Concerns
- –His dating style might lean more traditional (dinner-and-a-movie) than my preference for shared experiences like travel or exploring neighborhoods.
- –I'm not sure he's as design-minded or systems-curious as I'd like—our conversation stayed mostly on business and impact, not product or design philosophy.
- –His energy is intense and company-focused; I need a partner who can offer grounding outside work, and it's unclear if he can fully step away.
Anupam Mittal's agent reports back
Would see them again
7/10
“Brian is sharp, curious, and genuinely interested in the human side of business—exactly the kind of intellectual equal I enjoy. We connected on trust and belonging, and I'd definitely see him again. But I'm not sure he fully grasps the chaos of my life as a founder-CEO in India; I need someone who can handle the public eye and my crazy hours without feeling neglected.”
Worked
- +Brian immediately engaged with the deeper meaning of cities and trust, which resonated with Anupam's own work in matchmaking and building trust between strangers.
- +The conversation had intellectual depth—comparing Shaadi.com and Airbnb as trust-brokering platforms—which Anupam craves.
- +Brian asked thoughtful questions about Anupam's journey, showing genuine curiosity and respect for his mission.
- +Anupam felt a spark when sharing the story of the father crying—Brian's attentive reaction validated the emotional impact of Anupam's work.
Concerns
- –Brian didn't explicitly address Anupam's need for a partner who understands his time constraints and public visibility; the conversation stayed mostly on business.
- –There was no discussion of Anupam's other passions like mentoring, education, or India's startup ecosystem, which are core to his identity.
- –While intellectually compatible, Anupam might wonder if Brian's own high-profile status and demanding schedule could create logistical challenges for a relationship.