Why do smart investors repeat the same mistakes generation after generation? Because financial instincts — like fear, envy, and overconfidence — are ancient, stubborn, and terribly unsuited for modern markets. Fortunately, financial history leaves behind a paper trail of wisdom, wit, and hard-won lessons. Sometimes, a single quote can do more to correct a bad habit than a hundred charts.
That’s what brought us together. On March 19, 2025, I met Rachel Kloepfer. It was right after my keynote presentation at the Second Annual Institute of Advanced Investment Management (IAIM) conference at the University of Utah. My talk emphasized how investors can use financial history to gain a deeper understanding of current financial events and a clearer vision of the future. I closed with a few quotes from the past — concise and enduring truths which I hoped attendees could use to make better decisions.
Afterward, Rachel — a former journalist and fellow financial history enthusiast — suggested expanding the list. We sifted through hundreds of quotes. Some are serious, some are funny, but all come from people who lived through the financial highs and lows of the past 200 years.
The result is a curated set of 30 quotes exclusively for Enterprising Investor grouped by the vices to avoid, the virtues to adopt, and a little humor to stay sane through it all. We chose timeless quotes designed to resonate across generations, reminders that whether you’re new to investing or decades into your career, history still has something to teach you.
VICES
The most tragic mistakes in finance are those we could have avoided — if only we had learned from the past. Yet these errors persist because our instincts, once essential for survival, often backfire in markets. Until evolution catches up, our best remedy is historical awareness. The quotes that follow highlight some of the most damaging investor vices. Committing them to memory can help you resist these patterns — and free the mental capacity needed to cultivate more productive virtues.
Envy
“Nothing so undermines your financial judgement as the sight of your neighbor getting rich.”
—J. PIERPONT MORGAN, financier
Impatience
“The delusion lies in the conception of time. The great stock-market bull seeks to condense the future into a few days, to discount the long march of history, and capture the present value of all future riches. It is [their] strident demand for everything right now — to own the future in money right now — that cannot tolerate even the notion of futurity.”
—JAMES BUCHAN, author of Frozen Desire: The Meaning of Money
Dishonesty
“A business model that relies on trickery is doomed to fail.”
—CHARLIE MUNGER, late vice chairman of Berkshire Hathaway
Hubris
“The weakness of human nature prevents men from being good judges of their own deservings.”
—LOUIS BRANDEIS, author of Other People’s Money
Overconfidence
“When a speculator wins, he don’t stop till he loses.”
—GEORGE H. LORIMER, 19th century merchant
Complacency
“Always remember that somewhere someone is making a product that will make your product obsolete.”
—GEORGES DORIOT, founding father of venture capital
Denial
“Faced with the choice between changing one’s mind and proving that there is no need to do so, almost everybody gets busy on the proof.”
—JOHN KENNETH GALBRAITH, financial historian
Overthinking
It’s remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”
—CHARLIE MUNGER, late vice chairman of Berkshire Hathaway
Herd Behavior
“Once a majority of players adopts a heretofore contrarian position, the minority view becomes the widely held perspective.”
—DAVID SWENSEN, late CIO of the Yale University Endowment
Blind Faith
“The investing public is fascinated and captured by the great financial mind. That fascination derives, in turn, from the scale of the financial operations and the feeling that, with so much money involved, the mental resources behind them cannot be less.”
—JOHN KENNETH GALBRAITH, financial historian
VIRTUES
Shedding harmful instincts is only the beginning. The next step is to fill that space with virtues — a far more difficult task. Vices are common and instinctive; virtues are behavioral anomalies. The most powerful virtues are rare, easy to dismiss, and even easier to forget. The following 10 quotes come from financial minds who successfully navigated some of the most unforgiving markets in US history. Committing them to memory is a powerful next step toward becoming a more adept investor.
Passion
“All the genius I have lives in this: when I have a subject in hand, I study it profoundly. Day and night it is before me. My mind becomes pervaded with it. Then the effort that I’ve made is what people are pleased to call the fruit of genius. It is the fruit of labor and thought.”
—ALEXANDER HAMILTON, first US Secretary of the Treasury
Thrift
“I smoke four-cent cigars and I like them. If I were to smoke better ones, I might lose my taste for the cheap ones that I now find quite satisfactory.”
—EDWARD ROBINSON, father of Hetty Green, the Queen of Wall Street
Self-Discipline
“Several decades would pass, and many vicissitudes to be undergone before I could master the simplest and most important of all the rules of material welfare: The most brilliant financial strategy consists of living well within one’s means.”
—BENJAMIN GRAHAM, founder of the value investing philosophy
Competence
“A small bunch of people who know what they are doing can accomplish more than a big group of people who don’t know what they are doing.”
—ROBERT NOYCE, founder of Intel Corporation
Historical Awareness
“You can’t really understand what is going on now unless you understand what came before.”
