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Show Notes

Nancy Li Smith is the CEO and founder of Boop, a Seattle-based social travel platform, and previously led the AI platform behind the Meta Ray-Ban glasses, held CPO roles in enterprise AI, and ran global perception AI and augmented reality partnerships at Microsoft. On this episode, Nancy explains how a Venice honeymoon frustration crystallised a core insight: the best trips always come from a single trusted source — a well-travelled friend — and that trust signal is something no generic LLM can replicate. Boop lets users turn their camera roll into fully bookable itineraries by processing photo metadata entirely on-device, preserving privacy while automatically extracting locations, dates, and trip structure. Those itineraries can be shared, copied, and personalised by friends, with affiliate links auto-generated across hotels, experiences, and activity providers and commissions split 50/50 between Boop and the original creator. Nancy also addresses the long-tail creator phenomenon — a Chicago flight attendant's Japan itinerary and an Amsterdam local's Beyoncé-tour guide both outperformed influencer content — and the structural gap she sees as Boop's primary expansion surface: 80% of experience providers worldwide are still not bookable online, meaning the platform is targeting a market that affiliate infrastructure has barely touched.