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

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

    TLDW

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

    Thoughts

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

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

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

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

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

    Key Takeaways

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

    Detailed Summary

    The three sectors he actually invests in

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

    How the portfolio is really built: single stocks over ETFs

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

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

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

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

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

    The Warren Buffett handshake that backed Goldman in 2008

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

    Why you cannot legislate risk out of the system

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

    Small margins, big outcomes, and the role of luck

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

    Reputation is the real contract

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

    A supportive spouse as the highest return asset

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

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

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

    Robinhood, confetti, and the misses

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

    The obituary test, thick skin, and staying too long

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

    Why he reads history: it rhymes

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

    Notable Quotes

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

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

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

    Lloyd Blankfein, on why he stays concentrated in technology

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Related Reading

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

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

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

    TLDW

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

    Thoughts

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

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

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

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

    Key Takeaways

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

    Detailed Summary

    From activist trades to permanent capital

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

    The Wendy’s and Tim Hortons origin story

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

    Why a long-term shareholder on the board matters

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

    AI and the rising risk of disruption

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

    What the market is missing

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

    The SaaS question and AI-enabled software

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

    Underwriting SpaceX, xAI, and the AI labs like venture

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

    Founder-led companies and the authority to act

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

    Howard Hughes as Berkshire Hathaway 2.0

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

    Cost of capital, reflexivity, and going direct

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

    Notable Quotes

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

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

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

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

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

    Bill Ackman, on how prices revert at both extremes

    “People, opportunity, context, deal.”

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

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

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

    “A closed mouth gathers no foot.”

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

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

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

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

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

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

    Related Reading

  • Raoul Pal: Why the Crypto Bull Run Is Just Starting, the AI Economic Singularity, and Why You Should Never Sell Bitcoin

    Macro investor and Real Vision co-founder Raoul Pal returned to the When Shift Happens podcast for episode 173 to argue that the recent crypto drawdown is a nasty correction inside a much larger bull market, not the end of the cycle. Across an hour and a half he ties together the AI capital race, the coming economic singularity, why layer one blockchains are a kind of universal basic equity, and the deceptively simple discipline that actually compounds wealth: buy, hold, and almost never sell.

    TLDW

    Pal frames everything through what he calls the universal code, the conversion of units of energy into units of intelligence, and says the global race to fund AI is so large that no government or company can stop feeding it capital. That liquidity, plus relentless currency debasement, is the engine under both the AI stocks going vertical and the crypto market that has lagged them. He calls the Bitcoin slide from 126K toward 60K a normal correction in a bull market, says liquidity is now reaccelerating, and argues smart contract layer ones (Ethereum, Solana, Sui) are the best risk-adjusted bet because the entire financial system and a coming swarm of AI agents will run on those rails, giving crypto an effectively infinite total addressable market. He explains why he added Zcash as a Bitcoin-with-privacy and quantum-proof trade, lays out his plan to launch an NFT fund built around grail digital art and NFT-backed lending, and makes a data-backed case that buying oversold dips and never selling beats trying to trade cycles. The conversation closes on a 70/30 bullish framework for 2026 and 2027 and a reflection on kindness.

    Thoughts

    The strongest idea in this conversation is not a price target, it is a reframe. Pal keeps pulling the camera back from “what will Bitcoin do this quarter” to “what is the organizing principle of the entire economy right now,” and his answer is the funneling of all available capital into anything that produces intelligence. Once you accept that frame, the buy-the-dip behavior in both AI equities and crypto stops looking like mania and starts looking like a rational response to a one-way game. The part worth sitting with is his game-theory claim that neither the US nor China can stop, and that even a spectacular failure like an OpenAI blowup would simply trigger an instant asset auction rather than a collapse, because no single player can be allowed to win outright. Whether or not that is fully true, it is a genuinely different mental model than the recession-and-bust cycle most investors carry around.

