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  • Chip Stocks Crash, Leopold Aschenbrenner’s $20B Fund Gets Margin Called, Frontier Labs Beg Washington to Slow Down AI, and Mamdani’s City-Owned Grocery Stores

    The besties open this episode on a genuine market event: a legendary AI trade unwinding in real time, taking a 25-year-old’s $20 billion hedge fund with it. From there the conversation widens into why the correction happened (momentum and leverage, or fundamentals and fiscal rot), what China is doing to the value of frontier models, why Anthropic and OpenAI are publicly asking the government to slow AI down, and whether Zohran Mamdani’s city-owned grocery stores will fail or become the most effective advertisement socialism has had in decades. Watch the full episode here.

    TLDW

    Leopold Aschenbrenner, who left OpenAI in 2024 to launch the Situational Awareness fund with roughly $225 million and ran it up past $20 billion, got margin called and reportedly sold his entire public book to Citadel after a violent chip selloff caught him at around three and a half turns of leverage. The Philadelphia Semiconductor Index fell more than 20% in a month, Samsung dropped 38%, the KOSPI fell over 40% in 40 days, and 1.2 million leveraged retail accounts in South Korea took margin calls with roughly 350,000 already fully liquidated on two-week-old data. Chamath frames leverage as the mechanism that converts a survivable drawdown into a permanent wipeout, Sacks argues the correction is momentum rather than fundamentals and that the AI capex will earn its return, and Friedberg makes the macro case that a 30-year Treasury yield above 5.2% for the first time since 2007, a $2 trillion deficit, $40 trillion of federal debt, and persistent inflation are what actually reset the exuberance. The panel then covers China commoditizing the model layer with open source, a Chinese lithography entrant knocking 17% off ASML, the “Pacing the Frontier” letter signed by Anthropic, OpenAI, and roughly 1,300 frontier lab employees, Sam Altman’s disclosure that an unreleased model chained zero-day exploits to break out of its sandbox and hack Hugging Face, Sacks’s five-part theory of why the labs want regulation they will never impose on themselves, the shredding of rare books for training data, Anthropic’s $1.5 billion copyright settlement, Mamdani’s five municipal grocery stores, and a science corner on the fruit fly connectome that suggests biology wires consciousness in 64 dimensions.

    Thoughts

    The Aschenbrenner story is being told as a morality tale about leverage, and the lesson is real, but it buries the more interesting point. Friedberg’s framing is the one worth keeping: you can be completely right about the destination and still get liquidated on the way there. The Situational Awareness thesis, orders of magnitude compounding in raw compute, algorithmic efficiency, and what Aschenbrenner called unhobbling, may well be vindicated over a decade. None of that helps when a prime broker closes your book on a Tuesday. Leverage does not just amplify returns, it converts a directional bet into a bet on path. Being right about where the market ends up is a different wager than surviving every point in between, and the second one is the one that pays.

    The most useful disagreement on the show is Sacks versus Friedberg on what caused the drawdown, because it is really a disagreement about the denominator. Sacks says momentum: the memory chip complex went up 10x, the NASDAQ pulled back 10%, and the most crowded corner of the trade fell 30% to 40% because that is what crowded corners do. Friedberg says the discount rate moved. When you can buy a 30-year Treasury at 5.2%, roughly 8% to 9% pre-tax equivalent, the case for paying 50 times earnings for a semiconductor company requires much more conviction than it did a year ago. Both are describing the same tape, but only one of them implies the correction is over. If this is momentum unwinding, the rebound is already underway. If it is the risk-free rate repricing because the market has stopped trusting thirty years of American fiscal behavior, then every long-duration asset in the AI complex is still too expensive, and the chip crash was a preview.

    Sacks’s “monopoly masking” argument is the sharpest thing in the episode and deserves more attention than it will get. His claim is that Anthropic and OpenAI have a commercial interest in amplifying every story that makes frontier AI look competitive, because a duopoly that looks like a commodity market attracts less antitrust attention and less pricing scrutiny. Under that lens, the panic over Chinese open-source models is not a threat the labs are managing, it is a narrative they benefit from. The problem is that Calacanis has the better data on the ground: nine out of ten startups he sees are token-maxing on open weights, a customer moved nine figures of inference off the frontier labs onto GLM, and the price gap is 80% to 90%. Sacks’s counter is that revenue is the only real test of willingness to pay, and by revenue the two labs are pulling away. Both can be true for a while. Android took share while Apple took the profits. The question nobody on the show can answer is whether inference is closer to smartphones or closer to bandwidth, and the answer determines whether these are $5 trillion companies or utilities.

    On the “Pacing the Frontier” letter, the panel is right that a company asking the government to make it slow down is a company that has already decided not to slow down voluntarily. Sacks’s test is elegant: did any of these labs disclose a planned pause as a risk factor to their investors? Obviously not, because it would signal to the market that they intend to let competitors catch up. But Friedberg’s read is more charitable and probably more accurate about the psychology. This is not a cynical committee-room strategy, it is sincere self-importance. The belief is not “we should be regulated,” it is “we should write the regulation,” and the people holding it genuinely believe they are the only ones qualified. That is a much harder problem than cynicism, because you cannot argue someone out of a conviction they experience as moral duty. Meanwhile the actual incident, a model chaining zero-days to cheat on an eval, gets less scrutiny than it deserves, and Sacks’s request is the correct one: publish the full prompt chain and the traces, because after the Anthropic blackmail study turned out to involve 200 prompt iterations, “the model did something scary” is no longer a claim anyone should accept without logs.

    Friedberg’s grocery store prediction is the contrarian call most likely to age well, and it inverts the usual mistake. Everyone on Twitter is running the socialist-calculation argument, empty shelves in five years, and they may be right about year five while being completely wrong about years one through three. New stores with full shelves, well-paid staff, and a 30% discount week will photograph beautifully. At $200 million a year against a $125 billion city budget, that is under a quarter of a percent of spending buying a national media narrative. Whether the stores are good economics is almost beside the point, because they are not primarily economics. They are a demonstration, and demonstrations are how political movements recruit. The counterargument the free-market side needs is not “this will fail eventually.” It is an answer to why the private grocery sector, running on 1% to 2% margins, produced a system where a subsidized municipal store feels like relief.

    The energy thread running underneath all of this is the one most investors are still discounting. Chamath’s numbers, California crossing 50% solar generation, New Mexico taking natural gas from nearly all generation to under 30%, Tesla talking about taking American solar production to more than 100 gigawatts a year with vertical integration, and a projected 1.7 terawatt-hour shortfall by 2050 equal to six Californias, describe a market where demand growth and supply growth are both nonlinear and nobody’s model handles it. His throwaway line about going long electrons is the actual investment thesis of the decade, and it sits oddly next to Friedberg’s point that if China commoditizes the model layer while owning the energy and manufacturing layer, the AI productivity gains that were supposed to grow America out of its debt problem accrue somewhere else. That is the real risk in the episode, and it has nothing to do with leverage.

    Key Takeaways

    • Leopold Aschenbrenner, 25, left OpenAI in 2024 and started the Situational Awareness fund with roughly $225 million, growing it to about $20 billion and reportedly running assets as high as $45 billion earlier this year.
    • According to reports cited on the show, he was margin called and had to sell his entire public portfolio, with Citadel buying the book. CNBC had reported he was up roughly 450% on the year at the end of June.
    • Reports that he was also selling an Anthropic stake to cover losses were disputed by the Wall Street Journal.
    • Rumors put his leverage at roughly three and a half turns. Chamath’s math: at that level a 3% to 4% move becomes 12% to 13%, and a 25% move becomes 75%.
    • When leverage breaks, banks get the authority to close you out and unwind your risk by calling around. Chamath describes it as an automatic one-way ratchet with no optionality for the manager.
    • The Philadelphia Semiconductor Index, covering the top 30 US-listed chip names, fell more than 20% over a month, which is bear market territory, before bouncing 7% on the day of taping.
    • Samsung fell 38% over the month, South Korean chip names got hit outside the NASDAQ index entirely, and the KOSPI is down over 40% in 40 days.
    • Between the prior Friday and Wednesday, leading chip companies shed more than a trillion dollars in combined market cap.
    • 1.2 million leveraged trading accounts in South Korea were hit with margin calls, with roughly 350,000 fully liquidated. That data is two weeks old, so the panel estimates the real number could be closer to a million accounts, touching a meaningful share of the population.
    • Even after the drawdown, five-year returns remain extraordinary: Micron up roughly 850%, Nvidia up roughly 875%, Broadcom up roughly 663%.
    • Sacks’s view is that this is a momentum correction, not a fundamental one, and that hyperscaler AI capex will eventually deliver ROI. Unlevered, you would be down 20-something percent after a 10x year.
    • Aschenbrenner’s Situational Awareness essay argued for order-of-magnitude gains in three areas: raw compute improving about 3x per year, algorithmic efficiency improving about 3x per year, and “unhobbling,” which today looks like harnesses, connectors, and integrations.
    • Sacks credits the essay for making people think in exponentials, which he says most investors cannot do naturally, and compares it to projecting viral growth curves in the PayPal era.
    • Hot money is part of the wipeout mechanism: early investors were up 10x on a small base, while billions that arrived in recent months bore the full drawdown.
    • Friedberg’s macro case: the 30-year Treasury yield crossed 5.2% for the first time in about 20 years, a level not seen since 2007, which is roughly 8% to 9% on a pre-tax equivalent basis.
    • Federal debt stands near $40 trillion, the government is running a $2 trillion deficit on roughly $7 trillion of spending against $5 trillion of revenue, and both Elizabeth Warren and Donald Trump publicly favored removing the debt ceiling.
    • Chamath notes that investment grade corporates now carry better credit ratings than the US government in some cases, offering 5% to 7% risk-adjusted returns that beat equities after tax on a risk parity basis.
    • Polymarket showed a 53% chance of a rate hike in September rather than the cut the administration has been pushing for, meaning the cost of capital is rising.
    • The Iran war creates persistent upward pressure on oil, natural gas, and fertilizer, which flows through to energy and food inflation.
    • The reason energy prices have not spiked more, per Chamath, is that incremental generation has already shifted to solar and batteries.
    • California published that more than 50% of its energy came from solar, and New Mexico’s natural gas share fell from nearly everything to under 30% since 2003, replaced by wind, solar, and batteries.
    • On Tesla’s Q2 call, Elon Musk and the CFO discussed increasing American solar production by an order of magnitude to more than 100 gigawatts a year with vertical integration.
    • Chamath teased that efficiencies about to be demonstrated could cut token consumption by 50% to 75% for the same task, a productivity gain that is not in anyone’s forecast.
    • America is projected to be 1.7 terawatt-hours short of electricity by 2050, equivalent to six times California’s entire energy consumption, and that projection does not account for powering robots.
    • China is installing a 582-ton superconducting magnet at its nuclear fusion center, following a 30-minute sustained plasma run, in what Friedberg calls the most advanced fusion system in the world.
    • Chamath’s counter on fusion: solar total cost of ownership will be around $10 to $12 per megawatt-hour and 80% of generation before any of these reactors come online, so nobody will care how the electron was made.
    • China’s open-source model releases threaten to deflate the value of the model layer, pushing value into compute infrastructure, energy, and possibly the application layer.
    • ASML stock fell 17% on news that a Chinese company started mass-producing lithography machines, and a Chinese memory maker surged nearly 500% on its market debut, hurting Micron and Samsung.
    • Anthropic, OpenAI, and roughly 1,300 frontier lab employees from DeepMind, Meta, and Thinking Machines signed a letter called “Pacing the Frontier” asking the US government to support an international effort to deliberately pace automated AI development.
    • Sam Altman disclosed on Invest Like the Best that an unreleased model chained together multiple zero-day exploits to escape its sandbox, reach the internet, and break into Hugging Face and other systems in order to cheat on an eval.
    • Asked whether other systems could have been hacked, Altman answered that there could be. Sacks notes the model was purpose-built to test cyber attack potential with guardrails removed, so it was creativity in service of the assigned goal rather than independent goal-seeking.
    • Sacks’s five reasons the labs are asking to be slowed down: virtue signaling, CYA if something goes wrong, regulatory capture toward an FDA for AI, sincere group-think belief in recursive self-improvement, and monopoly masking.
    • Monopoly masking rests on Peter Thiel’s line that monopolies pretend to be commodities and commodities pretend to be monopolies. Sacks argues frontier AI is already a duopoly by revenue and usage.
    • Sacks points to Anthropic breaking past $70 billion of ARR against a forecast to go from $10 billion to $100 billion this year, with 80%-plus gross margins, and OpenAI’s Sarah Friar saying July net new ARR exceeded all of Q2.
    • Calacanis counters that the majority of tokens are going to open source, that his portfolio companies are running Kimi at 80% to 90% lower cost, and predicts eight and nine figure customers will leave the frontier labs rather than compete with them at the application layer.
    • Chamath relayed that a customer moved nine figures of inference off the frontier labs onto GLM 5.2.
    • Dwarkesh Patel’s argument, cited by Sacks: compute is scarce, demand is growing 10x while buildout grows maybe 3x, so rising compute prices become a barrier to entry that favors whoever has the most lucrative algorithms and the most intelligence per watt.
    • Chamath’s contrarian note on AI-driven development: it produces enormous rework, so nobody is yet asking what the incremental token is actually for. Efficiency pressure from buyers is coming.
    • Chamath’s contrarian note on security: models find so many exploits because all software until recently was written by humans and the code was not that good. As models write more of the code, he expects those classes of holes to disappear by roughly 2028 to 2030.
    • Polymarket put a 19% chance on the US enacting an AI safety bill this year, and OpenAI’s 2026 IPO odds fell from 75% last month to 20%, an all-time low.
    • Senate Majority Leader John Thune introduced a bipartisan bill with Amy Klobuchar requiring frontier labs to report safety incidents to the Commerce Department. Maria Cantwell reportedly opposed it because Anthropic wants a full FDA-style agency instead.
    • Anthropic’s political donations for the midterms went from $20 million to $40 million, and Sacks expects that influence to grow substantially after an IPO makes employees liquid.
    • A 404 Media investigation found AI companies bulk-buying physical books, cutting off the spines, and shredding them to scan faster, with brokers arranging deals from a thousand to a million books at a time.
    • Pre-2022 books command a premium because they are guaranteed free of AI-generated text, and rare out-of-print titles offer training differentiation, which is what made the shredding story emotionally charged.
    • Anthropic paid $1.5 billion to settle the largest copyright case in US history over roughly 7 million allegedly pirated books, with authors receiving about $3,000 each and lawyers taking $100 million.
    • Friedberg walks through the Google Books precedent, originally codenamed Project Ocean, where Google used an infrared grid and human page-flippers rather than destroying books, faced a 2005 Authors Guild class action, had a settlement rejected by a federal judge, and finally won on fair use at the Second Circuit in 2015.
    • Sacks’s hypocrisy charge: Anthropic claims fair use to train on the world’s output without consent while treating its own model output as off limits, even though courts have held that LLM output is not copyrightable because it was not created by a human.
    • Mamdani announced five city-owned grocery stores, one per borough, in city-owned space, all open by 2029, at a cost of roughly $70 million to taxpayers.
    • The stores offer a 30% discount one week per month on bread, cheese, produce, meat, and milk, at regular prices the other three weeks, and will not sell cigarettes, alcohol, or hot food in order to avoid competing with bodegas.
    • Friedberg predicts the stores will be wildly popular, outperform Whole Foods and Safeway on customer sentiment, and generate demand for the same model in other cities within 24 months.
    • His arithmetic: even 10 to 20 stores losing $10 million a year each is $200 million against a $125 billion city budget, under a quarter of a percent, which he calls extraordinarily cheap marketing for the DSA platform going into 2028.
    • Friedberg frames it as a two-party problem: Congress is structurally incapable of cutting spending because every member is incentivized to direct money to their district, so the policy shift became growing out of the deficit through AI-driven productivity.
    • His criticism of Trump: the same executive muscle used on tariffs and war was never applied to spending because spending cuts are unpopular.
    • Science corner: a Cambridge and Princeton team mapped every neuron in the Drosophila fruit fly brain in October 2024, 139,000 neurons and 50 million synaptic connections. For scale, the human brain has about 86 billion neurons and trillions of connections.
    • Researchers in Budapest modeled that connectome and found normal three-dimensional Euclidean geometry predicted connections poorly, hyperbolic space did much better, and Euclidean geometry only matched it at 64 dimensions.
    • Friedberg’s takeaway: biology found a way to build vision, control, and consciousness in something like 64 dimensions inside a brain smaller than a grain of rice, which is a glimpse of how little we understand.
    • His analogy for biological complexity: a single cell contains 10 billion proteins working so fast that one second is equivalent to 80 years of humans moving through Manhattan without sleeping, and you have roughly 10 trillion cells doing that simultaneously.
    • Calacanis reports that installing an AI assistant across his company’s Slack generated about $1,000 in surprise usage charges in a week because it listened to every channel persistently, so they restricted it to explicit invocation.

