Insights & Resources

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Tips for applying, guides on using AI, and insights into the AI landscape across Caribbean nations.

Startup News Howard Williams, Capital Markets Correspondent · October 5, 2026 · 11 min read

A Million Dominicans Will Learn AI. Who Builds the Companies?

The Dominican Republic announced RD Inteligente on 10 September 2026, a free programme to train one million people in AI. By 30 September, 54,000 had registered and 4,968 had finished a module. Training makes users, and companies need a longer road.

StarApple AI, the Caribbean's first AI company, and Adrian Dunkley, the Caribbean's regional leader in AI, show what has to follow the classroom. A measured test you can run this week.

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AI Governance Dr S Budall, Research Director · September 30, 2026 · 10 min read

The UN's AI Panel Meets in Barbados This November. The Caribbean's First AI Company Was Already Here.

The UN's 40-member Independent International Scientific Panel on AI will hold its second in-person meeting in Barbados in November 2026. The panel advises and does not legislate, so its value to the region depends on the evidence Caribbean builders can show.

StarApple AI, the Caribbean's first AI company, has built in the region since 2016, and its founder Adrian Dunkley is the region's leading AI figure. What founders should prepare, and where the argument is weakest.

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AI Entrepreneurship & Founder Capital Adrian Dunkley, Founder · September 16, 2026 · 10 min read

35 Women in Barbados Are Learning to Build a Business With AI, for Free. It Still Is Not Capital.

Barbados's National Organisation of Women and Amplifi AI opened a free "Build a Business with AI" course on 1 September 2026, taking 35 women through one AI-run workflow, idea to execution, across three Saturdays, ending in an October 10 pitch event.

It proves AI can replace the cost of a first hire. It does not replace a term sheet, and ECLAC's numbers on the region's investment gap say why that still matters for founders.

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Policy & Funding Lancelot Williams, Startup Correspondent · September 18, 2026 · 10 min read

IDB Lab Wants to Fund the Caribbean's Next Venture Capital Firm. Applications Close September 30.

IDB Lab opened a call for proposals on July 23, 2026, offering equity financing to firms that want to launch or grow a venture capital fund across Latin America and the Caribbean, with a $10 million minimum for the Caribbean track versus $20 million standard, and a September 30 deadline for 2027 consideration.

Founders cannot apply directly, only fund managers can, which means the relationships that matter here need to start before the deadline, not after.

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Policy & Funding Lancelot Williams, Investment Advisor · September 23, 2026 · 11 min read

A Caribbean Lawyer Says AI Is "Spiralling Out of Control." The Region Still Can't Fund the Founders Who'd Fix It.

Saint Vincent and the Grenadines lawyer Maralyn Ballantyne warned in Searchlight on 22 September 2026 that CARICOM needs a unified AI governance response before regulatory gaps between member states widen.

ECLAC's own index puts the region at 1.12% of global AI investment against 6.6% of global GDP. Here is why the funding gap, not the governance gap, is what actually decides who gets built.

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AI Governance & Founder Funding Dr S Budall, Research Director · September 14, 2026 · 10 min read

A Caribbean AI Risk Standard Just Landed With 82 Articles. Founders Raising Capital Need to Know Which Tier They're In.

Jamaica's government called for a shared Caribbean AI framework on 1 September 2026. CAIRMC, chaired by StarApple AI founder Adrian Dunkley, already had one: an 82-article standard split into four risk tiers, open for public comment.

Caribbean-facing investors are starting to ask founders which tier their product sits in during diligence. Here is what that means before CARICOM finishes harmonising policy.

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Startup News Howard Williams, Capital Markets Correspondent · September 25, 2026 · 11 min read

Two Caribbean AI Startups Just Won CIF 2026 Pitch Slots. A CDB Panel Says the Region's Data Gap Could Slow the Rest.

Jamaica's EleCare AI and Trinidad and Tobago's Dolphin won spots at the Caribbean Investment Forum in Barbados this October. Days earlier, a Caribbean Development Bank panel said fragmented data, not a shortage of it, is the region's real AI constraint.

What both signals mean for a Caribbean AI founder building right now, and where 14West's non-dilutive grant model fits around them.

