Ian grew up in Randallstown, Maryland, and played high school baseball in nearby Owings Mills for McDonogh School, where he spent three years on the Varsity team. During those three years, McDonogh made it to three championship series, winning one in 1992, only the second baseball championship in the school's history. Ian made the Baltimore Sun's All-Metro Team in 1993 and 1994.  During the summers, Ian worked as an instructor at the Elrod Hendricks Baseball Camp, and played for the Yankee Rebels Baseball Club.

After high school, Ian attended St. Andrews Presbyterian College in Laurinburg, North Carolina, where he was a four-year starter. He was elected Team Captain in his junior and senior years. While in college, Ian played in the Clark C. Griffith Collegiate Baseball League in Northern Virginia for the Arlington Senators in the summers following his sophomore and junior years.

In 1998, Ian signed as a free agent with the New York Mets organization. He played a season at the Rookie level with the Gulf Coast Mets before being released at the end of the following Spring Training.

After a very brief "retirement" Ian was talked back into the game by his brother, Ryan, and began playing in the Baltimore Baseball League (BBL). Ian played in the BBL from 1999-2002 for the Strongbow Brewers. During that time, the Brewers won four consecutive League Championships.

Ian followed his brother to the Chesapeake MSBL in 2003, where he played for the Chesapeake Dodgers.  The Dodgers won the League Championship in 2004, but lost in the championship game to the Chesapeake Braves in 2005. When the Dodger team folded after the 2005 season, Ian joined the Braves the following year, where he was a part of the last six of the Braves' seven consecutive championships.

During his Chesapeake MSBL career, Ian has played in five All-Star games (2006-2008, 2011, and 2012).

Since 2003, Ian has played in several MSBL national tournaments including the Las Vegas Kickoff Classic (with the Fedlock Falcons), the Caribbean Classic in Puerto Rico (with the Fedlock Falcons), and the Fall Classic (with the Boone County Braves). As a member of the Fedlock Falcons, Ian was a part of three championship teams in the Las Vegas Kickoff Classic.

Outside of the Chesapeake MSBL, baseball continued to play a large part in Ian's life. In 2000, he returned to his alma mater and began coaching at McDonogh School. Ian served as the Assistant JV Coach from 2000-2002 and served the same role on the Varsity team from 2003-2005. In 2006, Ian took over as the Head Varsity Coach, and held this position until 2012. During his coaching career at McDonogh, Ian, along with his team, volunteered at the Ronald McDonald House in Baltimore. He also organized and ran several baseball clinics each fall and winter, and ran a one-week camp during the summer.