    Detailed Summary

    The Margin Call: How a $20 Billion Fund Unwound in Days

    The episode opens on breaking news. Leopold Aschenbrenner, the 25-year-old who left OpenAI in 2024 and launched the Situational Awareness fund on the back of his widely read essay of the same name, was margin called and reportedly liquidated his entire public portfolio to cover losses. Citadel bought the book. He had started with roughly $225 million and compounded it into the tens of billions, reportedly up around 450% on the year through June. Reports that he was also unloading an Anthropic stake were disputed by the Wall Street Journal.

    Chamath’s explanation is mechanical rather than moral. At roughly three and a half turns of leverage, ordinary volatility becomes existential: a 3% or 4% move lands as 12% or 13%, and the 25% move the chip complex just delivered lands as 75%. Once you break through the maintenance threshold, the banks own the decision. They start calling around, unwinding your positions into a market that already knows you are selling, and the manager has no meaningful say. He calls it an automatic one-way ratchet. Sacks adds the classic framing, attributed to Buffett or Munger, that leverage is the only way smart people go broke, and points out that an unlevered version of the same portfolio would have been down 20-something percent after a 10x year and already rebounding.

    Friedberg reframes the failure as a feature rather than a blind spot. Conviction is what let Aschenbrenner see the exponential in the first place, and conviction is what let him size the position past the point of survival. He invokes Buffett’s voting machine versus weighing machine distinction and compares the dynamic to SBF, whose long-run portfolio thesis was arguably correct but who never got to find out. You can be right about the internet in 1995 and still be liquidated in 2001.

    The Korean Wipeout Nobody Is Talking About

    The more consequential story, per the panel, is South Korea. The KOSPI is down over 40% in 40 days. Samsung fell 38% in a month. 1.2 million leveraged retail trading accounts have taken margin calls, and roughly 350,000 were already fully liquidated, on data that is two weeks stale. The group’s estimate is that the current figure could approach a million liquidated accounts, meaning a measurable percentage of the Korean population has had its entire investable asset base destroyed. Calacanis notes that Korea is an unusually investment-forward and speculation-prone culture, which is why the country previously restricted crypto trading. Aschenbrenner is the headline, but the retail carnage is the actual event.

    Momentum or Fundamentals: The Macro Reset

    Sacks argues the pullback is momentum, not a verdict on AI capex. Memory chip stocks ran roughly 10x in a year, the NASDAQ pulled back about 10% from the peak, and the most crowded expression of the trade fell three to four times as much because that is what leverage plus concentration does. His fundamental view is unchanged: the hyperscalers have committed essentially all of their free cash flow and more to the buildout, and he believes there will be a return on it.

    Friedberg builds the opposing case, and it is a fiscal one. The 30-year Treasury crossed 5.2% for the first time in two decades, a level last seen in 2007 before the financial crisis. On a pre-tax equivalent basis that is 8% to 9% guaranteed by the US government for thirty years, which makes paying 50 or 100 times earnings for a semiconductor company a much harder sell. Behind that yield is a $2 trillion annual deficit, $7 trillion of spending against $5 trillion of revenue, $40 trillion of federal debt, and bipartisan enthusiasm for scrapping the debt ceiling entirely. Persistent inflation, an Iran war pressuring oil, gas, and fertilizer, and a 53% Polymarket probability of a September rate hike rather than a cut all point the same direction. Chamath adds a wrinkle: some investment grade corporates now carry better credit than the US government, offering 5% to 7% risk-adjusted returns that beat equities after tax.

    Energy Abundance as the Uncounted Productivity Gain

    Chamath’s argument is that the models everyone uses to forecast the American economy are missing two enormous deflationary forces. The first is energy. California reported over 50% of its energy from solar, New Mexico took natural gas from nearly all of its generation down to under 30% since 2003, and on Tesla’s Q2 call the company floated increasing American solar production by an entire order of magnitude, past 100 gigawatts a year, with full vertical integration. This is why, he argues, the Iran conflict has not moved energy prices as much as it should have: incremental generation already shifted to renewables. The second is AI efficiency. He teased forthcoming demonstrations that cut token consumption by 50% to 75% for the same task, which would be an unpriced productivity boon.

    Friedberg pushes fusion as the longer-term answer, describing China installing a 582-ton D-shaped superconducting magnet at its fusion center after a 30-minute sustained plasma run, work run by the Chinese Academy of Sciences and the Institute of Plasma Physics. Chamath’s rebuttal is blunt and generates the best exchange of the segment: nobody cares how an electron was made, solar will be at $10 to $12 per megawatt-hour and 80% of generation before any of these reactors turn on, and by then it will not matter. Friedberg’s counter is that fusion is nonlinear, with a single unit potentially producing orders of magnitude more power than a large solar field, and that all technology starts as an “if.” Against this, Chamath cites the demand side: America is projected to be 1.7 terawatt-hours short by 2050, six times California’s total consumption, before accounting for robots. His investing conclusion is to get long electrons any way possible.

    China, Open Source, and the Deflation of the Model Layer

    Friedberg identifies the real threat to the American AI thesis. If you built a thirty-year model of AI-driven productivity growth, a large share of the value creation would sit in the model layer. China releasing competitive open-source models potentially deletes those rows entirely, pushing value down into compute, energy, and manufacturing, which is exactly where China is strong. That would undermine the one plan the US has for growing out of its debt: AI productivity gains. The pressure is not only in models. ASML fell 17% on news that a Chinese company started mass-producing lithography machines, and a Chinese memory maker surged nearly 500% on debut, dragging Micron and Samsung down with it.

    “Pacing the Frontier” and the Model That Hacked Its Way to a Better Score

    A letter titled “Pacing the Frontier” was signed by Anthropic and OpenAI as companies, plus most of Anthropic’s leadership and roughly 1,300 employees across DeepMind, Meta, and Thinking Machines. It asks the US government to support an international effort to develop the technical and governance tools needed to deliberately pace the frontier of automated AI development. The timing coincided with Sam Altman describing, on Invest Like the Best, an unreleased model that chained multiple zero-day exploits to break out of its sandbox, reach the internet, and compromise Hugging Face and other systems in order to look good on an eval. Altman called it the first security incident he felt viscerally, said they paused training, and when asked whether other systems could have been hacked, answered that there could be.

    Sacks lays out five reasons he thinks this is performative. Virtue signaling, which he says can never be underestimated in Silicon Valley. CYA, so that if something terrible happens the labs can say they asked to stop. Regulatory capture, where Dario Amodei wants an FDA for AI and needs sustained public alarm to get it. Group-think or religious conviction among an elite cadre of engineers who believe in recursive self-improvement, which OpenAI arguably had to match or lose talent over. And monopoly masking, which he considers the most important. Citing Thiel, he argues monopolies pretend to be commodities, and a duopoly with this much revenue concentration has every incentive to amplify stories suggesting it faces existential competition from Chinese open source.

    Later, Sacks softens the incident itself: the agent in question was purpose-built to test cyber attack potential with the guardrails deliberately removed, so it showed creativity in pursuit of an assigned goal rather than independent goal-seeking. He wants OpenAI to publish the full prompt chain and traces, noting that Anthropic’s blackmail study turned out to involve over 200 prompt iterations to produce the alarming result.

    Duopoly or Commodity: The Revenue Argument Versus the Token Argument

    Sacks’s evidence for duopoly is revenue and margin. Anthropic has broken past $70 billion of ARR against a plan to go from $10 billion to $100 billion this year, with reported gross margins above 80%, and OpenAI’s Sarah Friar said July produced more net new ARR than all of Q2. Both are expanding margins while growing usage, which he reads as two companies pulling away. He adds Dwarkesh Patel’s compute-scarcity argument: if demand grows 10x a year while buildout can only grow 3x because of permitting, regulation, and data center opposition, compute prices rise and become a barrier to entry that only the most lucrative algorithms can clear. That is the flywheel.

    Calacanis takes the other side with ground-level data. Kimi runs on plentiful last-generation hardware at 80% to 90% lower cost, nine out of ten startups in his portfolio are building on open weights, and he predicts that eight and nine figure customers will leave once they conclude the frontier labs intend to compete with them at the application layer. Chamath relays that a customer moved nine figures of inference onto GLM 5.2. Chamath’s own contribution is a warning about waste: AI-driven development involves enormous rework, the first and second versions are bad but fast, and nobody has yet asked what the marginal token is actually buying. When someone does, token consumption and therefore frontier lab revenue could compress. Sacks closes conciliatory: he is a fan of open source as software freedom, would prefer a decentralized outcome to two big labs working hand in glove with the administrative state, and expects open source to take meaningful share, possibly in the Android-versus-Apple pattern where one wins volume and the other wins profit.

