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Caribbean Women < Caribbean Investing

Make Your First Investment.

You built the career, started the business, led the teams, poured into the community, and shattered every ceiling placed before you. Yet when it comes to investing beyond a retirement account, especially in the Caribbean, the message is still the same. Too complex. Too risky. Not for you. 

If you are anything like us, that just won’t do anymore. 

Introducing Women Invest, or WiN, the immersive investor readiness accelerator where women of Caribbean descent stop standing outside the capital conversation and step into their investing power.

How The WiN Accelerator Works

Each WiN cohort brings together high-earning Caribbean diaspora women and moves them through two phases of immersive learning and real investment action.

Learn
Lab

Phase 01

Where the program begins.

Phase One: The Investor Readiness Learning Lab is a two-day event where we begin to fill in the gap. We step into the capital conversation and understand how investment, ownership, and development actually move.

You will walk away knowing you own and our collective investment power and pathways.

The
Feild

Phase 02

Where the program expands.

Phase Two: The Ecosystem Immersion in Jamaica where eligible participants will engage with entrepreneurs, ecosystem leaders, and market opportunities.

The Jamaica experience is designed to deepen due diligence skills, strengthen market understanding, and help participants explore values-aligned investment opportunities in context.

WiN Accelerator Outcomes

Know exactly where you stand on the investor readiness pathway.

A values-aligned framework to evaluate real investment opportunities.

Gain a circle of women building investor confidence, capital fluency, and long-term collective power.

Get on a pathway to accredited investor status in the U.S.

Understand how Caribbean markets, development finance, entrepreneurship, and diaspora capital connect.

Assess your personal assets, investment capacity, and your financial edge.

Know the institutions shaping Caribbean economic development, including the World Bank, IMF, and Inter-American Development Bank.

Join us for Phase One in Washington, D.C., for our Investor Readiness Learning Lab. An immersive two-day experience where you and a curated group of investor-ready Caribbean women build the knowledge, confidence, and community needed to explore values-aligned investing across U.S. and Caribbean markets.

You will meet with our team of experts for hands-on workshops, fireside chats, and intimate labs where you assess your own capital capacity, understand your investor pathway, and examine how major financial institutions shape Caribbean economies.

Woven throughout, you and your fellow WiNvestors will enjoy VIP meals and the D.C. Investor Ecosystem Tour Experience.

  • You will learn how to map your assets, understand your investor readiness stage, explore values-aligned investment strategy, examine how capital flows into and around Caribbean markets, and identify your next steps toward more intentional investing.

    You will also gain exposure to institutions that shape Caribbean development and connect with women who are building similar investment capacity.

    By the End of the D.C. Learning Lab, You Will Have:

    • A clear understanding of where you are on the investor readiness pathway.

    • A stronger sense of your personal assets, investment capacity, and financial decision-making posture.

    • A values-aligned framework for thinking about investment opportunities.

    • A working understanding of how Caribbean markets, development finance, entrepreneurship, and diaspora capital connect.

    • A deeper awareness of the institutions shaping Caribbean economic development, including the World Bank, IMF, and Inter-American Development Bank.

    • A new circle of women who are also building investor confidence, capital fluency, and long-term collective power.

    • A next-step pathway toward Phase Two: the Jamaica ecosystem immersion in 2027.

  • This experience is designed for women of Caribbean descent who are executives, entrepreneurs, consultants, professionals, founders, wealth-builders, or emerging investors.

    It is especially relevant for women who have income or assets but want more confidence, structure, and community around investing.

  • The Two-Day Full Experience includes the Friday D.C. institutional investor ecosystem tour, VIP welcome reception dinner, and full Saturday Learning Lab access.

    Travel and lodging are not included unless specifically stated in your selected pass or future program materials.

  • No. This is an investor readiness learning lab.

    You will not sit through generic panels all day. You will participate in a structured learning experience designed to help you understand your investor identity, your capital capacity, your values, and your next steps.

