John J. Nail is an associate with the Firm’s Corporate and Tax Controversy groups. He practices in the areas of tax and business succession planning, state and federal tax controversy, and tax litigation. John’s work focuses on helping our clients develop efficient and innovative gift tax, estate tax and business succession plans to minimize taxes, preserve wealth, and manage risk for themselves, their families, and their businesses.

John represents entrepreneurs, successful individuals, and closely-held companies in business transactions of all types and has helped guide our clients through capital raises, asset purchases, and equity sales, and other transactions. John also represents taxpayers of all types at both the state and federal levels in civil tax controversy matters. In this capacity, he has helped our clients manage IRS and NC Department of Revenue audits, guided clients through state and federal administrative appeals, and participated in the litigation of significant tax cases in the U.S. Tax Court and Federal District Court.

  • Super Lawyers North Carolina Rising Stars, 2019 in Tax
  • Business North Carolina  Legal Elite Young Gun, 2016 and 2019
  • Member of the Order of the Coif
  • Wake Forest Law Review, Executive Editor
  • CALI Awards in Securities Regulation and Tax Policy
  • Advised closely-held businesses on various issues, including analysis of business structure, drafting limited liability company and partnership agreements, drafting asset purchase agreements, and managing business dissolutions.
  • Assisted a multi-million dollar medical device company in developing plans for raising capital through private investors and expanding to international markets.
  • Advised local business owners and real estate investors on sophisticated tax planning and deferral strategies.
  • Assisted in the litigation of complex issues of tax law and procedure in the United States Tax Court.
  • Assisted in the litigation of a case in the Western District of North Carolina District Court over the non-payment estate taxes, which was decided in favor of our client by summary judgment.
  • Appealed a sales and use tax case to the North Carolina Office of Administrative Hearings and negotiated with the North Carolina Department of Revenue in court-managed mediation proceedings.  
  • Represented clients in the disclosure of foreign bank accounts through the IRS’s Offshore Voluntary Disclosure Program and the Streamlined Filing Compliance Procedure.