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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

  • Jeremy Giffon on the Billion Dollar PDF, Peak Guy, and How Attention Became the New Capital

    In his second appearance on Invest Like the Best, investor Jeremy Giffon sits down with Patrick O’Shaughnessy for a wide-ranging conversation about how power, status, capital, and attention are being redrawn in real time. The organizing idea is the “billion dollar PDF,” the notion that a single well-timed document or post can crystallize a narrative and pull billions of dollars of capital toward it. From there the two range across the mechanics of the X timeline as market infrastructure, the decline of the billionaire class, the rise of the “poaster,” the economics of software in the age of compute, and what the next era of finance looks like when its founding act is seed investing rather than the leveraged buyout.

    TLDW

    Giffon argues that in private markets the real great filter for funds is storytelling, because the actual product (realized cash returns) takes a decade, so narrative is what you sell in the meantime. He and O’Shaughnessy unpack the “billion dollar PDF,” the way X functions as a single global newspaper (the uni-feed) that prices securities, dictates policy, and builds businesses, and how power laws now mean breaking containment on the timeline is worth more than steady performance. They discuss “peak guy” and the exhaustion of billionaire worship, the idea that the poaster has become the new priestly class, net worth as a surprisingly modern invention, and attention as the genuinely scarce asset. The back half turns practical: why AI job fears meet Giffon’s view that most white collar work is invented, why software is shifting from selling zero-marginal-cost strings to selling compute with thin margins and huge scale, why beating the market is easier for amateurs than professionals, how to underwrite emerging managers by studying the person, the feudal economics of SPVs and allocations, simplicity over complexity in investing, hiring through divisive job descriptions, and the hidden philosophers (from effective altruism to Curtis Yarvin and Nick Land) shaping Silicon Valley. Topics span venture capital, private equity, cap tables, SaaS, the Mag 7, Buffett and Bogle, East Coast versus West Coast finance, and the search for vocation.

    Thoughts

    The strongest thread in this conversation is that scarcity has moved. For most of the modern era, money was the scarce thing and attention was the byproduct of having it. Giffon flips that. Capital is now abundant, inflationary, and desperate for somewhere to go, which is why he can describe businesses and asset categories as “sponges” that get created downstream of capital rather than the other way around. What is actually scarce is a fixed slice of human attention, and whoever can command it (the “billion dollar PDF,” the breakout post, the person every billionaire wants to sit next to at dinner) captures the resource that money is now chasing. That reframing explains a lot of otherwise strange behavior, including why founders who already have wealth turn to posting, podcasting, and fame. They are not being vain. They are hedging out of a depreciating asset into the one that still appreciates.

    The most uncomfortable and clarifying claim is that narrative is not a distortion of markets, it is the market. Giffon walks through how the algorithm, driven by AI, selects which stories get shown, those stories set the consensus among the small group of posters who move capital, and securities get priced off that consensus. If you take that seriously, the efficient market hypothesis looks quaint. The marginal price of a security is being set, in part, by what an entertainment-optimizing model decided to surface to a few hundred thousand influential readers that morning. His line that “every other day someone writes some pornographic fanfic about AI and it moves the public markets” is a joke that is also a fairly precise description of 2026 price discovery.

    His software thesis deserves more attention than the culture commentary that will get clipped. The old SaaS miracle was selling copies of a string at near-zero marginal cost, which mechanically produced high gross margins. Giffon’s point is that the AI era sells compute, and you cannot write the prompt once and resell the output, so the marginal cost is no longer zero. The consequence is a structural regime change: lower gross margins, thinner net margins, and returns that accrue overwhelmingly to scale. He calls it a Walmart effect in software, and if he is right, a lot of the current sell-off in SaaS names is punishing the business model rather than the businesses, which is exactly the kind of nuance-free repricing he says markets specialize in.

    The optimistic surprise is his stance on AI and jobs, which cuts against the doom consensus without being naive about the short term. He concedes the near and medium term could be genuinely bad, but he refuses the “we will run out of jobs” framing because he thinks most white collar work is already invented to absorb our attention and capital, not to meet basic needs. Work-from-home Fridays, in his telling, are a quiet admission that many people have two or three hours of real work a day. If that is true, then automating the invented work is liberation rather than catastrophe, provided the transition does not crush people in the process. It is a bracing counterweight to the standard displacement panic, and it pairs well with his more personal note that the antidote to a priestly-class culture of looking outward for permission is the duty to steward your own gifts.

    The one place to push back is the tidiness of the “poaster as new priest” story. Giffon is careful to say he is describing, not endorsing, but the argument that status simply passes from scientists to billionaires to posters is cleaner than reality usually allows. Attention is scarce, yes, but it is also fickle and lotteryified in his own telling, which makes it a shaky foundation for a durable priestly class. Still, the underlying observation is sharp: when money becomes a “state of mind” label rather than a hard number, and when net worth itself is revealed as a recent invention (his Pride and Prejudice aside about Mr. Darcy’s income being cash flow, not a valuation, is the best illustration in the episode), the leaderboard everyone is actually competing on is real estate in other people’s minds.

    Key Takeaways

    • The great filter for private-market funds is storytelling ability, because the real product (realized cash returns) takes a decade, so narrative is what a fund actually sells in the interim through updates, events, and LP conversations.
    • The same business can be “cold” at seven years and $8 million in revenue but “hot” if you reset the clock and retell the story, so being flexible on narrative is itself a fix for a funding problem.
    • Insider bridge rounds are often surprisingly hostile (3x liquidation preferences, warrants, ratchets), and being extractive to the downside gets you booed while being extractive to the upside (pro rata rights) gets celebrated, even though both are similarly extractive.
    • In highly volatile times, optionality beats commitment: raise less, raise from investors with a wide mandate, and keep the ability to pivot the business model, run profitably, acquire, or even fire customers.
    • The “billion dollar PDF” is the idea that someone crystallizes a notion at the right time and it becomes the foundational viewpoint of an era, and capital follows it around like ten-year-olds chasing a soccer ball.
    • X is the “uni-feed”: everyone is served the same roughly 500 tweets a day across hundreds of millions of users, making it the global newspaper and a source of truth for capital markets, politics, and technology.
    • Institutions now survive only if they are “timeline native,” meaning reactive to and reflexive with the timeline, which describes the White House, venture capital, and public equities alike.
    • Posting has been lotteryified: a brand-new account can write one good post and get shown to hundreds of millions, so posting is described as the last great meritocracy.
    • Power laws have sharpened. Variance used to be low, but now breaking “containment” on the timeline means briefly taking over the world’s brain, and those few breakout events dwarf everything else combined.
    • Podcasts still underrate serving the algorithm; the video is recorded first for an LLM to review and decide whether to show, and only then do humans judge it.
    • A great post blends comedy, poetry, and writing, and great posters tend to be a bit tortured, closer to writers mixed with comedians.
    • “Peak guy”: society keeps searching for a priestly class, moved from scientists to the billionaire class, and Giffon thinks it has now moved to the poaster class, with billionaires increasingly deferential to posters.
    • Billionaire worship is exhausted partly because billionaires are far less scarce (state-of-mind billionaires have grown maybe 100x in 20 years) and money is less powerful than assumed, as the donor class has underperformed politically.
    • Net worth is a very new idea. In Pride and Prejudice, Mr. Darcy’s wealth is his estate’s annual cash flow, not a valuation, because no one would DCF or margin-loan an estate they would never sell.
    • “Billionaire,” like “millionaire” before it, is becoming a loose political and class label only tangentially related to actual liquid, inflation-adjusted wealth.
    • The most honest way to consume media is to admit it is entertainment, produced, selected, and edited to entertain, not to learn, no matter how productive it feels.
    • Going months off the timeline taught Giffon that you do not really miss anything; the filtered, secondhand version from smart people at dinner may be the most enlightened way to consume it.
    • On AI and jobs, the short to medium term could be bad, but the long-run worry is overblown because most white collar jobs are “made up” and not contingent on shelter, food, or medicine.
    • Work-from-home enthusiasm is evidence that many people have only two or three hours of real work a day, so work-from-home Fridays are a soft launch of the four day work week.
    • We have a moral duty to steward our gifts; the thing you spend most of your time on should spark and utilize your genius, and having fun at your job is a strong signal you have combined the two.
    • The largest finance firms (KKR, Blackstone, Apollo) were founded in a leveraged-buyout culture that is debt-driven and extractive; the next era’s giants may be founded on seed investing, which is equity-driven, optimistic, and qualitative.
    • West Coast venture is “eating” the East Coast: it created the biggest businesses in the world and functions as a civilizational technology, giving young people speculative capital with little downside.
    • Compensation has flipped: Silicon Valley now pays large liquid cash via mature secondary markets and yearly tenders, while Wall Street increasingly pays in RSUs tied to long-term firm value.
    • SaaS is just a business model, and while it is in trouble, that is often not what actually matters to a business being sold off out of fear.
    • Software is moving from selling near-zero-marginal-cost strings to selling compute, which means lower gross margins, razor-thin net margins, and returns accruing to scale, a Walmart effect in software.
    • Capital gets “blocked” when there are not enough great companies to absorb it, so high-capex AI and hardware categories arose in part as sponges for capital with nowhere else to go.
    • Markets lack nuance: the 52-week variance on the biggest companies is nearly 100%, so they are not priced well, and much private-market pricing reflects fund incentive structures rather than business quality.
    • Beating the market is easier for amateurs than professionals. Buffett’s S&P advice is for the average person, while pros are constrained by mandates, customers, and career risk (the Peter Lynch point).
    • A small principal writing a 500k check is the wrong customer for a large growth fund built to serve sovereigns and endowments; emerging managers, tightly aligned to returns, are underrated for that check.
    • Underwrite the person, not just the thesis. A manager’s personal financial situation matters enormously, and whether they are “looking up” or “looking down” at the fund size changes how they behave.
    • Modern finance is recreating a feudal system where lab founders (Elon, Zuckerberg, Dario, Sam) grant allocations like landed estates, and holders charge fees on this synthetic, purely relational, sometimes perpetual product.
    • The most generative activity is conversation, downstream of relationships, and being tolerant of weird, unpredictable people is a media diet advantage; chatbots can feel generative without actually being so.
    • Investors overvalue complexity to look clever; you should either do something so complex no one else will, or keep it simple (be long Elon, buy big companies at their 200-week moving average), and the real gift is selling the simple idea.
    • Richard Rainwater’s test: pitch your thesis on one page and state what percentage of your net worth you will put in, then yes or no. It is hard precisely because it forces clarity and conviction.
    • A job description is a sales pitch and an interview baked into a post; divisive, ambiguous statements (like “an ideological minority at a top 10 school”) self-select the right people and disqualify the wrong ones.
    • Silicon Valley’s hidden philosophy is underrated: a neo-Buddhist utilitarianism feeds effective altruism, and thinkers like Nick Land, Curtis Yarvin, and William MacAskill shape the culture without being named.
    • Where 1980s Wall Street was pagan, hedonistic, and nakedly about money, today’s tech views itself as self-righteous and positive-sum, treating the business itself as the ultimate philanthropy, with no felt need to launder gains through art or culture.