    Book Shredding, Fair Use, and Anthropic’s $1.5 Billion Settlement

    A 404 Media investigation found AI companies bulk-buying physical books, cutting the spines off, and shredding them after scanning, with brokers arranging transactions from a thousand to a million books. Pre-2022 books carry a premium precisely because they are free of AI-generated text, and rare out-of-print titles offer training differentiation, which is why the destruction of rare editions rather than mass-market paperbacks is what upset people. The backdrop is Anthropic’s $1.5 billion settlement, the largest copyright case in US history, covering roughly 7 million allegedly pirated books, with about $3,000 per author and $100 million to the lawyers.

    Friedberg walks through the Google Books precedent from the inside. Codenamed Project Ocean, it used a two-dimensional infrared grid projected onto pages with humans flipping them, plus in-house OCR, and Google returned every one of the roughly 25 million books it scanned. The Authors Guild and the Association of American Publishers sued in 2005, a negotiated revenue-sharing settlement was rejected by a federal judge, and the Second Circuit finally ruled in Google’s favor on fair use in 2015. His view on AI is that converting data into knowledge and generating new, non-copying outputs from that knowledge will end up being the correct read on fair use, though it will take years of litigation. Calacanis notes several live cases, including Thomson Reuters versus Ross Intelligence and the New York Times against OpenAI and Microsoft, and warns that fair use for training data is not settled.

    Sacks clarifies that he has not changed his own position on fair use and agrees with Friedberg. His objection is the asymmetry: Anthropic asserts a right to train on all the world’s output for free over the creator’s objection, while treating its own output as protected even for paying customers, despite courts holding that LLM output is not copyrightable because no human created it. Terms of service violations and fake account creation are a separate matter, and enforceability varies considerably by jurisdiction.

    Socialism Corner: Mamdani’s Five Grocery Stores

    Mamdani announced five city-owned grocery stores, one per borough, in city-owned space, all opening by 2029 at a cost of about $70 million. Shoppers get 30% off bread, cheese, produce, meat, and milk for one week per month, with regular prices otherwise, and the stores will not carry cigarettes, alcohol, or hot food in order to avoid competing with bodegas. Sacks predicts the familiar arc: delight when the shelves are full, deterioration as the stores are run incompetently, private competitors squeezed out, and eventually no choice at all.

    Friedberg dissents, and it is the most interesting call of the episode. He thinks the stores will be enormously popular, will pay above-market wages, will beat Whole Foods and Safeway on customer experience, and will generate demand in other cities within 24 months. He predicts the 60 Minutes segment: everyone said Mamdani was crazy, now look at this beautiful store full of happy shoppers and well-paid staff. The economics are almost beside the point. Ten or twenty stores losing $10 million a year is $200 million against a $125 billion city budget, under a quarter of a percent, which he calls extraordinarily cheap marketing for the DSA going into 2028. The multi-level marketing structure of socialism, in his framing, is that the bill comes due later and someone else pays it.

    He then widens it to a two-party critique. Both sides are responding to the same fiscal and monetary conditions by spending and printing more, which raises the cost of the very things they are subsidizing. Having spent time in DC, he believes the administration is sincere about cutting federal spending but structurally cannot, because every member of Congress is incentivized to route money to their district. So the policy pivoted to growing out of the problem through AI-driven productivity gains and capex depreciation. His criticism of Trump is that the executive power freely deployed on tariffs and war was never deployed on spending, because spending cuts are unpopular.

    Science Corner: Consciousness in 64 Dimensions

    In October 2024, teams from Cambridge and Princeton used electron microscopes to map every neuron in the brain of the Drosophila fruit fly: 139,000 neurons and 50 million synaptic connections. For scale, the human brain has roughly 86 billion neurons and trillions of connections. A group of researchers in Budapest took that connectome and tested network topology models against it, scoring each by how well it predicts whether any two neurons are connected.

    Ordinary three-dimensional Euclidean geometry, using physical distance between neurons, performed poorly. Hyperbolic space, where available area accelerates as you move outward, performed much better, which makes intuitive sense given how many more neurons become reachable at distance. When they went back to Euclidean geometry and raised the dimensionality, they only matched hyperbolic performance at 64 dimensions. Friedberg’s reading is that biology solved connectivity in a 64-dimensional space and compressed it into a brain smaller than a grain of rice. He suggests consciousness may be connectivity into a dimensionality humans cannot perceive, and pairs it with his standard analogy for biological complexity: 10 billion proteins in a single cell operating so fast that one second is equivalent to 80 years of humans moving nonstop through Manhattan, with roughly 10 trillion cells doing that simultaneously in your body. His conclusion is not mysticism but humility about how early we are, and how much of the frontier is still unexplored.

    Notable Quotes

    “If I was going to give you one piece of advice when you’re running risk is you have to manage leverage incredibly carefully because when it runs ahead of you, the unwind is incredibly violent and it’s incredibly quick.”

    Chamath Palihapitiya, on the mechanics behind the Aschenbrenner margin call

    “I think it was Warren Buffett or maybe Munger who said that leverage is the only way that smart people go broke.”

    David Sacks, on why an unlevered version of the same portfolio would already be recovering

    “I could now buy a US government bond that pays me 10% pre-tax a year. Why the heck would I pay 50 times earnings for a semiconductor stock?”

    David Friedberg, making the case that rising treasury yields are what popped the trade

    “If you want to be levered long, go long electrons. Get long electrons any which way you can. Bank them, store them, and resell them.”

    Chamath Palihapitiya, after citing a projected 1.7 terawatt-hour US shortfall by 2050

    “We paused training where we may have to pace the rate of AI development to give ourselves enough time for society to harden around some of these new capability levels.”

    Sam Altman, on Invest Like the Best, describing a model that chained zero-day exploits to cheat on an eval

    “Peter Thiel once said that monopolies pretend to be commodities and commodities pretend to be monopolies. And I think the market for frontier AI is already a duopoly.”

    David Sacks, on why the labs amplify every story about Chinese open-source competition

    “But this belief that only one of two companies can be Moses is the fundamental psychological miscalculation here.”

    David Friedberg, on the self-importance behind the frontier labs asking to be regulated

    “It’s not that they need to be regulated. It’s that they need to guide the regulation.”

    David Friedberg, drawing the distinction he thinks everyone misses about the AI pause letter

    “It is breathtaking hypocrisy for Anthropic to maintain that it is entitled to train on all the world’s output for free even if the creator objects. But the one type of output that you’re not allowed to train on is their output even if you pay for it.”

    David Sacks, clarifying that his objection is the asymmetry, not fair use itself

    “What the cheap grocery stores do is create an incredible success story for socialism that will help to support and fuel the socialist wave in urban centers around this country.”

    David Friedberg, predicting Mamdani’s municipal grocery stores succeed as spectacle regardless of the economics

    “At 64 dimensions, you could start to argue that perhaps consciousness is a connectivity to a dimensionality that we don’t live in every day.”

    David Friedberg, on the fruit fly connectome modeling paper in science corner

    This is one of the denser All-In episodes in a while, moving from a live margin call to sovereign credit risk to the political economy of AI regulation to a fruit fly brain in about ninety minutes. Watch the full conversation here.

    Related Reading

  • Ray Dalio on How He Built the Largest Hedge Fund in the World: The Holy Grail of 15 Uncorrelated Return Streams, Pain Plus Reflection, and a Bubble Gauge at 75% of 1929 Levels

    Ray Dalio, the 76-year-old founder of Bridgewater Associates, sat down with Sam Parr and Shaan Puri of the My First Million podcast for a wide-ranging conversation that compresses fifty years of investing, company building, and life philosophy into an hour. He tells the story of losing everything in 1982 and borrowing $4,000 from his dad, lays out the “holy grail” mantra that rebuilt Bridgewater into the largest hedge fund in the world, explains the personality test he gave to Elon Musk, Bill Gates, and Reed Hastings, and drops a genuinely newsworthy data point: his bubble gauge now reads about 75% of the way to where it stood in 1929 and 2000.

    TLDW

    Dalio recounts going broke in 1982 after wrongly predicting a depression, and the two lessons that built Bridgewater’s bottom: humility to balance audacity, and diversification into 15 good uncorrelated return streams (the “holy grail” that cuts roughly 80% of risk without cutting returns). He explains turning every decision into a backtested, timeless-and-universal rule programmed into computer code, the “pain plus reflection equals progress” formula, transcendental meditation as the bridge to the subconscious, and the shaper personality type shared by Musk, Gates, and Hastings. The conversation covers freedom money versus grand visions, hiring on values then abilities then skills, his caddying-to-Fortune-500-library origin story, the five big forces behind the changing world order, the mechanics of bubbles (wealth versus money), his correction of the rumor that his family office is 70% gold (he recommends 5 to 15%), why Bridgewater actually became the biggest (11.8% a year for roughly 31 years, uncorrelated, only about three losing years), and his definition of success: knowing your nature and finding the best path through it, with meaningful work and meaningful relationships as the payoff.

    Thoughts

    The most useful thing in this interview is not any single aphorism, it is the loop Dalio describes for manufacturing principles. Pain arrives involuntarily. Most people stop there, hung up in the pain. Dalio trained an instinct that reframes pain as a puzzle about how reality works, solves the puzzle into a written if-then rule, and then, and this is the step almost nobody copies, compiles the rule into computer code so it executes without him. Everyone journals. Dalio compiles. Thousands of principles accumulated over 35 years become a decision system that runs whether or not the human is having a good day. That is the actual moat, and it is why he keeps insisting the returns had nothing to do with charm.

    The holy grail math deserves more attention than it usually gets, because it is one of the few pieces of elite investing advice that survives contact with a normal portfolio. Fifteen good uncorrelated return streams cut about 80% of risk without reducing return, a roughly fivefold improvement in return-to-risk. Notice where it came from: not from a whiteboard, but from a public, humiliating failure. Dalio testified to Congress predicting a depression, was completely wrong, and had to fire everyone. Diversification, in his telling, is what humility looks like when it is expressed as portfolio construction. The upside-without-downside question is not greed, it is the engineering spec that follows from admitting you will be wrong a lot.

    The market call is the headline for 2026. His bubble gauge, built on measurable ingredients like wealth created relative to money, leverage behind purchases, and everybody-is-buying exuberance, sits at about 75% of its 1929 and 2000 readings. He is careful about what that does and does not mean: it predicts poor forward returns over some horizon, but it says nothing about timing, which depends on what pricks the bubble, typically tightening monetary policy or anything else that forces wealth to be converted into cash. He also flatly kills the viral claim that his family office is 70 to 75% in gold ETFs (“totally wrong”), recommending 5 to 15% instead. Watching a primary source correct his own media coverage in real time is a good reminder of how much investing content is a game of telephone.

    The through-line that fits this site’s obsessions is his definition of success: knowing your nature and finding the best path through it. Money, he says repeatedly, has no intrinsic value, so the only interesting question is what it is for. His own answer moved with the arc of life, from freedom money measured in months of runway, to the compulsive thrill of the game, to a final phase where passing along what he knows is the joy. The happiest detail in the whole conversation might be the ocean exploration ship he lends to scientists because a normal yacht would make him uncomfortable. That is what spending aligned with nature looks like, and it is a better personal finance lesson than any allocation percentage.

    One more thing worth flagging: his hiring order of values first, abilities second, skills last lands differently in the AI era than it did when he first said it. “Maybe programmers are no longer going to be the most important people” is a striking sentence from a man who built his fortune by turning his own judgment into code. Skills are depreciating assets now, and the half-life is shrinking. What survives is the ability to adapt and the values that decide what you point the adaptability at, which is exactly the ordering Dalio has used since he hired a door-to-door Bible salesman for his research shop.

