[Outliers] Hetty Green: The Witch of Wall Street

Hetty Green was the richest woman you’ve never heard of.

In the late 1800s, she built a fortune worth billions today in a world designed to stop her. Women couldn’t vote, couldn’t own property, and weren’t even allowed on the stock exchange floor.

She was a force that couldn’t be stopped. She bought entire towns, crushed railroad barons, and became the lender of last resort during financial panics. Her strategies still work today.

This is the story of how an unwanted daughter became “The Witch of Wall Street,” and a playbook for building lasting wealth and independence.

+ Members can read all 123 of my highlights here.

Listen Now: Apple Podcasts | Spotify | Transcript

Key Lessons:

1. Have a Detective’s Eye. Before buying anything, Hetty researched obsessively to uncover what others missed or ignored. When purchasing a horse and buggy, she found someone with a grudge against the seller to reveal every hidden flaw, getting it for half the asking price. This obsessive research gave her an information edge and set her apart from her contemporaries.
2. Positioning over Prediction. While others chased hot investments and bought on margin, Hetty always kept massive cash reserves and never went into debt. During the 1907 Panic, she had “a million dollars in cash on my desk every day” when banks were failing and credit was impossible to find. This liquidity allowed her to buy entire towns when others were forced to sell, and lend millions at reasonable rates when desperate borrowers would have paid anything. Everyone looks like a genius when they’re in a good position and even the smartest person looks like an idiot when they are in a bad position. 
3. Buy when others are fearful and sell when they are greedy. Hetty’s core investment philosophy was beautifully simple: “I buy when things are low and nobody wants them. I keep them until they go up and people are crazy to get them.” This wasn’t just a clever saying – she executed this strategy through every financial panic from 1857 to 1907.
4. Pay attention to the right side of the decimal. She often said, “Watch your pennies and the dollars will take care of themselves.”
5. Be fiercely independent. Hetty was completely comfortable trusting the results of her own thinking and judgment. She lived convinced that as a businesswoman, she was fundamentally alone and nobody else would watch out for her interests, so she had to. While others sought the safety of consensus, Hetty felt most comfortable making decisions on her own. This independence extended to how she lived – the rules she chose to live by were her own rather than society’s.
6. Structure matters. “I go my own way, take no partners, risk nobody else’s fortune.”
7. Mix patience with decisiveness. She would buy assets and “tuck them away” for years, sometimes waiting a decade for investments like greenbacks to pay off. Her extreme frugality – refusing to take carriages despite being worth millions – wasn’t miserliness but rather an understanding that every dollar spent was a dollar that couldn’t compound.
8. Stick to your circle of competence. Hetty concentrated on what she knew best: railroads, real estate, and government bonds. She avoided complexity and speculation, never borrowed money (following her father’s advice to “never owe anyone anything”), and kept her operations simple enough that she could manage everything herself from a desk at her bank.
9. Make work your passion. She said, “my work is my amusement,” and when asked why she didn’t retire, responded, “Why should I give up work?” Work wasn’t a burden; she was completely in love with the intellectual puzzle of investing and business.
10. Manage risk. Hetty’s approach to risk was sophisticated yet simple. She would only invest when she was satisfied that “the downside risk was low and the upside high”.
11. The storm doesn’t warn you. Don’t draw attention to yourself: “Hetty’s investments were not always known: she purchased property under fictitious names, bought stocks under other identities, and was praised by shrewd observers for how closely she held her positions.” She moved in silence.
12. Stay grounded. Her frugality served another purpose; she kept in touch with the real world.

Maxims for Life and Investing

Here is a list of ideas I took away from this episode and my research.

1. “I buy when things are low and nobody wants them. I keep them until they go up and people are crazy to get them.”
2. Position beats prediction. Always keep cash reserves.
3. “If you can manage your brain, you can manage your fortune.”
4. “Before deciding on an investment, seek out every kind of information about it.”
5. The skills to get rich and the skills to stay rich are not the same.
6. “In business generally, don’t close a bargain until you have reflected on it overnight.”
7. Only invest when downside risk is low and upside is high.
8. Self-reliance is the ultimate competitive advantage.
9. Everyone looks smart when they’re in a good position, and even the smartest person looks like a fool in a bad one.
10. Panics are temporary. Value is permanent.
11. Have a detective’s eye. Uncover what others miss or ignore.
12. “I go my own way, take no partners, risk nobody else’s fortune.”
13. “Never owe anyone anything. Not even a kindness.”
14. Mix extreme patience with extreme decisiveness.
15. Never bet against America.
16. “Watch your pennies and the dollars will take care of themselves.”
17. Move in silence. Keep your positions private.
18. Never take advantage of people, even when you could.
19. “When you try to do too much, you never get anywhere. Focus.”
20. Stay connected to reality. Frugality keeps you grounded.
21. “When it comes to spending your life, there have to be some things neglected. If you try to do too much, you can never get anywhere.”
22. “My work is my amusement.”
23. “Property is a trust to be enlarged for future generations.”
24. Live by your own rules, not society’s expectations.
25. Be fair in all things. Your conscience will haunt you otherwise.
26. “Don’t kick a man when he’s down.”
27. “Seek elegance rather than luxury, refinement rather than fashion.”
28. “When I see a good thing going cheap because nobody wants it, I buy a lot of it and tuck it away.”
29. From her favorite poem: “To live content with small means; To seek elegance rather than luxury, And refinement rather than fashion; To be worthy, not respectable, and wealthy, not rich.”

Things Not to Do

Hetty gave her children a list of things not to do.

• Don’t cheat in any of your business dealings, for sooner or later, your conscience will trouble you and you’ll worry yourself into an early grave.
• Don’t fail to be fair in all things business and otherwise.
• Don’t kick a man when he’s down.
• Don’t envy your neighbors.
• Don’t overdress, whether you have the means or not; this causes envy.
• Don’t fail to go to church, for the church needs you and you need the church.
• Don’t forget that riches dishonorably gained must be left behind someday, and when you depart, you will find the gates of heaven bolted against you.
• Don’t forget to be charitable.

Sources

• Wallach, Janet. The Richest Woman in America: Hetty Green in the Gilded Age. New York: Nan A. Talese/Doubleday, 2012.
• Slack, Charles. Hetty: The Genius and Madness of America’s First Female Tycoon.