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the late 1990s, many of the top performers came from entrepreneurial or technology careers. John Doerr of Kleiner Perkins, the best-known VC in the Valley, had been the number one salesman at Intel Corp., once throwing in a lawn mower to close a deal in the Midwest. His partner Vinod Khosla cofounded Sun Microsystems. Each had a deep understanding of how rapidly growing companies function on the inside. Another reasonable choice for preparation as a VC would be a career as a serious investor in public companies. Since almost no one before 1998 listed venture capital as an early career choice, “the only honest answer for the question, ‘How did you become a VC?’ is, ‘I got lucky,’” said Scott Sandell, of the venerable VC firm New Enterprise Associates.

That certainly applies to Richardson, who was one of many who got there quite by chance. But besides natural intelligence and ease with other people, two useful VC qualities, Richardson had a third, critical strength: a streak of independent thinking. Once everybody agrees that a given piece of technology or an idea is the right one, it’s too late to make a killing. Richardson had independent thinking in spades, despite a traditional upbringing near Middletown, New York. Her dock-builder father had worked on the Verrazano Narrows Bridge before he was permanently disabled in 1973. Her mother had emigrated from Ireland at twenty-seven, and they were poor enough that as a young girl, Richardson worried about the family losing its house. Often, Richardson’s mother emphasized the way out of poverty that had nearly worked for her: finding a good husband early. The lectures made an impression, and after high school, Richardson went to secretarial college, following her mother’s plan that she get a job where she could try to marry the boss.

Richardson’s first workplace superior, a seventy-year-old lawyer, wasn’t marriage material. Vivacious and driven, Richardson got bored with filing and other routine tasks, and she began doing some of his legal work. She soon realized that she could do a lot more than type. She entered St. Thomas Aquinas College in Sparkill, New York, then met a cadet at West Point and married him at age twenty-one. Without graduating herself from Aquinas, she left with him when he graduated and transferred to the first of a series of Army installations around the country. In each new town, she took an office job—once at an advertising firm, another time at a title-insurance firm. She kept thinking she could do

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