    His layer-one thesis is the most actionable takeaway and also the most quietly radical. The pitch is that for the first time ordinary people can own a piece of the core infrastructure that the machine economy will be built on, the way you never got to own a slice of TCP/IP or the open web. He calls this universal basic equity and treats it as humanity’s pension plan. The honest tension he admits is that the racy returns may not be in the boring base layer at all, and that the truly investable winners of this era, the private stablecoin companies, are largely closed off to retail. So the layer-one trade is partly a consolation prize for the fact that the best businesses are unreachable. That is a more candid admission than most crypto bulls will make.

    The behavioral core of the episode is the most useful for a normal reader, and it is almost embarrassingly simple. Pal has been in markets for 35 years and says he does not know a single person who reliably buys bottoms and sells tops, including the legends, who he points out made most of their money on management fees rather than heroic trades. His prescription is to add only when the asset is one to two standard deviations oversold on its long-term log trend, otherwise do nothing, and to treat patience as an action rather than inaction. The line that does the most work is “the market owes you nothing.” It quietly dismantles the entitlement that drives people to overtrade, chase, and burn emotional energy on a strategy that the data says underperforms simply holding.

    Where a reader should keep some skepticism is the certainty. Pal assigns the bull case a 70 percent probability and the bear case 30, but the bear case he sketches (Middle East war reignites, inflation forces tightening, liquidity gets starved, the intelligence buildout slows) is not a minor footnote, it is the whole structure failing at once. The thesis also leans hard on the assumption that AI agents will become massive on-chain economic actors, which is plausible but still mostly forward-looking rather than observed. The value here is the framework, not the forecast. If you take one thing, take the energy-into-intelligence lens and the standard-deviation discipline, and hold the specific tickers and timelines loosely.

