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Bobby Silvest began their career in 1993 as a Marketing Manager for Outback Steakhouse. Bobby was later promoted to VP of Sports Marketing, where they were responsible for Outback Bowl, NASCAR, and Outback Pro-Am. In 2008, they became the Owner of BWS Marketing. In 2010, they became the VP of Marketing/Owner of Tara Solutions, where they supplied and manufactured environmentally friendly growing solutions for agriculture, plants, and turf. In 2013, they were appointed as the Vice President of Marketing & Communications for Tampa Sports Authority.

Bobby Silvest attended the University of South Florida from 1980 to 1985, where they earned a BA in Marketing. Bobby then attended the IAVM Venue Management School from 2014 to 2015, and completed the Graduate Institute program in 2016.