Hetty Green

Henrietta "Hetty" Green was the richest woman in America at the turn of the 20th century and arguably the greatest female investor in history — Guinness World Records officially named her the "World's Greatest Miser." Her fortune of $200 million in 1900 (roughly $4.3 billion today) was built entirely through her own investment acumen, not inheritance, not marriage, not family money. She outperformed virtually every male investor of her era, including many of the robber barons.

Her investment strategy was elegant: buy bonds and real estate when markets panicked, hold them until recovery, and never sell at a loss. During the Panic of 1907, when even JP Morgan was scrambling, Hetty calmly lent money to the City of New York at favorable terms — she was so cash-rich that she could act as a one-woman central bank. Her real estate holdings in Chicago, New York, and San Francisco appreciated for decades.

The miser reputation was earned. Hetty wore the same black dress until it wore out, ate 15-cent pies for lunch, heated her oatmeal on the office radiator to save fuel costs, and famously moved between cheap apartments to avoid establishing residency for tax purposes. The most notorious story: when her son Ned broke his leg as a child, she reportedly tried to get treatment at a free clinic rather than pay a doctor. The leg eventually had to be amputated. Her frugality was pathological — but it's also why her $4.3 billion (adjusted) fortune represents pure investment returns with virtually zero lifestyle spending. She was the anti-celebrity, the opposite of every cautionary tale on this site.