    Key Takeaways

    • Pal’s central frame is the universal code: the universe, and now the economy, continuously converts units of energy into units of intelligence, and capital flows to whatever produces the most intelligence.
    • The AI buildout is a race of nations and corporations that nobody can exit. Game theory means neither the US nor China can stop, because the other side would gain a decisive advantage.
    • Even a catastrophic AI failure would not break the trend. If OpenAI ran out of money, its assets would be auctioned instantly to multiple buyers so no single company could double its compute and win the whole game.
    • The economic singularity is the point where institutions and the way we measure the economy can no longer keep up with the speed of technology, made worse when AI and robots are added to the population as economic actors.
    • AI is the first real-world example of Reed’s law, the exponential of the exponential, where most past technology followed the slower Metcalfe’s law log channel.
    • By around 2028, roughly five to six years after AI went mainstream, AI will have produced more words than all of humanity has produced in sum total since the Gutenberg press.
    • The current run is funded by cash flow, not debt. Unlike the late-1990s tech boom, the buildout is paid for out of the earnings of the most cash-generative firms in history.
    • Chips and energy are the binding constraints. Companies report being booked out three years and beyond, and xAI is reportedly handing older data centers to Anthropic because no one can get enough compute.
    • Pal expects the Fed to run a Greenspan-style playbook, cut rates and then get out of the way, letting a productivity miracle grow the economy faster than the debt pile so debt to GDP falls.
    • Bitcoin falling from 126K toward 60K is a nasty correction in a bull market, not a bear market. Pal has seen many 50 percent Bitcoin drawdowns since 2013, and altcoins always fall further on the risk curve.
    • The 2025 to 2026 correction has been choppy and slow rather than the fast V-shape of 2021, which is part of why sentiment feels so bad.
    • Crypto lagged because liquidity is finite. The government shutdown withdrew liquidity, which hits crypto with about a three-month lag, while AI capex and Chinese gold buying sucked capital away.
    • Liquidity is now reaccelerating in the US, China, and globally, which Pal sees as the reason the worst is likely over for crypto.
    • The birth of economic agents in late 2024 gives crypto an effectively infinite total addressable market, since agents will be economic actors that hold treasuries, make payments, and transact on-chain.
    • Smart contract layer ones are Pal’s preferred bet. He compares the structure to operating systems and cloud, where value concentrates into three to five major players plus a few specialists.
    • He calls owning layer ones universal basic equity and humanity’s pension plan, the chance to own the rails the agentic economy will run on, something the internet never offered retail.
    • Discounted cash flow analysis is the wrong tool for valuing a blockchain. The whole purpose of the network is to be the cheapest, fastest, and most programmable, so high fees are a bug, not a strength.
    • Pal measures layer ones by intelligence density: number of developers, programmability, speed to finality, applications per user, and the ratio of stablecoins to total value locked as stored energy.
    • Only three tokens maintained economic density when the market fell 80 percent: Ethereum, Solana, and Sui. ETH is the safe Microsoft-like choice, Solana is faster and cheaper, Sui is earlier but extremely fast and programmable.
    • Pal added Zcash in the correction as a Bitcoin-with-privacy trade. The left-curve case is simple privacy value, the right-curve case is that it is also quantum-proof and a hedge against AI-enabled state surveillance.
    • He admits he did not execute the Zcash buy well, kept meaning to add more while traveling, and watched it run up 50 percent. He treats it as a small position, not a portfolio overhaul.
    • On Hyperliquid he is complimentary but uninvested, because he does not trade, use perps, or use leverage, and he expects Robinhood and Coinbase to compete hard for that niche.
    • DeFi is better suited to machines than humans. Agents may not even need front ends or websites, just low-friction access to swap across multiple stablecoins and currencies instantly.
    • DeFi is not dead despite mega-hacks. Pal argues hacks force better products, and notes that banks quietly absorb theft losses too, so the answer is to build more secure systems.
    • The entire financial system is moving to blockchain rails because they are the most efficient way to operate, a prediction Pal first made in 2014 before smart contracts existed.
    • Pal is launching an NFT fund focused on grail assets (one-of-one alien CryptoPunks, top artists) trading from roughly 600K to tens of millions, plus a convex middle tier of artists with social consensus.
    • He names artists like Dies with the most likes (whom he compares to a Hunter S. Thompson of art) and Kim Asendorf, whose work uses tokens at the pixel level.
    • The fund will also lend against NFTs for yields around 15 percent or more, acquiring assets cheaply if borrowers default and recycling yield into emerging artists.
    • His real estate analogy: a smaller NFT in a great collection is like a modest apartment in a billionaire neighborhood, while grails are the 20 million dollar penthouses that actually compound.
    • Bitcoin is partly an AI proxy because global savings should rise as AI lifts economic growth, and Bitcoin targets a share of those savings as a digital store of value.
    • The core mindset shift: if you know where the world is going and roughly where market cap is heading on the log trend, you would never sell, you would only ever accumulate.
    • Selling well is nearly impossible. Even if you take profit at two standard deviations overbought, adding it back at the bottom is something almost no one actually manages.
    • The people who made the most money in crypto are the ones who did not trade it. Pal cites holders who profited by doing essentially nothing while active traders lost their edge.
    • Pal’s discipline requires roughly two to three actions every five years: add when one to two standard deviations oversold, optionally trim when two standard deviations overbought, otherwise nothing.
    • By his standard deviation measure, Bitcoin and crypto are as cheap as they have been in their long-term uptrend versus the NASDAQ, which he reads as a signal to allocate more to crypto.
    • Fear and greed sat below 10 for the longest stretch in the index’s history during this correction, hitting its lowest reading ever, a classic oversold extreme.
    • His 2026 to 2027 bull case stacks stablecoin explosion, the Clarity Act getting signed, rising global liquidity, debt rollovers forcing money printing, a strong business cycle, AI agents, and a cheap entry point. He puts it at roughly 70/30 to the upside.

    Detailed Summary

    Two economies and the money illusion

    The conversation opens loosely with travel, stablecoin spending, and a riff on why people agonize over a 75 dollar airport breakfast but happily lose money on an NFT that drops 80 percent. Pal’s explanation is that we live in two economies at once. The crypto and tech economy can grow 50 to 150 percent in a good year, while the real economy grows around 2 percent. Money earned in the fast economy does not feel real, which is why people spend and speculate so freely with it. This sets up the rest of the episode, where Pal treats the fast economy as the place serious capital is being forced to go.

