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Stephen J. Olsen

Stephen J. Olsen is a member of Gawthrop Greenwood’s Trusts &  Estates Department, practicing in the areas of Estate, Trust Administration, Estate Planning Taxation, and Business Transactions. He is also one of the few Pennsylvania attorneys in private practice with a wide breadth of experience supporting the legal needs of medical marijuana operators.

Recently Stephen’s Cannabis Law practice has expanded to provide support to medical marijuana permittees in operation after Pennsylvania issued 25 grower and 50 dispensary permits across the Commonwealth. What began as legal services for medical marijuana operators and executives in compliance and transactional matters has now grown to due diligence services for potential investors, as well as support in employment law, workplace issues, advising fiduciaries on investing in marijuana companies and advising nonprofits in accepting donations from marijuana companies. He has also assisted processors, distributors and retailers of hemp-derived CBD products in a wide array of transactional and compliance issues.

Stephen received his law degree, cum laude, and his Master of Laws in Taxation (3.97 GPA) from Villanova University School of Law.

During law school, he served in the Federal Tax Clinic representing low-income taxpayers before the IRS and Tax Court and participated in the VITA tax preparation program for low-income taxpayers. He received his undergraduate degree in economics, with honors, from Lycoming College, where he was a member of the scholars program.

In addition to working at Gawthrop Greenwood, Stephen is currently assisting in the preparation of supplements and the new edition of the seminal tax procedure treatise, IRS Practice and Procedure (Rev. 2d ed.) (WG&L 2002), written by Michael Saltzman and Leslie Book. He is also a past Chester County Coordinator for the Wills for Heroes program, serves as the co-chair of the steering committee of the Chester County Community Foundation’s (CCF) Imprints program, is a board member of The Hickman, and is a past board member for Aid then Trade.

Stephen is admitted to practice in Pennsylvania, Washington, DC and before the tax court. He is a member of the Chester County, Pennsylvania, Washington, DC, and American Bar Associations. He is also a member of the committees on taxation of the Pennsylvania and the American Bar Associations, and a member of the Chester County Estate Planning Council.

Stephen is a creator of and frequent poster on the popular blog Procedurally Taxing. He has also written many other articles over the years, including:

  • Chuck vs. Goliath: Basis of Stock Received in Demutualization of Mutual Insurance Companies (HBTLJ, 2009)
  • Temporary Repeal of the Federal Estate Tax
  • Pennsylvania Tax Amnesty Program 2010
  • Changes Abounded in 200 to Federal Tax Law
  • Recovery Act Tax Changes for Individuals
  • Recovery Act Tax Changes for Business Owners

Stephen also speaks at a variety of seminars on topics related to tax controversy, tax planning, marijuana law, charitable planning, estate planning, and estate and trust administration. He has been interviewed multiple times on Fox 29 News, speaking about tax issues and his work with the Wills For Heroes program.


  • Pennsylvania
  • U.S. Tax Court
  • Washington, D.C.


  • Villanova University School of Law, Villanova, Pennsylvania, LL.M., Taxation
  • Villanova University School of Law, J.D.
  • Honors: Cum Laude
  • Lycoming College, Williamsport, Pennsylvania, B.A., Economics


  • American Bar Association – Committee on Taxation
  • Pennsylvania Bar Association – Committee on Taxation
  • Chester County Bar Association
  • Washington, DC Bar Association
  • Chester County Estate Planning Council
  • Wills for Heroes
  • Chester County Community Foundation Imprints Program
  • The Hickman, board member
  • Aid then Trade


  • Super Lawyers, Rising Star, 2010, 2013-2021
  • Top Lawyers, Main Line Today, 2014-2022
  • Top Lawyers, Daily Local News, 2021-2022 Readers Choice Awards
  • 2016 Lawyers on the Fast Track, The Legal Intelligencer
  • Chester County Community Foundation Door Opener Award, 2013

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