About

Robert C. Vanderpool is a Senior Associate at our firm, primarily specializing in Business & Corporate Law, with a keen focus on tax planning. Robert specializes in handling the tax-related aspects of diverse legal areas, offering clients comprehensive tax strategies. His expertise spans Business Reorganizations, Mergers and Acquisitions, Entity Formations, Succession Planning for Closely-Held Business Entities, Real Estate Transactions, Estate Planning & Wealth Preservation, and Municipal, Land Use & Environmental matters. Additionally, he is well-versed in Tax Controversy matters, effectively handling disputes with the IRS or Maine Revenue Services.

Robert earned his Juris Doctorate (J.D.) from Stetson Law in Florida in 2021, complementing it with an LL.M. (Master of Laws) in Taxation from New York University in 2022. He then ventured to Boise, Idaho, delving into Tax Law, Corporate Transactions, and Estate/Wealth Preservation. This diverse experience laid the groundwork for his return to Maine, where he found his professional home at Rudman Winchell.  Robert is currently licensed to practice in Maine, Washington, and Idaho as well as before the U.S. Tax Court.

In the realm of tax planning, Robert shines. He employs a unique ‘tax trifecta’ approach, considering the effect of all income, property, and sales/use tax consequences to provide comprehensive solutions. Notably, Robert has worked on substantial business mergers and acquisitions involving large national corporations and successfully advocated major international tax controversy matters directly before the IRS.

Robert excels in client interactions with a personal approach, prioritizing a personal understanding of each individual’s situation. He skillfully navigates through the misconceptions regarding tax and business law found online and often perpetuated by tax preparers through emphasizing clear, relatable communication and analysis. He helps clients understand the tax consequences of their decisions, both past and future, and guides them to make choices that are well-informed and tax efficient. His blend of empathy, clarity, and strategic efficiency underscores his deep commitment to client service and satisfaction.

Beyond his legal expertise, Robert is an active community member, dedicating his time to volunteering through Pine Tree Legal Assistance assisting veterans residing in Northern Maine. He is multilingual, with a vast knowledge of international issues and complexities. Outside the office, Robert is an avid outdoor enthusiast, enjoying hikes, skiing, and mountain climbing.

As a first-generation college student and a military veteran with over 8 years of service under the Special Operations Command, Robert brings a unique perspective to his practice. For expert legal guidance in tax or business planning tailored to your personal needs, reach out to Robert today.