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Gary Winchester Martin has an extensive work experience beginning in 2006. Gary Winchester began their career with the Peace Corps as an Agri-Business Specialist Volunteer in the Republic of Moldova and also worked as Pro Business Nord, where they worked to strengthen the prevention of human trafficking of at risk women and children. In 2006, they also worked for Event Planning Associates as a Rural Corporate Finance-Peace Corps and for Drumul Spre Casa as the Director of Volunteer Mentor Program, where they were in charge of managing 45 community volunteers and 30 orphans matched one-on-one with volunteers. In 2008, they worked for NEW RULE PRODUCTS INC as the Director of Operations, where they were responsible for the design, manufacturing, implementation, marketing, and distribution of new proprietary ergonomic tools and processes for the commercial construction industry. In 2010, they worked for Apple Inc. as an Expert, where they built custom hardware and software solutions for business customers in OS X and iOS platforms. From 2013 to 2017, they worked for Fstoppers as a Staff Writer and from 2014 to 2020, they worked for PRO EDU as the CEO and Founder. In 2020, they also became the Owner of Resource Magazine and the Talk Show Host of The PRO EDU Photography Podcast.

Gary Winchester Martin has a diverse educational background. Gary Winchester began their studies at the University of Denver - Daniels College of Business, where they earned a BSBA in Finance in 2006. Gary Winchester then attended the University of Wollongong and earned a Certificate in Aboriginal Studies in 2006. In 2020, they began studying at the Massachusetts Institute of Technology and is expected to earn a Master's degree in Business Administration and Management, General in 2023. Gary Winchester is also pursuing a Master of Business Administration - MBA in Entrepreneurship/Entrepreneurial Studies at the same institution.