Stephanie M. Loughlin

Loughlin Stephanie

Stephanie Loughlin focuses her practice on advising businesses, their owners, and high-net-worth clients on federal income tax and partnership tax matters. She works with clients in real estate, hospitality, technology, consulting, and other industries on joint venture and business transactions, tax planning, tax controversy and advocacy, and charitable and estate planning.

Stephanie advises clients on structuring and negotiating joint ventures, acquisitions, and other business transactions. She has represented several private equity funds in the formation of their investment funds, and in their portfolio investments, including debt restructurings and asset sales. She counsels clients on day-to-day operational issues that arise in the context of joint ventures and other closely held businesses.

Stephanie has extensive experience representing businesses, individuals, and trusts and estates before the Internal Revenue Service (IRS) and federal courts in tax audits and controversies, many of which have involved the valuation of closely held media, entertainment, and real estate businesses. In addition, she assists clients with IRS private letter ruling requests.

Stephanie also helps clients achieve business succession, estate planning, and charitable giving objectives. She routinely collaborates with clients' accountants, investment advisors, appraisers, and other professional consultants to develop and implement efficient tax plans tailored to her clients' goals.


Representative Matters

Joint venture and business transactions

  • Represented the lead investor in the formation and subsequent funding rounds of a private biotechnology joint venture 
  • Served as tax counsel to the founder of a chain of U.S. specialty bakeries in negotiating with lead investors an equity compensation package and several amendments to the LLC agreement 
  • Represented a private equity fund in the sale of its portfolio company – a multistate cable television company – for more than $1 billion, including negotiating a purchase agreement, pre-sale tax planning, and foreign and state withholding matters

Tax controversy and advocacy matters

  • Represents clients before the IRS in a variety of matters, including LB&I, Small Business/Self-Employed, and GHW audits; Office of Appeals; technical advice; Offshore Voluntary Disclosure Program (OVDP); offers in compromise; penalty abatements; tax lien releases; and innocent spouse relief claims
  • Represents clients in income, employment, and gift and estate tax controversies, with a focus on complex business valuations, and the valuation and tax treatment of intangible assets; has collaborated on estate and gift tax litigation in Tax Court and U.S. Court of Federal Claims
  • Resolved at IRS Office of Appeals a years-long employment tax audit of a municipal parks and planning commission; successfully settled a seven-year, multi-million-dollar gift tax audit at IRS Appeals
  • Represented a state corporation commission in an IRS private letter ruling request regarding permissible state utility rate-making




  • J.D. University of Virginia School of Law 1988
    • Articles editor, Journal of Law & Politics
  • B.A. summa cum laude Catholic University of America 1985
    • Phi Beta Kappa

Bar Admissions

  • District of Columbia

Court Admissions

  • U.S. Tax Court

Professional Memberships and Activities

  • Member, District of Columbia Bar (DC Bar), Taxation Section


Pro Bono

  • Provides pro bono legal counsel to a public charity, Nurturing Minds in Africa, which funds the operations of a girls' secondary school in Tanzania
  • Provides pro bono legal assistance to indigent taxpayers in IRS audit and collection matters 


  • Volunteers with Montgomery County, MD/AARP Foundation Tax-Aide