During his recent interview with the Trinity Student Managed Fund Podcast, Howard Marks discussed a number of topics drawn from decades of experience that reveal a philosophy rooted in discipline, patience, and a steadfast commitment to values. “We didn’t have a napkin,” Marks quipped, reflecting on OakTree’s humble beginnings. “We … Read More
Howard Marks: Why Long-Term Investors Must Rely on Skill, Not Chance
In his book Mastering the Market Cycle, Howard Marks dedicates an entire chapter to Cycle Positioning. He explains, “Successfully positioning a portfolio for the market movements that lie ahead is dependent on what you do (turning aggressive or defensive) and when you do it (based on a superior understanding of what cycles … Read More
The Black Swan and Our Fatal Blindness to the Unexpected
One of my favorite investing-related books is The Black Swan: The Impact of the Highly Improbable by Nassim Nicholas Taleb. Recommended by both Jeff Bezos and Bill Gates, it offers a sharp, irreverent, and sweeping meditation on how rare, unpredictable events shape our world far more than the tidy stories … Read More
Ray Dalio: The 5 Step Process For Successful Portfolio Management
In this interview with The Deal, Ray Dalio, the founder of Bridgewater Associates and a titan of the investment world, distills his philosophy into a framework of timeless principles. His approach, rooted in pattern recognition and radical transparency, offers invaluable lessons for investors navigating volatile markets. “When I was making … Read More
Cliff Asness: Why Markets Have Gotten Less Efficient
During his recent interview with the Stigler Center, Cliff Asness, founder of AQR Capital Management, diagnosed the current state of markets saying. “Markets are assuredly not perfectly efficient,” channelling his mentor Gene Fama, but he warns they’ve grown “prone to bouts of extreme inefficiency.” Asness points to two glaring examples: … Read More
Michael Mauboussin: The Hard Truth About Drawdowns
Let’s cut to the chase: if you can’t stomach big drawdowns, you shouldn’t be investing in stocks. As Michael Mauboussin and Dan Callahan put it in their latest Morgan Stanley report, Drawdowns and Recoveries, Charlie Munger’s take on this is brutally clear: “I think it’s in the nature of long-term … Read More
Howard Marks: The Essence of Investing Is Risk for Profit
During his recent panel discussion at the 2025 Qatar Economic Forum on Bloomberg Live, Howard Marks said: “The essence of investing is appropriately bearing risk for profit.” In this conversation he laid bare how risk, uncertainty, and judgment shape the core of long-term investing. Marks emphasized the importance of understanding … Read More
Howard Marks on Luck, Integrity, and Being Unemotional
Listening to Howard Marks talk about his journey, you quickly realize he isn’t just sharing a career story — he’s explaining how to survive and thrive in investing and in life. One of the biggest lessons he repeats is simple but powerful: investing is a mental game. “Investment management is … Read More
Howard Marks: “Excessive Certainty Is The Enemy”
Howard Marks is the kind of investor who challenges the way you think. In this interview, he shares insight after insight, all with the steady, grounded perspective that only comes from decades of navigating real markets. What really stands out is his consistent focus on risk. “The challenge, the real … Read More
David Abrams: Focus on Multiple Future Paths in Investing
David Abrams, Founder of Abrams Capital and former Baupost Group investor, seldom speaks publicly. In a rare interview with Value Investing with Legends, he shared key principles behind his investing strategy. Investing begins with a simple but critical question: “What’s the risk?” As David Abrams explains, the first step is understanding … Read More
Warren Buffett: Why Concentration Beats Diversification
In his 1993 Berkshire Hathaway Annual Letter, Warren Buffett explained how he and Charlie Munger figured out early that trying to make dozens of brilliant investment decisions is a losing battle. As Buffett puts it, “Charlie and I decided long ago that in an investment lifetime, it’s just too hard … Read More
Luck vs. Skill in Investing: Why There Are No Gurus, Only Cycles
During their recent episode, Taylor, Carlisle, and Michael Gayed discussed Luck vs. Skill in Investing: Why There Are No Gurus, Only Cycles. Here’s an excerpt from the episode: Tobias: Self abnegnation. I don’t mind that as a strategy. Michael: Well, I’ll tell you something. Actually, I’m half joking about it, … Read More
Howard Marks: Is Now the Time to Exit the Market?
In this interview with The Market, Howard Marks suggests that stocks are currently overvalued by 20-30%, with a 60-65% probability the market will be lower in a year. However, there’s still a 35-40% chance it could rise, highlighting uncertainty. While a downward tendency exists, it’s not a certainty, and valuations … Read More
Mohnish Pabrai: How the Kelly Formula Can Improve Your Financial Strategy
In his book The Dhandho Investor, Mohnish Pabrai discusses the Kelly Formula, a strategy for determining the optimal fraction of a bankroll to bet on favorable odds. Using examples, Pabrai illustrates how to calculate the edge (expected value) and apply the formula to maximize returns while managing risk. For instance, … Read More
Cliff Asness: Investors Should Avoid These Two Extremes
In this interview with the Insightful Investor, Cliff Asness discusses the challenge of evaluating an investment strategy during difficult periods. He warns against two extremes: abandoning a strategy too quickly due to short-term losses or stubbornly refusing to adapt when necessary. He highlights Warren Buffett’s ability to stick to his … Read More
Howard Marks on Smart vs. Lucky: Lessons for Investors
In this Insight Conversation with Annie Duke, Howard Marks reflects on a key lesson he learned from his early studies in investment: the quality of a decision cannot be judged by its outcome. Success can result from poor decisions, and many investors are often “right for the wrong reasons.” He … Read More
Bill Nygren: How To Increase Your Odds Of Success
In this interview with Value Investing With Legends, Bill Nygren explains his investing strategy in simple terms. His team typically invests around 2% in each stock and avoids buying if the stock exceeds 3%. If a stock grows beyond 4%, they trim their holdings. They focus on managing risks sensibly … Read More
The Risks of Shorting MSTR and Long Bitcoin
During their recent episode, Taylor, Carlisle, and Jason Buck discussed The Risks of Shorting MSTR and Long Bitcoin. Here’s an excerpt from the episode: Jason: Well, the other thing we were talking about before, that I would caution everybody on and that’s what I’ve seen too much of on Twitter, … Read More
Mohnish Pabrai: Aim for a Home Run, Settle for Breaking Even
In this Q&A session with MBA students at Columbia Business School, Mohnish Pabrai discusses the importance of assessing potential risks and outcomes before making investments. He acknowledges that all businesses carry some level of uncertainty and a small probability of failure. Pabrai views investing as a game of probabilities, striving … Read More
Warren Buffett: Reaching For Yield Is Really Stupid, But It’s Very Human
In this interview with CNBC, Warren Buffett discusses the importance of aligning consumption with income rather than taking excessive risks to increase returns. He criticizes “reaching for yield,” calling it a dangerous and human tendency, as individuals often seek higher returns despite the risks. Instead, he advises adapting to lower … Read More
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