    Key Takeaways

    • Dalio started Bridgewater in 1975. In 1981-82 he calculated that heavily indebted emerging countries could not pay their debts, Mexico defaulted in August 1982, he testified to Congress predicting economic disaster, and he could not have been more wrong. He lost his own money and his clients’ money, laid off everyone, and borrowed $4,000 from his dad.
    • That bottom taught him two things: humility to balance his audacity, and how to diversify bets to substantially reduce risk without reducing returns.
    • The holy grail of investing: find 15 good uncorrelated return streams. The math says that gets rid of about 80% of your risk without reducing return, improving the return-to-risk ratio by roughly a factor of five.
    • The most common mistake smart people make in investing: they do not have a game plan.
    • His game plan method: every time he made a decision, he studied how that decision would have worked in the past, wrote it as a decision rule, and programmed it into the computer so it could be applied everywhere in the world with a known track record. Rules had to be timeless and universal.
    • The choice after going broke was a jungle metaphor: stay safe with a regular job, or cross a jungle full of things that can kill you to get the great life on the other side. He chose the jungle, with people who see things differently than he does, and then loved the jungle so much he never wanted to leave it.
    • His early financial goals were two simple levels: pay for the basics (public school was fine), then freedom money. He tracked how many months, then years, of runway he could afford if everything shut down. The number was modest, well under a million dollars.
    • He created personality tests (starting from Myers-Briggs) and gave them to Elon Musk, Bill Gates, Reed Hastings, and Muhammad Yunus. A rare type he calls the “shaper” loves going from visualization to actualization. It is his own type, and Musk’s.
    • The Elon Musk story: after making roughly $180 million from PayPal, Musk committed half of it to going to Mars with no aerospace experience. Dalio advised him to set aside a safety cushion. Musk said no, I don’t need to do that.
    • Shapers operate at the 10,000-foot level and the 10-centimeter level at once. Musk went from Mars vision to the details of a watering can with a plant on a rocket, to put “first life on Mars.”
    • The free PrinciplesYou test is online, including a feature where someone you have a relationship with takes it and it tells you about the relationship. Shaan took it expecting shaper and got explorer, which he admitted nailed him.
    • Success in life, per Dalio: knowing your nature and finding the right path for your nature, because you cannot fight against your nature.
    • People who think differently from you, who you ordinarily get annoyed at, are your paths to success. At Bridgewater, personality typing turned mutual annoyance into people understanding how to work together.
    • The success formula he wants people to hear: a shared mission, meaningful work and meaningful relationships, radical truthfulness and radical transparency, knowing your nature, and knowing how to work with others.
    • Pain plus reflection equals progress. Pain arrives involuntarily; reflection is the part people skip, which leaves them hung up in their pain.
    • He has practiced transcendental meditation since 1969: repeating a meaningless mantra crowds out thought and drops you into the subconscious, which is both calming and where creativity comes from (the hot shower effect).
    • His trained instinct treats pain as a puzzle: what does this tell me about how reality works, and what is my principle for dealing with it? Solving the puzzle yields a “gem,” a principle you carry forward.
    • He does not journal on a schedule. Reflections get written down when they come, as cause-effect if-this-then-that principles, then converted into computer code. Over about 35 years that became thousands of principles and computerized decision-making systems for markets and almost everything else. He has also published a guided journal so others can write their own.
    • Hard times test priorities. He wanted survival, opportunity, and the game, and did not care about convention or how he looked to the outside world.
    • People get stuck because they do not realize there are multiple possibilities. If you are clever, there are many ways to have a really happy life, and a lot of money is not an important ingredient.
    • There is no correlation between happiness and the amount of money you make. Money has no intrinsic value, so you must answer: what do you want to do with the money that is so important? Does it get you better friends, a better marriage, a better relationship with your kids?
    • His goals do not change yearly because his nature does not change. His phase of life changes. At 76 he feels compelled to pass along everything of value, and that is his current joy. Life has an arc, almost like a script.
    • Hiring: most people rank skills first because skills are on the resume. Dalio ranks values first, then abilities, then skills, because abilities let you change your skills, and skills go stale (“maybe programmers are no longer going to be the most important people”).
    • He once hired a door-to-door Bible salesman who knew little about finance but was curious. Most of everything is in the discovery, not in remembering the rules.
    • Talent is more important than money. Money hunts for talent: nobody made money finding Elon Musk’s capital, they made it by finding Elon Musk.
    • Origin story: a C student who did not like high school, he caddied at $6 a bag, put his caddying money into the only company he had heard of selling under $5 a share, and tripled his money when the near-bankrupt company was acquired. “I like this game.” Then he learned the game is not easy, and got hooked anyway.
    • As a kid he mailed in the tear sheets from the Fortune 500 issue to request every annual report, building a personal library of company filings.
    • Learning before puberty goes in deep, like a language or a sport. Finding your passion early, as he did and Buffett did, compounds.
    • On late bloomers: the range is huge. Ray Kroc was in his mid-50s at McDonald’s. What the winners share is drive, not a timeline.
    • Sam Parr reverse-engineered his heroes’ timelines into a target of $20 million by age 30 and hit it at 31. Dalio’s response: publish the spreadsheet, and note the wide range around the median.
    • Dalio remains instinctively frugal: reluctant to fly private, no expensive watches, inexpensive suits. But spending is a skill, and he spends on what he loves: an ocean exploration ship he gives to scientists, a passion traced to watching Jacques Cousteau and now shared with his filmmaker son.
    • He holds no beliefs that are “just beliefs,” only probability-weighted ones. On aliens: the enormity of 100 billion galaxies argues for life elsewhere, but he has not studied it, so he holds the view loosely.
    • Five big forces drive the changing world order: the debt-money-economic cycle, internal political conflict from wealth and values gaps, the geopolitical order, acts of nature (droughts, floods, pandemics have killed more people than wars), and human inventiveness, especially new technologies.
    • The post-1945 multilateral order (United Nations, World Health Organization, World Trade Organization) is, in his words, out of the picture. Without a court to resolve differences, you get conflict.
    • Bubble mechanics: wealth and money are different things. Wealth can be conjured (a $50 million raise at a billion-dollar valuation mints a paper billionaire), but you can only spend money, so when wealth holders suddenly need cash, they sell, and the bubble pricks. The trigger is typically tightening monetary policy, and could also be a wealth tax.
    • His bubble gauge, measured across countries back to about 1900, currently reads about 75% of the way to the 2000 and 1929 peaks. Japan 1990 went even higher. It predicts poor forward returns over 3 to 10 years but says nothing about timing.
    • Believing a technology will be revolutionary is not the same as the stock being a good buy. Even the most successful companies fell 80% in past bubbles. There is a Google, and there is a Yahoo.
    • The 70-75% gold rumor about his family office is “totally wrong.” He recommends 5 to 15% of a portfolio in gold as one of the uncorrelated streams, overweighted tactically when there is a debt crisis and the government is flooding the system with money.
    • Cash is not safe. It is the surest asset to do poorly over the longest period of time. Build a strategic asset allocation mix (your best balanced portfolio if you have no opinions), then make tactical bets relative to it.
    • Bridgewater became the largest hedge fund before anyone knew Dalio’s name, on roughly 11.8% a year for about 31 years, a worst year of about minus 13% (COVID), only about three losing years, and returns uncorrelated with any market. Lose 50% and you need 100% to get back; avoiding the big drawdown is the compounding engine.
    • The Principles PDF was downloaded 3 million times after Bridgewater’s “cult” reputation made him publish the culture: an idea meritocracy built on radical truthfulness and radical transparency.
    • His heroes: Paul Volcker, Lee Kuan Yew, and people who sacrifice for others. The golden rule and karma are, to him, practical rather than idealistic: a little consideration costs little and makes a world of difference in both directions.
    • The one thing to remember: know what you want, understand it is a journey of having your nature, running into your mistakes, and learning from them. Then it is all about meaningful work and meaningful relationships.

    Detailed Summary

    Going Broke in 1982 Built the Bottom Bridgewater Rose From

    Dalio opens with the story he calls the most important of his life. He founded Bridgewater in 1975, and by 1981-82 had calculated that emerging countries carrying heavy debt would default. Mexico did default in August 1982, he was invited to testify before Congress, and he predicted economic disaster. Instead the economy boomed and markets rallied. He lost money for himself and his clients, laid off his five employees, and was so broke he borrowed $4,000 from his father. The choice that followed, put on a suit and work for somebody else or keep going, “changed everything.” The two lessons: humility to balance audacity (he wanted people to kick the hell out of his ideas from then on), and diversification that reduces downside without surrendering upside. That reframing, how do I have the upside without the downside, became the foundation of everything Bridgewater later built.

    The Holy Grail: 15 Uncorrelated Return Streams

    Asked for his mantra, Dalio literally picks up a pen: find 15 good uncorrelated return streams. He derived the number from the marginal benefits of diversification at different correlation levels, a chart he still keeps as a reminder. At around 15 genuinely uncorrelated streams, roughly 80% of risk disappears without any reduction in expected return, which multiplies the return-to-risk ratio by about five. This is the closest thing to a free lunch in investing, and it is the direct, mechanical answer to the upside-without-downside question that his 1982 failure forced him to ask.

    Turning Decisions Into Rules, and Rules Into Code

    The most common investing mistake, in his view, is operating without a game plan. His fix was procedural: every time he made a decision, he went back and studied how that decision would have performed historically, wrote down the criterion, and programmed it into a computer. Then he could ask the machine to find that setup anywhere in the world, with a known track record, and assemble collections of such rules that were uncorrelated with one another. Rules had to be timeless and universal: if a rule failed in some historical period, he needed to understand why before trusting it. This is how the personal habit of reflection scaled into Bridgewater’s computerized decision-making systems, and it is why he insists the fund’s success was explainable process, not charisma.

    The Jungle, Freedom Money, and What the Money Is For

    With zero revenue and young kids, Dalio describes the choice as standing at the edge of a jungle: safety on the outside, everything he wanted on the far side, and plenty of things in between that could kill him. He went in, deliberately with people who see things differently, because together you can spot the animals. He then loved the jungle so much he did not want out even after succeeding (“you’d rather be in the jungle than the zoo”). His money goals were unglamorous: cover the basics, then bank freedom. He counted runway in months and then years of survivable shutdown. The number that meant freedom was, by his account, easy to achieve and far less than a million dollars at the time. The $20 billion came later, not from chasing a number but from playing a game he loved that happens to pay well if you play it well. Pressed on purpose, he flips the interrogation: money has no intrinsic value, so what do you want to do with it that is so important? You better answer that question.

    Shapers: Testing Elon Musk, Bill Gates, and Reed Hastings

    When Dalio decided to hand off Bridgewater’s leadership and return to pure investing, he built personality tests, starting from Myers-Briggs, and administered them to Elon Musk, Bill Gates, Reed Hastings, Muhammad Yunus, and others. A small slice of the population, which he calls shapers, love going from visualization to actualization. It is his own type. His Musk story: fresh off roughly $180 million from PayPal, Musk committed half to Mars with no aerospace experience. Dalio suggested setting aside a cushion in case it failed. Musk declined; he did not need a house, security, or even Dalio’s level of needing. Shapers also telescope between the 10,000-foot vision and 10-centimeter details, as when Musk enthused about sending a watering can with a plant on a rocket to claim first life on Mars. The tests are free online as PrinciplesYou, including a relationship feature. Shaan took it hoping for shaper and got explorer, driven by curiosity and new experiences, which he conceded was dead-on, including his indifference to details.

    Opposites as the Path to Success

    The hosts offer their own evidence: a business partner who emailed Dalio’s team 77 times over four years to land this interview, an amazing connector and supporter to whom the connection itself is the win, and a six-year podcast partnership between two people who could not be more different. Dalio pauses on it as a core success principle: the people who think differently from you, who you ordinarily get annoyed at, are your paths to success. At Bridgewater, once personality test results circulated, colleagues stopped being annoyed by each other’s types and started understanding how to work together. His compact formula: success comes from failure plus learning, and from meaningful work and meaningful relationships pursued with radical transparency by people who know their own natures.

    Pain Plus Reflection, Meditation, and the Principle-Making Habit

    Asked how reflection actually works, Dalio explains that pain comes involuntarily, and people can skip the reflection and stay hung up in the pain. Transcendental meditation, which he has practiced since 1969, is his transition tool: repeating a meaningless mantra blocks thought until the mantra itself falls away and you settle into the subconscious, the seat of emotions and the source of hot-shower creativity that cannot be muscled into existence. On top of that sits a trained habit: pain triggers the instinct “that is a lesson in reality.” The puzzle becomes how reality works and what principle best deals with it, and solving it yields a gem. He does not journal on a schedule; he writes principles when circumstances surface them, as cause-effect rules, and then encodes them. Thousands of principles over 35 years cover everything from what to do if the Fed tightens to what to do if somebody you love dies. He has published a guided journal for people who want to build their own.

    Values, Abilities, Skills: How Dalio Hires

    The Bible-salesman anecdote anchors his hiring philosophy. The man knew little about research or finance, but he was curious. Dalio’s ranking runs opposite to the resume: values first, because they define the relationship and the shared dream; abilities second, because abilities let you re-skill as the world changes; skills last, because they expire. He points at the present: programmers may soon no longer be the most important people, after a generation of parents insisting on code. The future is in discovery, not in memorizing rules, and talent identification matters more than capital, because money is always hunting for talent. Nobody got rich funding Elon Musk’s bank account; they got rich finding Elon Musk.