  • Yes.

    Your initial investment includes the D.C. Learning Lab  experience that will be focused on education, readiness, exposure, and community-building. It is designed to help you become more informed and prepared before investment decisions begin. The investor accelerator will first focus on a year of learning experience before directly investing in Caribbean commences. Starting Fall of 2027, the inaugural cohort will begin to evaluate values-aligned deal opportunities.

  • After D.C., participants will receive information about the next stage of the WiN pathway, including the 2027 Jamaica ecosystem immersion.

    The post-D.C. experience will include community follow-up, continued learning, and access to vetted values-aligned deal flow.

  • Yes, if you are financially ready and ready to act.

    You do not need to be an expert. You do need to be willing to learn, ask questions, examine your own financial position, and participate actively.

  • No.

    This experience is for women who are currently investing, preparing to invest, or building toward greater investor readiness.

    If you earn approximately $100K or more annually, have investable assets, own a business, hold equity, manage family wealth, or are actively building toward those milestones, this room was designed with you in mind.

Ready to make your first investment?

Make Your First Investment

D.C. Investor Readiness

Learning Lab

This is where your investor identity is born, and your first investment takes shape.

2026 WiN Accelerator Program

 September 11-12, 2026,  Washington, D.C. 

Featured Speakers & Faculty

Say hello to your 2026 Investor Readiness Learning Lab faculty. You will be learning from women working across wealth education, financial activism, global impact, entrepreneurship, and values-aligned investing.

This Is Bigger Than One Weekend or

WiN is building more than an accelerator.

We are cultivating a women-led investment and syndication network where relationships, knowledge, and capital compound over time.

The vision is simple.

  • More Caribbean and diaspora women understanding capital.

  • More women evaluating real opportunities.

  • More capital moving toward Caribbean entrepreneurs and markets with intention.

  • More women seeing themselves not only as earners, but as owners, allocators, and builders.

This is how we stop asking where the money is.

We become where the money moves.

Event Schedule

Check out your 2026 Investor Readiness Learning Lab Schedule.

  • Friday, August 28, 2026
    Virtual
    4:00 PM – 5:00 PM ET

    Class Is In Session: Where’s My Money At?

    Meet the WiN team, your instructors, and the women in your learning circle. This virtual session introduces the program pillars, sets expectations, and helps you begin locating yourself on the investor readiness pathway.

  • Friday, September 11, 2026

    Washington, D.C.

    1. Institutional Investor Ecosystem Tour: Step inside the spaces where global development, capital allocation, and Caribbean economic policy intersect. This guided experience introduces participants to the institutions influencing Caribbean development and investment flows.

    2. VIP Welcome Reception Dinner: Get dressed. Get connected. Get in the room. The VIP dinner is a curated relationship-building experience with fellow participants, speakers, ecosystem leaders, and invited guests. This is where the cohort begins to shift from individual ambition to collective investment power.

  • Saturday, September 12, 2026
    D.C. Haitian Embassy

    9:00 AM — Welcome Breakfast
    10:00 AM — Morning Learning Sessions
    12:00 PM — Ladies Luncheon
    1:00 PM — Afternoon Workshops
    3:00 PM — Send-Off

    Participants will engage in structured workshops, facilitated conversations, and practical readiness exercises designed to help women understand their investor profile, clarify their values, and prepare for future opportunities.

  • D.C. is phase one of the Accelerator Program.

    Phase Two takes the work into the field.

    In July 2027, eligible participants will travel to Jamaica for an ecosystem immersion focused on entrepreneurship, market context, due diligence, and values-aligned investment exploration. Participants will meet founders, learn from local ecosystem leaders, examine real business opportunities, and continue developing the collective investment muscle introduced in D.C. The goal is not to rush women into deals. The goal is to help women become more prepared, more discerning, and more connected before capital moves.

Sponsors‍ ‍

A Special thank you to all of your sponsors for bringing this program together.