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Michael McChesney has a diverse and extensive work experience. Michael is the founder and CEO at 86Borders, LLC., a position they have held since 2014. Prior to that, they founded and served as the CEO of StarPound Technologies, a communication-enablement platform, starting in 2004. Michael also founded and chaired WebTone Technologies, a banking software company that was acquired in 2004. Before that, they served as the chairman of Security First Network Bank, the first pure Internet bank in the United States, until its acquisition in 1998. Michael also founded and chaired S1 Corporation, a leading supplier of internet-based banking software, which was acquired in 1998. In addition, they co-founded and chaired Technologic, Inc., an internet security company, which was acquired in 1997. Prior to that, they founded and served as the CEO of SecureWare. Michael McChesney has been involved in various sectors, including technology, banking, and internet security.

Michael McChesney completed their Bachelor of Arts degree in Economics at Vanderbilt University from 1974 to 1978. Later, from 1979 to 1981, they pursued a Master of Business Administration (MBA) with a specialization in Finance at The Wharton School.