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Lindsay is a co-founder of The Pinnacle Benefits Group in Winston-Salem, NC. He is a graduate of Wake Forest University with a degree in mathematics and later earned an MBA from Temple University. Lindsay began his career in employee benefits, becoming an associate actuary, and then later moved into 401k consulting. In 1994 he partnered with Raymond Richard to form The Pinnacle Benefits Group. Quickly becoming a national leader in the marketing of major medical health insurance, Pinnacle later diversified into the life and senior markets. Lindsay is a Certified Public Accountant, enjoys golf, exercise, and occasionally appears in film and television productions.

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