Estes was born in Abilene, Texas, and graduated from the University of Texas at Austin in 1997. Estes manages the small community of The Village of Chevy Chase Section 5 in Maryland. The village is comprised of 227 houses and one restaurant. Her position is non-partisan, as she was appointed by the Town Council. From 2001 to 2005, she worked in the White House as George W Bush's personal secretary, but she was also Bush’s personal assistant from 1996 to 1999 while he was the governor of Texas. Estes was the personal assistant for the Bush-Cheney presidential campaign from 1996 to 2000. Both she and her now-husband were working for the Bushes in 2001 when they met. When the couple got married in 2004, the Bushes were just a few of the guests. The couple has two children, Margaret and Liza. Margaret was born just 13 months after they married, and Liza followed soon after.