3. Victoria Woodhull
Victoria Woodhull’s origins were straight out of a Horatio Alger story: She was born in 1838 in extreme poverty and had very little formal education. To make money, Victoria and her sister, Tennessee Claflin, performed spiritualist work, fortune-telling, and séances, at the behest of their father. It didn't directly amass her a fortune, but it helped contribute to it. The sisters moved to New York in 1868 and met Cornelius Vanderbilt, who gave them access to stock tips in exchange for Woodhull's services as his personal clairvoyant. In this role, Victoria held séances for Vanderbilt to contact his late wife and passed along financial advice from his dead partners. Tennessee, meanwhile, provided Vanderbilt with "magnetic healing"—she claimed her hands could pass positive and negative magnetic waves over a patient's troubled area to ease their pain—and later became his mistress.
In 1870, Vanderbilt helped to finance Woodhull, Claflin, & Co., a Wall Street brokerage firm founded and operated by the sisters (making them the first women to do so). That same year, the pair established a radical leftist paper, which was the first to publish The Communist Manifesto in America. Two years later, Woodhull became the first woman to run for president, though she wasn’t yet the Constitutionally required 35 years old. She campaigned on a platform of women’s suffrage, "free love," abolition of the death penalty, and other left-leaning ideals. Her bid was ultimately unsuccessful, and she later relocated to England, where, among other deeds, she ran a magazine and helped with the upkeep of Sulgrave Manor, George Washington's ancestral home in Northamptonshire.