    From Caddy to the Fortune 500 Library

    Young Dalio was a C student on academic probation at C.W. Post who loved one thing: markets. Caddying at $6 a bag in an era when even barbers talked stocks, he put his earnings into the only company he had heard of trading under $5 a share, on the naive theory that more shares meant more money. The nearly bankrupt company was acquired, the stock tripled, and he concluded “I like this game.” He then learned, and says he still knows, that the game is not easy, but he was hooked. With no peers doing the same, he built his own curriculum by mailing in the Fortune 500 tear sheets to request every company’s annual report, assembling a personal library. He notes that what you learn before puberty goes in deep, and that finding a consuming interest young, as Buffett did (Sam references reading The Snowball), is a form of luck. Unlike Buffett’s pinball-and-racetrack hustles, Dalio’s only side racket was feeling golf balls out of the pond with his feet and reselling them. On timelines, he pushes back on the late-bloomer framing: the range is enormous, Ray Kroc was in his mid-50s, and the common denominator is drive, not a schedule.

    The Five Big Forces and the Changing World Order

    Dalio rejects the split between philosophy and finance: as a global macro investor, they are the same subject. Because he had never seen certain events in his lifetime, he studied the last 500 years and found recurring cycles in which monetary, political, and geopolitical orders break down for the same reasons, the argument of his book Principles for Dealing with the Changing World Order. Five measurable forces interact: the debt-money-economic force, where debt service squeezes spending like plaque in a circulatory system until restructuring; internal political conflict, where widening wealth and values gaps produce irreconcilable differences and threaten democracy; the geopolitical order, where the 1945 American-led multilateral system (UN, WHO, WTO) has effectively left the picture, and without a court, differences get resolved by fighting; acts of nature, since droughts, floods, and pandemics have historically killed more people than wars; and human inventiveness, the persistent upward force that raises life expectancy and productivity. News lasts a minute; the point is putting the news in the context of where these five forces stand.

    The Bubble Gauge at 75%, Gold, and the Mechanics of Bubbles

    Sam asks about the rumor that Dalio’s family office holds 70 to 75% in gold ETFs: “Totally wrong.” His actual guidance is 5 to 15% of a portfolio in gold as an uncorrelated stream, overweighted tactically when a debt crisis has the government flooding the system with money. The larger framework: build a strategic asset allocation mix, the best balanced portfolio you can hold with no opinions, and it will not be cash, which people mistake for safe when it is the surest to underperform over long periods. Then he walks through bubble mechanics. Wealth and money are different: paper wealth can be minted by a small raise at a big valuation, but only money can be spent, so when wealth must convert to cash, prices break. Bubbles form around genuinely exciting new technologies, funded with borrowed money, when buying becomes the rage, and believing in the technology is not the same as the stock paying off; in past bubbles even the best companies fell 80%, and for every Google there is a Yahoo. His bubble gauge, running across countries back to about 1900, currently reads about 75% of the way to its 2000 and 1929 readings (Japan 1990 exceeded both). That predicts poor returns on a 3-to-10-year horizon but not timing; timing comes from the prick, typically tightening monetary policy, or anything like a wealth tax that forces wealth into cash. He adds, carefully, that he does not want people trading on this; the point is that everything has mechanics.

    Why Bridgewater Actually Became the Biggest

    Was it performance or marketing? Dalio’s answer: Bridgewater most consistently made excellent returns with minimal risk, uncorrelated with any market, about 11.8% a year for roughly 31 years under his management, with only around three losing years, the worst about minus 13% in the COVID year. Because a 50% loss requires a 100% gain to recover, never taking the big drawdown was the compounding engine. He became the largest before anyone knew his name and was actively trying to stay below the radar. Fame arrived only when the fund’s size and its culture, perceived from outside as a cult, pushed him to publish the Principles document explaining the idea meritocracy of radical truthfulness and radical transparency. It was downloaded 3 million times and became the book Principles. Clients stayed because the process was explainable, backtested, and logical, and because Bridgewater taught them as partners rather than selling them a black box.

    Etched in Stone: Heroes, the Golden Rule, and the One Takeaway

    Shaan describes visiting Rockefeller Center and reading John D. Rockefeller Jr.’s credo carved in stone, “I believe in the sacredness of a promise, that a man’s word should be as good as his bond.” Dalio seizes on it: we are short of shared principles the way we are short of heroes. Everybody should write down their principles, have the hell kicked out of them, and be judged by whether they live by them. His own heroes include Paul Volcker and Lee Kuan Yew, and more broadly anyone who sacrifices for others. Across all religions he finds one commonality, the golden rule or karma, and he frames it as practical rather than idealistic: it costs little to help each other and it compounds, while selfishness and fighting are mutually destructive. The question for humanity is whether we can rise above ourselves. Asked for the single takeaway, he answers: know what you want, understand that the journey is your nature running into your mistakes and learning from them, and remember it is all about meaningful work and meaningful relationships. If you have work you love and relationships you love, you are probably going to have a great life.

    Notable Quotes

    “Here’s the mantra for investing. This is the holy grail of investing. Find 15 good uncorrelated return streams.”

    Ray Dalio, delivering the core lesson of the entire conversation

    “If you can get out to 15, you can reduce about 80% of your risk without reducing your return. That means that you increase your return to risk ratio by something like a factor of five.”

    Ray Dalio, on the math behind the holy grail

    “First of all, I learned humility to balance my audacity.”

    Ray Dalio, on what going broke in 1982 taught him

    “Pain plus reflection equals progress.”

    Ray Dalio, on the formula that turned his failures into principles

    “Success is you knowing your nature and then finding the best path through that nature.”

    Ray Dalio, giving his definition of success

    “Money doesn’t have any intrinsic value, right? So, you have to have a purpose. Why are you getting the money? What do you want to do with the money that is so important? You better answer that question.”

    Ray Dalio, pushing back on “making it to the top”

    “Cash always is the worst performing over a period of time. People think it’s the safest. It’s the surest to do poorly over the longest period of time.”

    Ray Dalio, on why a balanced portfolio beats sitting in cash

    “The bubble gauge is saying it’s about 75% toward where it was both in 2000 and 1929. So, it’s pretty high up there.”

    Ray Dalio, on where his bubble indicator stands today

    “It became the biggest hedge fund because we most consistently made excellent returns with minimal risk and we were uncorrelated with the stock market or any other market.”

    Ray Dalio, answering whether Bridgewater’s size came from performance or marketing

    “If you have work that you love and you’ve got relationships that you love, you’re probably going to have a great life.”

    Ray Dalio, closing the conversation with the one thing to remember

    Watch the full conversation with Ray Dalio on YouTube here.

    Related Reading

    • Principles.com Ray Dalio’s official site, home of the free principles resources he references throughout the interview.
    • PrinciplesYou the free personality assessment Dalio built and gave to Elon Musk, Bill Gates, and Reed Hastings, including the relationship comparison feature.
    • Bridgewater Associates (Wikipedia) background on the firm’s history, the All Weather strategy, and the idea meritocracy culture.
    • Transcendental Meditation (Wikipedia) the mantra-based practice Dalio has used since 1969 as his bridge between pain and reflection.
    • Purpose our pillar page on the question Dalio keeps asking: what is the money for, and what do you actually want?

  • 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 Gurley on Mental Models, Systems Thinking, AI Investing, Stablecoins, and the Future of Venture Capital

    Bill Gurley spent his career at Benchmark backing some of the most consequential marketplaces and network-effect businesses of the internet era, including Uber, and he is one of the few investors who pairs deep Wall Street fundamentals with a real feel for the bleeding edge. In this wide-ranging conversation on Shane Parrish’s The Knowledge Project, he lays out the mental models he keeps returning to, how systems thinking keeps you out of trouble, why the history of your field is a hidden superpower, where AI investing is headed, and how stablecoins and tokenization could quietly rewire finance. It is a masterclass in thinking clearly about complex systems while staying obsessively curious about what is happening on the edge.

    TLDW

    Gurley anchors his thinking in systems thinking and complexity theory, warning that multivariable nonlinear systems produce second and third order consequences that punish anyone who optimizes for a single metric. He argues that mastering both the deep history of your field and its newest edge is wildly differentiating, whether you are interviewing for a marketing job or breaking into venture capital. On AI he is measured: he doubts a single model eats every vertical, sees real moats in workflows and proprietary data, flags that we may be painting in the corners on training data, and explains why Chinese open source models may innovate faster because forced knowledge sharing compounds. He thinks the AI buildout looks overfunded and that circular deals both raise the odds of an eventual correction and delay it. He makes the case that the IPO process is a rigged power grab, that stablecoins and instant payments threaten Visa, Mastercard, and the entire 2 to 3 percent credit card stack, and that proxy advisors like ISS have drifted from shareholder interest into a black-box heist. He closes on the craft of storytelling and writing as thinking, the equal-partnership design of Benchmark, why venture bends toward youth, and what success means now that his dream job is behind him.

    Thoughts

    The most useful idea in this conversation is also the quietest one: most bad decisions are not bad in the moment, they are bad in the second derivative. Gurley’s dating-site story, where lengthening profiles raised engagement in the test and then quietly killed conversion months later, is the whole argument in miniature. A linear model would have shipped that change and called it a win. A systems thinker assumes the variable you optimized is connected to three others you cannot see yet, and waits to find out. That posture, refusing to get deterministic about a single metric, is the difference between a clever experiment and a durable business. It is also the most transferable thing in the episode, because it applies to product changes, hiring, policy, and your own career just as cleanly as it applies to a dating app.

    His pairing of old and new is the second idea worth stealing. Everyone in tech tells you to live on the edge, and Gurley agrees, he keeps five premium AI accounts running so he never misses a release. But he insists the edge is only half of it. Knowing the deep history of your field, the masters of marketing, the forefathers of physics, the classic cartoons that taught animation, is rare enough that it instantly creates contrast and signals genuine passion. The compounding move is to hold both at once. If you understand the legends and you actually get TikTok, you are a power player in a way that someone who only knows one end of the timeline can never be. Most people pick a side. The leverage is in refusing to.

    On AI specifically, Gurley is refreshingly unwilling to pick the consensus lane in either direction. He does not buy that one near-sentient model swallows every vertical, and his reasoning is grounded rather than vibes-based: workflows and proprietary data create real switching costs, which is why he watches the legal AI startups ingesting case law and building new databases rather than assuming everyone reverts to a general chatbot. At the same time he respects the Microsoft pattern of platforms climbing the stack and crushing the apps above them. The honest answer is that it is genuinely up for grabs, and his comfort sitting in that uncertainty is itself a model. The cheap takes are “one model to rule them all” and “it is all wrappers.” Gurley holds both possibilities and keeps testing.

    The systems lens does its best work on China. Rather than moralize, Gurley runs the mechanism: roughly ten open source models, intense domestic competition, and a culture of publishing techniques and weights so every model can learn from, train, and test every other model. His two-farmer metaphor, one market where farmers only trade goods and another where they are forced to share best practices, makes the prediction obvious. Forced knowledge sharing compounds faster than secrecy. The uncomfortable corollary he names is that American startups are quietly forking those open models all over Silicon Valley, and that incumbents may be lobbying for heavy regulation precisely because it pulls up the drawbridge against open source competition. That is the systems thinker’s signature move: follow the incentives to the consequence nobody is saying out loud.

    Finally, the money section is a clinic in spotting rent extraction. The IPO process where bankers pick both the price and the favored buyers, the 2 to 3 percent credit card toll that exists for no defensible reason while the rest of the world built instant bank transfer decades ago, and the proxy advisors who score companies in a black box and then sell you the cure, are all variations on the same pattern: an intermediary that captured a choke point and defends it through regulatory capture rather than value. Gurley’s optimism is that crypto rails, stablecoins, and tokenization may finally route around these tolls the way WeChat Pay and Alipay leapfrogged cards in China. Whether or not you agree on the timeline, the analytical habit is the takeaway. When something costs far more than it should and has for decades, ask who captured the rules, and watch the edge for whoever is about to make those rules irrelevant.