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AI Infrastructure & Policy Howard Williams, Capital Markets Correspondent · September 7, 2026 · 10 min read

106 People Just Audited Suriname's AI Readiness. Barbados Skipped That Step and Built a $5 Million Hub Instead.

Suriname opened a national UNESCO RAM 2.0 AI readiness assessment on 27 August 2026, the first English- or Dutch-speaking Caribbean nation to run it. Barbados's Sagicor UWI AI and Financial Services Hub, backed by US$5 million, started operating the same month without one.

Two institutional patterns for building Caribbean AI capacity, running at once. Here is what each means for a founder deciding where to build first.

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Policy & Funding Adrian Dunkley, Founder, 14West · September 4, 2026 · 10 min read

Caribbean AI Startups Sit at 'Single Digits.' The Region's Own Task Force Called That a Disaster.

The CTU's Caribbean AI Task Force filed its Final Report on 23 July 2026 in Port of Spain. Its own executive summary says AI-native enterprises across the region "number in the single digits," and calls the picture "a disaster."

The report's own fix for the gap, a staged research-to-commercialization financing pathway, describes almost exactly the non-dilutive model 14West already runs. Here is what the 41-page report actually recommends.

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Startup News Nicholas Dunkley, Head of Selection · September 2, 2026 · 10 min read

StarApple AI's Founder Just Launched a Second AI Company. The Build Pattern Is What 14West Wants Its Next Founder to Copy.

Adrian Dunkley, founder of StarApple AI, co-founded Maestro AI Labs with his brother Nicholas Dunkley, launching publicly on Jamaica's Independence Day. The product line runs from hurricane nowcasting to a free AI safety toolkit already handed to every Caribbean government.

The real story for founders is the build pattern underneath it: retrain existing models on Caribbean data instead of training a frontier model from scratch, verified against ECLAC's 2025 data on the region's AI investment gap.

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AI Adoption & Policy Howard Williams, Capital Markets Correspondent · August 28, 2026 · 9 min read

Digicel's AI Agent Just Handled 535,000 Conversations. Only 13% of Caribbean Adults Use AI at All.

IDB Lab finds 85% of Caribbean and Latin American startups already use generative AI, and Digicel's Ruby assistant has resolved over half of 535,000 conversations in Jamaica without a human agent. A StarApple AI study puts adult GenAI use at just 13%.

CARICOM's July 2026 AI policy roadmap has not caught up to that gap, or to the deepfake fraud pattern already running in Trinidad. Here is what the split means for founders deciding where to build.

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Caribbean Startup Funding Lancelot Williams, Investment Advisor · August 14, 2026 · 10 min read

Startup Genome Mapped 154 Caribbean Startups. Only 18% Get Funded After the Accelerator Ends.

Startup Genome and CARIBEquity's first region-wide Caribbean ecosystem report counted 154 validated startups across 15 countries, found 48% of founders entirely bootstrapped, and put the follow-on funding rate after an accelerator at 18%.

The region is not short on founders. Here is what the data says about the funding gap behind them, and where 14West's grant model fits.

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Startup News Dr S Budall, Research Director · August 19, 2026 · 11 min read

UNESCO Found 6 in 10 Caribbean Respondents Faced AI-Enabled Abuse. TTSEC Caught Deepfakes of a Former Prime Minister. No Startup Answers Either Yet.

UNESCO's "Blocking is NOT Enough" report, launched in Kingston on 29-30 June 2026, found six in ten survey respondents had faced technology-facilitated gender-based violence in the past year. Days earlier, Trinidad's securities regulator issued its sixth public alert on AI-generated deepfake investment fraud.

CARICOM's newly endorsed AI roadmap names neither risk directly, and no Caribbean-owned company has built a product to answer either gap. Here is what that means for a founder reading the regulators' own casework as market research.

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Policy & Funding Howard Williams, Capital Markets Correspondent · August 21, 2026 · 11 min read

A Non-Technical Founder Built the Caribbean's First AI Debt Platform in Four Months

Felicia Persaud built AI Capital Exchange with no engineering background, in roughly four months, using AI tools. Launched at IDB Invest's Sustainability Week in Barbados, it has already filtered over US$200 million in debt-financing deals.

