Kirkland is a native of Bermuda, and grew up sailing there. He attended college in the United States at
Tufts University in
Massachusetts, and sailed while a student. He later moved to
Newport Beach, California, where he worked as youth sailing director for the
Newport Harbor Yacht Club and as sailing coach at Newport Harbor High School. Two years prior to the 2012 Summer Olympics in London, Kirkland and his brother Jesse Kirkland began training full-time in an attempt to qualify as Bermuda's representatives in the Olympics
49er competition. The 49er, a small two-person racing dinghy, is a relatively new sailing competition for the Olympics, having debuted for the first time at the
2000 Summer Olympics in
Sydney, Australia. At the 2012 World Championships in Croatia at the Sailing Club Uskok, the Kirkland brothers arrived early to gain experience sailing in local conditions. They advanced to the gold fleet after the preliminary qualifying races and later became the first team to secure one of the five remaining Olympic qualifying places that remained at the time after finishing in eighth place out of seventy-four in the final standings. After their success in Croatia, they likewise left early for
Weymouth, England, in order to get used to local sailing conditions prior to the start of the Olympic Games. They were one of twenty boats that competed in the 49er competition in the 2012 Olympics, finishing in 19th place. ==References==