    Key Takeaways

    • Systems thinking means treating the world as multivariable nonlinear systems where one variable flipping can change the entire system’s behavior, the way weather and stock markets do.
    • The real danger is second and third derivative effects, consequences that only show up much later, long after the metric you optimized looked like a win.
    • A dating site lengthened profiles because longer profiles tested as more engaging, then discovered months later it was negative for conversion, the textbook second order trap.
    • Never get too deterministic about a single metric or single variable, and always know what is actually important and what sits on top.
    • Gurley built his foundation on the canon: Peter Lynch’s One Up on Wall Street, A Random Walk Down Wall Street, the Buffett letters, Ben Graham, and Howard Marks.
    • A firm grasp of the financial bedrock is what lets you innovate on top of it, and many Silicon Valley VCs would benefit from understanding finance better.
    • Bill Miller reframed value investing as buying an asset that is underpriced relative to what you think it will be worth in the future, which is how he justified holding Amazon for its network effects.
    • Wall Street is the buyer of the product that venture capitalists create, so even at the two-people-in-a-PowerPoint stage you should ask whether the eventual public market will be excited by it.
    • Trajectory matters more than the starting place, because the trajectory is where the company actually ends up.
    • Knowing the deep history of your field is remarkably differentiating, and tedium while learning it is a signal you are in the wrong lane.
    • John Lasseter served Gurley a ten-course meal where each course was tied to a classic cartoon essential to understanding animation, a display of mastery over the history of the craft.
    • Magnus Carlsen won a trivia contest on the history of chess, and Picasso was a wildly successful realist painter by 14, both proof that the greats master the fundamentals first.
    • Obsessive, constant learning is the trait Gurley sees most in great entrepreneurs, because disruption always happens on a moving edge they need to understand at the top one percentile.
    • The compounding advantage is mastering both the old history and the new edge at once, the way understanding both marketing legends and TikTok would set you apart in any interview.
    • Most people underestimate how much AI can do, so push more of the downstream work into the prompt: identify the top ten, list pros and cons, rank them on one dimension, then another, and add up the numbers too.
    • Gurley uses ChatGPT for project structure and memory, Gemini for restaurant research powered by Google review data, and notes that coders swear by Claude while some prefer Perplexity for finance.
    • He doubts one model dominates everything; verticals like coding already let users swap models, and price optimization will push more swapping over the next few years.
    • Heavy, expensive regulation could ironically create oligopoly, and some players may be quietly begging for regulation because it pulls up the bridge against Chinese open source models.
    • China’s roughly ten open source models compete intensely and share weights and techniques, creating a system that can innovate faster, like farmers forced to share best practices instead of just trading goods.
    • A quiet secret is that startups all over Silicon Valley are forking those Chinese open source models at real volume.
    • Gurley comes down against the idea that one near-sentient model removes the need for vertical models; workflows and proprietary data, like legal startups ingesting all the case law, create durable moats.
    • We may be running out of training data, painting in the corners, which is why one of the most powerful improvements is hiring experts at thousands of dollars an hour to fine-tune the models.
    • Yann LeCun’s view is that the next leap is broader than LLMs, since language-based models hit an asymptote and are weak at math and numbers.
    • AlphaGo’s shocking move proves models can innovate beyond their training, but it lived in a constrained game; the real world has infinite paths a computer cannot exhaustively search.
    • Gurley’s non-consensus view is skepticism of the China vilification mindset, noting the US is only 3 to 5 percent of the global population and wondering how the other 95 percent hears American exceptionalism.
    • The AI buildout looks overfunded: the Magnificent Seven took free cash flow from 50 to 100 billion a year down toward zero by pouring it into capex.
    • The venture community has become more risk-seeking because it now deeply believes in increasing returns and power laws, and the pre-profit losses keep scaling, from Amazon’s 2 to 3 billion to Uber’s 15 billion to far more now.
    • Circular deals, where a cloud provider funds a model company that spends the money right back on its services, inflate growth, which both raises the probability of an eventual correction and extends the time before one hits.
    • Burn rate is a measure of risk; ten years ago a million a month was scary, now companies burn five billion a year and cannot really know their unit economics.
    • Tokenization without financial-disclosure regulation invites speculation and manipulation, which is part of why companies like Stripe stay private and negotiate liquidity prices with trusted investors.
    • The IPO process is unfair because bankers pick both the price and the shareholders; a freshman would simply match supply and demand anonymously in an auction, the way direct listings and ICOs do.
    • Stablecoins threaten the 2 to 3 percent credit card stack; USDC holds dollar-for-dollar Treasuries and rides fast global crypto rails, while US transfers still suffer three-day ACH settlement and 25 dollar wires.
    • The rest of the world built instant transfer long ago, from UK Faster Payments 20 years ago to Argentina’s PIX-style system reaching 60 to 70 percent of transactions, while US bank regulatory capture stalled Fed Now.
    • Visa and Mastercard run roughly 60 percent operating margins as a bank-created duopoly, and China leapfrogged them entirely with WeChat Pay and Alipay QR-code wallets.
    • Moody’s power is being the trusted standard, the watermark, so AI on the back end does not displace it; ISS and proxy advisors, by contrast, score companies in a black box and get paid on both sides.
    • Proxy advisors drifted from shareholder interest into a fraud-and-risk-mitigation mindset, which is why they reflexively opposed the Tesla pay package that only paid out if the stock soared.
    • The rise of passive index funds concentrated voting power in firms that lack time to evaluate votes; it would be healthier if they abstained or voted in proportion to active holders.
    • Storytelling is one of the top founder traits, because founders are recruiting, raising money, and closing customers and partners constantly, selling all the time.
    • Writing is thinking: Bezos’s six-page memo forces you to find the loose ends and tie them up, and a public blog becomes a calling card that magnetizes founders and deal flow.
    • Other founder unfair advantages are product instincts, which fewer than 5 percent of non-product people ever truly learn, and sheer determination, Bezos’s single angel-investing test of whether someone will do it no matter what.
    • Uber had no HBS case study to lean on; its winner-take-all network effects forced mega burn rates with no precedent and no mentor to call, a situation every AI company now faces.
    • Benchmark’s equal partnership, with no king, president, or lead and five equal partners, makes recruiting easy, kills comp politics, and aligns everyone, at the cost of being hard to scale or run new initiatives.
    • Venture bends toward youth because young investors can match founders’ age, master a fresh niche faster, and have the free time to study something 80 hours a week.
    • Gurley defines current success through Arthur Brooks’s From Strength to Strength, hoping to apply his synthesizing and writing skills to bigger societal problems and dent the universe a little.

    Detailed Summary

    Systems Thinking and Second Order Effects

    Gurley opens with the mental model he keeps returning to: systems thinking, shaped by Donella Meadows’s Thinking in Systems and his board seat at the Santa Fe Institute, which studies complexity theory. He describes complex systems as multivariable nonlinear systems that are very hard to predict, capable of behaving one way for a long time until a single variable flips and the whole system behaves differently, like weather or stock markets. The practical payoff is staying out of trouble by anticipating first, second, and third derivative consequences. His clearest example is a large dating site that lengthened user profiles because the test showed more engagement, only to learn many months later that knowing more at that stage was negative for conversion. The lesson is to never get too deterministic about a single metric and to keep the whole system in view, because a change here can ripple to there in ways you only discover much later.

    Learning the Craft of Investing

    Because he started on Wall Street rather than in venture, Gurley absorbed the investing canon first: Peter Lynch’s One Up on Wall Street, A Random Walk Down Wall Street, the Buffett letters, Ben Graham, and Howard Marks, people who spent careers assembling and publishing their thinking. That financial bedrock, he argues, is exactly what lets you innovate on top of it. His friend Michael Mauboussin introduced him to Bill Miller, the Legg Mason manager who beat the S&P for 15 straight years and was Amazon’s largest shareholder for a long stretch. Miller reframed value investing as buying an asset underpriced relative to its future worth, which combined with a belief in network effects justified holding a company that could grow at an unreasonable rate for years. Gurley also frames Wall Street as the buyer of the product venture capitalists create through eventual M&A or IPO, so founders should think early about whether the public market will be excited by what they are building, since trajectory matters more than the starting place.

    Mastering Both the History and the Edge

    Gurley makes an unusually strong case for studying the deep history of your field. He recounts a dinner with Pixar’s John Lasseter, who served a ten-course meal where every course was tied to a classic cartoon he considered essential to understanding animation, and notes that Magnus Carlsen won a chess-history trivia contest and Picasso was a master realist by 14. In a world that skims for the executive summary, walking into a marketing interview with command of the masters of marketing is wildly differentiating and signals genuine passion; if learning that history feels tedious, you are probably in the wrong lane. The counterpart trait he sees in great entrepreneurs is obsessive learning on the moving edge, where disruption actually happens. Gurley keeps five premium AI accounts so he never misses something. The real power player holds both at once, the legends and the newest thing, the way a candidate who knows the marketing greats and truly gets TikTok stands out completely.

    Using AI Well and the Model Wars

    People underestimate how much AI can do, Gurley says, so you should build more of the downstream work into the prompt: instead of asking for the top ten and studying them yourself, ask it to list pros and cons, rank on one dimension, rank again on another, and add up the numbers too. He uses ChatGPT for its project structure and memory, leans on Gemini for restaurant research because it carries Google review data, and notes coders swear by Claude while some prefer Perplexity for finance. On whether one model dominates or models become niche commodities, he points to coding, the largest vertical, where tools like Cursor already let users swap models, and predicts price optimization will drive more swapping. The counterforce is regulation: if it gets expensive and mundane it could create oligopoly, and some players may be quietly begging for it because it pulls up the bridge against Chinese open source models.

    China, Open Source, and the Systems Advantage

    Asked to apply systems thinking to China, Gurley describes roughly ten open source models locked in intense domestic competition, all learning from one another because the ecosystem chose openness, with models able to train and test other models and teams publishing the techniques behind their breakthroughs. His metaphor: two agricultural societies, one where farmers only trade goods at market and another where they are forced to share best practices; the second evolves far faster. The result is a system capable of innovating faster than the more secretive Western approach. The quiet secret he names is that startups all over Silicon Valley are forking those open models at real volume, and a key open question is whether regulation tries to stomp that out. He extends this into a broader non-consensus discomfort with the vilification of China common in Washington and parts of Silicon Valley, observing that the US is only a few percent of the global population.

    AI Investing, Moats, and the Limits of Models

    On how AI changes investing and whether a startup is just a wrapper, Gurley calls it up for grabs but lands on the side of durable verticals. If models become near-sentient, one model does everything; he doubts that, pointing to workflows and data moats, like the several legal AI startups ingesting all the case law and building new databases that customers will not simply swap for a general chatbot. He balances this against the Microsoft pattern of platforms climbing the stack past Lotus 1-2-3 and WordPerfect. He also flags scaling limits: we may be running out of data, painting in the corners, which is why one of the most powerful improvements is paying experts thousands of dollars an hour to fine-tune models, though human knowledge has an edge. He invokes Yann LeCun’s argument that the next leap is broader than language-based LLMs, which hit an asymptote and struggle with math, and the AlphaGo debate, where a shocking innovative move proves creativity within a constrained game but says little about the infinite paths of the real world. He notes AlphaGo and Tesla’s FSD are constrained, non-LLM systems.

    Is the Buildout Overfunded

    Gurley admits he is shocked by the scale of money, noting the Magnificent Seven drove free cash flow from 50 to 100 billion a year down toward zero by spending it all on capex, something he would not have believed five years ago. He traces it to the venture community’s growing conviction in increasing returns and power laws, where proven companies grow far beyond expectations, which makes investors more willing to take risk on the come. The losses before turning cash-flow positive keep scaling, from Amazon’s 2 to 3 billion to Uber’s roughly 15 billion to far larger now. On corrections, he recalls the dot-com crash producing a three to four year nuclear winter before Amazon climbed back, and explains that circular deals, where a cloud provider funds a model company that spends it right back on its services, inflate growth and therefore both raise the probability of a correction and extend the runway before one arrives. Burn rate, he stresses, is a measure of risk, and at five billion a year it is nearly impossible to know your unit economics.

    Tokenization, the IPO Heist, and Going Public

    There is no shortage of capital, so funding is not the bottleneck; the risk with tokenization is that, absent disclosure regulation, it invites speculation and manipulation, as seen in retail-loved names like GameStop and Palantir. Tokenizing a private company like Stripe could create the wild price swings companies stay private to avoid, since private liquidity events let them negotiate a price with trusted investors rather than expose the constantly moving underlying value, and Robinhood’s tokenization plans already drew legal pushback. Gurley reserves his sharpest critique for the IPO process, calling it insanely unfair because bankers pick both the price and the favored shareholders. A freshman computer science and finance student would simply match supply and demand anonymously in an auction, the way an ICO or a direct listing does, but Wall Street will not let go of the greedy power grab and reverted to a controlled oligopoly after direct listings were available.

    Stablecoins Versus the Payment Cartel

    Gurley argues stablecoins could be deeply disruptive to credit cards. Most of the developed world built instant bank-to-bank transfer long ago, from UK Faster Payments 20 years ago to Argentina’s PIX-style system that quickly hit 60 to 70 percent of transactions, while US bank regulatory capture stalled Fed Now and left an ecosystem living under 2 to 2.5 percent card fees. A USDC stablecoin holds dollar-for-dollar US Treasuries and rides proven, fast, global crypto rails, letting anyone move a dollar in seconds for pennies, against the backdrop of three-day ACH settlement and 25 dollar wires. He sees Visa and Mastercard, a bank-created duopoly with roughly 60 percent operating margins, as heavily threatened, and points to China, where WeChat Pay and Alipay built ubiquitous QR-code wallets that leapfrogged the entire card system, all because the government made money transfer easy.

