Scott was born and raised in Pinellas County. He moved to Gainesville in 1990 to attend the University of Florida. He sees himself as a serial entrepreneur, staring his first business at age 13. In 2003, Costello started his publishing company, now Costello Communications & Marketing. CCM has printed titles such as Guidel to Greater Gainesville, HOME: Living in Greater Gainesville and Guide to Greater Tampa Bay. Costello Communications & Marketing also created/hosted a number of community events such as CEO Power Hour, Forty Under 40 and Fierce Awards. Scott has served on numerous charity/civic board and in 2010, he started Taste Greater Gainesville, raising $1,700,000 for children Charities over 10 years.