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Ryan Bennett has held a variety of roles in the medical and sports industries since 1996. Ryan began their career as a catcher for the New York Mets, then moved on to become CEO of ProvidaCare Medical Supply in 2006. In 2011, they became a Partner at MD Cress and Associates, followed by Managing Partner at REM Sleep Labs in 2013. In 2014, they became Managing Partner at Transitions Geriatrics Group, and in 2020 they took on the roles of Chief Operating Officer and VP of Player Development at WIN Reality.

Ryan Bennett attended Austin Peay State University from 1992 to 1996, where they earned a degree in Management with a focus in Business.