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  • Howard Marks on AI Investing, Second-Level Thinking, Warren Buffett, and Why Waiting Until You Feel Safe Means the Opportunity Has Passed

    Howard Marks, co-founder of Oaktree Capital and author of the investing memos Warren Buffett says he reads first, returned to the My First Million podcast for a wide-ranging conversation with Shaan Puri and Sam Parr. Marks explains why he rewrote his AI memo after his son pushed back, what AI can and cannot take from professional investors, how Oaktree deployed $450 million a week while the world thought finance was ending, and why the sentence “I’m 100% convinced” is the most dangerous one in markets. Along the way he covers his 39-year partnership with Bruce Karsh, personal stories about Warren Buffett and Charlie Munger, parenting, career choice, and the two books that shaped his thinking.

    TLDW

    Marks updated his AI memo because his VC son Andrew told him too much had changed, and he now sees AI as unprecedented on two axes: autonomy (every prior technology was a tool; AI can be given a job and figure out how to do it) and unpredictability (he never felt the internet was beyond comprehension, but nobody knows the shape of an AI future). He expects AI to “defrock” mediocre active investors the way indexation did, while insight, judgment about people, and decisions with no historical precedent may remain human. He retells the Lehman Brothers moment: Oaktree raised an $11 billion distressed debt fund before the crisis, then invested $7 billion in a single quarter on the logic that if the world melted down nothing would matter, but if it did not and they had failed to invest, they had failed at their jobs. The through-line is acting despite fear: the battle hero is afraid and does it anyway, and if you wait until there is nothing to be afraid of, the opportunity has passed. He closes with the recipe for his partnership with Bruce Karsh (shared values, complementary skills, appreciation), stories about Buffett and Munger, advice to live your life your own way, and book recommendations: A Short History of Financial Euphoria and Fooled by Randomness.

    Thoughts

    The most valuable thing in this conversation is not any single call, it is watching a 79-year-old investor with five decades of pattern recognition publicly change his mind. Marks wrote an AI memo in December, his son told him in February that it was already stale, and he rewrote it entirely. When the host teases him that he sounds “a little seduced,” Marks does not get defensive. He distinguishes between upgrading an opinion on new evidence and getting emotional about an asset. That distinction is the whole game. Most people treat their published positions as identity; Marks treats his as drafts. The irony he would appreciate: the willingness to say “so much has happened, I have to update” is exactly the behavior that made his original reputation, and it is exactly what the “I’m 100% convinced” crowd cannot do.

    His AI framing is sharper than most full-time commentators manage. Every previous technology, from the railroad to the internet, was a tool that made humans faster. AI is the first with autonomy: you give it a job, not instructions. And it is the first innovation he has ever called genuinely unpredictable. Notice what that combination does to his old computer framework. Computers could only read, remember, add, subtract, and compare, a limited list that still beat most people. The question that decides everything, for investing and beyond, is whether AI’s list is limited or unlimited. Marks does not pretend to know, which is precisely why his answer is credible.

    The Lehman story deserves to be studied as decision-making under true uncertainty, not as a war story. There was no data and no historical analogy for the end of the financial system, only supposition. So Oaktree reframed the decision as an asymmetry: if the world melts down and we invest, it does not matter; if the world survives and we did not invest, we failed. That logic is available to anyone. What is not available to most people is the willingness to act on it while feeling terrible, and Marks is emphatic that he felt terrible. He read the same newspapers as everyone else. The lesson is that trepidation is not a signal to wait; it is the price of admission. Confidence is not the tell of a good decision. Structure is.

    The quietest and maybe most transferable idea here is the credibility flywheel. After a fund did well, Oaktree raised a smaller fund next, because great results meant assets had appreciated and the opportunity had shrunk. That is speaking against your own economic interest, repeatedly, for twenty years. The payoff came when they asked for $11 billion before the crisis and investors believed them, because Howard and Bruce do not cry wolf. Most people optimize each individual transaction and wonder why nobody trusts them at the moment trust matters. And it is not a coincidence that his partnership advice (shared values, complementary skills, appreciation), his parenting advice (let your kid be smarter than you, let them make choices), and his fundraising record all reduce to the same move: give up small ego wins now to compound trust for decades.