    The AI capital race nobody can stop

    Asked why the stock market only seems to go up, Pal gives two reasons: liquidity expansion and the most extraordinary capital event in human history, the funneling of all capital into intelligence. He frames it as a race of nations, corporations, and individuals that cannot be slowed because of game theory. No superpower can let another reach AGI alone, only the US and China can afford the race, and neither can stop without ceding the advantage. He even games out an OpenAI bankruptcy and concludes the US would instantly auction the assets across many buyers rather than let one firm double its compute and win, which is why he calls the whole thing too big to fail. The practical conclusion is blunt: buy the dip, because the structure forces capital to keep flowing.

    The economic singularity, Reed’s law, and electricity through sand

    Pal defines the economic singularity as the moment when institutions and our economic measurements can no longer cope with the speed of technology, especially once AI and robots count as population. He explains that almost all past technology adoption followed Metcalfe’s law, a log channel visible in the charts of Google, Facebook, and the NASDAQ, but AI is the first observed example of Reed’s law, the exponential of the exponential. To make it concrete he cites ARK research showing AI will, by roughly 2028, have produced more words per year than all of humanity, and notes Anthropic expected 10x growth and got 80x in a quarter. He marvels that we are putting electricity through silicon, the second most common element on Earth, and producing intelligence six orders of magnitude faster than a human neuron.

    Why crypto lagged and why the worst is over

    Pal explains the crypto underperformance mechanically. There is only so much liquidity, the government shutdown withdrew it, and that hits crypto with roughly a three-month lag, landing right in the middle of the October drawdown. At the same time, the AI buildout and Chinese gold buying pulled capital toward the longest-duration assets, leaving SaaS and crypto with nearly identical charts as they got left behind. His read for 2026 is that liquidity is now reaccelerating across the US, China, and the world, so there is nothing to worry about yet. The Bitcoin move from 126K toward 60K is, in his framing, a normal correction, comparable in length to the roughly six-month 2021 pullback that resolved into new highs.

    Layer ones as universal basic equity

    The heart of the investment thesis is that smart contract layer ones will accrue a growing share of crypto value as the investable infrastructure layer. Pal argues the entire financial system plus a coming swarm of AI agents will use these rails, giving crypto an infinite total addressable market. Like operating systems and cloud, value will concentrate into three to five chains plus specialists. He measures them by intelligence density rather than discounted cash flow, since the point of the network is to be cheapest and fastest. By his analysis only Ethereum, Solana, and Sui held economic density through an 80 percent drawdown. ETH wins on developers, security, and Lindy effects (the Microsoft you do not get fired for owning), Solana is faster and cheaper, and Sui is earlier but offers a different order of magnitude on speed, finality, and programmability. He frames owning a basket of four or five as humanity’s pension plan.

    Zcash, privacy, and the quantum hedge

    Pal reveals he added Zcash during the correction, alongside buying more Sui. He had said in December he would wait for it to pull back, and he did, though he admits he did not buy enough as it ran up 50 percent. His left-curve case is that privacy has real value and people will understand it more, making it essentially Bitcoin with privacy that could plausibly reach 5 to 10 percent of Bitcoin’s value. His right-curve case is that it is also quantum-proof and a hedge against governments wielding AI-enabled control over people. He dismisses the mid-curve worry that it will be banned, noting that the ban fear has shadowed crypto his entire career and never materialized.

    Agents, DeFi, and financial rails

    Pal argues the biggest future users of DeFi and crypto payments will be AI agents, whose scale is effectively infinite. Setting up agents himself, he keeps hitting walls that require small payments, and sees agents making endless micro-payments plus larger transactions, holding treasuries across multiple stablecoins and currencies, and rebalancing through DeFi instantly without any human involved. DeFi, he says, is actually better suited to machines than people, and may not even need front ends. On the wave of mega-hacks he is unbothered, arguing they force better products, that banks quietly absorb theft too, and that the financial system always migrates to the most efficient rails because that is how you make more money. He first predicted blockchain would become the financial industry’s infrastructure rail back in 2014.