    Detailed Summary

    The Billion Dollar PDF and Narrative-Driven Capital

    Giffon opens with what he has learned in his first 18 months running his own fund: in long-term private markets, the great filter is storytelling. Because a fund’s real product is realized cash returns that take a decade to arrive, what a manager sells in the meantime, through quarterly updates, events, and one-on-one LP conversations, is narrative. He describes situations where an older company that has recently inflected struggles to raise simply because its story (seven years old, $8 million in revenue) reads worse than the same numbers reframed as a two-year-old rocketship. The billion dollar PDF is the escalation of this: a single document or post that crystallizes the notion of an era, does not even have to be right, and pulls billions in capital toward it. Capital, he says, behaves like ten-year-olds playing soccer, all chasing the same ball.

    The Uni-Feed: X as Global Newspaper and Market Infrastructure

    The technological catalyst, in Giffon’s view, is the uni-feed. Everyone on X is served the same roughly 500 tweets a day, and the poster-to-lurker ratio is enormous, so people who do not post cannot feel the impact. X is the Lindy social network, unlikely to reach the scale of the others but filling a vital role as a global newspaper and near-source of truth. The most important people in capital markets, politics, entrepreneurship, and technology read it every morning, and it forms opinion, prices securities, and writes policy. Institutions survive only if they are timeline native, both reactive to the timeline and reflexive with it. Crucially, this is also where narratives get set, and the winning story is not a well-considered book but the most entertaining, novel, somewhat-correct thing, because people are on the timeline to be entertained and the algorithm selects for exactly that.

    Power Laws, Breaking Containment, and the LLM as First Filter

    O’Shaughnessy observes that variance used to be low, with the best performers only modestly ahead of the worst, and that this has changed completely. Now there is a threshold where breaching containment feels like taking over the world’s brain for a short window, and those handful of breakout events matter more than all the rest combined. Giffon attributes this to technology rather than any change in content or audience: RSS gave you a normal distribution, algorithms give you a power law. He notes that podcasts remain naive about serving the algorithm, unlike streamers and YouTubers, and delivers one of the episode’s sharpest structural points: the video is recorded first for an LLM to review and decide whether to show it, and only after that first, largely invisible filter do humans get to judge.

    Peak Guy: Billionaires, Priests, and the Poaster Class

    The “peak guy” segment is the episode’s philosophical core. Giffon traces how God moved from being in and around everything, to a guy above the clouds, to something conceptual and distant, leaving an ongoing search for priests. Society tried scientists, but the scientific project stalled and physics has not delivered meaning since the war, so status passed to a billionaire class treated as the new priesthood: successful at business, therefore smart and hardworking, therefore worth listening to on physics, theology, or health. That worship has now saturated. Billionaires are far less scarce, money looks less powerful (the donor class has underperformed politically), and a billionaire who posts the wrong thing has to resign where Andrew Carnegie could once take up arms. Giffon’s claim is that the priesthood has passed again, this time to the poaster, and you can see it in how the billionaire class defers to posters (his anecdote: billionaire investors fighting to sit next to Tyler Cowen because he was the most interesting person in the room).

    Net Worth as a Modern Invention and Attention as the New Scarcity

    Giffon frames net worth itself as a strikingly recent concept. In Pride and Prejudice, Mr. Darcy’s wealth is discussed as roughly 10,000 a year in cash flow from his estate, not as a valuation, because no one would sell the estate or borrow against it. Wealth as a mark-to-market number is new, and between illiquid private markets, net worth as a concept, and inflation, “billionaire” is becoming a loose label, much like “millionaire” already did. Since time is fixed, the new scarcity is attention you can draw on the screen, which is why founders who accrue wealth so predictably turn to posting, podcasts, and channels: partly to convert wealth into fame, partly because they sense money is depreciating and attention is what is actually scarce.

    Opting Out and Media as Entertainment

    Asked about going months off the timeline, Giffon’s takeaway is that you should not fool yourself that you are seeking anything other than entertainment. All of it is produced, selected, and edited to entertain, and just as Rolex or Nike can convince you a liability is an asset, posts and essays can convince you that consumption is productive. The question is simply how much you want to be entertained. He does not see the death of books as a crisis so much as a swan song for a technology that was the best way to deliver information until better, more compelling ways arrived, though he is careful to note the negative language we use (brain rot, terminally online) betrays a deeper sense that something is off. New media is less forgiving: better than ever for the disciplined, worse than ever for everyone else. His friend Jesse refuses all algorithms and simply lets people tell him what happened, which Giffon half-endorses as the most enlightened, filtered way to consume the radiation secondhand.

    AI, Fake Jobs, and Stewarding Your Gifts

    On AI and white collar displacement, Giffon concedes the short to medium term could be bad (he agrees with a friend who worries about kids in college but not the ten-year-old), but rejects the “peak jobs” panic. Anything that can be automated should be, and the prospect of never having to sit at a computer again strikes him as liberating. Most white collar jobs, he argues, are invented, not contingent on shelter, food, or medicine, and our economy runs on unquenchable desire, so we will simply invent new things to do. Work-from-home attachment is his evidence that many people have only a couple of hours of real work a day, making work-from-home Fridays a soft launch of the four day week. This connects to a more personal theme O’Shaughnessy draws out: the duty to steward your gifts. Waste is aesthetically bad, wasting your gifts is among the worst kinds, and the surest sign you have integrated your work with your genius is that you are having fun.

    The Next Era of Finance and the New Economics of Software

    Giffon notes that today’s largest firms (KKR, Blackstone, Apollo) were founded in a leveraged-buyout culture that is debt-driven, extractive, and financially engineered, and wonders what the next 30 years look like when the founding act of the biggest firms is instead seed investing: equity-driven, optimistic, power-law, and qualitative. He sees East and West Coast finance merging, with the West “eating” the East, and a compensation flip in which the Valley now pays large liquid cash through secondary markets while Wall Street pays RSUs. On software, his central economic argument is that SaaS sold copies of a string at near-zero marginal cost, which is why high gross margins were the norm. The new era sells compute, where you cannot write the prompt once and resell the output, so margins compress and returns accrue to scale, a Walmart effect. He also reframes the high-capex AI buildout as capital markets manufacturing somewhere for blocked capital to flow, with companies created downstream of capital rather than the reverse.

    Beating the Market, Emerging Managers, and the Feudal SPV System

    Giffon argues the myth that you cannot beat the market is overstated: Buffett’s S&P advice is aimed at the average person, and it is professionals, burdened by mandates and career risk, who struggle most, while amateurs who simply held Bitcoin, Tesla, or Apple outperformed. For LPs, he stresses knowing what customer you are. A 500k check is the wrong fit for a growth fund built to serve sovereigns, and emerging managers, tightly aligned to returns, are underrated. He urges underwriting the person over the thesis, paying special attention to a manager’s own financial situation and whether they are looking up or down at the fund size. He then describes the feudal economics of the labs, where founders grant allocations like landed estates, holders charge fees on a synthetic, relational, sometimes perpetual product, and the most egregious setups feature no GP commit, a 10% upfront fee, and carry with no term limit.

    Simplicity, Hiring, and Silicon Valley’s Hidden Philosophy

    On process, Giffon warns that investors prize complexity to look clever, when the choice is really to do something so complex no one else will or to keep it genuinely simple (be long Elon, buy big companies at their 200-week moving average), with the real gift being the ability to sell the simple idea. He praises Richard Rainwater’s one-page-thesis-plus-percentage-of-net-worth test as a brutal clarity forcing function. On hiring, he treats the job description as a sales pitch and a baked-in interview, using divisive, ambiguous statements like “an ideological minority at a top 10 school” to self-select the right people and repel the wrong ones. Finally, he makes the case that Silicon Valley’s underlying philosophy is badly underrated: a neo-Buddhist utilitarianism that flows into effective altruism, with thinkers like Nick Land, Curtis Yarvin, and William MacAskill shaping the culture unnamed. Where 1980s Wall Street was pagan and nakedly about money, today’s tech sees itself as self-righteous and positive-sum, treating the business as the ultimate philanthropy, with none of the old reflex to launder gains through art or culture.

    Notable Quotes

    “Every once in a while someone basically crystallizes a notion right at the right time in the right way that sort of becomes the foundational viewpoint or opinion on a certain era.”

    Jeremy Giffon, defining the billion dollar PDF

    “The capital just follows the billion dollar PDF around the field.”

    Jeremy Giffon, comparing capital to ten-year-olds chasing a soccer ball

    “Everyone gets served the same 500 tweets per day and it’s hundreds of millions of daily active users.”

    Jeremy Giffon, on the uni-feed that makes X the global newspaper

    “Posting changes your life if you’re good at it. That’s still true today, maybe more true than ever.”

    Jeremy Giffon, on posting as the last great meritocracy

    “Andrew Carnegie could take up arms against his workers, but now if you post the wrong thing as a billionaire, you have to resign.”

    Jeremy Giffon, on the shrinking power of the billionaire class

    “It’s this holy conceptual, just points on a leaderboard, truly, because you can’t spend it.”

    Jeremy Giffon, on net worth as a modern invention

    “One should not fool themselves that they are looking for anything other than entertainment in all the media that they consume, because it is produced to be entertaining.”

    Jeremy Giffon, on opting out of the timeline

    “We’re in an era where we’re selling compute. You can’t write the prompt once and then sell copies of the output. You have to do the compute every single time.”

    Jeremy Giffon, on the new economics of software

    “The most important media property won’t be watched. The most important author isn’t read. The most important philosopher is not understood. The most important stock has no fundamentals.”

    Jeremy Giffon, on a world where reputation floats free of the thing itself

    Watch the full conversation with Jeremy Giffon and Patrick O’Shaughnessy here on Invest Like the Best.

    Related Reading

  • Lloyd Blankfein on the 3 Sectors Where He Puts His Money Now: Big Tech, Energy, and Financial Services, Day Trading From an iPad, and the Warren Buffett Handshake That Backed Goldman in 2008

    Lloyd Blankfein spent almost 40 years at Goldman Sachs, the last dozen as its chairman and chief executive, and he still trades almost every day from an iPad. In this wide ranging conversation on the My First Million podcast, the former Goldman boss lays out exactly where he is putting his own money right now, why a supportive spouse beats nearly any investment, how Warren Buffett wired five billion dollars into Goldman on a handshake during the 2008 crisis, and why he reads medieval history to stay calm about the present. It is part stock picking, part risk philosophy, and part a frank accounting of money, marriage, and the scars of growing up in the projects.

    TLDW

    Blankfein says he is roughly 98 percent in risky assets, almost all equities, and concentrated in three sectors he knows cold: big tech, energy, and financial services. His personal book leans heavily into single stocks over ETFs, weighted toward the big hyperscalers and a few second tier names, and he trades daily, alone, from an iPad and a phone, using calls and texts as his research network. Yet the advice he gives a normal investor is the boring opposite: a diversified S&P 500 fund like VOO, more risk when you are young because you will outlive your mistakes, the same thing Warren Buffett would tell you. The conversation ranges across the 2008 Buffett investment in Goldman, the cost of trying to legislate risk out of markets, the thin margin between the best and the rest, luck and the myth of the genius, why reputation is the real contract on Wall Street, why a supportive spouse is the highest return asset he knows, the money anxiety he carried out of a Brooklyn housing project, the dignity of a 500 dollar financial aid check, giving with a warm hand versus a cold one, the dangers of gamified investing, the big misses like SpaceX and early cellular, the obituary test a senior partner once gave him, and why reading history keeps the present in proportion.