    Key Takeaways

    • Marks wrote his first AI memo around December 9th, then rewrote it entirely in early February after his son Andrew, a venture capitalist working with AI companies daily, told him too much had changed. Updating on new facts is a feature of good thinking, not a flip-flop.
    • He upgraded his opinion of AI because of qualities he considers unprecedented: it can discuss its own strengths and weaknesses, use humor, and put information in the context of the specific person it is talking to.
    • AI’s first unprecedented quality is autonomy. Every prior technological innovation, from the railroad to computers to the internet, was a tool to increase productivity. Nothing before could be given a job without being told how to do it.
    • AI’s second unprecedented quality is unpredictability. Marks never felt the internet was beyond comprehension or prediction. With AI, he says nobody knows the shape of the future, a feeling he has never had about any prior technology.
    • Indexation exposed that most active equity investors could not do what they claimed and pushed many out of the business. Marks expects AI to “defrock” another group of professionals whose talents are not as great as they purport.
    • His old framework for computers: they could only read, remember, add, subtract, and compare, but they did it with more data, faster, and without arithmetic or emotional mistakes, so the limited list still beat most people. The big question for AI is whether its list is limited or unlimited.
    • A large share of what AI does is knowing history and extrapolating patterns. There will always be events with no history to train on, and some people simply understand the probability distribution of future events better. That may be where human investors survive.
    • Part of Oaktree’s value has been refusing to invest with bad people based on undefinable signals, the “hair on the back of your neck” test. If AI has no hair on its neck, experienced judgment keeps a role.
    • Second-level thinking, the opening chapter of his first book, says that if you do not see anything different from everybody else, you cannot possibly be superior. You need a variant perception, you have to bet on it, and you have to be right.
    • Asked whether second-level thinking can be taught, Marks says probably not. He can teach its importance, but not how to have perceptions that are both at odds with consensus and correct. In basketball you cannot coach height; in investing there is something called insight, and some people have it.
    • He is genuinely unsure whether AGI, defined as AI doing everything a human can do, will arrive. Whether there are things AI will never do “even when it reaches full flower” is one of the central mysteries.
    • Before the 2008 crisis, the largest distressed debt fund in history had been Oaktree’s own $2.5 billion fund from 2002. In 2007-08 they raised $11 billion because they saw distress coming, and kept it on the shelf for deployment when the stuff hit the fan.
    • When Lehman went under in September 2008, there was no data and no prior experience for the end of the financial world, only supposition, borrowing the Harvard epidemiologist’s three bases for decisions: data, analogies to past experience, and supposition.
    • The deployment logic was an asymmetry: if the financial world melts down and we invest, it does not matter; if it does not melt down and we failed to invest, we did not do our job. So they had to invest.
    • Bruce Karsh invested an average of $450 million a week for 15 weeks, roughly $7 billion in a single quarter, buying debt of private-equity-owned companies at prices where Oaktree would break even if the companies were worth a fifth or a fourth of what buyers had paid a few years earlier.
    • They were “absolutely not confident.” Marks argues people who think probabilistically and admit ignorance and uncertainty cannot act without trepidation, and that acting anyway is the job.
    • His memo “Taking the Temperature” reviews the five major macro calls of his career; every one was made with doubt. Markets crash because the news is terrible, and he reads the same terrible news as everyone else, then overcomes it.
    • The battle hero framing: a hero is not someone who is unafraid, but someone who is afraid and does it anyway. If you are running into a hail of bullets without fear, something is wrong with you.
    • The signature line: if you wait until you have nothing to be afraid about, the opportunity has probably passed.
    • Raising $11 billion rested on a reservoir of goodwill built since 1988, a strategy purpose-built for crisis with proven results in 1991 and 2001-02, the pitch that a crisis fund hedges portfolios positioned for prosperity, and the ability to point at specific flaws: the market was failing at its main job of acting as a disciplinarian and saying no to dumb ideas.
    • From the Spy Game movie: when did Noah build the ark? Before the flood. You cannot raise money during a crisis because the news is too terrible, so you build the ark in advance.
    • Oaktree’s contrarian fund sizing built its credibility: after a fund produced great results, the next fund was smaller, because great results meant assets had appreciated and opportunities had shrunk. Most managers raise bigger funds on the back of good numbers. Twenty years of that earned them trust when it counted, and sometimes you have to speak against your own interest.
    • During the 1998 LTCM meltdown, a young portfolio manager told Marks “I think this is it, we’re melting down.” Marks heard him out, then said: now go back to your desk and do your job.
    • He and Bruce Karsh have been partners for 39 years and have never had a fight, partly because neither is a financial maximizer and most fights are about money. They have intellectual disagreements, not fights.
    • The keys to partnership, from his 2002 memo: shared values and complementary skills. One aggressive partner and one timid one, or one ethical partner and one corner-cutter, cannot last.
    • The cowboys-and-chickens story: of the roughly 40 investment banks on the AT&T tombstone ad, almost all eventually disappeared. In bad times the chickens say the cowboys are getting us killed; in good times the cowboys say the chickens are holding us back. Mismatched values kill firms.
    • Complementary skills mean each partner can do things the other cannot, so both are additive. If one partner can do everything, the other is eventually seen as overpaid. Bruce manages the money; Howard goes on the road and does the podcasts. The third element: be appreciative, and thank your lucky stars your partner does the things you do not want to do.
    • On parenting: a Wall Street psychiatrist observed that his patients’ problems were inversely proportional to the support they got from their fathers. Marks finds it terrible how many successful men need to assert superiority over their sons, and says he always let Andrew be smarter than him in some things.
    • When his daughter had to choose between two good schools, he and his wife let her decide, on the logic that neither option was bad and kids need experience making choices, including incorrect ones.
    • His favorite quote, from Christopher Morley: there is only one success, to live your life your own way. You cannot let friends, parents, or society decide what you should do. Find something that plays to your strengths, avoids your weaknesses, and makes you happy, while knowing that in 20 years you will be a different person.
    • By his own account, Marks made his early career decisions unconsciously and haphazardly until about age 49-50, when he left to start Oaktree in 1995. He landed in high yield bonds because a boss called him in 1978 about “a guy named Milken in California,” and if that call had come at lunchtime, someone else would have gotten the career.
    • The Mark Twain rule: it ain’t what you don’t know that gets you into trouble, it’s what you know for certain that just ain’t true. No sentence starting with “I could be wrong, but” ever hurt anyone; the dangerous sentence is “I’m 100% convinced.” If you bet like you are 100% right and it was really 80/20 and the 20 comes up, that is how you get into big trouble.
    • The Buffett relationship began with Enron’s collapse: Oaktree was the largest holder of the debt of off-balance-sheet entity Osprey, Buffett was second largest, and Buffett gave Oaktree his proxy to run the position. Bruce’s masterful restructuring led to a thank-you letter, a lunch in Omaha, and a friendship.
    • Buffett is the reason the first book exists: in 2009 he told Marks “you should write a book, and if you do, I’ll give you a blurb.” Marks had planned to write one in retirement, but you cannot let a note like that sit. The result was The Most Important Thing.
    • What people do not know about Buffett: the depth of his love for Charlie Munger. Buffett’s farewell note described Charlie as the big brother and himself as the little brother, and their relationship was suffused with humor. Marks says the same dynamic describes him and Bruce.
    • Munger’s greatest credited contribution was talking Buffett out of cigar butt investing (picking up discarded companies with three free puffs left) and convincing him to buy great companies at a good price instead of any company at a great price.
    • Buffett and Munger probably had the highest combined IQ of any partnership in history, but different kinds: Munger a classicist, humanist, and man of letters who talked about ideas rather than money; Buffett an incredible computing machine.
    • Book recommendations: A Short History of Financial Euphoria by John Kenneth Galbraith, on the mental weakness that gives rise to booms and busts, and Fooled by Randomness by Nassim Nicholas Taleb, on why in the short run anything can happen, which shapes attitudes toward risk, portfolio construction, and whether a great published track record means skill or luck.

