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    Miles Abraham

    OPERATOR · OWNER · FOUNDER

    I build businesses
    in markets people
    underestimate.

    I've been doing it in the Caribbean for 25 years.

    Work With MeWhat I'm Building
    Miles Abraham
    1994Digital Builder for 32 years
    22Regional Awards
    2023Real Estate Pivot

    What I'm Building

    Three lines of work. One method.

    Engineer the system. Understand the person at the end of it. Hold for the long term.

    Now

    SI.Ventures

    Acquisitions

    Buys and partners with founder-led businesses in the Caribbean, then operates them for the long term.

    Sourcingsi.ventures

    Now

    SI.Sprint

    AI Deployment

    Fixes one workflow in ten working days, on the business's own data. Handover is the default: the team keeps what we build and runs it. Optional support after that, if they want it improved.

    Running nowSee how a Sprint works

    Since 2023

    The Villas Tobago

    Real Assets

    Villas in Tobago. The brand, the bookings and the operations all run in-house.

    OperatingVisit the villas

    Since 2006

    SI.Media

    Technology & Media

    A regional agency for brand, digital, communications and PR. 19 regional Addy Awards. It also builds the technology the other two run on.

    Operating since 2006simplyintense.com

    Other projects are in development. They are listed here once they operate.

    SI.Sprint

    One workflow. Ten working days.

    Somebody on your team is retyping a WhatsApp order, then checking it against the invoice. A Sprint fixes one workflow like that. Fixed fee, scoped on a 30-minute call. Built on your own data.

    Handover is the default. Your team keeps what we build and runs it. If you want us to keep improving it, there is an optional plan, with no lock-in.

    Days 1–2

    Name what eats the week

    We list the workflows that take the team's time and score them on value, whether the data is there, and the risk.

    Days 3–4

    Pick one and write it down

    One workflow. One page: the problem, the data, the approach, and the person who owns it.

    Days 5–8

    Build it on your data

    We build and test on the real email, WhatsApp, invoices and systems. Your people are in the room so they can run it after we leave.

    Days 9–10

    Hand it over, working

    Your team sees it live, with the notes they need to run it. What to automate next is a later decision.

    SI is short for superintelligence, which on this work means one system your own team can run after we leave.

    Describe the workflowBook a 30-minute call

    Proof

    AI built inside my own companies

    These run inside businesses I operate. I had them built for our own work: the same kind of fix, on our own data, before offering it to anyone else.

    Support ticketing

    A request has an owner, inside a company I operate.

    Cash flow reporting

    The cash position, assembled from records the business already keeps.

    Sales follow-up

    A lead has a next step the person who owns it can see.

    Villa operations automation

    Bookings and the day-to-day handoffs at The Villas Tobago, run in-house.

    SI.Sprint is that same kind of work, done inside someone else's business, then handed back.

    Work With Me

    Four ways in.

    01

    Have you ever thought of selling your business?

    SI.Ventures buys and partners with established, profitable, founder-led businesses in the Caribbean. A full sale is one option. Staying on with a partner is another.

    Start a private conversation

    First conversations are private and stay that way.

    02

    One workflow. Fixed scope. Fixed fee.

    Somebody on your team is retyping a WhatsApp order, then checking it against the invoice. We fix that kind of thing. One workflow, in ten working days, handed back working. Your team keeps it and runs it. Optional support if you want it improved after that.

    Describe the workflowBook a 30-minute call

    03

    Long-term exposure, alongside the operator.

    I own and operate what I invest in. For capital partners who want real assets in the Caribbean and have the patience to hold them, I share the detail in private.

    Request an introduction

    04

    Agency work goes through SI.Media.

    Brand, digital, communications and PR for companies across the Caribbean. Operating since 2006.

    Go to simplyintense.com

    Who I Am

    I find where value is mispriced and build into it.

    For 25 years that has meant technology, then media, and now real assets and business acquisitions. The medium changed. The method did not. Engineer the system. Understand the person at the end of it. Keep building until it works.

    I trained as an interaction designer, so I care how things feel as much as how they function. In hospitality and property that is not decoration. It is the margin.

    Most people see the Caribbean as a small market. I see assets and businesses priced below what they can become. That gap is the work.

    Credentials

    • BA (Hons) Interaction Design, Ravensbourne

    • Kellogg School of Management Executive Education

      • Artificial Intelligence Strategies for Leading Business Transformation (2020). Verify
      • Digital Marketing Strategies (2019). Verify

    Executive education

    • MIT Innovation of Products and Services (2022)
    • Hyper Island Leading Teams (2016)
    • Hyper Island Digital Strategy (2012)
    • Econsultancy Agile Marketing and Conversion Optimisation (2016)

    Member, Forbes Technology Council.

    2026 to 1994

    The Long Game.

    The record, newest entry first.

    2026

    Hospitality, acquisitions, twenty years.

    Villa operations in Tobago, run end to end. SI.Ventures is sourcing its first acquisitions. SI.Media turns twenty.

    2023

    Into hospitality.

    Moved into hospitality in Tobago and ran it like a product. The brand, the bookings and the operations, all in-house.

    2021

    A food delivery exit.

    Co-founded a food delivery business in 2020, before the international platforms reached the region. Built it to profit. Sold it the next year.

    2013

    19 Addy Awards.

    Between 2013 and 2021 the agency's work won 19 regional Addy Awards. Seven gold, twelve silver.

    2006

    Founding the agency.

    Came home and started SI.Media in Port of Spain. It grew into a regional agency working for companies in energy, banking, telecoms, retail and government.

    2001

    London.

    Studied Interaction Design at Ravensbourne. Then web production at London agencies, on national retail and drinks brands.

    1999

    Hong Kong.

    Built websites at an interactive agency for international drinks brands.

    1998

    Málaga.

    First work abroad. Web design and development in southern Spain.

    1994

    The country's first internet provider, age twelve.

    The internet reached Trinidad. I got a summer job on the web team at the country's first internet provider, and it turned into contract work. First paid web work, the same year.

    How I Build

    Five principles. They decide what I buy, what I fix first and what I leave alone.

    01

    Own What Appreciates

    Real assets. Scarce land. Businesses whose customers come back. As AI makes digital work cheaper, value moves to what cannot be copied.

    02

    Engineer for Humans

    Every system has a person at the end of it. What they respond to, and what brings them back, decides whether the work performs.

    03

    Taste Is the Margin

    In hospitality, property and brand, how something feels is the product. Many can engineer. Some understand people. Few have taste. That gap is the premium.

    04

    One Region. One Playbook.

    The Caribbean is one market with shared culture, shared demand and shared gaps. I operate across it that way.

    05

    Decades, Not Exits

    I buy and build to hold. A longer horizon changes every decision, from who you hire to what you fix first.

    Insights

    Notes from the work.

    All insights

    Speaking

    I talk about what I have run, not what I have read.

    • Building businesses in markets people underestimate
    • Where value goes as AI makes digital work cheap
    • Taste as a business advantage
    • Owning and operating real assets in the Caribbean

    Member, Forbes Technology Council. Most recent keynote: Innovation in Action, AmCham T&T.

    Invite me to speak

    Contact

    Get in touch.

    Tell me which door you came through and what you have in mind. Every message is read. My office replies.

    Or email team@si.ventures

    Your details are used to reply to you. Nothing else.