    The NFT fund and grail digital art

    Pal is launching an NFT fund because so many people told him they want exposure but do not know how. The fund targets grail assets, the scarce one-of-one pieces with proven social consensus that trade from around 600K into the tens of millions, plus a convex middle tier of artists who have long-term proven value and could be wildly re-rated. He names Dies with the most likes, an Indiana artist cataloging the decline of middle America whom he likens to Hunter S. Thompson, and German artist Kim Asendorf, whose 3D works are built from individually tokenized pixels. The math of convexity is the draw: an artist re-rating from 20 to 200 ETH while ETH itself multiplies could compound into a 100x. The fund will also lend against NFTs for yields above 15 percent, acquiring assets cheaply on default and recycling yield into emerging artists, and will build a club connecting investors to artists. His real estate framing reassures smaller holders: owning a lesser piece in a top collection is like a modest flat in a billionaire neighborhood.

    Never sell, and the math of patience

    The behavioral spine of the episode is Pal’s argument that buying, holding, and accumulating beats trading cycles. He has built a Real Vision indicator that signals a buy when an asset is one to two standard deviations oversold on its log regression channel, and says it compounds at a stupid rate. The problem with selling is deciding how much and then having the discipline to buy it back at the bottom, which almost no one does. In 35 years he says he has never met anyone who reliably buys bottoms and sells tops, and notes the trading legends made most of their money on management fees. The people who made the most in crypto are the ones who did nothing. He reframes holding as patience, an active stance, and ties it back to the universal code: buying Bitcoin and doing nothing is the most energy-efficient trade you can make, while overtrading burns mental and emotional energy for a worse outcome. His advice to those tempted by AI’s vertical charts is to go play with AI and just hold your Bitcoin.

    The 2026 to 2027 outlook

    Pal closes the macro case by stacking the bull factors: a massive stablecoin expansion over the next 24 months, the Clarity Act getting signed and freeing builders, rising global liquidity, trillions in interest payments that force more money printing, a strong business cycle recycling earnings into speculative assets, the arrival of AI agents, and a cheap entry point with fear and greed at historic lows. He even floats a permanent resolution of Middle East conflict as part of the upside. The bear case is the mirror image: war reignites, inflation runs hotter, tightening starves capital, and the intelligence buildout slows. He puts the odds at roughly 70 percent bullish, 30 percent bearish, and says he does not see the bear case yet. The episode ends on a personal note about kindness, with Pal unable to name a single kindest act because, he says, everything is made of kindness.

    Notable Quotes

    “We’re going through the most extraordinary time in human history. Nothing else matters. This whole funneling of all capital into intelligence is the biggest race that’s ever happened.”

    Raoul Pal, on why capital keeps flooding into AI

    “The game is so big that nobody will stop.”

    Raoul Pal, on the game theory of the US and China AI race

    “This is how amazing it is. We’re putting electricity through sand and creating intelligence.”

    Raoul Pal, on silicon and the universal code

    “It’s a nasty correction in a bull market. I’ve been in crypto since 2013. I’ve seen many corrections, non-bear markets of 50% in Bitcoin.”

    Raoul Pal, on Bitcoin falling from 126K toward 60K

    “The market owes you nothing. You would just have to be better at doing a job.”

    Raoul Pal, on the entitlement that ruins crypto investors

    “This is humanity’s pension plan. We get to invest in the infrastructure rails of which all the agentic economy will run.”

    Raoul Pal, on owning layer one blockchains

    “The people who’ve made the most money out of crypto are the people who don’t trade it.”

    Raoul Pal, on why holding beats trading

    “Your job is to be a mercenary for your own capital. You want to make the most money over time.”

    Raoul Pal, on why no one has to stay loyal to crypto

    “Bitcoin and crypto is as cheap as it has been in its long-term uptrend versus NASDAQ.”

    Raoul Pal, on the relative value signal he watches

    This is a compressed look at a wide-ranging conversation. Watch the full episode on When Shift Happens here for Pal’s complete reasoning, the charts he references, and the back-and-forth that the summary above leaves out.