    Detailed Summary

    Changing His Mind on AI

    The conversation opens with the story behind Marks’s updated AI memo. He wrote the first version around December 9th. In early February his son Andrew, a venture capitalist whose portfolio companies use and build AI, told him: “Dad, so much has happened. You have to update the memo.” Marks rewrote it entirely. When the hosts needle him that the sequel sounds “a little seduced,” he pushes back on the framing: he upgraded his opinion because of observable capabilities, including AI’s ability to discuss its own strengths and weaknesses, use humor, and contextualize information to the specific person using it. He identifies two qualities he considers historically unprecedented. First, autonomy: everything from the railroad to the internet was a tool to speed humans up, while AI can be handed a job without being told how to do it, which is also the source of the nagging concern that it may take over. Second, unpredictability: he never once thought the internet was beyond comprehension or prediction, but with AI he says nobody knows the shape of the future.

    What AI Does to Investors

    Asked whether AI will be able to do what he does, Marks reaches for the indexation precedent: index funds revealed that most active equity managers could not do what they claimed, and pushed many out of the business. AI, he says, will “defrock another group of people whose talents are not as great as they purport.” He recalls his old line about computers, which could only read, remember, add, subtract, and compare, yet still beat most people because they did those five things with more data, faster, and without arithmetic or emotional errors. The decisive question for AI is whether its list of capabilities is limited or unlimited, and he admits he does not know. The hosts note that Buffett reading the Moody’s manual page by page is now a task AI does in a heartbeat. What might remain human: events with no history to train on, since so much of AI is pattern recognition over history; superior intuition about the probability distribution of future events; and people judgment, the undefinable signal when the hair on the back of your neck goes up about someone. If AI has no hair on its neck, experienced investors with judgment keep a role.

    Second-Level Thinking and the Limits of Teaching Insight

    Marks retells the origin of his first book: Columbia asked for a sample chapter, he sat down and wrote one he had never consciously thought about, and it became chapter one, on second-level thinking. The idea: if you do not see anything different from everybody else, you cannot possibly be superior. You need a variant perception, a belief that consensus overstates or understates a company’s quality, growth, earning power, or deserved multiple; you must bet on that perception; and you must be right. Can it be taught? He says the answer is more no than yes. He can teach the importance of second-level thinking, but not how to have perceptions that are both contrarian and correct. His analogy: in basketball you cannot coach height, and in investing there is something called insight that some people simply have. Whether AI can have it is, for him, bound up with the AGI question and genuinely unknown.

