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Winston Gilpin has a diverse work experience spanning over several years. Winston is currently a Founding Partner at The Collectiv, a Houston-based sports-tech venture capital fund. Prior to this, they were a Co-Founder at GSQR Consulting, LLC, a consulting company catering to startups and investment partnership groups.

In terms of executive roles, Winston has served as the Chief Operating Officer at Mercury since 2005. Winston has also held the position of Chief Financial Officer at MPACT Strategic Consulting LLC, inerG, Inc., SEP Acquisition Corp, Performix Inc., and Imagination Campus.

In addition to their executive roles, Winston has founded their own consulting company called Gilpin Consulting, LLC. This company specializes in providing financial and operational consulting services to startups and early-stage companies seeking funding or guidance.

Overall, Winston Gilpin's work experience showcases a strong background in finance, operational management, and consulting expertise.

Winston Gilpin began their education at JHS 192 in the year 1969, but the field of study is unspecified. Winston then attended August Martin H.S. from 1970 to 1975, where they focused on Accounting. Following high school, Winston pursued further education at St. John's University, The Peter J. Tobin College of Business from 1975 to 1979. Although the degree name is not provided, their area of specialization remained Accounting. In addition to their formal education, Winston Gilpin obtained a license as a Texas Certified Public Accountant (CPA) from the Texas State Board of Accountancy, although no specific information regarding the month or year of obtaining the license is given.