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Joshua D. Headley

Joshua D. Headley


Nonprofit Organizations Practice Group Leader

Washington, DC
Alexandria, VA
Philadelphia, PA

How Josh Helps Clients

Josh serves in the Tax, Wealth and Succession Planning, and Nonprofit Organizations groups. His primary focus is advising high-net-worth individuals on sophisticated estate planning matters, including mitigating death taxes. He also regularly works with executors and trustees on large, complex trust and estate administration and tax compliance matters. On the nonprofit side, Josh works closely with private individuals and large charitable institutions in structuring and operating planned giving vehicles, including private foundations (operating and grant-making) and public charities. He is the leader for the firm's Nonprofit Organizations Practice Group.

Josh co-chairs Buchanan's C.A.R.E.s Affinity Group, supporting employees who are caregivers or working parents. He is also an active volunteer with Wills for Heroes, a nonprofit organization providing essential legal documents free of charge to the nation's first responders, including wills, living wills, and powers of attorney.

What Clients Can Expect

A friendly demeanor, responsiveness and hard work are the cornerstones of Josh’s practice style. He enjoys helping people navigate complex issues by distilling what matters most to them to make an informed decision.

There is no better feeling than helping make your client’s goals become a reality, whether it be a legacy for their loved ones or some other noble cause.

Outside the Office

Josh grew up in the Shenandoah Valley of Virginia. He is the descendant of four generations of furniture makers. To his surprise, Josh discovered that the practice of law was his calling. He lives in Virginia with his wife, Caroline, and three children, Maisie Lee, August and Louisa.

An active member of his local community, Josh volunteers as a business coach for "E Squared," a program hosted by the 501(c)(3) nonprofit organization Career Partners, Inc. in Culpeper, Virginia. The semester-long program provides local high school students the opportunity to partner with coaches, create new business ventures and pitch them to hypothetical investors for a chance at receiving $10,000 in scholarship funds. Josh also serves on the Parking Authority for the Town of Culpeper, which promotes economic development in Downtown Culpeper by providing convenient, attractive and safe parking at a reasonable cost to residents, property owners, merchants, businesses and customers.

Proof Points

  • Developed a comprehensive estate plan for successful real estate developer that included restructuring numerous business entities to reduce estate taxes, avoid probate and provide for the seamless transition of business operations to the next generation.
  • Advised fiduciaries in the administration of multimillion dollar estate, including navigating the probate process and tax compliance matters relating to asset protection trusts, insurance trusts and other dynasty trusts.
  • Advised board of directors of public charity with multibillion-dollar endowment regarding the adoption of new investment policies in light of recent changes in charitable laws.
  • Established employee relief fund for national retailer including advising on formational and governance matters and obtaining recognition of tax-exempt status from the IRS.
  • Received a 2021, 2022 and 2023 Best Lawyers: Ones To Watch recognition for Tax Law.
  • Named to the Washington, D.C. Super Lawyers Rising Stars® list in 2022.