Sheldon Gray is an experienced professional in the field of asset management and real estate investments. Currently, Sheldon is employed at The Milestone Group in an asset management role since June 2025. Previously, Sheldon worked at S2 Capital as an investments professional from June 2024 to June 2025 and served as a portfolio manager for the Colonnade Fund focusing on real estate at Darden Capital Management from April 2023 to May 2024. Notably, Sheldon also gained experience as a real estate summer associate at Blackstone in the summer of 2023. Earlier career roles include strategist and associate strategist at DeSantis Breindel from November 2019 to June 2022 and operations at M.M.LaFleur from June 2018 to October 2019. Sheldon holds a Master of Business Administration from the University of Virginia Darden School of Business (2022-2024) and a Bachelor of Arts with Distinction in English and Spanish from the University of Virginia (2014-2018). Education was initiated at Strake Jesuit College Preparatory (2010-2014).
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