    Thoughts

    The most useful tension in this interview is the gap between what Blankfein practices and what he preaches. He tells young people to buy a diversified S&P 500 index fund, he holds VOO himself, and he calls the host’s plain 90 percent stocks and 10 percent bonds split sensible. Then he admits his own portfolio is something like 90 percent single stocks that he trades by hand every day. The honest read is that his edge is not a transferable tip. It is a 40 year information network of phone calls and a tolerance for risk that most people neither have nor should want. The replicable lesson is the boring half, not the day trading half.

    The most contrarian idea here is not a stock pick, it is his defense of risk itself. His argument that regulators trying to prevent the hundred year storm also forfeit the 99 normal years of growth in between is a serious claim about the price of safety, and it travels far beyond Wall Street. The same goes for his point that a good risk manager sometimes has to push people to take more risk, not less. The moment after a loss, when everyone goes gunshy, is exactly when the best operators lean back in. That is an uncomfortable thing for a former bank CEO to say out loud, and it is the part of the conversation most worth sitting with.

    The Warren Buffett story is a master class in what actually moves markets, and it is not cash. Goldman did not need the five billion dollars. Blankfein says the money was almost irrelevant because the firm already had money. What it could not manufacture was confidence, and Buffett’s name supplied it. The handshake, the commitment with no paperwork, the line about worrying enough for the both of us, all point to the same thing. At the top, reputation is the collateral. His aside that most trades are never written down because you will never eat lunch in this town again is the same idea wearing street clothes.

    Quietly, the personal finance thread may be the most valuable part for a normal listener. A former Goldman CEO saying that a supportive partner is more game changing than any investment, that a bad marriage is financially worse than being lonely, and that he has not paid a bill in over 40 years because his wife runs the household economy, is a reminder that household stability is itself an asset class. The 500 dollar financial aid check he still remembers half a century later, and his give with your warm hand philosophy, reframe wealth as something measured by how it feels to give and to receive, not just by the size of a pie chart.

    Finally, the history obsession is not a side hobby, it is his risk model. Reading about the black plague, the McCarthy era, and the Vietnam draft is how he keeps the present in proportion. His Mark Twain line, that history does not repeat but it rhymes, is the direct antidote to the in this economy defeatism he and the host both complain about. For an investor, that long view is close to the whole game. It is what lets you hold through the drawdowns that scare everyone else out of the market.

    Key Takeaways

    • Blankfein estimates he is about 98 percent in risky assets, with roughly 95 of those 98 points in equities, and the rest spread thin. He invests in risky assets because, in his words, that is what is fun for him.
    • Within his equities, he is heavily tilted toward single stocks rather than ETFs. He frames it as roughly a quarter to a third in ETFs and the rest in single names, and concedes it could be as lopsided as 90 percent single stocks because picking names is what he enjoys.
    • The three sectors he has concentrated in for years are big tech, energy, and financial services, and he says his outperformance comes from where he focused, not from any special genius.
    • On tech he owns the big hyperscalers, the Googles, Microsofts, and Nvidias of the world, plus a tier just below them, naming Oracle and Larry Ellison as an example of a slightly riskier second tier name. He thinks in categories, not fixed tickers, because he changes positions constantly.
    • He says he has a background in trading energy, which is why energy is a core sleeve, and he knows financial services from the inside after almost 40 years at Goldman, so those are natural areas of edge.
    • He still owns a lot of Goldman Sachs stock, out of affection for the firm he spent his career building.
    • He is bullish on big tech and plans to stay bullish until it stops going up. His foreseeable future, he jokes, lasts until he finishes the conversation and checks the screen again.
    • He trades every single day, alone, with no team. He does it from an iPad and a phone, not a computer, and treats the market like background music rather than a job.
    • His research is human, not algorithmic. He chats and texts with people, then calls them because he is tired of fixing typos, and he reads the New York Post, the Wall Street Journal, the New York Times, the Financial Times, and Bloomberg.
    • The advice he gives ordinary investors is deliberately boring and different from his own behavior: hold a diversified equity portfolio like an S&P 500 fund, with VOO as his own example, and tilt more aggressively when you are young because you have time to outlive mistakes.
    • He notes that broad indexes are already heavily weighted toward tech because of market cap, so a plain index gives meaningful tech exposure, and a tech focused ETF on top can add a disproportionate tilt for believers.
    • He calls the host’s simple 90 percent index and 10 percent bonds allocation sensible, and says this is essentially the same advice Warren Buffett would give a normal person.
    • The older you get, the more conservative you should become, shifting from maximizing gains toward not losing what you have. Young people can afford more risk precisely because they will outlive their errors.
    • During the 2008 financial crisis, Warren Buffett invested about five billion dollars in Goldman through a preferred stock structure, essentially on a phone call and a handshake, with no demand for due diligence.
    • Buffett’s real value was confidence, not capital. Goldman already had money, but it had lost the confidence of the market while peers were failing. Buffett’s name signaled the firm was a good investment being beaten down by circumstances that would reverse.
    • Buffett asked for a verbal commitment that Goldman would not sell shares before he did, and declined to put it in writing. He waved off the worry with the line that five billion dollars going bad would not even be a bad hurricane for Berkshire, an insurer.
    • Most trading is done on reputation, not paper. Blankfein says people buy and sell bonds worth enormous sums without written contracts, relying on probity, because anyone who reneges will never eat lunch in this town again.
    • On risk and regulation, he argues you cannot legislate risk away. Trying to prevent the hundred year storm also forgoes the 99 in between years of growth, and a good risk manager sometimes has to encourage people to take risk, not suppress it.
    • The best traders have resilience. They bounce back, focus on new information rather than the past, and adapt quickly instead of staying gunshy after a loss.
    • The difference between someone who is really good and someone who cannot make it is small. He compares it to a golf tournament won by one stroke with six people tied for second, and notes much of life is winner take all at razor thin margins.
    • Luck matters enormously. He became Goldman CEO partly because his predecessor was nominated to be Treasury Secretary, a reference to Hank Paulson, and the timing of opportunities is often out of your control.
    • He is skeptical of the word genius. He says he can usually see how successful people do what they do, with Elon Musk as a rare exception, and that powerful people are more normal, more insecure, and more flawed than outsiders assume.
    • On democratized investing, he thinks apps that make markets accessible are good in their own terms, but gamifying trading with confetti and high fives can mask real danger for people who can lose more than they can afford.
    • He has missed plenty. He thought SpaceX was overpriced at a 100 billion dollar valuation, now discussed near a trillion and three quarters, and passed on early cellular because he could not imagine why anyone would carry a bulky phone when payphones existed. He says he missed far more than he got.
    • He frames a supportive spouse as more game changing than almost any investment, and warns that a bad marriage, with custody fights and property settlements, is financially and personally worse than being lonely.
    • He has not paid a bill in over 40 years. His wife Laura, a former lawyer he says now chairs Barnard College, runs a bill paying service and manages the household economy. He generates the money, she distributes it.
    • He grew up in an East New York, Brooklyn housing project, the son of a postal worker, and carried money anxiety well into his 30s. He recalls buying a vacation home that cost more than all their savings, with his wife unable to make the math work until they remembered the down payment.
    • A 500 dollar financial aid check, handed to him without shame as a college freshman around 1971, shaped his philosophy on giving. He learned it is not enough to give people what they need, you have to give it in a way that feels dignified.
    • He embraces the give with your warm hand, not your cold hand idea, the notion of giving while alive so you can experience the joy, which connects to the spirit of the book Die With Zero.
    • He admits ambivalence about giving to his kids, the strange feeling of resenting that they have what he provided, and notes the heavy burden carried by children of prominent people who must prove they earned their place.
    • He describes himself as wired for anxiety, inherited from his father, and says looking around corners for what could go wrong actually suited a career in a risky business with a big balance sheet.
    • When he made partner, a senior partner gave him rules of the road, including avoiding misconduct, being conservative on taxes, setting up a charitable foundation, and living so that no more than three of the nine paragraphs in his eventual obituary would be about Goldman. He says he stayed too long to pass that test.
    • He reads history as a discipline, favoring Barbara Tuchman, Robert Caro’s The Power Broker, Ron Chernow, Rick Atkinson, and Stephen Ambrose. His core belief, borrowed from Mark Twain, is that history does not repeat but it rhymes, which is why he would not bet against America.

    Detailed Summary

    The three sectors he actually invests in

    The headline answer to where the former Goldman CEO is putting his money is simple: big tech, energy, and financial services. He says he has been focused on those three areas for a long time, and that his outperformance is a function of where he aimed rather than any unusual investing gift. Energy is natural because he has a background trading it. Financial services is natural because he spent nearly 40 years inside the industry. Tech is where he is most heavily concentrated, and he expects to stay there for good reason, citing the threshold of large changes in technology. He owns the major hyperscalers by category, the Googles, Microsofts, and Nvidias, plus a tier just below, offering Oracle and Larry Ellison as a polite example of a slightly riskier second tier name. He is careful to say he thinks in categories rather than fixed tickers because he changes his positions all the time.

    How the portfolio is really built: single stocks over ETFs

    Asked to describe his portfolio as a pie chart, Blankfein says he is about 98 percent in risky assets, with roughly 95 of those points in equities. He pushes back on the idea that index funds are safe, pointing out that a diversified equity ETF is still equities and still risky, just spread out, and very different from debt or short term money markets. Within his equity sleeve he leans into single stocks, framing it as somewhere between a quarter and a third in ETFs and the rest in individual names, and conceding it might be as extreme as 10 percent ETFs and 90 percent single stocks. The reason is preference, not theory. Picking and trading names is what he likes to do, and he is honest that this is a hobby pursued by a professional, not a model for someone investing for a living.

    How he actually trades: an iPad, a phone, and a network

    He trades every day, by himself, with no team. There is no Bloomberg terminal and no desk of analysts. He uses an iPad and a phone, and admits it takes discipline not to glance at his screen mid conversation. The market, he says, is like music playing in the background while he does other things. His information edge is relational. People text him, he texts back, and then he calls because he is tired of fixing typos with what he calls his fat fingers. He follows general and business news, reads a stack of newspapers starting with the New York Post, and treats companies like little stories, almost like gossip. He even notes, with some delight, that he still watches commercials on Netflix, a small window into a frugality that never fully left him.

    The advice he gives young investors, and what Buffett would say

    For a normal person, his counsel is the opposite of his own behavior. He would hold a diversified portfolio of equities like an S&P 500 fund, naming the SPY and VOO tickers and saying he personally uses VOO. Because of the importance of technology, he might add a tech oriented ETF for extra tilt, while noting the broad index is already tech heavy by market cap. He endorses the host’s plain 90 percent index and 10 percent bonds split as sensible and says it mirrors what Warren Buffett would advise. His one piece of age based guidance is that younger investors should accept more risk through equities, because they have time to recover, while older investors should grow more conservative and focus on not losing what they have rather than maximizing returns.

    The Warren Buffett handshake that backed Goldman in 2008

    The most cinematic story in the conversation is Buffett’s roughly five billion dollar investment in Goldman during the financial crisis, structured as a preferred stock that sits between a loan and equity. Blankfein describes a deal done largely on trust. When he offered to walk Buffett through everything he was worried about, Buffett replied that he knew Lloyd well enough to know he worried enough for the both of them. Buffett also asked, verbally and without writing, for a commitment that Goldman would not sell shares before he did. Blankfein is clear that the cash itself was almost irrelevant, since Goldman had money. What the firm lacked was the confidence of a frightened market, and Buffett’s willingness to invest before things improved supplied exactly that signal. Buffett, he stresses, was acting for his own shareholders, not as a rescuer, which is precisely what made the vote of confidence credible.

