Law Office of Andrew L. Gradman, APC

I am a tax lawyer, focusing on transactions (as opposed to audit/controversy). This means that:
◦ I help non-tax lawyers to draft documents which maximize after-tax value.
◦ I help CPAs to reflect these events on tax returns.
◦ I advise individuals and businesses directly when their lawyers and CPAs refer them with discrete questions.

Download my CV for links to my publications and presentations.

Representative Projects

• Qualified Opportunity Zones (QOZs). Help investors, QOFs, and QOZBs qualify and maximize benefits.
• Qualified Small Business Stock (QSBS / §1202 stock). Help investors and businesses qualify and maximize benefits.
• Corporation and partnership structuring. Advise on M&A, waterfalls, compensation, deductions and credits, etc.
• Estate and gift tax planning. Advise on trusts, gifts, valuation discounts, partnership freezes, etc.
• Litigation planning. Draft complaints and settlement agreements to reduce taxes and clarify filing responsibilities.

Education and Credentials

• Certified Tax Specialist, California Board of Legal Specialization; CA bar # 277-237
• NYU School of Law, LL.M. in Taxation, 2016.
• NYU Stern School of Business, Advanced Professional Certificate in Law & Business, 2016.
• Columbia Law School, J.D., 2011.
• Stanford University, B.A. (History), 2006.

When do you need a transactional tax lawyer?

First, you should be considering a transaction—a contract of any kind. For example, a merger, an estate plan, a litigation settlement. And you should know the terms you care about most—the terms I should not change. My job is to improve your after-tax results, by proposing changes to every other term. Often, my proposals will look unattractive to you, but for the tax savings. I like to say: “Tax planning is the art of the sacrifice.” And also: “Tax planning is not a coat of paint—it’s a change to the blueprints.” This is why it helps to seek tax advice early.

I do my best work when you are already working with another professional who is responsible for the project (e.g.: corporate attorney, estate planning attorney, plaintiff’s attorney, tax return preparer). I give them a recipe, which they know how to follow—i.e., a tweak to a document, or something to put in a tax return. I have a harder time helping people who aren’t considering a particular transaction and who simply want help lowering their taxes. However, if you are considering a tax-motivated transaction which I did not propose, I can point out the risks.

While I can advise your CPA on how to prepare your tax return, I do not prepare or file returns myself. If this service is needed, you must work with a CPA or other return preparer.

Why do you need a tax opinion?

Most of my time is spent forming opinions. That is: You are paying me to convince myself that, if you make a particular change to your proposed transaction (often, a change which I proposed), the hoped-for tax result would survive IRS challenge. To help you make an informed decision—and also for my own protection—my standard client agreement states that “you should not rely on advice given orally unless subsequently confirmed in an email or other writing.”

My opinions are not guarantees. If the IRS disagrees with my position, it may then decide whether to impose certain penalties. When it does so, it may consider your reliance on my opinion as a favorable factor. This is a second benefit of having my opinion. However, my ability to issue an opinion for this purpose is limited by the rules which regulate tax professionals (US Treasury Circular 230). Accordingly, my standard client agreement states: “If I offer a tax opinion, you should not rely on it for avoiding tax penalties unless I expressly confirm it is proper to do so.”

What to expect from our first call

Most of my clients are referred to me by professionals who know my work and have in mind specific questions I can answer. On our first call, clients tend to expect me to answer these questions. I strive to do that, and often do. Answering these questions is what I do for a living. For all these reasons, I typically do charge for initial calls. The fee is a flat one hour of my time, payable online before we speak. This covers the call and, if appropriate, a follow-up email summarizing my advice.

If there is a need for further work, I request a deposit and bill hourly. I will try to give an estimate, but in many cases I can’t give a meaningful estimate until I’ve been hired and made some progress. If the engagement is terminated, any unearned deposit will be refunded to you. If the final amount due exceeds the deposit on hand, the excess will be invoiced.

Other Downloads

• OBBBA Redlines
• Tax Holiday Calendars: 2024, 2026