While he has typically fielded at shortstop in his professional career, Ryan has been known to play at second and third base and on a rare occasion as a first baseman. Ryan has earned a reputation as one of the finest defensive players in the league.

Ryan was born in Los Angeles on March 26, 1982, to Katie and Jim Ryan. He is the youngest of their four children. Ryan attended Notre Dame High School in Sherman Oaks, California. His father was an infielder for Loyola Marymount University and holds the school's single season record for most hits with a wooden bat. His uncle, Willie Ryan, was a National Champion First Team All-American first baseman for the USC Trojans baseball team; his other uncle, Dr. Patrick Ryan, was a college sprinter at UCLA and Michigan State.

In the fall of 2000, Ryan enrolled at Lewis–Clark State College to play college baseball in the National Association of Intercollegiate Athletics. In his first season, he batted .375 with 5 triples, the third most ever by a Warrior. As a sophomore shortstop, he hit .359 with 34 RBIs and hit .378 with runners on. During the 2002 season, he hit safely in 18 straight games. Beyond his solid offensive numbers, Ryan gained a reputation as a good defensive infielder.

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