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Jayson Dubin began their work experience in 1998 as an Account Executive at Yahoo.com. Jayson worked there until 2001. In 2001, they founded JKD Media and served as the CEO until 2004. From 2004 to 2005, they held the position of Vice President and Publisher at Theglobe.com. Jayson then became the President and Publisher of the Media Division of Theglobe.com from 2005 to 2007. Since 2007, they have been the CEO and President of Playwire.

Jayson Dubin attended the University of Maryland from 1992 to 1997. During this period, they did not receive a specific degree or focus in any particular field of study. Prior to that, from 1988 to 1992, Jayson completed their Bachelor of Science (BS) degree in Advertising at Syosset.