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. 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.