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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

  • From Broke to Billions: Ray Dalio’s Raw Truths on Building an Empire

    Ray Dalio shares his journey from a $50 stock market bet at age 12 to building Bridgewater Associates into a $14 billion empire, revealing how failure, radical transparency, and the formula “Pain + Reflection = Progress” fueled his success, alongside tips for entrepreneurs on decision-making, team-building, and thriving through adversity.

    Ray Dalio—billionaire investor, founder of Bridgewater Associates, and the mastermind behind the world’s largest hedge fund—didn’t stumble into his $14 billion empire. He clawed his way there through brutal failures, radical transparency, and a relentless obsession with turning pain into progress. In a jaw-dropping episode of The Foundr Podcast hosted by Nathan Chan on February 28, 2025, Dalio pulls back the curtain on the gritty principles that transformed him from a kid with $50 in the stock market to a titan of finance. Spoiler: It’s not about luck—it’s about learning to “struggle well.”

    The Punch That Changed Everything

    Dalio’s story isn’t all polished suits and Wall Street swagger. It’s raw, messy, and real. Picture this: New Year’s Eve, a young Dalio, drunk and rambunctious, decks his boss at Shearson Hayden Stone. The next day, he’s out of a job. Most would call it a career-ending disaster. Dalio calls it the spark that lit Bridgewater’s fire. “That big punch in the face did me a lot of good,” he admits with a chuckle. From a two-bedroom apartment in 1975, with a rugby buddy and a dream, he built a hedge fund juggernaut managing hundreds of billions. But the real turning point? A colossal failure years later that nearly wiped him out.

    The $4,000 Lifeline and a Lesson in Humility

    Fast forward to 1982. Dalio’s riding high, predicting a debt crisis after Mexico’s default. He’s wrong—dead wrong. The Federal Reserve pumps money into the system, the stock market soars, and Dalio’s left with nothing. “I was so broke I had to borrow $4,000 from my dad to take care of my family,” he recalls. Clients ditch him. His team evaporates. Yet, in that gut punch of a moment, he finds gold: humility. “It made me think, ‘How do I know I’m right?’” That question became the bedrock of Bridgewater’s success—an “idea meritocracy” where the best ideas win, no matter who they come from.

    Pain + Reflection = Progress

    Dalio’s mantra isn’t just a catchy phrase—it’s a battle-tested formula. “Struggling in ideas and getting ahead in life is just like struggling in the gym. No pain, no gain,” he says. Take 1982: He could’ve sulked. Instead, he reflected, wrote down his lessons, and built a system to never repeat the mistake. That’s the essence of his iconic book Principles—a playbook of hard-won wisdom distilled over decades. “Every mistake is a puzzle,” he explains. “Solve it, and you get a gem—a principle for the future.” Entrepreneurs, take note: Success isn’t avoiding failure; it’s mastering it.

    Radical Transparency: The Secret Sauce

    Bridgewater’s culture isn’t for the faint-hearted. Radical truthfulness and transparency rule. Decisions are recorded, debated, and stress-tested by the sharpest minds—ego be damned. “The greatest tragedy of mankind is individuals attached to wrong opinions who don’t understand thoughtful disagreement,” Dalio warns. He’s seen it politically, socially, and in business. His antidote? Surround yourself with people who challenge you, not coddle you. It’s why he’s giving away tools like the PrinciplesYou personality test for free—because knowing your weaknesses and pairing them with others’ strengths is how empires are built.

    From Jungle Risks to Zen Productivity

    How does a guy who’s managed billions stay sane? Meditation, nature, and a love for the grind. “I saw life as a jungle,” Dalio says. “Stay safe, and it’s boring. Cross it, and you’ll get banged up—but that’s the adventure.” Burnout? He’s felt it, but transcendental meditation and a walk in the woods pull him back. Productivity? It’s not about working harder—it’s about leverage. With 25 direct reports, he turns one hour into 50 through trust and delegation. “You can increase your productivity 10 times,” he insists. “Cram more life into life.”

    The Next Chapter: Oceans, Giving, and Legacy

    At 75, Dalio’s not slowing down—he’s shifting gears. After stepping back from Bridgewater (46 years strong), he’s diving into ocean exploration with OceanX, uncovering the planet’s last frontier. He’s pouring wealth into philanthropy—education, healthcare, microfinance—because “meaningful relationships beat money every time.” And he’s watching the world with a historian’s eye, warning of debt cycles, wealth gaps, and superpower clashes echoing the 1930s. His advice? Study history. It’s all happened before.

    A Banger Takeaway for Founders

    Dalio’s final words to early-stage entrepreneurs hit like a freight train: “You’re on an arc. Build a team, a culture, a mission. Money’s great, but meaningful work with people you love—that’s the real payoff.” Grab his free Principles in Action app or hit principles.com for the tools that took him from zero to billions. Because if a kid who punched his boss and borrowed $4,000 from his dad can do it, so can you.