    Why you cannot legislate risk out of the system

    Reflecting on the post crisis regulatory push to make sure 2008 never happened again, Blankfein makes a careful argument about the price of safety. Once you are in the business of taking risk, anything can happen, and trying to legislate it away has a hidden cost. You may think you are protecting the world from the hundred year storm, but you also forgo the 99 years of growth in between. He extends this inside the firm too. After a period of big losses, partners had become gunshy and were talking themselves out of every idea. A good risk manager, he argues, sometimes has to promote risk taking rather than repress it, because without risk there is no growth, no entrepreneurship, and no progress. The flip side is real: take risk and there is a meaningful chance you fail and lose other people’s money, which is a terrible outcome. But the alternative, never risking anything, buys comfort at the cost of ever moving forward.

    Small margins, big outcomes, and the role of luck

    Asked what separated the traders who could not outperform from the rest, Blankfein says the gap between the very good and those who cannot make it is surprisingly small. He likens it to a golf tournament decided by a single stroke with six players tied for second, and to acting, where the best performer gets every role and the second best waits tables. Much of life, he says, is winner take all at tiny margins. Luck compounds this. He freely credits fortune for his own rise, noting he became CEO in part because his predecessor was tapped to be Treasury Secretary. He is also skeptical of the genius label. He can usually see how accomplished people do what they do, with Elon Musk a rare exception, and insists the powerful are more normal, more insecure, and more driven by their flaws than outsiders imagine.

    Reputation is the real contract

    A recurring theme is that the financial world runs on reputation more than paperwork. Blankfein notes that most of what traders do is not written down. People buy and sell bonds and other instruments that settle days later, relying on probity rather than signed contracts, because anyone who lies or reneges will never eat lunch in this town again. He references the casual texts between Elon Musk and Larry Ellison around the Twitter acquisition as proof that big does not mean complicated. There are big things that are simple and little things that are complicated. Documentation is good when execution is far off, but when a deal will be performed in two days, dotting every i is often pointless. The point is not that documents do not matter, it is that trust and reputation are the load bearing structure.

    A supportive spouse as the highest return asset

    The conversation turns personal when both men agree that a supportive partner may be the single most game changing factor in a life, more than any investment. Blankfein adds the inverse warning: a bad marriage, with breakups, custody battles, and property settlements, is worse than loneliness. He credits his wife Laura, a former big firm lawyer he says now chairs Barnard College, with handling everything when his career moved the family overseas, from the car to the house to the kids’ schooling, while he took the visible victory laps at work. He has not paid a bill in over 40 years. Laura manages a bill paying service and runs the household finances. As he puts it, he is in charge of generating the money and she is in charge of distributing it. The host contrasts this with his own monthly money meetings with his wife, a discipline he picked up from a personal finance author friend.

    Money scars, the 500 dollar check, and giving with a warm hand

    Blankfein grew up in an East New York housing project, the son of a postal worker who had earlier lost a job, in a household where rent was scarce. He calls himself an urban hick who barely left Brooklyn as a kid. That scarcity left a mark that lasted into his 30s. He tells the story of buying a small beach house that cost more than all their savings, and of his wife driving 30 miles while failing to make the closing math work, until they realized she had forgotten to count the 10 percent down payment. The most resonant memory is a 500 dollar financial aid check handed to him as a freshman around 1971, made out on the spot by a clerk with a generosity of spirit that let him receive it without shame. That experience shaped a lifelong view that giving well means preserving dignity, and he now co chairs a financial aid campaign at his university. It also connects to his embrace of the idea of giving with your warm hand rather than your cold hand, giving while alive so you can feel the joy, the same spirit as the book Die With Zero. He is candid about a strange ambivalence, the way he can resent that his kids enjoy what he himself gave them.

    Robinhood, confetti, and the misses

    On apps like Robinhood, Blankfein takes a balanced view. Democratizing investing and making assets accessible is good in its own terms, and advertising can pull people toward markets they would otherwise ignore. But if you make trading too much like a video game, with confetti and high fives, you can mask the danger and lure people who cannot afford to lose into losing more than they can. He is equally frank about his own misses. He thought SpaceX was overpriced at a 100 billion dollar valuation, a figure now discussed near a trillion and three quarters. He passed on early cellular because he could not imagine why anyone would carry a bulky phone with payphones everywhere. His blunt summary is that he missed far more than he got, and that nobody is great at predicting the future.

    The obituary test, thick skin, and staying too long

    When Blankfein made partner, a senior partner assigned to acculturate new partners gave him rules of the road: avoid anything that would today be called misconduct, be rigorous and conservative on taxes, set up and actually use a charitable foundation, and keep enough balance that, if your obituary runs nine paragraphs, no more than three are about Goldman. Blankfein says he failed that last test by staying too long, even titling his memoir around the firm. He also reflects on having a thick skin, recalling unflattering press and concluding that he could take a punch, a trait not everyone has and one he did not know he possessed until he was tested. He is careful to say this does not make people who cannot take a punch bad, just differently wired.

    Why he reads history: it rhymes

    The final stretch is a love letter to reading history. Blankfein favors Barbara Tuchman, whose A Distant Mirror he has read twice and whose Guns of August he calls fantastic and influential, along with Robert Caro’s The Power Broker on Robert Moses, Ron Chernow’s biographies, Rick Atkinson’s Revolution series, and Stephen Ambrose’s Undaunted Courage. He describes rereading the Robert Moses book after 40 years of trying to get things done and finding his appreciation for the achievements rise, even as the flaws stayed the same, because he had changed. He ties history directly to markets through the Mark Twain line that history does not repeat but it rhymes. Patterns recur, every generation maximizes its own crises and minimizes resolved ones, and reading about the black plague, the McCarthy era, or the Vietnam draft is how he stays calm. His conclusion, echoing a sentiment often attributed to Buffett, is that he would not bet against America, a country he describes as mostly good and able to improve.

    Notable Quotes

    “I invest in risky assets. That’s what’s fun for me.”

    Lloyd Blankfein, describing his own portfolio, which he says is roughly 98 percent risky assets

    “It’s been good to be bullish on big tech, and I’ll stop being bullish on it when it stops going up.”

    Lloyd Blankfein, on why he stays concentrated in technology

    “I’m not at a computer. I don’t have a computer. I have an iPad.”

    Lloyd Blankfein, on how he day trades every day, alone and with no team

    “To me, the market is like music. It’s out there. It’s going on.”

    Lloyd Blankfein, on why trading daily feels like a hobby rather than work

    “Look, $5 billion if it all goes bad, that’s not even a bad hurricane on the East Coast.”

    Warren Buffett to Lloyd Blankfein, waving off the risk of his 2008 investment in Goldman Sachs

    “The difference between somebody who’s really, really good and somebody who can’t make it is not that great.”

    Lloyd Blankfein, on the thin margin between the best and the rest

    “You may think you’re protecting the world from the hundred-year storm, but you’re also going to forego the 99 years of in between when there was growth.”

    Lloyd Blankfein, on the cost of trying to legislate risk out of markets after 2008

    “I’m in charge of generating the money, and she’s in charge of distributing it.”

    Lloyd Blankfein, on his 40-plus-year marriage to Laura and why he has not paid a bill in decades

    “History doesn’t repeat, but to paraphrase Mark Twain, it rhymes.”

    Lloyd Blankfein, on why reading history keeps the present in proportion

    Watch the full conversation with Lloyd Blankfein on the My First Million podcast here.

    Related Reading

    • Lloyd Blankfein (Wikipedia) background on the former Goldman Sachs chairman and CEO whose investing views anchor the conversation.
    • My First Million podcast the show where this interview took place, for the full back catalog of investor and founder conversations.
    • Berkshire Hathaway primary source on Warren Buffett’s company, which made the roughly five billion dollar Goldman investment in 2008.
    • Vanguard S&P 500 ETF (VOO) the diversified index fund Blankfein names as the sensible core holding for a normal investor.
    • Die With Zero by Bill Perkins the book behind the give with your warm hand, not your cold hand philosophy discussed near the end.

  • Bill Ackman on Investment Strategy, What the Market Is Missing, and How AI Breaks Businesses

    Bill Ackman, founder and CEO of Pershing Square, joined the All-In Podcast for a conversation about how his investment approach has shifted toward permanent, long-term ownership, why he believes the highest-quality companies are being left behind by a market chasing the new new thing, and how AI is raising the risk of disruption for almost every business. He also lays out his plan to turn Howard Hughes into a Berkshire Hathaway-style compounding machine built on insurance. You can watch the full conversation here. Below is a structured breakdown of the ideas, the stories, and the frameworks he uses to underwrite a business.

    TLDW

    Ackman explains how his philosophy evolved from a smaller, more liquid activist toward concentrated, permanent ownership of durable, non-disruptible businesses, with much of his activism now playing out on X rather than in the boardroom. He tells the origin story of his first big trade, Wendy’s and the Tim Hortons spin-off, and explains why a large long-term shareholder on a board is an antidote to short-term markets. On AI, he argues that this is the greatest era in history to build a company, which means the risk of being disrupted has gone up enormously, and that the market is mispricing high-quality compounders like Microsoft, Meta, and Amazon while crowding into chips, semiconductors, and energy. He works through the SaaS question and why niche software is more at risk than platforms, how he underwrites SpaceX, xAI, OpenAI, Anthropic, and Palantir like late-stage venture bets using a people, opportunity, context, deal framework, and why founder-led companies have an edge in making radical calls. The back half covers his Howard Hughes plan to copy Buffett’s insurance-float model, the role of cost of capital and reflexivity in markets, the meme-stock era, going direct on social media, and the three different ways an investor can put money to work with Pershing Square.

    Thoughts

    The most useful idea in the interview is the way Ackman reframes disruption as the central investing problem of the AI era. His point is that the same forces making this the best time in history to start a company, meaning near-unlimited compute, capital, and talent, also raise the odds that any given incumbent gets disrupted. That reframes the word quality. It is no longer mostly about margins and moats. It becomes about non-disruptibility, which is a much higher bar than most quality investors were using a decade ago, and it is why he says most of his research time now goes into assessing that single risk.

    The what-the-market-is-missing thesis is classic contrarian Ackman. Arguing that Microsoft, Meta, and Amazon are the new old-fashioned, undervalued names while capital piles into semiconductors and energy is a direct echo of 2000, when Berkshire Hathaway bottomed precisely because money was chasing internet stocks. It is worth keeping in mind that he owns all three, so the call is also his book. The durable signal here is the framework, not the specific tickers: capital reliably chases the new new thing, and genuinely high-quality businesses get left behind during those rotations.

    The Howard Hughes plan is the most concrete bet in the conversation. Copying Buffett’s insurance-float playbook, short-term treasuries for policyholder money and equities for the surplus, onto a discounted real-estate holding company is elegant. The hard part is exactly what Ackman flags about insurance as an industry: the best investors go to hedge funds, not insurers, so most insurance companies only ever manage the liability side well. Pershing Square’s edge is that Ackman can both write the business and invest the float, which is the same reason it worked for Buffett. The framing of going from a four billion dollar company to a trillion over fifty years is a statement of intent, not a forecast, and should be read that way.