    Related Reading

    • Real Vision the financial media platform Raoul Pal co-founded, where his Global Macro Investor research and exponential age thesis live.
    • Metcalfe’s law (Wikipedia) the network-value relationship Pal uses to model the log regression channel for crypto.
    • Reed’s law (Wikipedia) background on the exponential-of-the-exponential growth Pal says AI is the first real-world example of.
    • Technological singularity (Wikipedia) context for the economic singularity Pal argues is now only about four years away.
    • Zcash the privacy coin Pal added in the correction as a Bitcoin-with-privacy and quantum-proof trade.

  • The Paradox of Skill in Financial Investing: A Comprehensive Exploration

    In the complex world of financial markets, the elusive quest for consistent outperformance often leads both professionals and individual investors deep into the realm of skill enhancement, strategy refinement, and rigorous data analysis. Yet, somewhat counterintuitively, an established concept known as the “paradox of skill” suggests that the more competitive and knowledgeable investors become, the harder it is to distinguish skill-driven successes from random chance. At its core, the paradox of skill in financial investing is the phenomenon whereby increasing levels of competence among market participants paradoxically amplify the role of luck in determining outcomes. Understanding this paradox offers valuable insight into why it can feel so difficult to beat the market, even—or especially—when market participants are more skilled than ever before.

    Conceptual Foundations and Historical Context

    1. Early Recognition of the Paradox:
      Although the paradox of skill is a relatively modern label, the underlying idea traces its roots back to the earliest meditations on probability, competition, and merit. Thinkers as diverse as the 19th-century statistician Francis Galton, sports analyst Bill James, and contemporary researchers like Michael Mauboussin have invoked variations of this concept. In the financial sphere, it surfaces whenever analysts and portfolio managers question why superior training and technology have not, on aggregate, led to uniformly superior returns.
    2. Statistical Insights and the “Tightening” of Performance Distributions:
      Financial markets have grown vastly more sophisticated over the last century. Information is disseminated at lightning speed. Countless professionals hold advanced degrees in mathematics, economics, and finance; entire armies of data scientists and quantitative analysts employ algorithms to price securities with astonishing precision. With each incremental gain in the average skill level, the distribution of possible outcomes narrows. Think of it as a race where all the runners have adopted world-class training methods. When everyone is faster, the difference between finishing first and second might hinge not on training, but on a gust of wind or a slight miscalculation in strategy. The margin of victory shrinks, and thus randomness plays a relatively larger role in deciding winners and losers.

    Defining the Paradox

    1. What Is the Paradox of Skill?
      The paradox of skill can be stated succinctly: as the baseline skill level of all competitors rises, individual outcomes among those competitors become more influenced by luck, rather than less. This paradox is not about skill being irrelevant. On the contrary, skill remains an essential component of any long-term success. Instead, it highlights that when everyone in a competitive environment is extremely skilled, marginal advantages diminish. In other words, even slight strokes of good fortune or unlucky breaks can have disproportionately large effects on relative performance.
    2. Why Does This Paradox Occur?
      • Market Efficiency: The Efficient Market Hypothesis (EMH) argues that securities prices reflect all known information. As more and more skilled investors enter the market, and as technology makes informational edges more fleeting, it becomes increasingly difficult for any single participant to have a lasting information advantage. With fewer opportunities to exploit genuine mispricings, variations in performance owe more to short-term randomness.
      • Competitive Equilibrium: The concept of equilibrium in economic theory implies that profit opportunities are arbitraged away by skilled participants. If many intelligent players are hunting for alpha (excess returns above a benchmark), their collective actions often cancel one another out. In doing so, the distribution of returns converges, making any outperformance increasingly subtle and less attributable solely to skill.
      • Law of Large Numbers and Mean Reversion: Over time, statistical principles like mean reversion ensure that excessively high or low performance tends to move back towards the average. As skill levels rise and stabilize, individual performers find their results inching toward the mean. In this stable, more predictable environment, the small residual differences that remain are more easily chalked up to random fluctuations rather than meaningful distinctions in ability.

