Mr. Shapiro advises individuals and business entities on a broad range of federal, state, and international tax planning and tax controversy matters. A native of the San Francisco area, he received his undergraduate degree and law degree from the University of Chicago. At the law school, he served as Comment Editor for the University of Chicago Legal Forum.
Mr. Shapiro has successfully represented individuals and companies at all stages of tax controversy, from sensitive audit inquiries to administrative protests and appeals. He has significant experience litigating matters before California’s Board of Equalization and Office of Tax Appeals, the United States Tax Court, and in federal district courts in both civil and criminal tax matters. He has obtained favorable outcomes for taxpayers in a variety of settings, including no-change audit determinations, transitional relief acceptance within the Offshore Voluntary Disclosure Program (OVDP), and 100% concessions of tax and penalties in IRS audit examinations and appeals.
In 2014, he appeared before the California State Board of Equalization and obtained the Board’s full reversal of a $10 million constructive receipt determination made by the Franchise Tax Board. He appeared again before the Board of Equalization in 2017 and obtained a decision overturning California’s policy of imposing sales and use tax on destination management companies, and the full reversal of taxes, penalties, and interest.
Prior to moving into private practice, Mr. Shapiro spent a total of seven years at the U.S. Department of Justice Tax Division litigating tax controversies in federal courts across the country. At the Department of Justice, he gained broad experience in all aspects of tax controversy practice in federal district and bankruptcy courts, including trial work and evidentiary hearings, depositions and written discovery, pleadings, motions practice, appeals, and settlements. He regularly handled a docket of 60 to 70 cases, and worked on a variety of matters including tax shelters, statutes of limitation, employment tax disputes, tax liens and collection cases, international tax disputes, summons enforcement in criminal matters, interpretation and defense of Treasury Regulations, and many others. For his achievements, the Department of Justice awarded Dashiell with a Special Commendation Award and an Outstanding Trial Attorney Award.
Mr. Shapiro regularly publishes articles on tax litigation, the tax treatment of cryptocurrency transactions, and the taxation of financial products and investments.