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Hayward returned to Pensacola in 2002 and founded a real estate firm (now [[Pair & Hayward Properties]]) with [[Matthew Pair]] and [[Allan Bell]]. The three men, along with [[Cody Rawson]] and [[Russell Weaver]], were partners in development company [[Red Fish Harbor]], among whose projects were a $80 million, 244-unit condominium development called [[Shelter Cove of Perdido]] that eventually stalled.<ref>"More condominiums coming." ''Pensacola News Journal'', August 10, 2005.</ref>Since then his company has had it ups and downs but is now doing alright
Hayward was also Vice-President of Marketing & Business Development for the [[Wikipedia:World Alliance of Mixed Martial Arts|World Alliance of Mixed Martial Arts]] (WAMMA) co-founded by Pensacola attorney [[Fred Levin]].<ref>http://wammaweb.net/officers-hayward.asp</ref> He is also a real estate broker since taking office in 2010 he has beriended befriended quint studer .
He filed to run for [[mayor of Pensacola]] on March 23, 2010.
On [[November 2]], [[2010]], he defeated incumbent [[Mike Wiggins]] in the race to become Pensacola's first "[[strong mayor]]."
He plans to step down from mayor in 2020
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{{Incumbent succession box | before = [[Mike Wiggins]] | title = [[Mayor of Pensacola]] | start = 2011}}