    Implications for Investors

    1. Professional Money Managers:
      For professional portfolio managers, the paradox of skill presents a conundrum. Decades of professional training, sophisticated analysis tools, and diligently followed investment processes still fail to guarantee outperformance. In fact, as the entire industry professionalizes, it collectively drives away easy arbitrage opportunities and mispriced assets, thereby shrinking the payoff for intensive research. This is one reason why an increasing number of professional investors find it difficult to beat simple benchmarks, such as a broad market index, over long horizons.
    2. Individual Investors:
      Many retail investors assume that by educating themselves, following the market more closely, or subscribing to premium research services, they can improve their odds of substantial outperformance. While financial literacy and disciplined investing practices are undeniably beneficial—especially for risk management and avoiding glaring mistakes—these improvements do not guarantee beating the market. As the professional sphere grows ever more sophisticated, and as information becomes abundant, the advantage of being simply “well-informed” diminishes. Therefore, even smart and well-prepared individual investors may see their fates influenced disproportionately by short-term randomness.
    3. Indexing and Passive Strategies:
      The paradox of skill offers a rational explanation for the rise of passive investment strategies such as index funds and ETFs. As skill differentials narrow, investors realize that paying high fees for active management that cannot reliably secure excess returns may be suboptimal. Passive investors accept average market returns and minimize costs, thus often outstripping the net performance of their more active but ultimately luck-constrained peers.

    Nuances and Counterarguments

    1. Skill Still Matters:
      It is critical not to misinterpret the paradox. The conclusion that as skill increases, luck becomes more important in determining outliers does not imply that skill is meaningless or that luck entirely governs outcomes. Over the very long run, consistently skillful investors can and do achieve superior risk-adjusted returns—Warren Buffett’s performance over decades provides a notable example. The paradox simply states that it is much more challenging to isolate and prove skill as the driving factor in any short to medium-term performance measurement because the competitive field has narrowed the skill gap.
    2. Different Markets, Different Conditions:
      Not all markets or asset classes are equally efficient. Some corners of the global market—like small-cap stocks, certain emerging markets, or specialized niches such as micro-credit or distressed debt—may still be less crowded with equally skilled participants. In these market segments, the paradox of skill might be less pronounced, and skilled investors might have a clearer advantage. Thus, an investor’s ability to find fertile ground for alpha generation may depend on choosing markets or strategies where the skill gap remains wide.
    3. Behavioral Considerations:
      While the paradox of skill primarily addresses technical and informational advantages, human behavior and psychological biases remain potent sources of exploitable inefficiencies. Even if all participants have similar levels of technical skill, some are better at maintaining emotional discipline, resisting herd mentality, or exploiting behavioral anomalies. Here, the “skill” may not lie purely in analytic prowess, but in behavioral mastery. Those who excel at understanding market psychology can still carve out meaningful edges, though as awareness of these behavioral edges grows, they too may become more limited.

    Mathematical and Statistical Perspectives

    From a mathematical standpoint, the paradox of skill often emerges from the interplay of variance, standard deviation, and the normal distribution of outcomes. When a large number of very skilled participants compete, their performance distribution is “tight.” A tight distribution means that the spread between top and bottom performers is relatively small. When spreads are small, random factors—market sentiment shifts, sudden economic news, regulatory changes—can have an outsized impact on who ends up “winning” in any given period. Over a large sample of observations, we might see that no single participant consistently outperforms without facing stretches of underperformance, making it statistically challenging to confirm a true skill edge.

    Strategic Takeaways and Adaptations

    1. Focus on Process Over Short-Term Outcomes:
      If outcomes become harder to distinguish from luck, a prudent response is to emphasize the robustness of one’s investment process rather than short-term performance. The paradox of skill suggests that a thoughtful, evidence-based, and risk-aware approach is more sustainable than chasing volatile market trends. Over long horizons, good processes can still add value, even if that value is subtle and only apparent in retrospect.
    2. Cost Management and Efficiency:
      Recognizing how fiercely competitive and skilled the marketplace has become, many investors double down on controlling what they can: costs, taxes, and risk exposure. Reducing fees and avoiding unnecessary complexity can improve net returns and mitigate the random shocks that come from luck-influenced outcomes.
    3. Niche Specialization and Innovation:
      If the broad equity market is too efficient, skillful investors might look elsewhere—towards complex derivatives, private markets, alternative credit structures, or frontier economies—where skill still has a clear advantage. This strategy relies on the insight that the paradox of skill is environment-specific, and that unique and less populated segments of the financial ecosystem might still reward superior acumen.
    4. Long-Term Horizons:
      Over short periods, luck can dominate. Over long periods, skill should have more opportunities to manifest. Investors who genuinely possess an edge may focus on patient, long-term strategies, letting the law of large numbers work in their favor. By lengthening their time horizon and reducing the emphasis on short-term swings, they increase the probability that true skill will eventually triumph over transient luck.

