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Ingram Leedy began their work experience as the CEO at Protected Trust, with no specific start year indicated. Ingram remained in this role until at least 2011 when they also became the CEO at Protected Trust, LLC. In 2010, Leedy joined Inland Fiber & Data as a Partner and held this position until 2013. Prior to that, in 2001, they founded Elephant Outlook and served as the President until 2013. Leedy's work history also includes founding iThink, Inc. - Imaginative Thinking in 1996 and holding the position of Founder until 2000.

Ingram Leedy attended the University of Florida from 1990 to 1996, where they studied Computer Information Science and Engineering. Ingram did not obtain a degree during this time. In addition, they are certified as a Private Pilot in ASEL, ASES, and Instrument by the Federal Aviation Administration, although the specific month and year of obtaining this certification are unknown.