Brian Cheslack advises high net worth individuals and families regarding the preservation, management and transfer of wealth. Certified in Wills, Trusts and Estates by the Florida Bar Board of Legal Specialization and Education, Brian is experienced in the design and implementation of advanced asset preservation techniques, including transfer tax planning. A family man himself, Brian understands the importance of compassion, respect and creativity when guiding clients through the complex decisions involving their loved ones.

With clients that range from tens of millions to over a billion dollars in net wealth, Brian strives to provide integrated asset conservation and succession solutions that reflect clients’ personal goals, values, convictions and distinct preferences. He advises on sophisticated personal, business progression and overarching wealth planning. Brian remains dedicated to client and family wide communications that are constructive rather than disruptive, as well as clear and understandable. He focuses on knowing clients and their needs, and to establishing the rapport, trust and confidence required to maintain long term relationships.

Curious by nature, Brian remains at the forefront of understanding businesses and economics at the local, state, national and international levels to serve clients and guide them through the challenges they face. A team player, Brian believes in collaboration, maintaining a positive stance to problem solving, and above all never compromising your integrity.

Brian graduated from the United States Naval Academy then served as a nuclear engineering officer for the United States Navy onboard fast attack submarines. Following eight years on active duty, he continued to serve as a Navy Reserve officer. He served in leadership roles in both the Pacific and Atlantic theater representing the United States in conference in South America and NATO.

A Delray resident and committed volunteer, Brian cares deeply about the development and prosperity of the community he calls home. Through service and dedication, Brian seeks to improve his community through action that incorporates good acts, fairness and sound ideals. At his core, he believes in supporting education and true change requires personal involvement.

  • Greater Delray Beach Chamber of Commerce Ken Ellingsworth Community Service Award, 2011
  • Florida Bar Association
    • Real Property, Probate & Trust Section, 2000-present
    • Tax Section, 2000-present
  • American Bar Association
    • Probate Law and Tax Law Sections
  • South Palm Beach County Bar Association
  • Boca Raton Tax Institute
  • Delray Beach Public Library, Vice President, 2004-present
  • Delray Beach Centre for the Arts at Old School Square, Inc.
    • Executive Board, 2003-05
    • President, 2006-09
  • Bethesda Memorial Hospital Foundation
    • Board Member, 2001-09
    • Executive Committee Member, 2007-09
  • Delray Beach Soccer Club, 2006-16
    • Board Member
    • Executive Committee
  • Riptide Lacrosse, Founding Board Member, 2008-16
  • Youth Soccer Coach, 2002-10
  • Youth Lacrosse Coach, 2008-12
  • Delray Beach Chamber of Commerce, 2009-13, Chairman, 2010
  • DEL-PAC, Delray Beach Business Political Action Committee, Chair, 2010-12
  • Delray Beach Community Redevelopment Agency Commissioner, 2011



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