    Lehman, the $11 Billion Fund, and Investing at the End of the World

    Oaktree’s biggest call illustrates decision-making with no precedent. Before 2007, the largest distressed debt fund in history was Oaktree’s own $2.5 billion 2002 fund. Sensing distress coming, they raised $11 billion in 2007-08 and kept it on the shelf. Then Lehman Brothers failed on September 15, 2008, and people were talking about the end of the world, all financial institutions melting down, everything having to do with money atomizing. Marks cites a Harvard epidemiologist: decisions rest on data, analogies to past experience, and supposition, and at that moment there was no data and no past experience. The reframe that unlocked action: if the financial world melts down and we invest, it does not matter; if it does not melt down and we did not invest, we did not do our job. Bruce Karsh deployed an average of $450 million a week for 15 weeks, about $7 billion in a quarter, buying debt of companies bought by private equity years earlier at prices where Oaktree would break even even if the companies were worth a quarter or a fifth of the buyout price. Quantitatively easy, emotionally brutal: they were, in his words, absolutely not confident.

    Trepidation Is the Price of Admission

    Marks generalizes the feeling in his memo “Taking the Temperature,” which reviews the five major macro calls of his career: all were made with doubt. Markets crash because the news is terrible, and he consumes the same news feeds as everyone else, so the terrible news looks terrible to him too. The difference is overcoming it. People who look at the world probabilistically and admit ignorance and uncertainty cannot act without trepidation, and if you act without any, something may be wrong with you. He recalls the 1998 LTCM and Russian ruble crisis, when a young portfolio manager came to him convinced everything was melting down; Marks heard his concerns and sent him back to his desk to do his job. The battle hero is not unafraid; he is afraid and does it anyway. And the line that anchors the episode: if you wait until you have nothing to be afraid about, the opportunity has probably passed.

    How You Actually Raise $11 Billion

    Pressed on the mechanics of raising the fund, Marks lists the ingredients. Twenty years of managing money well since 1988 created a reservoir of goodwill. The strategy was purpose-built for crisis, with excellent results through the 1991 and 2001-02 downturns. The pitch positioned the fund as a hedge: most investor portfolios are set up for prosperity, so it makes sense to own something that does particularly well when the stuff hits the fan. And Oaktree could point at specific flaws in the environment, chiefly that the market was failing at its main job of acting as a disciplinarian, the job of telling people that a dumb idea does not make sense and will not be funded. When the market stops saying no, dumb ideas get financed, and when they turn out to be dumb, people lose money. He adds the Spy Game line he and his wife love: when did Noah build the ark? Before the flood. You cannot raise money during a crisis because the news is too terrible. Finally, credibility compounding: Oaktree repeatedly raised smaller funds after successful ones, reasoning that great results meant opportunities had shrunk. Two decades of speaking against their own interest meant that when Howard and Bruce said there was a great opportunity, investors believed they meant it.

    39 Years with Bruce Karsh: Shared Values, Complementary Skills, Appreciation

    Marks calls his partnership with Bruce Karsh, 39 years old that month, one of the greatest things in his life after family and close friendships. They have never had a fight, which he attributes partly to neither being a financial maximizer, since most fights are about money. His 2002 memo formula: shared values and complementary skills. Mismatched values, like one cowboy and one chicken, or one ethical partner and one corner-cutter, doom a firm; he illustrates with the AT&T tombstone ad listing roughly 40 investment banks, nearly all of which eventually vanished as the chickens blamed the cowboys in bad times and the cowboys mocked the chickens in good times. Complementary skills mean each partner does what the other cannot: Bruce approached Marks in 1987 with the novel idea of a distressed debt fund, and from the beginning Bruce stayed back managing money while Howard went on the road and, later, on podcasts. The third element is appreciation: thank your lucky stars you have a partner who will do the stuff you do not want to do.

    Parenting Without Asserting Superiority

    Asked how he raised a son he not only loves but enjoys, Marks cites a decades-old Forbes profile of the only psychiatrist with an office on Wall Street, whose patients’ problems were inversely proportional to the support they got from their fathers. He marvels at how many successful men need to prove they are smarter than their sons, and says he always let Andrew be smarter than him in some things while giving full support to whatever his kids wanted to do, provided it was not injurious. When his daughter got into both good Los Angeles schools, he and his wife had a preference but let her choose, reasoning that they could be wrong, neither option was bad, and children need experience making choices, including incorrect ones.

    Live Your Life Your Own Way

    On career choice, Marks confesses he did a terrible job himself: his decisions for his first decades were unconscious and haphazard, and by his own account he did not really make intentional choices until he left to co-found Oaktree in 1995, around age 49. He went to Citibank because of a good summer job, moved from equities to bonds because his equity research was unsuccessful and he was told to get out, and moved to California for sunshine and palm trees. In 1978 the head of the bond department called the fairly idle Marks about “a guy named Milken or something in California” dealing in high yield bonds, and a legendary career resulted from being at his desk when the phone rang, a story straight out of Outliers. His advice to students at Wharton, Harvard, and Columbia is built on his favorite quote, from writer Christopher Morley: there is only one success, to live your life your own way. Find something that plays to your strengths, avoids your weaknesses, and makes you happy, which really means refusing to let friends, society, or parents decide for you, while accepting the hard truth that you will be a different person in 20 years and must choose anyway.

