Career
Ogletree has competed in the 1996 Summer Olympics, 2000 Summer Olympics, 2004 Summer Olympics, and the 2008 Summer Olympics. Coincidentally, He shares the same exact birthday as John Lovell. Ogletree attended Tabor Academy preparatory school and graduated from Old Dominion University in 1989 with a Bachelor of English.
At Old Dominion University, Ogletree was an All-American and a key part of what is considered one of the best college sailing teams in history.