—STEVE JOBS, founder of Apple Computer
Education
“Proper education is one long exercise in augmentation of high cognition so that our wisdom becomes strong enough to destroy wrong thinking maintained by resistance to change.”
—CHARLIE MUNGER, late vice chairman of Berkshire Hathaway
Humility
“There is a prudent maxim of the economic forecaster’s trade that is too often ignored: Pick a number or pick a date, but never both.”
—PAUL A. VOLCKER, late chairman of the Federal Reserve
Caution
“In business, don’t close a bargain until you have reflected upon it overnight.”
—HETTY GREEN, the Queen of Wall Street
Perspective
“A calm and modest life brings more happiness than the pursuit of success combined with constant restlessness.”
—ALBERT EINSTEIN, Nobel Prize Winning Physicist
Self-Awareness
“There is one set of management skills needed to start a company and another set needed to manage a bigger company. They are rarely resident in the same person.”
—DON VALENTINE, founder of Sequoia Capital
HUMOR
Finance and investing are not commonly associated with humor, but when human vices are stretched to their limits, they often produce situations so outrageous it’s hard not to laugh. The following set of quotes comes from witnesses to some of the more insane moments in U.S. financial history. We hope you can find humor in the insanity.
“I try to invest in businesses that are so wonderful that an idiot can run them. Because sooner or later, one will.”
—WARREN BUFFETT, chairman of Berkshire Hathaway
“In the history of every great catastrophe, you will find some masterly bit of stupidity set fire to the oil-soaked rags.”
—EDWIN LEFEVRE, financial journalist
“Periods of speculative frenzy always draw both scoundrels and suckers to Wall Street, the way a three-alarm fire attracts onlookers and pickpockets.”
—ROBERT SOBEL, financial historian
“I’ve lots of enemies…I tell you the devil would fear me, as many of his satellites do here.”
—HETTY GREEN, the Queen of Wall Street
“It was an absurd sign of the times that ‘enhanced leverage’ had become a selling point for an investment vehicle, instead of a warning; it was like naming a new car model after its faulty brakes.”
—TIMOTHY GEITHNER, former secretary of the Treasury
“Upon discovering the nature of the ruse, their rage was, as may well be imagined, unbounded but fruitless, and they were obliged to content themselves with asserting in a very emphatic manner that if [Jacob] Little ever visited Boston, he would inevitably part company with his ears.”
—WILLIAM ARMSTRONG, a reformed stock gambler (1848)
“If you have any money in that place [the Knickerbocker Trust], get it out the first thing tomorrow. The men in that bank are too good looking. You mark my words.”
—HETTY GREEN, the Queen of Wall Street
“Men have been swindled by other men on many occasions. The Autumn of 1929 was, perhaps, the first occasion when men succeeded on a large scale in swindling themselves.”
—JOHN KENNETH GALBRAITH, financial historian
“As a general rule of thumb, the more complexity in a Wall Street creation, the faster and further investors should run.”
—DAVID SWENSEN, late CIO of the Yale Investments Office
“The most common exit strategy was that we lost all our money.”
—JACK MELCHOR, venture capitalist
CLOSING THOUGHTS
The 235-year history of US finance is filled with scoundrels, schemes, and spectacular missteps. So it’s fair to ask: How can we remain confident in such a system? The answer is that financial history is also rich with heroism, ingenuity, and selflessness — forces that have steadily driven progress. The path forward is never linear, but over time, this system has worked better than the alternatives.
That’s why it’s essential to bridge generational gaps in the investment industry and ensure that future leaders benefit from the hard-earned lessons of the past. As knowledge compounds, so too can a more historically informed and self-aware financial system.
Like many of the insights shared here, this one isn’t new. In 1940, Fred Schwed Jr. wrote Where Are the Customers’ Yachts?, a classic that skewered Wall Street with unmatched humor — and still arrived at the same conclusion we have. Capitalism is flawed, but it works. So we’ll let Schwed Jr. have the final word. Despite our best efforts, we simply couldn’t say it better.
“I have a sneaking fondness for that wretched old hag, the capitalistic system, after watching the performance of her temperamental younger rivals. I believe we had better preserve our financial machinery even with much of the nonsense still adhering to it. The way we have been brought up, we all have a fondness for articles which can only be made in plants costing millions of dollars. Few of these articles can be produced by a fellow and his uncle working behind the garage. The only successful method so far devised for getting millions out of the public, for enterprises both good and bad, is some system similar to the devious mechanisms of Wall Street. . (Money has occasionally been raised from the public by smacking the citizens with the broad side of a saber, but the results of this were always less than satisfactory).
I am willing to submit an idea to the SEC that perhaps they have thought of themselves: they are in the position of a doctor who has only one patient, with no prospect of getting another. It would be a tactical error to kill this patient, even though a commendable scientific zeal prompts the doctor to try out his whole shelf of pharmacopoeia on him. After all, there is no real danger in this case of the patient ever becoming cured.”
—FRED SCHWED JR., author of Where are the Customers’ Yachts