Liz Ann Sonders on investing vs. gambling

When you invest, the odds are in your favor.  When you gamble, the odds are not in your favor.

~ Liz Ann Sonders, "Energy Prices Aren't Matching With Reality," RiskReversal Media, 7:20 mark, April 10, 2026

 

Kevin Duffy on pursuit of the truth

Once you realize pursuit of the truth - dedication to reality at all costs - is the key to investing and life, you realize there is no other choice.  Being uncomfortable then becomes your comfort zone.  Since others prefer comforting lies, this becomes a massive, durable edge in both games (life and investing).

~ Kevin Duffy

 

Michael Weeks on when to sell

When should I sell? 

Ask an economist, an investor, and a business owner this question and you will get three different answers: a theory, a formula, and a decision.

The theory is universal and true, but not practical.

The formula is universal and practical, but not true.

The decision is true and practical, but not universal.

My answer is simple: You sell when it makes sense. 

Not a theory.  Not a formula.  Always a judgment call, based entirely on experience and circumstance.

~ Michael Weeks, Edelweiss Holdings, Twitter/X post, October 15, 2025

 

Howard Marks on investing errors

The biggest investing errors come not from factors that are informational or analytical, but from those that are psychological.

~ Howard Marks

 

Joe Austin on investing

If you want to invest it should be fun.  It should be something you like or love, where you think you can make money, where you can understand where you went wrong.  If you can't understand where you went wrong, you're never going to learn.

~ Joe Austin, "The Alternative Way to Invest in AI and Still Win Big," Stansberry Investor Hour, June 30, 2025

Dan Rasmussen: "Investing is a game of meta-analysis"

Investing is not a game of analysis, it's a game of meta-analysis.  It's not what you think, it's what you think relative to what everyone else thinks...  Instead of saying, "How positive do I feel about this stock or its prospects?," flip it and ask, "How positive does everyone else think about this?" and then look for the places where you're most likely to disagree.  And that is the place where the best investments are found.

~ Dan Rasmussen, "The Private-Equity Reckoning is Here," Stansberry Investor Hour, 50:35 mark, March 17, 2025

Pieter Slegers on investing and learning

Keep growing and be a learning machine.  I definitely don't consider myself, for example, the smartest guy in the room...  How can you offset it?  Just by reading as much as you possibly can...  The first thing I do, every first two hours - I'm a morning person, an early bird - every day between 5 am and 7 am, I just read...  Last year I read 91 books...  Everything can be found in books and by reading, buying a $20 book, and basically learning from the best person in the world about a certain topic.  That's amazing.  And when you combine these books with having some great mentors in your life, people who are maybe farther than you in what you are doing, well that's a very powerful combination...  If you reach out to people asking for help, asking for advice, you will be surprised how many people are willing to help you, especially people with a lot of experience.  They love to help you, especially people with a lot of experience.  They love to help other people get along the way.

~ Pieter Slegers, "How to Spot Rare Quality Businesses Among All the Losers," Stansberry Investor Hour, 55:15 mark, February 18, 2025

Tony Deden on investing

I'm not so sure that the business of deploying your capital is something that anybody could do just because they want to or because they're intelligent and smart and they have a medical degree or whatever it is they do.  I think it's a matter of common sense and temperament more than it is one of knowledge and intellect.

~ Tony Deden, "Tony Deden - Master Value Investor," State of the Markets, 1:14:50 mark, January 10, 2025

Herb Greenberg on investing and being willing to make mistakes

When I look back I think "gosh, what I've learned."  Because of the mistakes I've made.  It's all because of the mistakes.  That's how you learn.  I think that's how you learn how to be an investor.  And if you approach it thinking, "oh my god, I'm going to make a mistake," you're not going to move forward.

~ Herb Greenberg, "Gunslinging Gambler or Cautious Investor: Which One Are You?," Stansberry Investor Hour, 10:00 mark, December 30, 2024

Kevin Duffy on investing: using the past to inform the future

But enough about the past.  Investing, to paraphrase Danish philosopher Søren Kierkegaard, must be understood backwards, but lived forward. 

Where some see randomness and others statistical certainty, the economic historian and forward-looking investor sees patterns and probabilities, motivations and biases, individual calculation and group error.  At times, and to no one’s surprise, guesses about the future can diverge wildly.

~ Kevin Duffy, "Countervailing Forces," The Coffee Can Portfolio, p. 3, October 22, 2024

Benjamin Graham on stock investing

Although there are good and bad companies, there is no such thing as a good stock; there are only good stock prices, which come and go.

~ Benjamin Graham

Seth Klarman on contrary investing

Generally, the greater the stigma or revulsion, the better the bargain.

~ Seth Klarman

Simon Handrahan on two keys to investing

Investing requires the arrogance to go it alone and the humility to follow others’ better ideas. 

~ Simon Handrahan, MOS Capital, tweet, March 28, 2024

Stanley Druckenmiller on patience and investing

I think it's one of the most important things to do is not to play when you don't see a fat pitch.

~ Stan Druckenmiller

Charlie Munger on how investing isn't like physics

I think [Warren and I] have had some effect [on investing and thinking], but they’re still teaching the Efficient Market Theory at business schools.  The old ideas die hard. And by the way, it’s roughly right.  It’s just the very hard form, which everybody believed.  They believed it was impossible, they didn’t think it was rare.  They thought efficiency was absolutely inevitable, like physics.  I call it physics envy.  That’s what they had in the finance field, they wanted to make their subject like physics.  Now, what kind of a nut would want to make stock markets like physics?  It ain’t like physics.  It’s more like a mob at a football game.

~ Charlie Munger

January 1, 1924 - November 28, 2023

John Hempton on risk management and position sizing

The size of the position has to be determined by what you can lose because it's the fat ugly tails that kill you in this business.  It's not that I don't like to win.  It's that I hate losing.  "Hate losing" is necessary for survival.  I do like to win.  Believe me, I like to win.  The business is built around taking care of the losses.

~ John Hempton, interview, HedgeD, With A Capital "D", March 22, 2023

Kevin Duffy on the predictive value of financial markets

Most times financial markets are vaguely right, sometimes wildly wrong.  The key to successful investing is recognizing the difference.

~ Kevin Duffy, tweet, August 19, 2023

Morgan Housel on the investment game

The biggest thing is realizing that there are a million different games to play and you have to figure out the game that works for you.  A lot of investors get tripped up because they start to emulate maybe somebody on TV, maybe somebody on Twitter, maybe someone in their own household, and they start playing a game that is the wrong game for them.

~ Morgan Housel, "The Secret to Good Investing? Look Within" by Lauren Foster, Barron's, August 5, 2023

Seth Klarman on investing

Investing is the intersection of economics and psychology.

~ Seth Klarman, interview with Charlie Rose, The Great Investors, 4:30 mark, July 9, 2023

Joel Tillinghast shares lessons for investors

Q: When you think about your own influence on the firm [Fidelity Investments] and the people who will be there after you've retired, what do you hope your main lessons will be for them?

A: Stick to the long view.  Compare price with value.  Think about risks that are not immediately in view.  Favor founder-led companies that offer something the customers think is very valuable.  Dare to explore companies where management doesn't give much guidance and where there aren't many analysts.  I think a lot of analysts are afraid to go where management doesn't spoon feed them and the Street isn't there to say, "$3.45 is the consensus number."  Don't hold too many path-dependent companies, especially if they don't have moats.  I hope that they'll take some of that, especially the "take the longer view."

~ Joel Tillinghast, "The Art of Investing" interview, Morningstar's The Long View, 25:35 mark, May 31, 2023