Meet David Dolitsky

My foundation is a Bachelor of Science in Accounting. I started my career in the United States working in corporate accounting — financial reporting, reconciliations, internal controls, the full cycle. Over time, I gravitated toward more complex work: businesses with multi-entity structures, cross-border operations, and situations where getting the structure right mattered enormously to the outcome.

What kept pulling me deeper into the advisory side was the human element. Tax and compliance aren't abstract — they shape how people build wealth, protect what they've earned, and plan their futures. When you help a business owner structure their company correctly from day one, or guide a retiree into a legally compliant framework that dramatically reduces their effective tax rate, the impact is real and measurable. That's what I find deeply satisfying about this work.

Over the years I became proficient in systems like QuickBooks and Peachtree (Sage), and built experience across industries including hospitality, real estate, and professional services — industries that are very much the backbone of the Sint Maarten economy today.

I hold a dual leadership role: Financial Controller of BrightPath Caribbean, and General Manager of CaribTax. The two roles are complementary. BrightPath Caribbean is the parent firm — it handles a broader range of professional services for clients on the island. CaribTax is the specialized tax and accounting advisory arm, and that's where much of the day-to-day client work lives.

What attracted me to this opportunity was the chance to build something meaningful in a jurisdiction that genuinely rewards doing things correctly. Sint Maarten has a legitimate, favorable tax environment for those who qualify and comply — particularly the Penshonado program, which offers a flat 10% tax rate on worldwide income for eligible residents. Being part of a team that helps clients access that benefit lawfully and sustainably is motivating work. It's not a gray area — it's a legitimate statutory program, and helping clients navigate it properly is exactly the kind of substantive work I enjoy.

Start early. The single biggest cost in tax and compliance work is almost always delay. Whether it's delaying entity formation, delaying a Penshonado application, or delaying a filing — the longer someone waits, the more they pay. In some cases, the window for a favorable structure closes entirely.

Documentation is everything. Courts and tax authorities operate on evidence. A well-constructed position that can't be supported with paperwork is worth nothing under audit. I've seen clients lose defensible positions because they couldn't produce supporting records. The discipline of maintaining documentation from day one is not bureaucratic overhead — it's protection.

Complexity compounds. A compliance gap in year one becomes two gaps in year two when it isn't corrected. I've seen small oversights — a missed annual filing, an improperly classified transaction — snowball into significant back-tax exposure because nobody addressed them when they were manageable. The best time to fix a problem is the first day you know about it.

The most prevalent misconception is that Sint Maarten is informal or low-enforcement because it's a small island. That is simply not true. Sint Maarten has a full tax code — the Landsverordening op de inkomstenbelasting (LvIB) — an active and growing Belastingdienst (Tax Authority), and real consequences for non-compliance, including penalties, interest, and in serious cases, prosecution. The island is small; the obligations are not.

The second biggest misconception involves the Penshonado program specifically. Many people arrive believing that the 10% flat-rate benefit is automatic for any foreign retiree who moves here. It isn't. It requires a formal application to the Tax Authority, documented proof of eligibility (foreign-sourced income, the 183-day residency requirement, and in some cases a property requirement), and ongoing compliance obligations after approval. The benefit is real and substantial — but it is earned through proper process, not assumed by default.

A third one: people sometimes assume that income earned on the French side of the island is outside the Dutch Sint Maarten tax system. It isn't. Sint Maarten taxes residents on worldwide income — including anything earned in Saint-Martin. Failing to report cross-border income is one of the most common and serious errors we see.

Under-structuring. This is by far the most common mistake. Someone arrives with a solid business concept, finds a location, starts operating — and skips the entity formation or chooses the wrong structure. On Sint Maarten, the choice between an NV (Naamloze Vennootschap), a BV (Besloten Vennootschap), a Stichting (foundation), or operating as a sole trader has real tax, liability, and banking consequences. These are not interchangeable. Each structure carries different registration costs, governance requirements, and tax treatment. Getting it right upfront costs a fraction of correcting it later.

Mixing personal and business finances. Extraordinarily common, and creates significant complications during audits or when seeking financing. When business income flows through personal accounts, and personal expenses appear in business records, there is no clean picture of the business's actual performance — and no clean separation of personal liability. Banks don't like it and the Belastingdienst certainly doesn't either.

Missing deadlines. Sint Maarten has a defined tax calendar. Personal income tax, corporate profit tax, turnover tax (ABB) — each has its own filing and payment deadlines. Late submissions attract penalties and interest regardless of whether you owe tax. We see this most often with newly arrived expats who don't yet understand the local filing calendar, and with small business owners managing everything alone.