    Underneath all of it sits cost of capital and reflexivity. His observation that a higher stock price literally makes a company more valuable, because it lowers the cost of capital and creates acquisition currency, is the mechanism behind both Elon Musk’s empire and the meme-stock era he is wary of. Going direct on X is the same lever pointed at himself: communicate the vision, lower your own cost of capital, and make the bet easier for other people to place. It is a coherent worldview in which narrative and balance sheet continuously feed each other, and it explains a lot of his behavior over the last few years.

    Key Takeaways

    • The biggest change in Ackman’s approach over time is an appreciation for business quality, meaning long-term, durable, protected, non-disruptible growth as the most important factor.
    • He says he is as activist as ever, but more of it now happens on X than in the traditional corporate context.
    • His first big investment was Wendy’s, which owned Tim Hortons. The simple thesis was to buy Wendy’s, spin off Tim Hortons, and double the money.
    • Early on no one returned his calls, so he had Steve Schwarzman’s Blackstone write a fairness opinion, filed it publicly, and the company spun off Tim Hortons six weeks later. The CEO later thanked him after being fired with a large exit package.
    • Reputation compounds. Where Pershing Square once had to bang down the door, companies now sometimes tweet a welcome when it buys a stake.
    • A large long-term shareholder on a board is a counterweight to short-term markets, letting management test ideas privately and pursue initiatives that hurt the next few quarters of earnings.
    • Pershing Square owns Microsoft, Meta, and Amazon. Ackman argues you are either invested in AI directly or indirectly, or it is a threat, so you have to understand it.
    • The hardest and most important job for a concentrated investor is judging the risk of disruption, and that risk has risen dramatically.
    • This is the greatest era in history to build a business because of near-unlimited access to compute, capital, and talent, which is exactly why the probability of being disrupted has gone up enormously.
    • Markets bring their eye to the new new thing, currently chips, semiconductors, and energy, while high-quality companies get left behind.
    • He draws an analogy to 2000, when Berkshire Hathaway traded at one of its lowest valuations because everyone chased internet stocks. He sees a similar dynamic around Amazon, Meta, and Microsoft today.
    • On the SaaS question, he worries more about a Salesforce than a platform like Microsoft, because niche software charging high per-seat or per-year prices is most exposed, while low-priced platforms are safer.
    • Any software company today has to be as AI-enabled as possible, or risk losing the monopolistic pricing it once enjoyed.
    • His famous March 2020 CNBC appearance was an attempt to reach President Trump and argue for a short shutdown, paired with the view that stocks were incredibly cheap and worth buying.
    • He describes valuation as a tether on the market: when prices stretch too high they snap back, and when they get too cheap the same rubber band pulls valuations up. Calling that out publicly can trigger a psychological reset.
    • His recent bullish call came because stocks of really high-quality companies had gotten crazy cheap on fundamentals, meaning the present value of the cash they generate.
    • He underwrites high-multiple names like SpaceX as venture investments using a framework from business school: people, opportunity, context, deal.
    • On SpaceX, people and opportunity are one of one, the context is incredible, and Starlink plus near-monopoly low-cost launch make it strategically valuable. The complicated part is the deal, meaning the valuation. He invested via an SPV after Ron Baron’s nudge, and also invested in xAI.
    • He treats OpenAI, Anthropic, and Palantir as late-stage venture bets that have proven they can generate real revenue, and says OpenAI should do a better job communicating how it thinks about its enormous capital commitments.
    • Every CEO in America is asking how to use AI, how it applies to their business, and how it is a threat. It is top of mind and boards open every meeting with it.
    • He has not seen much enterprise AI success yet, citing a McKinsey study that 95 percent of enterprise initiatives fail and the rise of the forward deployed engineer as the hot role bridging promise and ROI. Pershing Square itself uses AI mainly for legal, compliance, and back-office work.
    • Founder-led companies have an advantage because founders have the authority and the economic stake to make radical calls, while the average S&P 500 CEO has a roughly three to four year tenure and is incentivized not to make mistakes.
    • He cites Mark Zuckerberg buying Instagram and WhatsApp as the kind of shocking-at-the-time calls that a founder with a track record can make.
    • Ben Graham’s enduring lesson is that a stock is an interest in a business, not a piece of paper, but Graham mostly invested in liquidations and cash-rich shells, and made most of his money on Geico.
    • Most of Buffett’s value at Berkshire came from owning insurance operations and focusing on the asset side of the balance sheet, not just the liability side.
    • Insurance is hard to copy because top investors do not go to work for insurers. Buffett owned half his company and was a great investor, which is why it worked.
    • Howard Hughes came out of the General Growth bankruptcy and owns master-planned cities like Summerlin, with 26,000 acres in the Las Vegas area, comparable to the Irvine Company that built roughly a hundred billion dollars of wealth for Donald Bren.
    • The plan is to reinvest the cash Howard Hughes generates into insurance, put policyholder float in short-term treasuries and the surplus in common stocks, and build a compounding machine over fifty years, buying it at roughly sixty cents on the dollar.
    • A company must earn a return above its cost of capital for the stock to rise. Elon Musk has kept his companies’ cost of capital extremely low, and a SpaceX IPO near a 1.75 trillion dollar valuation could be one of the lowest cost of equity capital transactions ever.
    • Markets have changed less because of Ackman and more because of figures like Ryan Cohen and GameStop, where a stock can trade well above its value on personality and an army of followers.
    • Higher valuations are reflexive: a rising stock price lowers cost of capital and creates currency to issue stock and acquire businesses, which is part of how Elon built Tesla.
    • There are three ways to invest with Pershing Square: the management company itself (a royalty on compounding assets with no capex), PSUS (a portfolio of best ideas trading at an 18 percent discount), and Howard Hughes (a bet on building the next Berkshire). A dollar invested 22 years ago became roughly 27 to 28 times net of fees.
    • Going direct on X, with 2.2 million followers, lets him communicate his vision and lower the friction for others to back his bets, even as his very long tweets have become a running meme.

    Detailed Summary

    From activist trades to permanent capital

    Ackman frames the evolution of his career as a steady move toward business quality. As a smaller, more liquid investor early on, he did not have to think as long-term. As Pershing Square became a bigger, more concentrated investor, durable growth became the dominant factor in every decision. He insists he is still as activist as ever, but a lot of that energy has shifted to X, where he can argue a position publicly rather than only inside a boardroom. The best investments, he notes, are the ones where you do not need to join the board and do anything at all.

    The Wendy’s and Tim Hortons origin story

    One of Pershing Square’s first investments was Wendy’s, which owned the Canadian coffee and donut chain Tim Hortons. The value of Tim Hortons alone was greater than the entire value of Wendy’s, so the idea was simple: buy Wendy’s, spin off Tim Hortons, and double the money. Ackman bought ten percent of the company and could not get the CEO to return a single call, so he had a contact at Blackstone, with Steve Schwarzman’s sign-off, write a fairness opinion on what Wendy’s would be worth after a spin-off, filed it publicly, and watched the spin-off happen six weeks later. The CEO eventually called back to thank him, having been fired but rewarded with a large exit package. Over the years that scrappy approach gave way to a reputation that now opens doors on its own.

    Why a long-term shareholder on the board matters

    The core problem of being a public company, in Ackman’s telling, is the short-term nature of markets and analysts, when a good business should be run in the context of years and even decades. A large, supportive shareholder on the board gives management a place to test ideas before exposing them to the public and a credible voice willing to back initiatives that hurt earnings for a few quarters. That is the value-add he believes a constructive activist can bring to a mature public company, as opposed to a startup where the best outcome is simply to own a great business and stay out of the way.

    AI and the rising risk of disruption

    For a concentrated, long-term investor, the most challenging task is judging the risk that two people from Stanford in a garage build something that destroys your thesis. Ackman argues that risk has climbed dramatically because this is the greatest era in history to build a company, with near-unlimited access to compute, capital, and talent. The paradox is that the conditions that make building easier also make incumbents more fragile, so the bulk of his research now centers on assessing how disruptible a business really is.

    What the market is missing

    Investors bring their attention to the new new thing, currently chips, semiconductors, and energy, which leaves high-quality companies behind. Ackman compares the moment to 2000, when Berkshire Hathaway traded at one of its lowest valuations ever because capital was chasing internet stocks. He sees an echo today in how Amazon, Meta, and Microsoft are treated as old-fashioned, and he considers them undervalued on fundamentals, where value is the present value of the cash a business generates over its life. His recent bullish call, like his March 2020 appearance, came because stocks of really high-quality companies had simply gotten too cheap.

    The SaaS question and AI-enabled software

    On the so-called SaaS apocalypse, Ackman says it is a company-by-company analysis. He worries more about something like Salesforce than about a low-priced platform. The companies most at risk are those that extracted near-monopolistic profits by charging a high annual price for a niche product, because AI lowers the barrier to replicating that functionality. A platform where the average customer pays a small amount per seat, like Microsoft, is far less exposed. The takeaway for any software company is to become as AI-enabled as it possibly can.

    Underwriting SpaceX, xAI, and the AI labs like venture

    For the highest-multiple private companies, Ackman uses a venture lens and a framework a business school professor taught him: people, opportunity, context, deal. SpaceX scores as one of one on people and opportunity, with an incredible context and a near-monopoly in low-cost launch through Starlink, which makes even Amazon a likely customer. The complicated variable is the deal, meaning the valuation, and he admits he has not done all the math, having invested through an SPV after Ron Baron encouraged him, along with a position in xAI. He treats OpenAI, Anthropic, and Palantir as late-stage venture bets that have proven real revenue, and argues OpenAI in particular should communicate more clearly how it justifies capital commitments that vastly exceed current revenue.

    Founder-led companies and the authority to act

    Ackman agrees that founder-led companies have a structural advantage in a fast-changing environment. The average S&P 500 CEO has a tenure of roughly three to four years, a small economic stake, and an incentive not to make a career-ending mistake. A founder is betting an entire life and reputation, has the authority of a major voting and economic position, and has usually made several hard, contrarian calls that turned out right. He points to Mark Zuckerberg’s acquisitions of Instagram and WhatsApp, which looked shocking at the time, as exactly the kind of decision a founder with a track record can make and a hired manager often cannot.

    Howard Hughes as Berkshire Hathaway 2.0

    Ackman points to a detailed financial history of Berkshire Hathaway showing that the vast majority of Buffett’s value creation came from owning insurance and focusing on the asset side of the balance sheet, not just the liability side. Insurance is hard to replicate because skilled investors join hedge funds rather than insurers, but Buffett owned half his company and was a great investor. Pershing Square is applying the same idea to Howard Hughes, a company created out of the General Growth bankruptcy that owns master-planned cities such as Summerlin, with 26,000 acres around Las Vegas, in the spirit of the Irvine Company that made Donald Bren roughly a hundred billion dollars. The plan is to reinvest the company’s cash into insurance, place policyholder float in short-term treasuries and the surplus in common stocks, avoid issuing stock the way Buffett did, and compound for fifty years, all bought at around sixty cents on the dollar.

    Cost of capital, reflexivity, and going direct

    A company only creates value when it earns above its cost of capital, which is why Howard Hughes, seen as a high-cost-of-capital real-estate business, has long traded at a discount, and why Ackman is repurposing its assets into a higher-returning model. He highlights how reflexive markets are: a higher stock price itself makes a company more valuable by lowering its cost of capital and creating currency to raise money and acquire businesses, a lever Elon Musk used to build Tesla. He attributes real market change less to himself and more to figures like Ryan Cohen and GameStop, where personality and a following can lift a stock far above its value. His own going-direct strategy on X, with 2.2 million followers and famously long posts, is the same mechanism applied to communicating a vision and lowering friction for investors. He closes by laying out three ways to invest with Pershing Square: the management company as a royalty on compounding assets, the PSUS portfolio trading at an 18 percent discount, and Howard Hughes as a bet on building the next Berkshire.