    Humility as Risk Management

    When the hosts remark on his humility, Marks turns it into a risk framework via Mark Twain: it ain’t what you don’t know that gets you into trouble, it’s what you know for certain that just ain’t true. No sentence beginning “I could be wrong, but” or “I don’t know, but” ever got anybody into trouble; the dangerous sentences begin “I’m 100% convinced that.” If you bet as though you are certain and the odds were really 80/20 and the 20 comes up, that is how you get into big trouble. You make the investment because you believe in it, but you must see the other side.

    Buffett and Munger Stories

    The Buffett friendship began in the wreckage of Enron, which did most of its misbehavior through off-balance-sheet entities. Oaktree became the largest holder of the debt of one called Osprey; Warren Buffett was the second largest, gave Oaktree his proxy, and let Bruce run the position, which Bruce restructured masterfully for a big win. Around 2003-04 Buffett wrote Bruce a note saying nice job, and if you find yourself in Omaha, we’ll have lunch; Bruce and Howard promptly found themselves in Omaha. In 2009, Buffett told Marks he should write a book and promised a blurb, which is why The Most Important Thing exists years before the retirement book Marks had planned. What people do not know about Buffett, Marks says, is the depth of his love for Charlie Munger, expressed in Buffett’s farewell note describing Charlie as the big brother and himself as the little brother. Munger’s celebrated contribution was talking Buffett out of cigar butt investing, the practice of picking up discarded companies for three free puffs, and toward great companies at a good price. They probably had the highest combined IQ of any partnership in history, but of different kinds: Munger the classicist and man of letters who preferred talking about ideas over money, Buffett the incredible computing machine.

    Homework from Howard Marks

    His two book recommendations: A Short History of Financial Euphoria by John Kenneth Galbraith, which shaped his objective view of cycles by teaching the mental weakness that gives rise to booms and busts (he was lucky enough to meet Galbraith), and Fooled by Randomness by Nassim Nicholas Taleb, which argues that in the short run anything can happen because of randomness, with consequences for how we think about risk, portfolio construction, and whether a hot track record reflects skill or luck. He notes, with characteristic self-awareness, that his belief in randomness may be his rationale for not being a decisive thinker, and offers his own memos as the “classic comic” version of Taleb. The episode closes with a nod to his January 2021 memo Something of Value, written after three generations of the Marks family spent the pandemic under one roof arguing about value investing with Andrew.

    Notable Quotes

    “If you wait until you have nothing to be afraid about, probably the opportunity has passed.”

    Howard Marks, on why great investments are made with fear intact

    The thesis of the whole conversation, delivered in the cold open and again in the LTCM story.

    “Second level thinking basically says if you don’t see anything different from everybody else, you can’t possibly be superior.”

    Howard Marks, explaining the first chapter of The Most Important Thing

    The variant perception requirement: see it, bet on it, and be right.

    “In basketball there’s a saying, you can’t coach height. And I think there’s something called insight. And I think some people have it.”

    Howard Marks, on why second-level thinking probably cannot be taught

    Also his open question about AI: whether machines can ever have insight.

    “But if we don’t invest and the financial world doesn’t melt down, then we didn’t do our job. So, we have to do it.”

    Howard Marks, on Oaktree’s reasoning the week Lehman Brothers failed

    The asymmetry that justified investing $450 million a week for 15 weeks.

    “A battle hero is not somebody who’s unafraid. It’s somebody who’s afraid but does it anyway.”

    Howard Marks, sending a panicked portfolio manager back to his desk in 1998

    His answer to the LTCM-era fear that everything was melting down.

    “When did Noah build the ark? Before the flood. You got to build the ark before the flood.”

    Howard Marks, quoting the movie Spy Game on raising crisis funds in advance

    Why the $11 billion was raised in 2007-08 and kept on the shelf.

    “No sentence that starts with I could be wrong but or I don’t know but ever got anybody into trouble. The sentences that get people into trouble are I’m 100% convinced that.”

    Howard Marks, channeling Mark Twain on certainty

    His practical definition of humility as a risk-management tool.

    “The key to a successful partnership is shared values and complementary skills.”

    Howard Marks, on 39 years with Bruce Karsh, from his 2002 memo

    Plus the third element he adds now: appreciation for the partner who does what you will not.

    “There is only one success to live your life your own way.”

    Howard Marks, quoting writer Christopher Morley, his favorite line for students

    The advice he gives at Wharton, Harvard, and Columbia, and admits he did not follow until age 49.

    Watch the full conversation with Howard Marks on My First Million here.

