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, a trust, a litigation settlement. And you should know the terms which matter most to you—the ones which I should not change. My job is to improve your after-tax results, by considering changes to every other term.

I am most productive when I am helping your CPA or non-tax attorney; these professionals know how to use my work. I have a harder time helping people 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.

Typically, you cannot “have your cake and eat it too.” Aside from some tax elections, my proposals will look unattractive to you, but for the tax savings. If it didn’t, you would have thought of it yourself. Instead, 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.

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, 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.” I can also provide instructions to your CPA and non-tax-attorney on what must be drafted and what tax forms must be filed.

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.”

Other Downloads

• OBBBA Redlines
• Tax Holiday Calendars: 2024, 2026