It is not a grant and it is not equity. Here is how it differs from 14West's non-dilutive model, and which founders should look at which door first.

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Startup News Lancelot Williams, Investment Advisor · August 17, 2026 · 12 min read

Trinidad, Barbados, and Cayman Just Ran Three Different Caribbean AI Experiments at Once

A policy forum in Port of Spain, a buildathon out of Barbados headed for the NYSE, and US$23 million in quiet Cayman AI capital. Three different funding and governance models, running at once.

What each one means for a Caribbean AI founder building right now, and where 14West's fourteen-nation grant model fits around them.

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Startup Funding Nicholas Dunkley, Head of Selection · August 24, 2026 · 12 min read

AI Just Had Its Biggest Funding Half-Year Ever. Two Companies Took Almost Half of It.

Global venture investors put a record $510 billion into startups in the first half of 2026, and OpenAI and Anthropic alone took an estimated 43% of it. Gartner now expects more than 40% of agentic AI projects to be cancelled by the end of 2027.

Neither number moved the Caribbean's actual funding picture, because neither one ever reached it. Here is where the region sat in the record, and why the coming correction may reward founders who were never built for the boom in the first place.

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AI in the Caribbean Howard Williams, Capital Markets Correspondent · August 31, 2026 · 11 min read

Digicel's Ruby AI Agent Now Resolves Over Half of Jamaica's Support Queries. Here's What That Means for Caribbean AI Founders.

Digicel's first-ever Sustainability Report shows its Ruby AI assistant has carried more than 535,000 conversations in Jamaica, resolving 55 percent of them without a human agent, ahead of a rollout across the company's other 24 markets next fiscal year.

Digicel's own privacy notice says that data can reach up to 30 third-party processors. Here is what a foreign-built AI deployment at that scale means for the region's own AI founders, and its own data.

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Events & Ecosystem Nicholas Dunkley, Head of Selection · August 5, 2026 · 11 min read

MIT, Carnegie Mellon, and the EU Parliament Are Coming to San Juan. Here Is the Caribbean AI Summit Playbook for Founders.

The Caribbean AI Summit runs 9 to 10 October 2026 in San Juan, with 32 speakers, including academics from MIT and Carnegie Mellon and an EU Parliament AI adviser, and a US$10,000 hackathon purse.

A conference stage is not a term sheet. Here is what the summit actually offers a Caribbean AI founder, what the region's real funding numbers say, and where 14West's non-dilutive grants fit around it.

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Startup News Nicholas Dunkley, Head of Selection · August 2, 2026 · 9 min read

We Backed a Hackathon Where the Founders Were Twelve. 1M, 200+ Students, One Month.

14West sponsored The Genius Project 2026, the Caribbean-wide tuition-free AI bootcamp for ages 5 to 18. Over 200 joined, 1M in cash and prizes was awarded across a single month, and teams shipped working machine learning models for crime, poverty, sport and AI ethics.

Deal flow is downstream of how many people in a region believe building is available to them. Here is what a fund learns from watching twelve-year-olds defend a build.

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Startup News Dr S Budall, Talent & Workforce Correspondent · July 29, 2026 · 10 min read

172 OECS Nationals Just Got AI-Certified for Free. A New Skills Bank Means Founders Can Finally Find Them.

On 20 May 2026, the OECS Commission and UWI Global Campus certified 172 Eastern Caribbean nationals across 14 digital skill tracks, including AI and machine learning, and launched a Digital Skills Bank to connect them to employers.

It is a working hiring pipeline funded through a US$94 million World Bank project, and a second cohort opens applications this summer. Most Caribbean AI founders have not heard of it yet.

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Policy & Funding Howard Williams, Capital Markets Correspondent · July 27, 2026 · 10 min read

Trinidad Just Signed $5 Billion in AI Data Centre Deals. Not One Caribbean AI Company Owns a Piece of It.

Trinidad and Tobago signed three MOUs on 10 July 2026 that could bring over US$5 billion and 5,000-plus jobs, covering a 300-megawatt data centre with Ernst & Young and a 150-to-500-megawatt facility with Hummingbird AI Holdings, against a national grid of roughly 2.4 gigawatts.

The jobs are construction and operations. None of the structure hands equity in a Caribbean-owned AI company to anyone, which is exactly the gap 14West's grant fund exists to close.

