Martin Hanna series to detail journey of Caribbean startup

Published on October 7, 2025

For the last seven years, I’ve been in the trenches, building and scaling a tech venture across the unique, fragmented markets of the Caribbean. It wasn’t just a hustle; it was a war against infrastructure, regulation, and market inertia.

This experience taught me that the challenges of the region, from regulatory complexity and fractured cross-border payment systems to a fragmented talent pool are often underestimated by both founders and international investors. The sheer willpower that works in Silicon Valley often breaks against the geopolitical and logistical realities of island economies.

This piece is the first in a series that will distill those seven years of gut-wrenching facts and hard-won lessons into actionable strategies. We will move beyond the hype and reveal the Strategic Realities of building high-growth companies in this market.

If there is one core truth I’ve taken from this journey, it’s this: The solo founder model is an almost guaranteed path to failure in the Caribbean context. The sheer number of domain-specific pitfalls requires a distributed and specialized team to navigate.

My goal is to build a playbook for the next generation of regional founders  a comprehensive guide to navigating the unique cultural, financial, and logistical landmines that sink otherwise promising ventures.

This series is for those who are serious about building and those who are serious about investing successfully in the next generation of Caribbean tech.

Source Martin Hanna LinkedIn