    Notable Quotes

    “The best investments are one where you don’t need to join the board and do anything.”

    Bill Ackman, on the kind of business he most wants to own

    “The probability of your being disrupted has gone up enormously.”

    Bill Ackman, on why assessing disruption risk now dominates his research

    “Valuation is like a tether on the market, right? When it gets too high, it’s like this rubber band that’s stretching and inevitably it bounces back.”

    Bill Ackman, on how prices revert at both extremes

    “People, opportunity, context, deal.”

    Bill Ackman, on the business school framework he uses to underwrite companies like SpaceX

    “Every CEO in America today is like, how do I use AI?”

    Bill Ackman, on AI as the top opportunity and threat in every boardroom

    “A closed mouth gathers no foot.”

    Bill Ackman, quoting the line a friend put next to his name in his high school yearbook

    “The increase in value of the company increases the value of the company, right? Because it lowers the cost of capital, it gives you more flexibility, gives you the ability to issue stock, raise capital, acquire other businesses.”

    Bill Ackman, on the reflexivity between stock price and corporate value

    “The company’s got like a $4 billion market cap and the goal is to build it into a trillion dollar thing over time compounding.”

    Bill Ackman, on his fifty-year plan for Howard Hughes

    Taken together, the conversation is a tour of how Ackman now thinks about quality, disruption, and compounding, and a preview of the Berkshire-style machine he wants to build out of Howard Hughes. Watch the full conversation here.

    Related Reading

  • Charles Koch and Chase Koch on Koch Industries: 130K Employees, 60 Countries, and a $150B Private Empire Built on Principle-Based Management

    Charles Koch and his son Chase Koch sat down with David Friedberg for a long, candid Forbes/All-In conversation about how a small crude-oil gathering operation in southern Oklahoma became Koch Industries, a privately held company with more than 130,000 employees across 60 countries and revenue that would land it comfortably in the top 25 of the Fortune 500 if it were public. They walked through the founding story, the management principles that drove a 9,000x increase in value since the early 1960s, the failures that almost wiped out the company, and the philanthropic and political work being done through Stand Together. Watch the full conversation on YouTube.

    TLDW

    Charles Koch took over a roughly 300-person family business in 1961 at age 25, fired the bureaucratic president, and built it into one of the most profitable private companies in the world by applying what he calls Principle-Based Management. The core insight is to be capability bounded rather than industry bounded, to run an internal “republic of science” that rewards contribution over credentials, and to treat failure as the price of experimental discovery. Koch grew through both organic capability extension and large acquisitions like Georgia Pacific in 2005 and Molex in 2013, mostly by replacing top-down hierarchies with bottom-up empowerment. The conversation covers the founding by Fred Koch, the near-death failures of the late 1990s “gas to bread spread,” the Pine Bend Minnesota refinery turnaround, the role of Wichita as a competitive advantage, Chase Koch’s path from feed-yard laborer to leader of Koch Disruptive Technologies, the launch of Stand Together as a long-running social-change platform, the rejection of single-party politics, the case against entitlements and occupational licensing, and the principles for using AI as a permissionless empowerment tool rather than a top-down control system. The throughline is Viktor Frankl: more people have the means to live and less meaning to live for, and the remedy is helping every individual find a gift and apply it in a way that creates value for others.

    Key Takeaways

    • Koch Industries today has more than 130,000 employees across 60 countries and has increased in value roughly 9,000 times since Charles took over in the early 1960s, when headcount was about 300.
    • Founded in 1940 by Fred Koch in Wichita, Kansas. The two starting businesses were designing fractionating trays (separating liquids by boiling point) and crude oil gathering in Oklahoma.
    • Charles got three engineering degrees at MIT, worked at Arthur D. Little, and reluctantly came back at 25 only after his father said he would otherwise sell the company. His father gave him full autonomy over every decision except selling.
    • His first move was firing the controlling, memo-driven president and replacing protectionism with three pillars: create value for customers, empower employees, and own end-to-end execution. They built their own plant in Italy instead of stitching together European subcontractors.
    • The defining mental model is “capability bounded, not industry bounded.” You expand into adjacent industries where the capabilities you have already proven (operations, logistics, trading, refining, branding) create more value than incumbents, not because the new industry is in the same SIC code.
    • Wholly owned business platforms today include engineered projects and construction, solar plants, commodity trading and distribution, fertilizers, refined products, chemicals and polymers, glass, forest and consumer products, electrical products (Molex), and management software, plus four distinct investment firms.
    • Koch is explicitly not a Berkshire-style conglomerate of independent silos. Chase frames it as an integrated republic of science, an integrated set of capabilities that share knowledge and people across business lines.
    • “If you are not failing at anything, you are not doing anything new.” Failure is treated as the cost of experimental discovery, but only when the learning value exceeds the cost.
    • The worst failures came from violating the hiring rule. Hire on values first, talent second. People with destructive motivation (power and control over contribution) hide failures and invent successes, and the damage compounds when those people get promoted into leadership.
    • The 1973 trading blowup nearly bankrupted the company. The late 1990s “gas to bread spread” strategy, an attempt to vertically integrate from natural gas through fertilizer to pizza crust, nearly wiped out all of Koch’s earnings. Lesson repeated, then internalized.
    • One acquisition shipped hundreds of millions of dollars in out-of-the-money hog feed contracts that nobody bothered to read before closing. Apply the scientific method: try as hard to disprove your hypothesis as to prove it.
    • Georgia Pacific was acquired in 2005 for roughly $20 billion when Koch was much smaller. They originally tried to buy only the commodity pulp piece so GP could re-rate as a pure consumer-products company at a higher P/E. When legal blockers killed that path, they bought the whole thing.
    • The Georgia Pacific culture change started with sending Joe Moeller in as CEO. He gutted the 51st-floor coat-and-tie executive suite, fired the most bureaucratic managers, moved everyone to working floors, and converted the executive floor into open meeting rooms. Signals like that drive culture more than memos do.
    • The Pine Bend, Minnesota refinery, bought in 1969, was one of the hardest cultural turnarounds. The union strike was violent (rifles fired, switch engines used to ram units), Charles ran it nine months without union labor on his honeymoon, the work rules finally changed, and once empowered, the workforce built its own machine shop, cut spare-part costs, and grew capacity tenfold. It is now one of the best refineries in the country.
    • Molex, bought in 2013, took years to transform. The dominant paradigm was top-line growth rather than bottom-line value creation, partly because it had been public for 30 years and the market rewarded the wrong things. Almost every successful turnaround required swapping in leadership with a bottom-up empowerment paradigm.
    • Sheep-dipping does not work. Pushing 130,000 people through the same seminar will not rewire habits. Coaching one struggling team until it succeeds creates social mimicry. Other teams ask to be next. Demand for Principle-Based Management coaches now exceeds supply inside the company.
    • The talent doctrine is values first, skills second, credentials last. Wichita and the farm-team labor pool are deliberate competitive advantages because farm kids tend to show up contribution-motivated rather than entitlement-motivated.
    • The current Koch CIO, Jared Benson, joined as a contractor striping lines in the parking lot and has no college degree. He learned data science, built the cyber-security capability, and ran circles around credentialed peers.
    • Public-company pressure to IPO was the biggest external threat. Charles refused. Staying private was the only way to keep reinvesting roughly 90 percent of profits, to maintain the capability-bounded model that no analyst would underwrite, and to keep accepting low P/E optics on commodity businesses inside the portfolio.
    • Three things any lasting partnership requires (marriage, business, employment): shared vision, shared values, and complementary capabilities. Miss any one and it does not last.
    • Chase Koch started at age 15 throwing tennis matches to escape practice, got shipped to a feed yard the next morning, shared a single-wide trailer with his boss, shoveled manure, and discovered the “glorious feeling of accomplishment” that his grandfather Fred had written about in his famous letter to the next generation.
    • At one point Chase was promoted to president of Koch Fertilizer, realized after nine months he was a builder and not an optimization operator, walked into his boss’s office, and fired himself. The role went to someone with the right comparative advantage and the business grew faster. Chase went on to launch Koch Disruptive Technologies (KDT).
    • KDT would have been shut down on a normal three-to-four-year venture timeline. Koch kept investing through the losses because of two principles: experimental discovery and creative destruction. They also valued the knowledge inflow about disruptive technologies that might one day eat the core business.
    • Comparative advantage applies to careers. The job of 20,000 plus Koch supervisors is to keep moving people into roles where they can actually contribute. Beating people up in the wrong seat is destructive.
    • Viktor Frankl frames the moral problem of the era: ever more people have the means to live and no meaning to live for. Without meaning, people default to either power or pleasure. Both lead, at scale, to totalitarianism, authoritarianism, or socialism.
    • Charles credits Maslow’s Eupsychian Management, Polanyi’s Personal Knowledge, Hayek’s price-signal work, and Frankl’s logotherapy as the intellectual foundations of Principle-Based Management. The five dimensions: vision, virtue and talents, knowledge processes, decision rights, and incentives.
    • Stand Together, founded in 2003, is a community of close to a thousand business leaders pooling effort on social change rather than working in philanthropic silos. The thesis: every human has a gift and the institutions are putting up barriers (broken schools, broken criminal justice, bad policy, occupational licensing).
    • Education is one of Stand Together’s biggest fronts. Pre-COVID, around 20 percent of families were open to a new model. Post-COVID, it is 70 to 80 percent. They back Alpha School (Joe Liemandt), Khan Academy (Sal Khan), and the VELA Education Fund alongside the Walton family. Roughly 5,000 micro-schools have been seeded.
    • The model for social change mirrors the business model: bet on the person closest to the problem who already shows results. Scott Strode and The Phoenix gym went from a couple of Colorado locations to one million people overcoming addiction, with relapse rates under 10 percent, by combining community and exercise rather than top-down treatment programs.
    • Charles says the biggest mistake of the first 50 years was trying to drive social change through a single political party, first the Libertarians and later just the Republicans. The current rule, from Frederick Douglass, is “I will unite with anybody to do right and with nobody to do wrong.”
    • His policy critique cuts in every direction: occupational licensing locks out newcomers, the treatment of working illegal immigrants is wrong, tariffs undermine division of labor by comparative advantage and raise prices, and entitlements once created are nearly impossible to dismantle.
    • Asked whether capitalism inevitably compounds into monopoly, Charles answers that the fix is removing barriers to others realizing their potential, not capping the winners.
    • On AI: the principle is permissionless innovation. Cost is collapsing, access is widening, and the right use is empowering individuals to learn 1000x faster, not concentrating power.
    • Koch backs Cosmos and other AI efforts that apply market-based management principles. Internally, they launched an AI app called Principal Companion that uses the Socratic method to walk users through problems using the book’s principles, from business to parenting.
    • Writing the new book (Charles’s fifth, Chase’s first) was the most important project Chase has worked on. They went through 27 versions of the stewardship chapter. Charles still corrects Koch leaders who say “the proof is in the pudding” instead of “the proof of the pudding is in the eating.”
    • When asked about legacy, Charles answered in one sentence: he wants the country to more fully live up to the promise in the Declaration of Independence.