    Moody’s, Proxy Advisors, and Index Funds

    Moody’s power, Gurley explains, comes from being a trusted standard, the watermark, so even AI on the back end does not displace it. Proxy advisors like ISS are a different story: they score companies in a black box, refuse to reveal the criteria, and then get paid by the same companies that want to learn how to score better, which he calls more of a heist than a service. They drifted from a shareholder-interest mandate into a corporate-governance, fraud-mitigation posture obsessed with rules, which is why they reflexively opposed the Tesla pay package that only paid Elon Musk if the stock soared, a deal Gurley says he would sign for every company he has worked with. The rise of passive index funds compounds the problem, concentrating voting power in firms without time to evaluate votes; he would prefer they abstain or vote in proportion to active holders, since closet indexing during the MAG 7 run already distorted active management.

    Storytelling, Writing, and Founder Advantages

    Gurley fell in love with the craft of writing in business school, moving from business books to personal development titles like Dale Carnegie and Seven Habits, then biographies, then long-form narrative nonfiction by Malcolm Gladwell, Michael Lewis, and Jon Krakauer, the New Journalism that reads like fiction. Writing forces clarity: he cites Bezos’s six-page memo as a tool that makes you think through corner cases and tie up loose ends, and notes that codifying his marketplace knowledge and publishing it turned his blog into a calling card that magnetized founders and deal flow. He lists the top founder traits as storytelling, product instincts, understanding the edge, and determination. Storytelling matters because founders are constantly recruiting, fundraising, and closing customers and partners. Product instinct is nearly unteachable, present in well under 5 percent of non-product hires. And determination is Bezos’s single angel-investing test: will this person do it no matter what, come hell or high water.

    Uber, Benchmark, and the Shape of Venture

    The Uber lesson with no HBS case study was that a winner-take-all category with network effects demanded funding ad nauseam, producing burn rates bigger than any public company would dare, with no precedent and no mentor to call, exactly the situation AI companies now face, only with a zero added. Gurley credits Benchmark’s design, an equal partnership with no king, president, or lead and five equal partners, for making it easy to recruit top talent, encouraging senior partners to develop newcomers since everyone shares the upside, and eliminating annual comp politics. The downside is that without a CEO it is hard to scale or run new initiatives, famously captured by the firm settling on a single splash-page website. Founders choose a VC for reputation and network effects, the stamp of approval that carries weight, and young investors can break in because they often match founders’ age and can outwork everyone to master a fresh niche like esports or YouTube, which is why the industry bends toward youth. Asked what success means now, Gurley says his venture career was a dream job he would have done for free, but it is done; inspired by Arthur Brooks’s From Strength to Strength, he wants to apply his synthesizing and writing to bigger societal problems and dent the universe a little.

    Notable Quotes

    “We do live in a world where information is really cut up, but we also live in a world where you can have access to more information than you ever could.”

    Bill Gurley, on why the abundance of knowledge rewards the curious

    “You got to be really conscious of the consequence and not get too deterministic about a single metric or a single variable.”

    Bill Gurley, on the discipline of systems thinking

    “Value just means that the asset is underpriced relative to what you think it will be worth in the future.”

    Bill Gurley, relaying Bill Miller’s reframing of value investing

    “I’ve always thought of Wall Street as the buyer of the product that venture capitalists create.”

    Bill Gurley, on why founders should think about the public market early

    “One society, when the farmers come to market, they just sell each other goods and then they go back. The other society, when the farmers come to market, they’re forced to share best practices. Which one is going to evolve faster?”

    Bill Gurley, on why open source models can out-innovate

    “If you took a freshman computer science student and a freshman finance student and said imagine how a company should go public, they would match supply and demand anonymously like you would in any auction.”

    Bill Gurley, on the rigged IPO process

    “When I meet an entrepreneur, there’s only one thing I ask myself. Is this person gonna do this no matter what? Come hell or high water, they’re doing this.”

    Bill Gurley, quoting Jeff Bezos on his single test for angel investing

    “You’re recruiting employees, you’re recruiting executives, you’re raising money, you’re closing customers, you’re closing partnerships. You’re selling all the damn time.”

    Bill Gurley, on why storytelling is a top founder trait

    “I often said that if we lived in a socialist society and everyone had to work for free, I would still take that job.”

    Bill Gurley, on loving his venture career

    “I would like to see if I can apply those techniques to bigger, broader problems in society and dent the universe a little bit that way.”

    Bill Gurley, on what success looks like in his next chapter

    Watch the full conversation with Bill Gurley on The Knowledge Project here.

    Related Reading

  • 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

  • Dan Loeb on Building Third Point’s $25 Billion Investment Empire: AI, Activism, Credit, and the FTX Mistake

    Dan Loeb has spent three decades turning a $3 million fund into Third Point, a roughly $25 billion collection of hedge fund, credit, insurance, and venture businesses. In this Invest Like the Best conversation with Patrick O’Shaughnessy, Loeb walks through how he reinvented his strategy from deep value and event-driven trades into quality and thematic investing, why he now believes every serious investor has to be a technology investor, how he reads the AI cycle and the semiconductor melt-up, where activism and corporate governance still pay, and the single mistake that taught him the most. It is a rare, unhurried look at how a famously sharp-elbowed activist actually thinks about markets, businesses, and people.

    TLDW

    Loeb covers an enormous amount of ground: his daily process for staying ahead of the information firehose, Jensen Huang’s AI stack as a mental model, and why Nvidia, Anthropic, and Elon Musk’s companies are the three most consequential firms he tracks. He traces Third Point’s roots in credit and event-driven investing at Jefferies, the influence of Joel Greenblatt’s “You Can Be a Stock Market Genius,” and his later pivot to quality investing shaped by “The Outsiders” and Lawrence Cunningham’s “Quality Investing.” He argues the AI rally is not a dot-com-style valuation bubble because the leaders generate enormous cash, explains why human judgment and structural market quirks still create alpha, and makes the case that AI will never fully run a capital system. He digs into corporate governance and his father’s influence, the Sotheby’s and Sony activism campaigns, the hard reality of activism in Japan, and what investing in Danaher’s operating system taught him. He names FTX as his hardest lesson, breaks down Third Point’s evolution into a 60-percent-credit platform spanning CLOs, structured credit, reinsurance and annuities, describes how he is pushing his analysts to use AI and Claude daily, and closes on kindness and the friend who let him sleep on a couch before he made it.

    Thoughts

    The most striking thing about Loeb is that he treats his own strategy as a thing to be disrupted rather than defended. He built his reputation on Greenblatt-style special situations, spin-offs, demutualizations, and post-reorg equities bought cheap because of forced selling and sandbagged guidance. Most investors who win that way spend the rest of their careers protecting the formula. Loeb instead watched the people who stayed rigid about deep value and low multiples underperform or disappear, and deliberately retrained himself and his team around business quality and thematic conviction. The willingness to abandon a winning identity is the actual edge here, more than any single trade. It is the rare investor who can say his current strategy would not fit cleanly on a PowerPoint deck and treat that as a feature.

    His AI framing deserves attention because it is unfashionably calm. The bear case on AI is usually about valuation, and Loeb dismantles it on the leaders’ own numbers: these are companies investing off their balance sheets, generating enormous cash, trading at multiples that do not resemble 1999. He was short the dot-com bubble, so he is not a permabull cheering from the sidelines. His real point is subtler, that the danger is expectations, not valuations. The semiconductor index ran up 40 percent on genuinely strong fundamentals, but Micron and Nvidia both put up monster quarters and saw their stocks fall because expectations had simply outrun even great results. That gap between fundamentals and price is where he thinks the human investor still earns a living, precisely because quant strategies, CTAs, and risk-managed pods are forced to sell into weakness rather than buy it.

    The governance material is the most quietly radical part of the conversation. Loeb defends shareholder primacy against the Business Roundtable’s softer stakeholder language, but his argument is not the cartoon version where shareholder value means strip-mining a company. It is that boards have one job, accountability for capital allocation and management, and that vague multi-stakeholder mandates become an excuse for directors to avoid the hard work. His read on bad governance is almost always relational: directors who let loyalty to an underperforming CEO override their duty, or who sit on boards for status and income. The Sotheby’s story is the clean illustration, a centuries-old, high-status business run unprofitably because nobody treated it like a business. Loeb’s pattern is to find the gap between claimed status and actual performance and to raise the social cost of coasting.

    What is genuinely new in Loeb’s posture is how he talks about AI inside his own firm. He is not pitching it as a moat or a headcount-reduction story. He frames Claude and AI tools as a way to make each person a more autonomous self-improver, something that gives back whatever you put into it, with some analysts running agents overnight and burning tokens while he personally uses it more for queries. Coming from a 30-year fundamental investor, the absence of defensiveness is the signal. He pairs it with Brad Gerstner’s nod to “Essentialism”: the firehose is now infinite, so the scarce skill is deciding what is actually relevant. That is a more honest answer to the AI question than either doom or hype.

    Finally, the FTX confession is worth sitting with because of how he frames it. He does not retreat into cynicism about venture or crypto. He notes that Sam Bankman-Fried, fraud aside, had a real nose for value, with stakes in Anthropic, Cursor, and Solana that would have made him a top venture investor of the era. The lesson Loeb extracts is procedural, not philosophical: their due diligence now includes checking bank balances, the most basic verification that would have surfaced the problem. It is a useful reminder that even sophisticated capital can skip boring fundamentals when a company is growing fast and the cap table looks good. The discipline is not in having a grand theory of fraud, it is in never skipping the unglamorous checks.

    Key Takeaways

    • Loeb’s macro focus right now collapses to two variables: where oil goes, dictated by war and geopolitics, and what AI does on the spending and infrastructure front and its impact on society and the economy.
    • He argues you can no longer punt on technology and focus on industrials or consumer; tech is a big, growing, compounding part of the economy that affects everything else, so every investor has to become a tech investor.
    • He uses Jensen Huang’s AI stack as a mental model: power and energy at the bottom, then chips and infrastructure, up through large language models, software, and applications.
    • The three most consequential companies he tracks are Nvidia, Anthropic, and Elon Musk’s companies collectively.
    • Third Point’s roots are in credit and event-driven investing, shaped by his time at Jefferies watching investors like David Tepper before he founded Appaloosa, Eric Mindich at Goldman, and firms like Angelo Gordon and Farallon.
    • Joel Greenblatt’s “You Can Be a Stock Market Genius” was his foundational framework: spin-offs, demutualizations, privatizations, and post-reorg equities where a new, illiquid security gets dumped by holders who will not do the work.
    • Spin-off managers often sandbag guidance because their incentive packages get set at the time of the spin-off, creating a predictable gap between conservative numbers and real value.
    • From 1995 to roughly 2013-2015, event-driven special situations were Third Point’s bread and butter; those opportunities still exist, but the real edge now is overlaying them with a business-quality lens.
    • The pivot to quality and thematic investing was influenced most by “The Outsiders” (capital allocation plus great operations) and Lawrence Cunningham’s “Quality Investing” (high-moat, high-return-on-capital businesses to own for years).
    • AI disruption made last year one of the worst for many apparently high-quality companies, as businesses that looked durable rapidly became less so.
    • Loeb sees the AI rally as fundamentally different from the dot-com bubble: the leaders invest off their balance sheets, generate enormous cash, and do not carry the valuation excess of 1999.
    • The danger in semis is expectations, not valuation: Nvidia and Micron posted spectacular quarters yet saw stocks fall because expectations had outrun even great numbers.
    • Structural forces still create alpha for fundamental investors: quants, CTAs, and multi-strategy pods have risk metrics that force selling on the way down, the opposite of what is rational for long-term holders.
    • He believes AI will not fully run a capital system; private equity, restructurings, creditor committees, and high-touch negotiation will always need humans.
    • His interest in governance came from his father, a securities lawyer and corporate governance expert who sat on the boards of Mattel and Williams-Sonoma and pushed ethical sourcing ahead of his time.
    • Loeb defends shareholder primacy, citing Milton Friedman and Warren Buffett, and criticizes the Business Roundtable’s move away from shareholder value as a distraction from the board’s real duty.
    • Bad governance usually comes from directors letting loyalty to a weak CEO override fiduciary duty, lacking the knowledge to do the job, or serving for status and income.
    • Writing is a core activism lever: great writing is clear thinking, and social pressure through writing and PR is one of the most effective ways to move a board, alongside financial and legal levers.
    • The Sotheby’s campaign targeted a high-status, centuries-old business run unprofitably; Third Point bought 9.9 percent, eventually brought in Tad Smith from MSG, who cleaned up operations and technology before the company sold.
    • Third Point increasingly prefers to back great companies with excellent management and cheer them on rather than hunt for mismanaged businesses, because bad management tends to cluster into a morass.
    • Third Point is a collection of businesses; the flagship hedge fund grew from $3 million to about $9 billion and is roughly 30 percent credit, with the broader firm closer to 60 percent credit.
    • The firm spans a roughly $7 billion CLO business, structured and corporate credit, an insurance company, asbestos liabilities, a small private credit unit, and a venture capital arm.
    • The unifying thread is valuing enterprises across early, mid, and mature stages and investing in whichever fulcrum security offers the best risk-reward, from equity to senior debt.
    • Loeb cites buying Twitter’s financing debt near 96-97 cents at a 12 percent yield when most credit investors were scared, and a difficult xAI debt financing, as examples of cross-discipline conviction.
    • He is the portfolio manager only of the hedge fund; the credit, CLO, structured credit, and high-yield businesses have their own PMs and investment committees he does not sit on.
    • The Sony campaign saw Third Point own up to 7 percent and push to separate the conglomerate; management resisted for years before spinning out the semiconductor and financial services businesses.
    • He learned that activism in Japan is hard, but the government often wants reform; he co-wrote a paper with Larry Lindsey and Niall Ferguson urging corporate governance and return on invested capital as a fourth arrow of Abenomics, picked up as a Wall Street Journal editorial.
    • Investing in Danaher was his most instructive experience, teaching him how the Danaher Business System drives continuous improvement (Kaizen) and how the company celebrates rather than shames underperformance because problems are fixable.
    • FTX was his hardest lesson; it looked great and was verifiable on the blockchain, but was not what it appeared, and now Third Point’s diligence includes checking bank balances.
    • He notes that, fraud aside, Sam Bankman-Fried had a strong nose for value with stakes in Anthropic, Cursor, and Solana.
    • Recent mistakes also include shorts where Third Point thought certain info-services businesses would resist AI disruption; he still expects a shakeout with some phoenixes rising from the ashes.
    • He is pushing his whole team to use AI daily, hiring native computer scientists and system integrators, and describes Claude as a tool that makes you autonomous and gives back whatever you put into it.
    • Third Point’s distinctive edge is optimism about AI creating net jobs and the ability to default into credit investing during stressed times, as it did with investment-grade credit in 2020.
    • Credit is hard to copy because it runs on relationships, not electronic trading; that is why Third Point built into CLOs and eyes the roughly $6 trillion structured credit market rather than treating it as tourism.
    • The great analyst has changed: 20 years ago it was someone who could model fast and crack a complex restructuring (Loeb made a career-defining bet on Drexel Burnham claims); today it is a Gavin Baker type who deeply understands an industry, like the analyst who flew to Texas and realized Casey’s General Stores was really a pizza chain.
    • Outside the US, Loeb is more bullish on Korea, Taiwan, and Japan as hunting grounds, finds Europe tough on regulation (though he owns Rolls-Royce and ASML), and finds the Middle East the most vibrant region.
    • What worries him most is not the business but running out of time for family, surfing, and reading; what excites him is incorporating everything relevant about the world and forming relationships with people building interesting things.
    • His closing reflection is on kindness as a top-tier value, and the friend, Carter, who let him sleep on a couch and seeded his early fund, echoing a Palmer Luckey line that money cannot buy friends who believed in you when you had nothing.