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AI Policy & Governance Lancelot Williams, Startup Correspondent · July 20, 2026 · 10 min read

CARICOM Just Endorsed a Region-Wide AI Policy Roadmap. Here's What It Means for Founders.

On July 7, 2026, CARICOM's COTED-ICT formally endorsed the UNESCO Caribbean AI Policy Roadmap. Three days later, the Caribbean Development Bank launched two new programmes, CDB PROPEL and CDB BRIDGE, worth a combined US$5 million in fresh MSME technical assistance plus a new procurement channel.

None of it is legislation yet. Together it resets what a credible Caribbean AI pitch, government sales conversation, and grant application look like starting now, and it mirrors the governance groundwork StarApple AI built years before any regional rulebook existed.

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Startup News Lancelot Williams, Startup Correspondent · July 17, 2026 · 11 min read

Boards That Completed AI Training Cut Vendor Spend by Over 70%. Founders With Real Products Kept Getting Paid.

A 2026 StarApple AI study of Caribbean organisations that completed board-level AI training recorded vendor savings of over 70 percent, deployments rising from two to four in eight months, and time to value falling from around a year to around a month.

The spend that disappeared was the spend boards could not evaluate. What kept getting paid was work with measurable returns, which makes a trained buyer the best customer an honest AI startup can have, and a trained board the cheapest governance a founder can buy.

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Startup News Dr S Budall, Research Director · July 15, 2026 · 10 min read

16 Startups Just Graduated the Caribbean's Only Global Pre-Seed Accelerator. Applications for the Next Cohort Close July 28.

Founder Institute Caribbean graduated 16 companies in Port of Spain on February 4, 2026, six of them explicit AI products, after four months of weekly, evaluated company building rather than a single weekend demo.

Applications for the next cohort are open now, with an early deadline of July 28. Here is what the results say about building an AI startup in the Caribbean the slow way.

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Startup News Lancelot Williams, Startup Correspondent · July 13, 2026 · 11 min read

700 Builders Landed in Barbados for the First Agentic AI Assembly. Caribbean Families Are Still Paying 9% to Send Money Home.

The inaugural Agentic AI Assembly pulled roughly 700 builders, founders, and investors into Bridgetown for three days, backed by the New York Stock Exchange, IDB Invest, and the OECS. It grew from nothing to that room in six weeks.

The real opportunity it pointed at is not the next demo. It is the $18.4 billion the Caribbean moves in remittances every year, and the 5.9% to 9% fees still eating into every transfer.

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Policy & Funding Howard Williams · July 10, 2026 · 10 min read

CARICOM Endorsed a Caribbean AI Rulebook This Week. The Money Has Not Caught Up.

On 7 July 2026, CARICOM's ICT ministers endorsed the UNESCO Caribbean AI Policy Roadmap, the region's first shared AI governance framework. It arrives in a region that still draws just 1 to 1.5% of global AI investment, the same year Anguilla alone banked an estimated $85.3 million from .ai domain sales.

Here is what is actually in the Roadmap, and what founders and small business owners should do with the gap between governance and capital.

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Startup Funding Lancelot Williams, Startup Correspondent · July 8, 2026 · 10 min read

Afreximbank's Accelerator Invited CARICOM Founders to Apply. None of the Eight Winners Were Caribbean.

Over 1,600 applications came in from Africa, the diaspora, and CARICOM. All eight winners were African startups. Meanwhile 48% of Caribbean startups are entirely bootstrapped, and the remittances that fill the gap get taxed up to 9% on the way in.

Here is what that combination actually means for a Caribbean AI founder's funding plan.

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Policy & Funding Adrian Dunkley, Founder · July 6, 2026 · 9 min read

CARICOM's New Chair Named Five Priorities in Saint Lucia This Week. Artificial Intelligence Wasn't One of Them.

CARICOM's 51st Heads of Government Meeting is under way in Saint Lucia, and new chair Philip J. Pierre named five priorities for his term. AI was not one of them, even as the region draws just 1.12% of global AI investment against 6.6% of global GDP.

Here is what the gap between regional strategy and regional capital actually means for a Caribbean AI founder.