    Related Reading

  • Howard Marks on Why Most Investors Lose, the AI Bubble, India, and the Hunt for the $10 Bill Nobody Picked Up

    TLDW

    Howard Marks, co-founder of Oaktree Capital and the author of the memos every serious investor reads first, sat down with Nikhil Kamath for a wide-ranging conversation on his 50+ year career, the philosophy of Mujo (the inevitability of change), why he chose bonds over stocks, the difference between drifting down the river and seeing it, where we sit in the current cycle, AI as both threat and opportunity, why active management lost to indexation, and why the only way to outperform in a world full of smart, motivated, computer-literate competitors is “superior insight.” His core message: investing is a puzzle that cannot be solved by formula, and the only edge that lasts is being more right than the other person, more often, with the discipline to stay calm when everyone else is panicking or partying.

    Key Takeaways

    • Mujo is the operating system. Marks took Japanese literature at Wharton and walked away with one idea that shaped his whole career: change is inevitable, unpredictable, and uncontrollable. You cannot predict the future, but you can prepare for it.
    • Cycles are excesses and corrections, not ups and downs. The S&P 500 has averaged about 10% per year for 100 years, but it is almost never between 8% and 12% in any given year. The norm is not the average. Greed and fear push the pendulum past equilibrium every time.
    • The recovery is two years older. When asked where we are in the cycle, Marks notes the bull market continued from April 2024 through January 2026, so by definition we are deeper into the cycle, with a recovery distorted by the unique man-made COVID recession.
    • Drifting versus seeing the river. Marks describes the first 35 years of his career (roughly age 14 to 49) as drifting. Starting Oaktree in 1995 was the first truly intentional decision he made. Entrepreneurship forced proactivity on him.
    • Why bonds over equities. The contractual, predictable nature of debt suited his conservative temperament (his parents were adults during the Depression). He was not voluntarily moved to bonds in 1978; a boss reassigned him just in time for the birth of the high-yield bond market.
    • Distressed debt is the bigger story. Bruce Karsh joined in 1987 and has run roughly $70 billion in distressed debt since 1988, with profits well over 90% of the total profit and loss.
    • Excess return is getting paid more than the risk warrants. If the market thinks a borrower has a 5% default probability and you correctly conclude it is 2%, you collect interest priced for 5% risk while taking 2% risk. That gap is the alpha.
    • Oaktree’s default rate is about a third of the market. Over 40 years, roughly 3.6% to 3.7% of high-yield bonds default each year. Oaktree’s rate is roughly one-third of that, achieved through process discipline, institutional memory, and analysts who stay analysts for life.
    • If you are starting a career today, understand AI. Marks says the investor who will make the most money over the next 10 years is the one who best understands AI and its capabilities, whether they bet for or against it.
    • AI is excellent at pattern matching, but cannot create new patterns. Can AI pick the Amazon out of five business plans? The Steve Jobs out of five CEOs? Marks bets no. Most humans cannot either, which means there is still a role for exceptional people.
    • Indexation won because active management lost. Passive did not become dominant because it is brilliant. It dominated because most active managers failed and charged high fees for the privilege.
    • Bad times create openings for active managers, but most cannot take them. Panic drives prices down, but the same panic prevents most investors from buying. Wally Deemer: when the time comes to buy, you will not want to.
    • The job is simple but not easy. Find the best managers, the best companies, the best ideas. Charlie Munger told Marks: anyone who thinks it is easy is stupid.
    • Where is the $10 bill nobody picked up? Marks thinks it is around AI, but only for those with insight above the average. If you are average and you crowd into AI, you get average results in a bull case and worse in a bear case.
    • Quantitative information about the present cannot produce alpha. Andrew Marks (howards son) pointed this out to his father during the COVID lockdown. Everyone has the same data. Outperformance has to come from somewhere else.
    • Buffett’s edge was reading Moody’s Manuals when nobody else would. The pre-internet research process favored those willing to do tedious work alone. The format of the edge changes; the fact that edge requires doing what others will not, does not.
    • You cannot coach height. Marks can tell you that second-level thinking, contrarian insight, and the ability to evolve at 80 are essential. He cannot tell you how to acquire any of them.
    • India: Marks declines to opine. He has deployed roughly $4 billion in India but refuses to claim expertise on the Indian stock market or recommend a sector.
    • History rhymes. Marks credits Mark Twain. The lessons that repeat are lessons of human nature, which changes incredibly slowly.
    • Investing is a puzzle, not dentistry. Quoting Taleb, Marks observes that engineers and dentists succeed by repeating the right answer. Investors face a problem with no certain solution. If you need to be right every time, do not become an investor.

    Detailed Summary

    From Queens to Wharton: The Accidental Investor

    Howard Marks grew up in Queens, New York, in a middle-class family. Neither of his parents went to college, but his father was an intelligent accountant. Marks discovered accounting in high school, fell in love with its orderliness, and chose Wharton because he was told it was the best undergraduate business school in America. Wharton required a literature class in a foreign country and a non-business minor. For reasons he no longer remembers, Marks chose Japanese studies, then took Japanese civilization and Japanese art. He calls it the most important academic decision of his life because of one concept he encountered: Mujo.

