Exclusive: Trinidad Startups Gain Momentum, Insights from 24SIX9 Ambassador

Jarryon Paul, Ambassador for 24SIX9 in Trinidad & Tobago, reflects on the inaugural Caribbean Tech Week and its impact on local founders. From inspiring entrepreneurial stories to identifying structural gaps, he shares insights on Trinidad’s evolving startup ecosystem, the opportunities ahead, and the steps needed to sustain momentum in 2026.

1. As 24SIX9 Ambassador for Trinidad & Tobago, what stood out most about the local participation at Caribbean Tech Week? There was definitely an appetite from local founders within the 24SIX9 Community. Our event, in collaboration with the inaugural Caribbean Tech Week, was our most heavily attended since we launched the Chapter in September 2025! What stood out most was seeing entrepreneurs and those considering entrepreneurship fully engage during my interview with Dwight Housend—and even afterward, during informal discussions over drinks.

2. How would you assess Trinidad’s startup ecosystem today, following the conversations and connections made during the event? Trinidad and Tobago is still early in its entrepreneurial ecosystem development. Many support organisations are emerging, which is positive, but their impact remains to be seen. We need to do more to support entrepreneurs and educate them on the realities of the journey, especially navigating the challenges unique to our local context.

3. Were there any standout founders or sectors from Trinidad that impressed you during Caribbean Tech Week? Dwight Housend was particularly impressive. His venture, TTRS (a local ride-sharing platform), is widely known locally. Hearing his story and asking questions revealed many valuable insights—not only for my own understanding but for the benefit of all entrepreneurs present.

4. What real opportunities—investment, partnerships, market access—emerged for Trinidad-based entrepreneurs? The event was primarily an opportunity to inspire entrepreneurs and show what’s possible. Any investment, partnerships, or market access that may arise will likely come from the connections formed among the entrepreneurs who attended.

5. Did the event expose any structural gaps in Trinidad’s ecosystem that now need urgent attention? Yes. Our ecosystem is still in an early stage. We need to increase both the quantity and quality of startups and founders. This should be the first priority to create more successful businesses and entrepreneurs.

6. How did the energy and ambition of Trinidad’s founders compare to previous years? As the inaugural Caribbean Tech Week, this year reflects cautious optimism. Our ecosystem has faced many false starts, but we are seeing both newcomers and experienced participants stepping up. I’m optimistic—Trinidad and Tobago is moving past status-driven entrepreneurship toward tangible, grounded ventures.

7. Post–Caribbean Tech Week, what concrete next steps should Trinidad’s startup community prioritise to maintain momentum? Starting with the 24SIX9 Trinidad & Tobago Chapter, we aim to finalise our 2026 Strategic Plan and mobilise a core group of members to lead the Chapter, making it a space where entrepreneurs feel safe, seen, and supported. Other organisations should align their goals similarly.

For entrepreneurs, the focus must be on reality: understanding what entrepreneurship truly entails, identifying real problems, and solving them for the benefit of customers. Transformation in Trinidad and Tobago won’t come from spotlights, hubris, or external grants—it will come from within, and from the communities and people we serve.