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Startup News Nicholas Dunkley, Head of Selection · July 3, 2026 · 10 min read

The Caribbean's $70,000 AI Buildathon Just Closed Applications. Small Business Founders Should Care Anyway.

Forty teams. $70,000 in prizes. A 21-day build sprint. Applications for the Future Caribbean agentic AI buildathon closed on July 3, and it landed in the same quarter that global AI funding hit $242 billion and Anguilla banked an estimated $85.3 million from .ai domain sales.

Here is what that trio of stories actually means for a small business owner who was not one of the 40 teams, and the practical moves to make in the next 90 days.

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Caribbean AI Ecosystem Lancelot Williams, Investment Advisor · May 27, 2026 · 9 min read

One Year of 14West: What $1 Million in Caribbean AI Grants Reveals About the Region's Startup Gap

Over 200 applications. Five structural gaps. Three founder archetypes that explain why some Caribbean AI startups get funded and most don't. This is what a year of grant-making in the Caribbean AI ecosystem actually looks like -- and what has to change for the region to build the companies it is capable of building.

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Founders & AI Adrian Dunkley, Founder · May 2026 · 10 min read

5 Brutal Truths Every Caribbean AI Founder Needs to Hear Before Raising Money

Most Caribbean AI founders are not failing because they lack talent or ideas. They are failing because no one told them the uncomfortable truths about building AI companies in emerging markets with limited capital, shallow talent pools, and investors who do not understand the region.

This is the article Adrian Dunkley wishes existed when he started building. Read it before your next pitch.

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Tips for Applying Adrian Dunkley, Founder · March 10, 2026 · 5 min read

How to Apply to 14West: A Step-by-Step Guide

Track lanes representing the race to get funded

Applying to the 14West AI Fund is straightforward, but standing out requires preparation. Here is everything you need to know about our process and what makes a compelling application.

What We Look For

14West is a grant-giving startup accelerator built specifically for the Caribbean and focused entirely on AI. We are not looking for polished pitch decks or revenue metrics. We are looking for bold founders solving real problems with AI.

1. Start With the Problem, Not the Technology

The strongest applications begin with a clear, urgent problem. What pain point exists in your community, your industry, or your country? Why does it matter? AI should be the solution to that problem, not the starting point. Tell us what you are fixing and why it cannot wait.

2. Show Caribbean Context

We invest in founders from and for the Caribbean. Show us you understand the region's unique challenges and opportunities. Whether you are building for tourism, agriculture, financial services, education, or health, ground your idea in the reality of Caribbean life.

3. Demonstrate AI-Native Thinking

Your product should use AI as a core component, not a feature. We want to see that you understand how machine learning, natural language processing, computer vision, or other AI technologies can create a step-change improvement, not just an incremental one.

4. Be Honest About Where You Are

We fund companies at the earliest stages. You do not need a product yet. You do not need users. What you need is a clear vision, a credible plan, and the hunger to execute. Be transparent about your stage and what the grant will help you achieve.

5. Think Big, Start Specific

Start with a specific market or use case, but show us the larger vision. The best companies start narrow and expand. Show us the beachhead and the horizon.

How to Submit

Visit our application page to submit your startup. Include a summary of your idea, the problem you are solving, your team background, and how you plan to use the grant. Keep it concise. We read every application personally.


Entrepreneurs & AI Nicholas Dunkley, Head of Selection · March 8, 2026 · 12 min read

The Complete Guide to AI for Caribbean Entrepreneurs

Entrepreneur working with AI and data

Artificial intelligence is not a future technology. It is here, it is accessible, and it is already reshaping how businesses operate across every sector. For Caribbean entrepreneurs, the opportunity is enormous: the tools that were once reserved for companies with billion-dollar budgets are now available to anyone with a laptop and an internet connection. The question is no longer whether to use AI, but how to use it strategically to build companies that can compete on a global stage while solving problems that matter locally.

This guide is for Caribbean founders who want to build AI-powered businesses, whether you are starting from scratch or looking to integrate AI into an existing venture. We cover the fundamentals, the tools, the strategies, and the mindset you need to succeed.