Tax is typically the single largest variable cost in any financial plan — more so in international relocation, where the gap between a well-structured and a poorly structured arrangement can be enormous. Let me give you a concrete example: a Penshonado resident who qualifies and properly applies pays a flat 10% rate on worldwide income. The standard progressive personal income tax rate in Sint Maarten goes up to 47.5%. The difference between those two outcomes — for the same person, earning the same income — is not recoverable retroactively. The window for the right structure had to be accessed at the right time.

For real estate investors, the structure matters too. Property purchases in Sint Maarten attract a transfer tax of 4%. Holding property through a properly structured NV versus personally can affect estate planning outcomes, liability, and how the asset is treated upon sale. These are not details you can optimize after the fact.

For retirement planning, the sequencing of income — when you draw pensions, how foreign income is declared, how the Penshonado application is timed — all of this affects the effective tax rate you'll pay for decades. Proper planning done once, correctly, delivers compounding returns on that investment every year thereafter.

Sint Maarten is genuinely underserved in high-quality professional services. There is significant demand — from the growing expat community, from established businesses, and from incoming investors — for accounting, legal, compliance, healthcare, and financial advisory services at a professional level. That's a real opportunity for skilled professionals who want to relocate and practice here.

Tourism and hospitality remain the core of the economy and continue to expand, particularly in the premium accommodation and yacht charter segments. Real estate is active — Sint Maarten has a dynamic property market with buyers from Europe, North America, and South America all participating. And digital and remote businesses are increasingly viable: the island has reliable infrastructure, English as a primary language, and a favorable time zone that overlaps with both US Eastern and European business hours.

What I tell people is that Sint Maarten rewards those who do their homework. The Penshonado benefit, the corporate structures, the real estate opportunities — they are all real. But they are accessible to those who plan properly and execute through the right channels, not to those who arrive and improvise.

The opportunity at BrightPath Caribbean was the catalyst — but the island itself made the decision easy to commit to. I came to take on the Financial Controller role, and once I was here, I understood quickly why so many people who come for a year end up building a life.

The quality of life is genuinely high. The community is international, multilingual, and remarkably welcoming to professionals who bring real expertise. There's a sense that the island is still building — the infrastructure is developing, the business community is growing — and that creates real opportunity for people who want to be part of something rather than just arrive after the fact.

Living here as an expat also makes me a better advisor to our clients. I've gone through the residency process. I've opened local bank accounts, navigated the permit system, filed taxes as a local resident. When a client asks me what it's actually like to live here and comply with local obligations, I can answer from personal experience — not just from a textbook.

Come with a plan, not just a vision. Sint Maarten is an exceptional place to live and build — but it is not a tax-free jurisdiction, it is not without regulatory requirements, and it is not somewhere you can navigate successfully by improvising. The Penshonado program, the residency process, the corporate structures — all of them require deliberate preparation.

Work with advisors who are physically here. There is a meaningful difference between receiving advice from a firm located in a distant financial center and working with professionals who have active relationships with the local Belastingdienst, know the immigration authorities, and have filed returns locally for years. The regulations, as written, leave room for interpretation — and how that interpretation plays out depends heavily on local knowledge and established relationships.

Understand that Sint Maarten has two sides. If you live on the Dutch side and work, own property, or earn income on the French side, your tax situation is more complex than you may realize. Cross-border income reporting is a real obligation, and the absence of a tax treaty between Sint Maarten and France means the relief mechanisms are internal — and must be claimed correctly.

Most importantly: give yourself time to understand the island before making large financial commitments. The due diligence phase is well worth the investment.

CaribTax is embedded in BrightPath Caribbean — we're not a seasonal advisory service, we're not remote, and we're not a pop-up operation. Our team lives and works on this island. We have active, ongoing relationships with the local Belastingdienst. We know how regulations are applied in practice — which is not always identical to how they read on paper — and that practical knowledge is what protects our clients.

We also take a genuinely holistic approach. Tax planning in Sint Maarten doesn't exist in isolation. Entity structure, real estate ownership, residency status, Penshonado eligibility, US expat obligations — these are interconnected. A change in one affects the others. We look at the full picture for each client and build a strategy accordingly, rather than handling a single transaction and walking away.

What I hear most often from clients who've worked with other advisors before coming to us is that they were given technically correct information that turned out to be strategically incomplete. The letter of the law was followed, but the structure wasn't optimized for their actual situation. That's the gap CaribTax closes — not just compliance, but compliance designed around your specific goals.