    Mujo, Independence of Events, and Why You Cannot Predict

    Mujo, the turning of the wheel of the law, teaches that change is inevitable, unpredictable, and uncontrollable, and that humans must accommodate it rather than try to control it. Marks pairs this with his deep belief in the independence of events: ten heads in a row do not change the odds on flip eleven. Roughly 20 years ago he wrote a memo titled “You Can’t Predict. You Can Prepare.” A portfolio cannot be optimized for both extreme upside and extreme downside, but it can be built to perform respectably across many possible futures, if you suboptimize for the middle of the probability distribution.

    Why Cycles Exist

    If GDP averages 2% growth, why is it never simply 2%? Marks’s answer is excesses and corrections. Optimism leads producers to overbuild and consumers to overspend, growth runs above trend, then satiation and oversupply pull it back below trend. The S&P 500 averages 10% per year over a century, but the return in any given year is almost never between 8% and 12%. The norm is not the average because human beings are not average; they are alternately greedy and fearful.

    Where Are We Now?

    Two years ago Marks told the Norwegian Sovereign Wealth Fund’s Nicolai Tangen that we were near the middle of the cycle. Two years later, the bull market in stocks continued through January 2026, so by simple math the recovery is older. The COVID recession was a man-made anomaly: one quarter of negative growth followed by the best quarter in history, triggered by a deliberate global shutdown rather than by accumulated excess. That distorts every traditional cycle metric.

    Drifting Versus Seeing the River

    One of the most personal moments in the conversation is Marks’s confession that he drifted for the first 35 years of his career. He did not pick his career, his first job, or his transition from equities to bonds in any deliberate way. Other people pushed him; he said yes. The first proactive decision of his life was co-founding Oaktree in 1995 at age 49, and even that came largely because his wife and his partner Bruce Karsh pushed him into it. Once he had to lead, he had to be intentional. Leadership cannot be passive.

    The Bond Decision

    Marks did not choose bonds; bonds chose him. In May 1978 his boss at Citibank moved him to the bond department to start a convertible fund. Three months later another phone call asked him to figure out something called high-yield bonds being run by a guy in California named Milken. Marks said yes both times. He arrived at the front of the line for high-yield in 1978 and has been there for 48 years.

    The conservative temperament fit. Marks’s parents were adults during the Depression, so he grew up hearing “don’t put all your eggs in one basket” and “save for a rainy day.” Bonds offered contractual, predictable returns. The phrase “junk bonds” was a bias that made the asset class cheaply available to anyone willing to do the analytical work.

    Distressed Debt and Excess Return

    When Bruce Karsh joined in 1987, Oaktree launched what Marks believes was the first distressed debt fund from a mainstream institution. Karsh has managed about $70 billion since 1988 with well over 90% of the total being profit. The core skill is predicting default probability better than the market. If consensus prices a borrower at a 5% default risk and you correctly assess 2%, the interest you receive is overpaid relative to actual risk. Marks calls this “excess return” and credits Mike Milken with the foundational insight: lend to borrowers others will not, demand interest beyond what compensates you, and the math works.

    Over 40 years, roughly 3.6% to 3.7% of high-yield bonds default annually on average. Oaktree’s default rate has been roughly one-third of that. Marks credits institutional culture (analysts who stay analysts for life), psychological stability in volatile periods, and a process that forces every analyst to ask the same eight questions of every company every time. In equity research, you can buy a stock for great management without examining the product, or for a great product without examining the management. In Oaktree’s bond process, you cover every base every time.

    Beginning a Career Today: The AI Question

    Asked what he would do today, Marks says the front of the line is AI. The investor who will succeed most over the next decade is the one who best understands AI, whether they bet for or against it. He notes that he was shocked by his own experience using Claude, but adds that he has not fired a single person and does not intend to.

    His view: AI excels at extracting patterns from history and applying them with discipline and without psychological wobble. But investing also requires creating new patterns. Can AI sit with five business plans and identify the future Amazon? Can it sit with five CEOs and pick Steve Jobs? Marks bets not. Then he adds the killer line: most humans cannot either. Which means the role for exceptional humans survives, but the bar gets higher.

    Why Indexation Won

    When Marks went to graduate school at the University of Chicago in 1968, his professor pointed out that most mutual funds underperformed the S&P after fees. Index funds did not exist yet; Jack Bogle launched the first one in 1974. Today, most equity mutual fund capital is passive. Marks’s controversial take: indexation did not win because it is great. It won because active management was so bad and so expensive. Even at equal fees, if active decisions are inferior, passive wins.

    Bad times create openings for active managers because panic drives prices down, but the same panic prevents most people from buying. Marks quotes the old trader Wally Deemer: when the time comes to buy, you will not want to. The advantage of an AI nudge that says “this is one of those moments, get your ass in gear and buy something” might genuinely add value, because it removes the emotion.

    Second-Level Thinking and Why You Cannot Coach It

    Marks’s first book, The Most Important Thing, has 21 chapters, each titled “The Most Important Thing Is…” Each one is different because so many things matter. The chapter on second-level thinking came to him spontaneously while writing a sample chapter for Columbia University Press. The argument is simple: if you think like everyone else, you act like everyone else, and you get the same results. To outperform, you must deviate from the herd and be more right than the herd. Different is not enough. Different and better is the bar.

