He is also a professional sports team owner of Futbol Longshots, a San Francisco based fantasy football franchise.

Following college, two years prior to the 2012 Summer Olympics in London, Kirkland and his brother Zander Kirkland began training full-time in an attempt to qualify as Bermuda's representatives in the Olympics 49er competition.

[2] During the 2012 49er World Championship in Croatia, 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.

[3] After their success in Croatia, they likewise left early for Weymouth, England in order to get used to local sailing conditions.