    Detailed Summary

    From 300 Employees to 130,000 Across 60 Countries

    Koch Industries was founded in 1940 by Fred Koch in Wichita, Kansas. When Charles took over full-time in 1961, the company had about 300 employees and two main businesses: designing fractionating trays for separating liquids by boiling point, and a crude oil gathering system in Oklahoma. Today the company has more than 130,000 employees in 60 countries and has grown in value roughly 9,000 times over that period. If Koch were public, revenue would put it easily in the top 25 of the Fortune 500. The portfolio spans engineered projects and construction, solar plants, commodity trading and distribution, fertilizers, refined products, chemicals and polymers, glass, forest and consumer products, electrical products through Molex, management software, and four distinct investment vehicles. Roughly 90 percent of profits are reinvested.

    Charles Coming In at 25

    Charles describes himself as a poor engineer who happened to be good at math, science, and theory and bad at making or operating things. After three MIT degrees and a stint at Arthur D. Little doing what he calls “absurd” management consulting at 25, his father called and said the company was struggling and his health was failing. Either Charles came back or it would be sold. He came back. The condition was full autonomy: Charles could run it any way he wanted, the only decision requiring approval was selling. Within a short time he fired the previous president, a top-down memo-writer obsessed with controlling spending, and rewrote the operating philosophy around three things: create value for customers, empower employees, and own the value chain end to end. Instead of farming European fractionating trays out to multiple subcontractors and then re-assembling, Koch built its own plant in Italy.

    Capability Bounded, Not Industry Bounded

    This is the single most important strategic idea in the interview. Conventional advice told Koch to become an integrated oil major because they were in crude oil gathering. Charles rejected that and ran on Hayek and Adam Smith instead: division of labor by comparative advantage. Be in the part of any value chain where you can create more value than anyone else. From crude oil gathering, Koch leveraged operations, logistics, and trading into pipelines, refineries, natural gas, chemicals, fertilizers. Georgia Pacific looked like a non sequitur, wood products, but the underlying capability set transferred, and the acquisition also added branding as a new capability that fed back into the system. Chase calls the result not a Berkshire-style conglomerate of independent businesses but a republic of science: an integrated set of capabilities that share talent, knowledge, and laboratories.

    The Failures That Almost Killed the Company

    Charles spends a long stretch on failures, because he says the strength is in them. The 1973 trading blowup tied to the Middle East war could have bankrupted the company. The late 1990s “gas to bread spread” was an attempt to control the entire chain from natural gas to nitrogen fertilizer to grain to pizza crust. It violated almost every principle in the book at once and wiped out most of Koch Industries earnings for the decade. One acquisition closed before anyone read the hog-feed contracts, and on closing day they discovered hundreds of millions of dollars of out-of-the-money positions. Every failure traced back to two violations: hiring leaders with destructive motivation (power and control instead of contribution), and skipping the scientific method (trying to prove a hypothesis instead of disprove it). Charles says “repetition penetrates even the dullest of minds,” and he had to be punished enough times before the lesson took.

    Georgia Pacific, Molex, and the Pine Bend Refinery

    Three acquisition stories show how Koch transfers culture into businesses ten times larger than the corporate playbook would normally allow. Georgia Pacific in 2005 was a $20 billion bet on a company much larger than Koch at the time. Joe Moeller, sent in as CEO, immediately fired the most bureaucratic managers, gutted the 51st-floor private-elevator executive suite (coat and tie required to visit), moved everyone to working floors, and turned the old executive floor into open meeting rooms. Molex, bought in 2013, had been public for 30 years and ran on top-line growth thinking because that is what the market rewarded. Changing the paradigm to bottom-up empowerment and bottom-line value creation took years and required new leadership. Pine Bend, Minnesota, bought in 1969, was the hardest. The union ran the refinery, ignored work rules, and went on a violent strike when Koch tried to change them, firing rifles and ramming switch engines into units. Charles ran the refinery nine months without union labor (during his honeymoon), eventually got the work rules changed, then spent years rebuilding the culture. The empowered workforce designed and built its own machine shop, cut spare-part costs, and grew capacity tenfold. Pine Bend is now one of the best refineries in the country.

    How Principle-Based Management Actually Diffuses

    Charles is blunt that they tried “sheep dipping” first, hauling everyone through a seminar. It did not work, because changing a habit means rewiring the brain through work at intensity over time, the way a weightlifter has to retrain to become a marathoner. The model that did work was small. Find one team that is struggling, coach them with principles, let them succeed, and the rest of the company asks to be next. Social mimicry replaces top-down rollout. Internally the Principle-Based Management group is now in higher demand than any other function.

    Talent: Values First, Skills Second, Credentials Last

    Koch deliberately stayed in Wichita partly to access a “farm team” labor pool of people who grew up contribution-motivated. Chase tells the story of Jared Benson, who started as a contractor striping lines in the Koch parking lot, taught himself data science, built the company’s cyber-security capability, and is now CIO with no college degree. The lesson runs against the prestige-school default of most large companies. Contribution motivation, not credentials, predicts long-run output, and Charles is willing to “hire slow and stupid” for anyone with bad values so the company can flush them quickly. Aligning incentives matters as much as hiring: reward people on overall long-run contribution to Koch’s future, including the value of what was learned from a failed experiment, not on near-term P&L.

    Why Koch Stayed Private

    Multiple parties pushed hard for an IPO over the decades. Charles refused. Going public would have made the capability-bounded model impossible to communicate to analysts, would have forced a higher payout ratio and broken the reinvestment compounding, and would have introduced the short-termism that wrecks bottom-up empowerment. Buffett gets credit, but Berkshire does not try to integrate its businesses the way Koch does. Asked whether a non-owner public CEO could ever apply the principles, Charles allows it is possible if they can sell a different durable story (as Buffett did), but it is much harder.

    Chase Koch’s Path

    Chase tells two formative stories. The first is being shipped to a feed yard at 15, sharing a single-wide trailer with his boss, shoveling manure for minimum wage, and finding, for the first time, what his grandfather Fred had called “the glorious feeling of accomplishment.” The second is firing himself as president of Koch Fertilizer after nine months because he realized he was a builder, not an operator. The business outgrew where he would have taken it, and he went on to launch Koch Disruptive Technologies, the venture and innovation arm that now feeds technological insight back into every Koch business line. The comparative-advantage principle applied to a career, in public, by the boss’s son.

    Stand Together and Social Change

    Stand Together, founded in 2003, is the Koch family’s social-change platform. It now includes close to a thousand aligned business leaders. The animating belief is that every human has a gift and institutional barriers (broken schools, broken criminal justice, occupational licensing, bad policy) prevent most people from finding and applying it. The Phoenix gym founded by Scott Strode is the canonical Stand Together bet: a person closest to the problem, with results (relapse rates under 10 percent), funded to scale. In seven or eight years it has gone from a couple of Colorado locations to one million people. On education, post-COVID openness to new models jumped from roughly 20 percent of families to 70 to 80 percent. Stand Together backs Alpha School, Khan Academy, and the VELA Education Fund alongside the Walton family, and has helped seed roughly 5,000 micro-schools.

    Politics: The Single-Party Mistake

    Charles says for the first 50 of his 60 years in this work he avoided major-party politics, then concluded the country needed principle-based policies badly enough that engagement was required. The mistake was trying to do it through one party. The Libertarian Party turned into purity tests reminiscent of the early Communist Party. Doing it through Republicans blew up too. The rule going forward is Frederick Douglass’s: unite with anybody to do right and with nobody to do wrong. He is openly critical of both parties on occupational licensing, immigration policy, tariffs, entitlements, and the treatment of working illegal immigrants. He invokes Jefferson on slavery to describe his current mood: “If God is just, I despair for the future of our country.”

    Capitalism, Compounding, and AI

    Asked whether capitalism inevitably ends in monopoly because successful operators compound, Charles flips the framing. The remedy is not to cap the winners, it is to remove the barriers preventing everyone else from realizing their potential. Occupational licensing, immigration restriction on contributors, tariffs that undermine comparative advantage. On AI, Koch’s principle is permissionless innovation: cost is collapsing, access is widening, and the right outcome is individual empowerment and 1000x faster learning, not power concentration. Internally they launched Principal Companion, an AI app built on the principles in the book that uses the Socratic method to walk users through problems rather than handing out answers. Koch backs Cosmos and other AI ventures applying market-based management.

    The Philosophical Spine

    Charles cites four foundational thinkers. Polanyi’s Personal Knowledge gave him the model for how habits encode knowledge in the brain and why retraining is bodily work. Maslow’s Eupsychian Management supplied the empirical link between self-actualization and organizational performance. Hayek supplied the price system and the case against central planning. Frankl supplied the diagnosis: more means to live, less meaning to live for, and in that vacuum people drift to either power or pleasure, both paths to the slippery slope of authoritarianism and socialism. The Principle-Based Management answer is to design the company (and the country) so that everyone can find a gift and apply it to help others succeed.

    Thoughts

    The most useful concept in the conversation, the one worth stealing for any operator regardless of industry, is “capability bounded, not industry bounded.” Most companies define their addressable market by SIC code or competitive set. Koch defines it by the actual transferable skills they have demonstrated: operations, logistics, trading, refining, branding, cyber-security. Each acquisition is a probe to see whether the capability set creates more value than incumbents, and each acquisition that works hands back new capabilities (branding from Georgia Pacific, electronic-components engineering from Molex) that compound the option space. This is the same logic that makes Amazon’s AWS, advertising, and logistics businesses adjacent rather than diversifications. Industry conglomerates collapse. Capability conglomerates do not, because the capabilities reinforce each other.

    The honest treatment of failure is rarer than it sounds. Most CEOs who say “we celebrate failure” mean something performative. Charles’s version has teeth because the failures he names (the 1973 trade, the late 1990s vertical-integration push, the unread hog contracts) were almost terminal, and the lesson he draws is not “fail fast” but a specific causal claim about hiring leaders with destructive motivation. The asymmetry between contribution-motivated and destructively motivated employees, with the latter capable of hiding losses and inventing successes until the damage compounds, is the kind of insight that only comes from forty years of post-mortems. The remedy, hire slow and dumb if values are bad so you can purge fast, is uncomfortable enough to be real advice.

    The case for staying private is also harder than the founder-flex version usually heard from private operators. Charles is not arguing that private is better for everyone. He is arguing that a specific operating model (high reinvestment, cross-business capability sharing, willingness to take long P/E hits on commodity legs, leadership succession over decades) cannot be communicated to public markets without distortion. If you do not run that model, going public is fine. If you do, going public would have killed the system. That distinction is worth holding on to when reading the founder-control discourse in tech, because most “stay private forever” arguments do not actually meet that bar.

    The political reflection is the most surprising part of the conversation, particularly given the public reputation. Charles plainly says the biggest mistake of his life in social change was trying to do it through one party, that the Libertarians collapsed into purity-test factionalism, that the Republican approach failed in similar ways, and that the current operating rule is the one Frederick Douglass actually wrote down. He criticizes the current administration’s treatment of working illegal immigrants and the tariff regime by name. Whether one agrees or disagrees on policy, the willingness to grade your own past work in public, decades after the bets were placed, is rare at this level.

    Finally, the Frankl framing deserves a longer hearing than a podcast can give it. “Ever more people have the means to live and no meaning to live for” is the most economical statement of the malaise running through politics, addiction, education, and labor data right now. Koch’s bet is that the answer is not policy alone but a design problem: build institutions (companies, schools, philanthropies, AI tools) that let each individual find a gift and apply it in a way that creates value for others. That is the through-line connecting Principle-Based Management, Stand Together, the Alpha School partnership, The Phoenix gym, and Principal Companion. Whether it scales is an open question. The fact that one family business has spent 60 years pressure-testing it makes the experiment worth paying attention to.