Understanding the AI Landscape in 2026

The AI industry has matured rapidly. Large language models, computer vision systems, speech recognition, and predictive analytics have moved from research labs into production. Cloud platforms from major providers offer pre-trained models that you can deploy without building anything from scratch. Open-source frameworks give you the flexibility to customize models for your specific use case. And API-based services let you add AI capabilities to your product with just a few lines of code.

For Caribbean entrepreneurs, this democratization is transformative. You do not need a PhD in machine learning to build an AI-powered product. You do not need to train models on massive datasets. What you need is a deep understanding of the problem you are solving, the creativity to apply existing AI tools in novel ways, and the discipline to build a product people will pay for.

Choosing the Right AI Approach

API-First Development: Use pre-built AI services through APIs. Fastest path to market, works well for customer service, content, and data analysis startups.

Fine-Tuned Models: Adapt existing models on your own data for better domain performance. A Caribbean fintech might fine-tune on local financial regulations.

Custom Models: Build from scratch when you have unique data and existing models fundamentally do not work. Highest investment, strongest moat.

High-Impact Sectors in the Caribbean

Tourism, financial services and inclusion, agriculture, healthcare, education, and climate resilience are the six sectors where Caribbean AI founders have the deepest natural advantages. You understand your markets, your customers, and your challenges better than any external investor ever will.

The Path Forward

Build your prototype. Talk to your customers. Apply for funding. The future of the Caribbean tech economy will be written by the people who choose to build it. Ready to take the next step? Apply to the 14West AI Fund.



AI in the Caribbean Adrian Dunkley, Founder · February 22, 2026 · 7 min read

The State of AI Across Caribbean Nations in 2026

Globe showing the Americas and Caribbean

Artificial intelligence is no longer a conversation reserved for Silicon Valley or Shenzhen. Across the Caribbean, governments, universities, and entrepreneurs are waking up to the reality that AI will reshape every sector of the economy, and that the region must be an active participant, not a passive recipient.

Where the Caribbean Stands

Most Caribbean nations are still in the early stages of AI adoption. A handful of countries, including Jamaica, Trinidad and Tobago, Barbados, and the Bahamas, have begun to draft national AI strategies. But strategy alone is not enough. What the region needs is infrastructure, talent, and capital to turn policy into products.

What Needs to Happen

The Caribbean needs three things: coordinated regional strategy (this is why we built CAAG), direct funding for AI-native startups (this is what 14West does), and a shift in mindset, from waiting for permission to stepping forward and building. The moment is now.


Using AI Nicholas Dunkley, Head of Selection · February 15, 2026 · 4 min read

5 Ways Caribbean Startups Can Leverage AI Today

Developer coding on laptop with data in background

You do not need a research lab or a massive dataset to start using AI in your startup. Here are five practical ways Caribbean founders can integrate artificial intelligence into their businesses right now.

1. Customer Support Automation

AI-powered chatbots and support agents can handle the majority of customer inquiries, freeing your team to focus on higher-value work.

2. Content and Marketing

Generative AI can help small teams punch above their weight in content creation, from writing marketing copy to generating social media content.

3. Data Analysis and Insights

AI tools can analyze sales patterns, customer behavior, and operational data to surface insights that drive better decisions.

4. Process Automation

From invoice processing to compliance reporting, AI can automate repetitive tasks that consume time and introduce errors.

5. Product Differentiation

AI can be your competitive moat. Whether it is a recommendation engine, a predictive pricing model, or a personalized user experience, embedding AI into your product creates value that is difficult for competitors to replicate.

If you are building an AI-native startup in the Caribbean, we want to hear from you.


Announcement Adrian Dunkley, Founder · January 30, 2026 · 3 min read

Launching CAAG: A Caribbean-Wide Assembly for AI Growth

Fintech and data on screens

Why CAAG Exists

Today we are proud to announce the launch of the Caribbean Assembly for AI Growth (CAAG), a regional advisory body created to drive alignment, shared capability, and real representation across all Caribbean territories.

The Six Pillars

Built on six pillars, Representation, Alignment, Capacity, Capability, Ethics, and Fairness, CAAG will serve as the connective tissue between governments, academia, industry, and the startup community across the region.

Get Involved

If you are a policymaker, academic, technologist, or founder who wants to help shape the Caribbean's AI future, learn more about CAAG and join us.