Sears was born in Washington, D.C and raised in Chevy Chase, Maryland in a close-knit family that can be traced back to Plymouth, Massachusetts in the year 1630.[citation needed] He attended high school at Landon School in Bethesda, MD. In high school, he was captain of the varsity football team and was awarded all-state honors as a tight end, as well as receiving a national top-ten ranking in the 100-yard breaststroke.Sears played varsity football for the University of Maryland. carrying on the family tradition of athletic excellence inspired by his great-grandfather who won a gold medal in the 1912 Olympics for pistol shooting, and again by his aunt who took home a bronze in the 1956 Olympics for the 100-yard butterfly. He transferred and graduated from the University of Virginia with a degree in business management in 1999.