investing in a crisis

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.

Tag: investing in a crisis

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