Tax Planning

The clients I do the most tax planning work for share a common frustration: they have a CPA who prepares the return, a financial advisor who manages the investments, and an attorney who handles the estate plan, and none of those people talk to each other. The result is a tax position that’s the sum of three independent decisions instead of one coordinated one. Most of the meaningful tax savings I find for new clients aren’t from clever maneuvers – they’re from the gaps between professionals that nobody owns.

I’m Lawrence Israeloff. I’m a tax attorney and a CPA, and I’ve been doing this work for clients across Long Island and the New York City metro for over two decades. The dual credential is genuinely useful in tax planning specifically. Tax law sits at the intersection of statutory interpretation, financial structuring, and operational reality, and it’s hard to do well without seeing all three at once.

Tax planning happens during the year, not at filing time. By the time a client is sitting in their CPA’s office in March looking at last year’s return, most of the meaningful decisions have already been made – for better or worse. The work I do is mostly about making those decisions intentionally instead of accidentally. A few areas where the leverage is highest:

Some of this work is straightforwardly CPA work, some is straightforwardly attorney work, and some sits in the middle. The middle is where most clients lose money.

A CPA preparing returns generally won’t draft a trust agreement to capture a planning idea. An attorney drafting a trust generally won’t run the multi-year tax projections to confirm the trust actually saves money. A financial advisor recommending a portfolio change generally won’t model the realization implications across federal, state, and NIIT brackets. When all three pieces sit with one professional, or when one professional serves as the coordinator across all three, the planning gets sharper and the gaps disappear.

Concretely, the work I do often involves: drafting or reviewing the legal documents that implement a tax strategy (trust agreements, partnership operating agreements, family entity structures); running the actual tax projections that compare the current path to the proposed path; preparing or reviewing the returns that report the strategy correctly; and representing the client if the IRS or NY DTF later questions any of it. That’s a different scope than what either a pure CPA or a pure tax attorney typically offers.

The recurring patterns: high-income individuals and couples in NY’s top brackets where the tax cost is large enough to justify proactive work; closely-held business owners thinking about owner comp, entity structure, and eventual sale; professionals (physicians, attorneys, executives) with concentrated equity compensation, deferred comp, or unusual income patterns; real estate investors with depreciation, basis, and §1031 considerations; clients in the year of a liquidity event (a business sale, an inheritance, a large equity vesting) where the planning window is short and the stakes are high; and trustees and executors looking at the income tax and estate tax aspects of fiduciary administration.

If your tax situation is straightforward (W-2 income, standard deductions, no business interests, no large taxable account) you may not need this level of planning, and I’ll tell you that. The work I do has the most value where the complexity is.

I work out of Melville, NY and serve clients across Long Island, the five boroughs, and Westchester. New York’s tax landscape is genuinely complicated and aggressively enforced – the state’s residency audits are well-known among practitioners, and the NY DTF is active in challenging filing positions on issues from residency to pass-through entity tax. Useful starting points if you want to read on your own: the IRS, the New York State Department of Taxation and Finance, and the American Institute of CPAs. None of those replace advice tied to your specific facts.

If your tax situation is complex enough that you have multiple professionals involved, or if you’re approaching a year where the tax stakes are unusually high (a business sale, a relocation, a large bonus, an inheritance, retirement) that’s typically when proactive tax planning pays for itself. Schedule a consultation and we’ll talk through where you are and what the highest-leverage decisions look like.