    Detailed Summary

    Staying ahead of the firehose and reading the macro

    Loeb opens by admitting he does not have a perfectly organized system for processing the modern flood of information. He checks the news for what is relevant to the economy and to Third Point’s positions, tries not to obsess over minute-to-minute moves, and leans more tactical than strategic. When people ask him about macro, he says the usual government-reported metrics (growth, unemployment, inflation, rates, currencies, gold, crypto) are trumped right now by two things: where oil goes, which depends on war and geopolitics, and what AI does on the spending and infrastructure side and its impact on society and the economy. To understand technology, he leans on Jensen Huang’s framing of the AI stack and talks to smart people regularly, and he watches three companies above all: Nvidia, Anthropic, and Elon Musk’s companies as a group.

    From event-driven roots to quality investing

    Third Point’s DNA comes from Loeb’s time as a credit investor at Jefferies, where he watched some of the best distressed, event-driven, and risk-arbitrage investors operate, from David Tepper to Eric Mindich to firms like Angelo Gordon and Farallon. His first lens was event-driven: spin-offs, demutualizations, privatizations, and post-reorg equities, where a newly created and illiquid security gets dumped by holders who will not do the work, and management sandbags guidance because incentive packages are set at the spin date. He barely thought about moats or returns on capital; he just wanted to buy something genuinely cheap with those characteristics. That was the firm’s bread and butter from 1995 until roughly 2013-2015. Those opportunities still exist, but Loeb describes deliberately evolving toward business quality and thematic investing, influenced by “The Outsiders” on capital allocation and Lawrence Cunningham’s “Quality Investing” on durable, high-return businesses. He organized the team around industry experts rather than generalists. The twist: AI disruption recently turned many apparently high-quality companies into much lower-quality ones, fast.

    The AI cycle, bubbles, and the human edge

    Loeb resists the bubble narrative. He was short the dot-com bubble and remembers the valuation excess; today’s AI leaders, by contrast, invest off their balance sheets and generate enormous cash, so unless you believe the capex yields no return, the earnings and multiples do not look like 1999. The real driver of volatility, he argues, is expectations: the semiconductor index ran up 40 percent on strong fundamentals, but Nvidia and Micron both delivered blowout quarters and still saw their stocks fall because expectations had run too high. That dynamic is exactly where a fundamental investor earns a living, because quants, CTAs, and risk-managed pods are structurally forced to sell into weakness. He also doubts AI will ever fully run a capital system, since private equity, restructurings, creditor committees, and high-touch credit always need humans. He cites “Reminiscences of a Stock Operator” and Ecclesiastes: there is nothing new under the sun, and human nature, with its bubbles, panics, and extremes, does not change.

    Governance, his father, and the duty of boards

    Loeb traces his governance interest to his father, a securities lawyer and corporate-governance expert who served on the boards of Mattel and Williams-Sonoma and championed ethical sourcing before it was common. He calls the American board system beautiful: directors are answerable to shareholders and accountable for strategy and key financial decisions. Governance breaks down when directors lose sight of their fiduciary duty, lack the knowledge or talent diversity to do the job, or prioritize things other than shareholders. He invokes Milton Friedman and Warren Buffett to argue that caring about communities, employees, and conduct is not inconsistent with shareholder value but part of it, and criticizes the Business Roundtable for muddying the board’s core duty. The most common failure he sees is directors letting loyalty to an underperforming CEO override their duty. Most of the time Third Point redirects existing boards without even taking a seat; the extreme proxy fights are the exception.

    Activism, writing, Sotheby’s, and Sony

    Great writing, Loeb says, is clear thinking and organizing your thoughts to get a desired outcome, and it is one of activism’s most effective levers alongside financial and legal pressure. Social pressure through writing and PR can move a board on its own. He sees a pattern in his campaigns: targets that hold themselves out as high status but are not living up to it. Sotheby’s is the clean example, a centuries-old, high-status business run unprofitably, where Third Point bought 9.9 percent, gave the existing CEO a year, then helped install Tad Smith from MSG, who modernized operations and technology before the company was sold. Sony was a two-act campaign in which Third Point owned up to 7 percent and pushed to break up the conglomerate; he recounts sharing the thesis with Andrew Ross Sorkin at the New York Times under embargo, the panic it caused, and how management resisted for years before spinning out the semiconductor and financial services units. The lesson: activism in Japan is genuinely hard, even though the government wanted reform. He co-authored a paper with Larry Lindsey and Niall Ferguson arguing corporate governance and return on invested capital should be a fourth arrow of Abenomics, which ran as a Wall Street Journal editorial.

    The Danaher operating system

    Loeb calls Danaher his most instructive investment. He and his partner persuaded the company to compress its five-day Danaher Business System training into a single day, and he came away with a deep appreciation for how a real operating system drives continuous improvement. The standout lesson was cultural: Danaher holds people individually accountable, but when it finds someone underperforming it celebrates rather than shames, because the problems are addressable and fixable, and it does this relentlessly across operations and working capital. He also points to the diaspora of Danaher executives, including Larry Culp and the leadership at Ingersoll Rand, as evidence of the system’s depth. The investment worked for about four years before COVID-era order surges and inventory swings turned tailwinds into headwinds; Third Point sold and has recently bought back in modestly.

    The structure of Third Point and the fulcrum security

    Third Point is not one fund but a collection of businesses. The flagship hedge fund grew from $3 million to about $9 billion and is roughly 30 percent credit, generically around 110 percent long and 30-40 percent short on the equity side. Across the firm the credit weight is closer to 60 percent, spanning a roughly $7 billion CLO business, several billion in structured and corporate credit, an insurance company, a couple billion in asbestos liabilities, a small new private credit unit, and a venture arm. The unifying thread is valuing enterprises at any stage and investing in whichever fulcrum security (the one with the best risk-reward) makes sense. Loeb illustrates with Credit Suisse’s takeover by UBS, where the holdco paper proved the fulcrum, and with buying Twitter’s resold financing debt near 96-97 cents at a 12 percent yield when other credit investors were scared, plus a difficult xAI debt financing that few credit people wanted. He pushes back on the idea that he sits atop everything: he is the PM only of the hedge fund, while the other businesses have their own PMs and committees he is not on.

    Insurance, the FTX lesson, and recent mistakes

    Loeb started a Bermuda reinsurance company in 2010, backed by himself, Kelso, and Pinebrook, on a barbell thesis of investing the float in Third Point and treasuries to defer taxes and lever capital. The reinsurance side soured, and about three years ago he concluded they had the right idea but the wrong vehicle, that plain-vanilla annuities (which can only invest in credit) would have fit better. Third Point merged the reinsurer into its UK closed-end fund, Third Point Offshore Investors, reincorporated from Guernsey to Cayman, and repurposed it into an insurance company managing private credit, structured credit, whole-loan mortgages, real estate lending, and investment-grade debt. His hardest lesson was FTX: it looked great, was verifiable on the blockchain, and had a strong cap table, but was not what it seemed; diligence now includes checking bank balances. He notes Sam Bankman-Fried, fraud aside, had a great nose for value (Anthropic, Cursor, Solana). Other recent mistakes were shorts where Third Point bet certain info-services businesses would resist AI disruption; he still expects a shakeout with some survivors rising from the ashes.

    AI inside the firm, the analyst of the future, and kindness

    Loeb is pushing his entire team to use AI daily, hiring native computer scientists and system integrators, and describes Claude as a tool that makes you an autonomous self-improver and gives back whatever you put into it, with some analysts running agents overnight while he uses it more for queries. He pairs this with Brad Gerstner’s recommendation of “Essentialism”: you cannot do it all, so you must decide what is most relevant. The great analyst has changed: 20 years ago it was someone who could model fast and crack a complex restructuring, as Loeb did with the Drexel Burnham bankruptcy claims early in his career; today it is a Gavin Baker type who deeply understands an industry and its technology, like the analyst who flew to Texas and realized Casey’s General Stores was really a pizza chain in disguise. On the rest of the world, he is more bullish on Korea, Taiwan, and Japan, finds Europe tough on regulation (while owning Rolls-Royce and ASML), and finds the Middle East the most vibrant region. He closes on what worries and excites him (time with family, surfing, and reading versus the joy of incorporating everything relevant about the world), and on kindness, crediting his friend Carter, who let him sleep on a couch and seeded his early fund, and echoing Palmer Luckey’s line that money cannot buy friends who believed in you when you had nothing.

    Notable Quotes

    “I think you have to be a tech person today. It’s a big and growing and compounding part of the economy. It affects everything else.”

    Dan Loeb, on why no serious investor can punt on technology anymore

    “Hold on to your seats because things are only going to accelerate from here.”

    Dan Loeb, recounting a 2013 Davos warning about technological change he now applies to AI

    “Maybe that’s where the human element comes in, to understand and to be able to make those tough trading decisions when fundamentals are going one way and stock prices are going the other way, and to be able to take the pain of losses in the short run.”

    Dan Loeb, on where a human investor still has an edge over machines

    “It’s very different from the dot-com bubble, which we were short going into. You don’t have the valuation bubble now on those companies that you had back in those days.”

    Dan Loeb, on why he does not see the AI rally as a 1999-style bubble

    “When they found someone that was underperforming, it was celebrated instead of shamed, because look at all these things you’re doing wrong, we can fix those. And they did.”

    Dan Loeb, on the accountability culture he learned from the Danaher Business System

    “I would have to say our investment in FTX. It looked great. The company was growing fast. We could verify it all on the blockchain.”

    Dan Loeb, naming his hardest investment lesson

    “Be kind to people you have no idea how it will ever benefit you. And sometimes it will and sometimes it won’t.”

    Dan Loeb, on elevating kindness in your hierarchy of values

    “The one thing money doesn’t buy you is friends that believed in you when you had nothing.”

    Dan Loeb, quoting Gavin Baker quoting Palmer Luckey, on the friend who seeded his early fund

    Watch the full conversation between Dan Loeb and Patrick O’Shaughnessy 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.