Amy Phelan was born in Dallas, where her stay-at-home mom cared for Amy and her brother while her father (a former champion bull rider) embarked on a variety of businesses, ranging from construction to oil. She attended Southern Methodist University and graduated “on the five- or six-year track, if I’m honest,” with a degree in marketing and finance. (Cheerleading, she admits, was a bit of a distraction from her studies: “It was during the glory years, when we were winning back-to-back Super Bowls.”) After graduating, she worked in marketing at a medical mattress company for three years. When the company was sold, she went into management consulting at the Dallas-based firm Blythe-Nelson. In the meantime, she was briefly married to L.B. Moon, a former football player for the Miami Dolphins. The two had a daughter, Makenzie, but divorced in 1997. In 2000 she was set up on a blind date with John, also an SMU graduate, whose fraternity brother had married a cheerleading teammate of Amy’s. They hit it off: In late 2000 Amy and her daughter moved to New York to be with John, who runs MSD Capital, the highly successful investment fund that manages Michael Dell’s fortune. They married in 2002.