    Watch the full Charles Koch and Chase Koch conversation on All-In and Forbes.

  • Warren Buffett’s Final Thanksgiving Letter: A Historic Farewell from the Oracle of Omaha

    Warren Buffett’s Final Thanksgiving Letter: A Historic Farewell from the Oracle of Omaha

    On November 10, 2025, Berkshire Hathaway released an 8-page document that instantly became one of the most important shareholder letters in the history of American capitalism.

    This is not just another annual report update. This is Warren Buffett’s official retirement announcement at age 95, his last direct message to shareholders, and the clearest blueprint yet for the future of his $1 trillion empire and his remaining $150+ billion fortune.

    In one sweeping move, Buffett converted 1,800 Class A shares into 2.7 million Class B shares and donated them immediately — the largest single-day charitable gift in Berkshire history:

    • 1.5 million B shares → The Susan Thompson Buffett Foundation
    • 400,000 B shares each → The Sherwood Foundation, Howard G. Buffett Foundation, and NoVo Foundation

    That’s over $13 billion at today’s prices, delivered the same day.

    The End of an Era

    In his trademark folksy style, Buffett declares: “I will no longer be writing Berkshire’s annual report or talking endlessly at the annual meeting. As the British would say, I’m ‘going quiet.’ Sort of.”

    He confirms what insiders have known for years: Greg Abel takes over as CEO at year-end 2025. Buffett’s praise is unequivocal: “I can’t think of a CEO, a management consultant, an academic, a member of government — you name it — that I would select over Greg to handle your savings and mine.”

    The Most Personal Letter Ever Written by a Billionaire

    Unlike any previous letter, this one is deeply autobiographical. Buffett recounts:

    • Nearly dying at age 8 from a burst appendix in 1938
    • Fingerprinting Catholic nuns during recovery (and fantasizing about helping J. Edgar Hoover catch a “criminal nun”)
    • Missing Charlie Munger by a whisker — Munger worked at Buffett’s grandfather’s grocery store in 1940; Warren took the same $2-for-10-hours job in 1941
    • Living one block away from Munger, six blocks from future Berkshire legends, and across the street from Coca-Cola president Don Keough — all without knowing it

    His conclusion? “Can it be that there is some magic ingredient in Omaha’s water?”

    Lady Luck, Father Time, and the Acceleration of Giving

    At 95, Buffett is blunt about aging: “Father Time, to the contrary, now finds me more interesting as I age. And he is undefeated.”

    He acknowledges his children (Susie, Howie, and Peter — ages 72, 70, and 67) are entering the zone where “the honeymoon period will not last forever.” To avoid the chaos of post-mortem estate battles, he is accelerating lifetime gifts at warp speed while keeping enough A shares to ease the transition to Greg Abel.

    Most powerful line on wealth and luck:

    “I was born in 1930 healthy, reasonably intelligent, white, male and in America. Wow! Thank you, Lady Luck.”

    Warnings to Corporate America

    Buffett eviscerates CEO pay inflation, dementia in the C-suite, and dynastic wealth. Highlights:

    • CEO pay-disclosure rules “produced envy, not moderation”
    • Boards must fire CEOs who develop dementia — he and Munger failed to act several times
    • Berkshire will never tolerate “look-at-me rich” or dynastic CEOs

    Why This Document Will Be Studied for Centuries

    This letter is the capitalist equivalent of a papal encyclical. It combines:

    • A formal leadership handoff after 60 years
    • The largest ongoing wealth transfer in history
    • A philosophical treatise on luck, aging, kindness, and corporate governance
    • A love letter to Omaha and middle America
    • Buffett’s final ethical will: “Decide what you would like your obituary to say and live the life to deserve it.”

    Business schools will teach this. Biographers will mine it. Investors will quote it for decades.

    Download the full PDF here: Warren Buffett Thanksgiving Letter 2025 (PDF)

    As Buffett signs off:

    “I wish all who read this a very happy Thanksgiving. Yes, even the jerks; it’s never too late to change.”

    The Oracle has spoken — one last time. And the world is listening.

  • Diverging Paths: Marks and Buffett’s Contrasting Investment Philosophies

    Diverging Paths: Marks and Buffett's Contrasting Investment Philosophies

    While Howard Marks and Warren Buffett share a deep respect for intrinsic value and long-term investing, their approaches diverge in several key areas. These differences, while subtle, offer valuable insights into the diverse strategies that can lead to success in the financial markets.

    Risk Management

    Marks is known for his emphasis on risk management and avoiding losses. He believes that “if we avoid the losers, the winners will take care of themselves.” This focus on capital preservation is evident in Oaktree’s investment strategies, which often involve buying distressed debt or other undervalued assets with a margin of safety. Buffett, while also risk-averse, is more focused on the long-term growth potential of his investments. He is willing to take on more concentrated positions in companies he believes have a durable competitive advantage, even if it means accepting more short-term volatility.

    Investment Philosophy

    Marks is a proponent of value investing, but he also emphasizes the importance of understanding market cycles and investor psychology. He believes that these factors can create opportunities for outsized returns, but they can also lead to significant losses if not properly understood. Buffett, on the other hand, is a more traditional value investor who focuses on buying high-quality businesses at reasonable prices. He is less concerned with market cycles and investor psychology, believing that the long-term performance of a business is the most important factor in determining its value.

    Investment Universe

    Marks, through Oaktree Capital Management, has a broader investment mandate than Buffett. Oaktree invests in a variety of asset classes, including distressed debt, real estate, and private equity. This allows Marks to take advantage of opportunities in different markets and to diversify his portfolio. Buffett, on the other hand, primarily invests in publicly traded stocks of large, well-established companies. He has a more concentrated portfolio than Marks, and he is less likely to invest in alternative asset classes.

    Communication Style

    Marks is known for his clear and concise communication style. He regularly publishes memos to his clients that share his insights on the market and his investment philosophy. These memos are widely read and respected in the investment community. Buffett also communicates regularly with his shareholders through his annual letters, but his writing style is more folksy and anecdotal. He often uses stories and analogies to explain his investment philosophy, and he is less likely to share specific investment ideas.

    The divergent paths of Howard Marks and Warren Buffett highlight the diverse approaches that can lead to success in investing. While their shared principles provide a solid foundation, their differences in focusing on macroeconomic factors, investment universe, portfolio concentration, investment style, and communication offer valuable lessons for investors seeking to develop their own unique strategies. By understanding these nuances, investors can tailor their approach to their individual risk tolerance, investment goals, and areas of expertise, ultimately increasing their chances of achieving long-term success in the market.

    If you want to know where Marks and Buffett converge on investment philosophy read this.

  • Converging on Investment Philosophy: Marks and Buffett’s Shared Wisdom

    In the world of investing, few figures command as much respect as Howard Marks and Warren Buffett. While their individual styles and approaches may differ, a careful analysis of their writings reveals a remarkable convergence of key investment principles. This exploration of the shared wisdom found in Marks’ memos and Buffett’s letters offers a roadmap for navigating the complexities of the market.

    Intrinsic Value: The North Star of Investing

    Both Marks and Buffett unequivocally stress the importance of intrinsic value as the bedrock of investment decisions. Intrinsic value, they argue, is the true worth of a business, determined by the present value of its future cash flows. This principle serves as a guiding light, leading investors toward assets that are genuinely undervalued and shielding them from the capriciousness of market sentiment.

    Long-Term Orientation: The Antidote to Short-Termism

    In a world often fixated on short-term gains and quarterly earnings, Marks and Buffett champion the virtues of long-term thinking. They recognize that true value creation is a gradual process, and succumbing to the allure of quick profits can lead to devastating consequences. By maintaining an unwavering focus on the long-term potential of their investments, they navigate through market turbulence and emerge stronger.

    Tuning Out Market Noise: The Path to Rationality

    The daily fluctuations of the market can be a source of anxiety for many investors. However, Marks and Buffett counsel against being swayed by the noise. They posit that short-term price movements are often fueled by irrational exuberance or fear, and astute investors should concentrate on the underlying value of their holdings, not the fleeting whims of the ticker tape.

    Margin of Safety: The Investor’s Fortress

    The concept of margin of safety is deeply embedded in both Marks’ and Buffett’s investment strategies. It entails acquiring assets at a substantial discount to their intrinsic value, creating a buffer against potential losses. This approach not only safeguards against downside risk but also amplifies the potential for extraordinary gains when the market eventually aligns with the investment’s true worth.

    Circle of Competence: Knowing Your Limits

    Both investors underscore the importance of operating within one’s circle of competence. This means investing in businesses and industries that you genuinely comprehend, acknowledging the boundaries of your knowledge. By adhering to this principle, Marks and Buffett sidestep costly errors and seize upon opportunities that others may miss due to a lack of understanding.

    Temperament and Discipline: The Investor’s Emotional Rudder

    Successful investing transcends mere intellect; it necessitates the cultivation of the right temperament and discipline. Marks and Buffett emphasize the significance of remaining patient, rational, and emotionally composed amidst market volatility. By eschewing impulsive decisions fueled by fear or greed, they maintain a steady course and make judicious choices that endure.

    Prioritizing Loss Avoidance: The Foundation of Winning

    While the pursuit of gains is a natural inclination for investors, Marks and Buffett prioritize the avoidance of losses. They understand that by safeguarding capital and mitigating downside risk, the winning investments will naturally reveal themselves over time. This prudent approach ensures that their portfolios are resilient and capable of withstanding market downturns.

    The Importance of Management: The Human Element

    Both investors acknowledge that the caliber of a company’s management team is a pivotal factor in its long-term success. They seek out companies helmed by competent, ethical, and shareholder-oriented leaders who are dedicated to creating value for their investors. By investing in companies with robust leadership, Marks and Buffett align themselves with the paragons of the business world.

    Opportunistic Investing: Seizing the Right Moment

    Marks and Buffett are opportunistic investors, perpetually vigilant for undervalued assets and market dislocations. They exercise patience, waiting for the right opportunities to emerge, rather than succumbing to the allure of fleeting trends. When the market presents them with a bargain, they act decisively and with unwavering conviction.

    Financial Strength and Conservatism: The Bedrock of Stability

    Both investors stress the importance of maintaining financial strength and eschewing excessive debt. They believe that a conservative approach is paramount for long-term survival and prosperity in the unpredictable world of investing. By prioritizing financial stability, they fortify their portfolios against unforeseen challenges.

    Skepticism of Forecasts: Embracing the Unknown

    Marks and Buffett share a healthy skepticism towards macroeconomic forecasts and market predictions. They acknowledge the inherent uncertainty of the future and the limitations of human foresight. Instead of relying on speculative prognostications, they concentrate on what is knowable and controllable, such as the intrinsic value of their investments and the quality of the businesses they own.

    Value Investing Philosophy: The Time-Tested Path

    Both Marks and Buffett are ardent proponents of the value investing philosophy, which entails acquiring assets at a discount to their intrinsic value. This approach, championed by Benjamin Graham and refined by Buffett, has consistently proven to be a reliable path to enduring investment success. By adhering to this philosophy, they consistently unearth and acquire undervalued assets poised to deliver superior returns over time.

    If you want to know where Marks and Buffett diverge on investment philosophy read this.