    Wrapping Up

    The paradox of skill in financial investing is a nuanced and thought-provoking concept that resonates deeply in today’s hyper-competitive markets. It underscores a crucial point: as collective skill rises, outperforming others becomes more about random breaks than the fundamental superiority of one’s methods. This does not diminish the value of skill or knowledge. Instead, it encourages investors, both professional and individual, to understand the limits of their advantages, to manage expectations more realistically, and to place a premium on disciplined, cost-effective, and long-term investment approaches. Ultimately, recognizing the paradox of skill can help market participants navigate a world where everyone is smart and well-informed, but luck still holds powerful sway.

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

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

    Intrinsic Value: The North Star of Investing

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

    Long-Term Orientation: The Antidote to Short-Termism

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

    Tuning Out Market Noise: The Path to Rationality

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

    Margin of Safety: The Investor’s Fortress

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

    Circle of Competence: Knowing Your Limits

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

    Temperament and Discipline: The Investor’s Emotional Rudder

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

    Prioritizing Loss Avoidance: The Foundation of Winning

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

    The Importance of Management: The Human Element

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

    Opportunistic Investing: Seizing the Right Moment

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

    Financial Strength and Conservatism: The Bedrock of Stability

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

    Skepticism of Forecasts: Embracing the Unknown

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

    Value Investing Philosophy: The Time-Tested Path

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

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

  • Warren Buffett and Charlie Munger on Index Funds

    In the world of investing, few names command as much respect as Warren Buffett and Charlie Munger. Their investment philosophy has been a guiding light for many, offering a blend of wisdom, simplicity, and practicality. Central to their approach is the endorsement of index funds, which they regard as a prudent choice for most individual investors. Let’s delve into their perspectives:

    Simplicity and Effectiveness

    Warren Buffett, known for his straightforward approach to investing, has long been an advocate of the simplicity and effectiveness of index funds. His recommendation for most individual investors, especially those who are not investment professionals, is to opt for a low-cost S&P 500 index fund. Buffett’s rationale is rooted in the difficulty of consistently outperforming the market. For the average investor, attempting to beat the market is often a futile endeavor fraught with unnecessary risks and costs.

    Cost Efficiency

    Both Buffett and Munger have been vocal critics of the hefty fees charged by many actively managed funds. They argue that these fees significantly diminish returns, contributing to the often lackluster performance of active funds compared to their benchmarks. In contrast, index funds are known for their low-cost structure, making them a more efficient choice for investors.

    Long-Term Investing

    The investment strategy espoused by Buffett and Munger emphasizes long-term thinking. This philosophy aligns perfectly with the nature of index funds, which are designed to mirror the performance of the broader market over extended periods. Such funds are less susceptible to the short-term volatility that can affect individual stocks, making them suitable for long-term investment strategies.

    Diversification

    A cornerstone of risk management in investing is diversification, and index funds excel in this area. By investing in a broad market index fund, one gains exposure to a diverse array of sectors and companies. This diversification minimizes the risks associated with single-stock investments and offers a more balanced portfolio.

    Passive Management

    Finally, the Buffett-Munger investment ethos criticizes excessive trading and speculation, favoring instead a passive, buy-and-hold approach. Index funds embody this philosophy, as they involve purchasing and holding a diversified portfolio that reflects the market index.

    Wrap Up

    In essence, the advocacy of Warren Buffett and Charlie Munger for index funds is a natural extension of their broader investment philosophy. They champion index funds for their simplicity, cost-efficiency, long-term growth potential, diversification benefits, and passive management style. For the average investor seeking a sensible, low-cost route to market returns, Buffett.