    Can AI become a contrarian thinker? You can prompt Claude to give you only non-consensus answers, but the catch is that consensus is often close to right because the people building consensus are intelligent, educated, computer-literate, and motivated. Forcing non-consensus often forces wrong. The real edge is being non-consensus AND correct, which is a much narrower target.

    The $10 Bill That Nobody Has Picked Up

    Marks references the joke about the efficient market hypothesis: there is no $10 bill on the sidewalk because if there were, somebody would have already picked it up. He then concedes that the bill is probably around AI today, but only for those whose insight rises above the average. If you are average and you crowd into AI, you go along with the tide if it works and get crushed if it does not. Quoting Garrison Keillor’s Lake Wobegon, “where all the children are above average,” Marks notes that the math does not allow it. Most investors will not be above average, and acknowledging that is the first step toward becoming one of the few who are.

    Learning From Andrew, Buffett, and Onion-Skin Manuals

    Marks lived with his son Andrew during COVID and wrote a memo about it called “Something of Value” in January 2021. Andrew’s most important contribution was a near-revelation: readily available quantitative information about the present cannot be the source of investment alpha because everyone has it. Buffett’s edge in the 1950s was reading Moody’s Manuals (giant books printed on onion-skin paper with tiny type and zero narrative) when nobody else would. The medium changes; the principle that edge requires doing what others will not, does not.

    India

    Kamath asks Marks directly about India. Marks has deployed roughly $4 billion there but politely declines to claim any expertise on the Indian stock market or recommend a sector. He cautions Kamath about taking advice from people who do not know what they are talking about, and includes himself in that category on the question of India. The honesty is striking and is itself an investment lesson.

    History Rhymes, and Final Advice

    Marks reads Andrew Ross Sorkin’s 1929 and references it in an upcoming memo on private credit. He likes Mark Twain’s reputed line that history does not repeat but it rhymes, and Napoleon’s line that history is written by the winners of tomorrow. The lessons that rhyme are lessons of human nature, which evolves incredibly slowly. Fight or flight from the watering hole still drives behavior in financial markets.

    His final advice: investing is a puzzle, not engineering. A civil engineer calculates steel and concrete, builds the bridge, and the bridge stands. Every time. A dentist fills the cavity correctly and it stays filled. Every time. If you need that kind of reliability in your work, become a dentist. Investing is the act of positioning capital for a future that cannot be predicted accurately. You will be wrong sometimes. If something in your makeup cannot tolerate being wrong sometimes, do not become an investor. The puzzle has no final solution, which is exactly what makes it endlessly interesting.

    Thoughts

    The most useful thing Marks does in this conversation is admit, repeatedly and without ego, what he does not know. He does not know whether AI models differ in real intelligence. He does not know which sector in India to bet on. He does not know how to teach second-level thinking. He drifted for 35 years and only began making intentional decisions at 49. This honesty is the inverse of every guru selling certainty, and it is the actual content of the lesson he is trying to convey: epistemic humility is the precondition for superior insight, because you cannot acquire what you already think you have.

    The deepest insight in the conversation might be the one Andrew Marks (Howard’s son) gave his father during COVID: readily available quantitative information about the present cannot produce alpha because everyone has it. This is devastating in the AI era. If everyone is asking the same large language model the same question, the answers converge, and convergence is consensus, and consensus does not pay. The arms race for proprietary data, novel framings, and unconventional questions is the only thing that can break the convergence.

    Marks’s framing of cycles as excesses and corrections rather than ups and downs is genuinely useful. It reframes volatility from something to fear into something to expect, and reframes the question from “where are we going?” to “how far past trend have we already gone?” The 8 to 12 percent observation about the S&P (that the average return is almost never the actual return) is the kind of fact that should be taught in every introductory finance class but is almost never mentioned.

    The most contrarian claim in the conversation is the one about indexation: that it won because active was bad, not because passive is great. This is a useful inversion. Most defenders of passive investing argue from efficient market theory; Marks argues from the empirical failure of active managers. The implication is that if you can find the small population of active managers who genuinely outperform, the indexation argument falls apart for that subset. Most cannot. The hardest job in investing is the meta-job of identifying the few who can.

    The exchange about AI as a contrarian engine is one of the most clarifying short discussions of AI’s investment limits I have read. Different from consensus is easy. Different and better is the actual goal. Forcing different gets you wrong more often than right because consensus, built by smart, motivated, educated competitors, is usually close to correct. This is why “use AI to find non-consensus ideas” is a worse strategy than it sounds.

    Finally, the Buffett-Moody’s-Manual story is the most quietly profound moment in the interview. The edge in 1955 was the willingness to read tiny type on onion-skin paper alone in an office in Omaha when no one else would. The edge in 2026 is whatever the modern equivalent of that is, and the only honest answer is: nobody knows yet, which is precisely why finding it is worth so much money.