James grew up and learned to play golf in Northern Indiana, where he was ranked in the top 20 high school golfers in the state. He attended the Kelley School of Business at Indiana University and moved to Columbia, South Carolina, after graduating. James started at the Membership Director at Wildewood and Woodcreek Farms Country Club in 2007 before he was promoted to Club Controller at the facility. In February 2010, James joined the Ipswich team as the new Membership Director. That same year, he helped Ipswich attain one of the best membership sales totals since 2006.