Evaluating only HabanaTech’s profile at its peak — without knowing the outcome — the model ranked Macro / political as the #1 likely cause. Documented cause: Regulation.
Key Events Timeline
FOUNDING
FUNDING
CRISIS
SHUTDOWN
Full Analysis
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Documented cause
HabanaTech launched in the window of Obama-era Cuba opening, building a booking and discovery platform for independent travelers to Cuba — connecting tourists with casa particular hosts, private restaurants (paladares), and local guides outside the state tourism system. The platform was timed to capture the surge in American travelers after the 2015 normalization. By 2017 it had 600+ listed experiences and was processing 200+ monthly bookings. The Trump administration reversed US-Cuba travel policies in 2019, prohibiting people-to-people travel licenses — the primary legal basis on which Americans visited Cuba independently. US-Cuba travelers collapsed 75%. The platform had no viable market without US tourists.
Lesson
“If your entire addressable market depends on a single bilateral diplomatic relationship, the geopolitical risk is not diversifiable. Build multi-origin tourist models or accept the binary outcome.”