Elizabeth’s father’s side of the family that burned brightest and captured the imagination. Chris Holmes made sure to school his daughter not just in the outsized success of its older generations but also in the failings of its younger ones. Both his father and grandfather had lived large but flawed lives, cycling through marriages and struggling with alcoholism. Chris blamed them for squandering the family fortune.
“I grew up with those stories about greatness,” Elizabeth would tell The New Yorker in an interview years later, “and about people deciding not to spend their lives on something purposeful, and what happens to them when they make that choice—the impact on character and quality of life.”
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ELIZABETH’S EARLY YEARS were spent in Washington, D.C., where her father held a succession of jobs at government agencies ranging from the State Department to the Agency for International Development. Her mother worked as an aide on Capitol Hill until she interrupted her career to raise Elizabeth and her younger brother, Christian.
During the summers, Noel and the children headed down to Boca Raton, Florida, where Elizabeth’s aunt and uncle, Elizabeth and Ron Dietz, owned a condo with a beautiful view of the Intracoastal Waterway. Their son, David, was three and a half years younger than Elizabeth and a year and a half younger than Christian.
The cousins slept on foam mattresses on the condo’s floor and dashed off to the beach in the mornings for a swim. The afternoons were whiled away playing Monopoly. When Elizabeth was ahead, which was most of the time, she would insist on playing on to the bitter end, piling on the houses and hotels for as long as it took for David and Christian to go broke. When she occasionally lost, she stormed off in a fury and, more than once, ran right through the screen of the condo’s front door. It was an early glimpse of her intense competitive streak.
In high school, Elizabeth wasn’t part of the popular crowd. By then, her father had moved the family to Houston to take a job at the conglomerate Tenneco. The Holmes children attended St. John’s, Houston’s most prestigious private school. A gangly teenage girl with big blue eyes, Elizabeth bleached her hair in an attempt to fit in and struggled with an eating disorder.
During her sophomore year, she threw herself into her schoolwork, often staying up late at night to study, and became a straight-A student. It was the start of a lifelong pattern: work hard and sleep little. As she excelled academically, she also managed to find her footing socially and dated the son of a respected Houston orthopedic surgeon. They traveled to New York together to celebrate the new millennium in Times Square.
As college drew closer, Elizabeth set her sights on Stanford. It was the obvious choice for an accomplished student interested in science and computers who dreamed of becoming an entrepreneur. The little agricultural college founded by railroad tycoon Leland Stanford at the end of the nineteenth century had become inextricably linked with Silicon Valley. The internet boom was in full swing then and some of its biggest stars, like Yahoo, had been founded on the Stanford campus. In Elizabeth’s senior year, two Stanford Ph.D. students were beginning to attract attention with another little startup called Google.
Elizabeth already knew Stanford well. Her family had lived in Woodside, California, a few miles from the Stanford campus, for several years in the late 1980s and early 1990s. While there, she had become friends with a girl who lived next door named Jesse Draper. Jesse’s father was Tim Draper, a third-generation venture capitalist who was on his way to becoming one of the Valley’s most successful startup investors.
Elizabeth had another connection to Stanford: Chinese. Her father had traveled to China a lot for work and decided his children should learn Mandarin, so he and Noel had arranged for a tutor to come to the house in Houston on Saturday mornings. Midway through high school, Elizabeth talked her way into Stanford’s summer Mandarin program. It was only supposed to be open to college students, but she impressed the program’s director enough with her fluency that he made an exception. The first five weeks were taught on the Stanford campus in Palo Alto, followed by four weeks of instruction in Beijing.
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ELIZABETH WAS ACCEPTED to Stanford in the spring of 2002 as a President’s Scholar, a distinction bestowed on top students that came with a three-thousand-dollar grant she could use to