    Struggle well. Reflect. Win. That’s the Dalio way.

  • The Dhandho Investor: A Low-Risk Path to High Returns

    The Dhandho Investor: A Low-Risk Path to High Returns

    Mohnish Pabrai’s The Dhandho Investor offers a compelling and practical framework for building wealth through low-risk, high-return investments. Inspired by the entrepreneurial spirit of the Patel community and the investment wisdom of Warren Buffett and Charlie Munger, Pabrai distills principles that challenge traditional notions of risk and return. Here’s an in-depth look at the Dhandho philosophy and its application.

    The Dhandho Philosophy

    The Gujarati term “Dhandho” translates to “business” and signifies endeavors that create wealth with minimal risk. Pabrai flips the traditional idea that high returns require high risk. Instead, the Dhandho framework focuses on reducing downside risk while maximizing upside potential. It is a disciplined, pragmatic approach to investing and entrepreneurship.

    Nine Core Principles of the Dhandho Framework

    1. Buy Existing Businesses
      Avoid the risks of startups by acquiring or investing in established businesses with a proven track record and stable cash flows. In public markets, you can own fractions of such businesses without running them yourself.
    2. Invest in Simple, Predictable Businesses
      Simple businesses are easier to understand and analyze. Focus on industries with enduring demand and slow change, such as motels, consumer goods, or basic services.
    3. Target Distressed Businesses or Industries
      Look for businesses experiencing temporary setbacks or industries undergoing downturns. Distressed assets often sell at a significant discount, creating opportunities for outsized returns.
    4. Seek Durable Competitive Advantages (Moats)
      Invest in companies with lasting advantages, such as brand strength, cost leadership, or regulatory barriers. Durable moats ensure that a business can fend off competition and sustain profitability.
    5. Make Few, Big, Infrequent Bets
      Concentrated bets on high-conviction opportunities yield better returns than spreading investments thin. Use tools like the Kelly Criterion to determine optimal bet sizes.
    6. Exploit Arbitrage Opportunities
      Take advantage of price disparities or inefficiencies, such as undervalued stocks, geographic advantages, or business model quirks, to secure low-risk, high-reward outcomes.
    7. Ensure a Margin of Safety
      Purchase assets significantly below their intrinsic value. This cushion protects against downside risk even if things don’t go as planned.
    8. Embrace Low-Risk, High-Uncertainty Investments
      Investments with uncertain outcomes but limited downside risk often offer the best opportunities for substantial returns.
    9. Copy Proven Ideas Instead of Innovating
      Innovation can be risky. Copying successful models and adapting them reduces risk and increases the likelihood of success.

    Case Studies: Dhandho in Action

    The Patel Motel Model

    The Patel community in the U.S. demonstrated the Dhandho mindset by buying distressed motels, cutting costs with family labor, and reinvesting profits. This low-risk, high-return strategy helped them dominate the motel industry.

    Lakshmi Mittal and Steel Arbitrage

    Lakshmi Mittal turned a small steel mill into a global empire by buying distressed mills at steep discounts. His ability to streamline operations and scale created immense value from challenging industries.

    Warren Buffett’s Bet on American Express

    In the 1960s, Buffett invested 40% of his portfolio in American Express during the “salad oil scandal,” when its stock was halved. He recognized that its core business was unaffected and reaped significant returns when the market corrected.

    Richard Branson’s Virgin Empire

    Branson’s ventures, like Virgin Atlantic, exemplify creative arbitrage. By leasing planes and leveraging partnerships, he minimized downside risk while capitalizing on unmet market needs.

    Applying the Dhandho Framework to Investing

    Intrinsic Value and Margin of Safety

    Estimate the intrinsic value of a business using discounted cash flow (DCF) analysis. Only invest when the stock trades at a significant discount to this value, ensuring a margin of safety.

    Finding Opportunities

    Identify distressed businesses or industries through:

    • News and market reports.
    • Value-focused investor filings (e.g., Warren Buffett, Seth Klarman).
    • Resources like Value Investors Club or Joel Greenblatt’s Magic Formula Investing.

    Portfolio Management

    Maintain a concentrated portfolio of a few high-conviction bets. This approach mitigates dilution of returns and allows for meaningful gains when bets succeed.

    Mindset for Dhandho Investing

    1. Think Probabilistically
      Treat investing like betting on favorable odds. Use probabilities to assess risks and returns, ensuring that potential upside far outweighs downside.
    2. Be Patient and Disciplined
      Wait for rare opportunities where the odds are overwhelmingly in your favor. Avoid emotional reactions to market fluctuations.
    3. Focus on Simplicity
      Stick to businesses you can fully understand. Complexity increases the likelihood of mistakes.

    Closing Wisdom: The Dhandho Edge

    The Dhandho framework is a powerful tool for building wealth by minimizing risk while maximizing returns. By focusing on undervalued assets, leveraging durable competitive advantages, and exercising patience and discipline, investors can achieve outsized success. As Pabrai emphasizes, the key lies in embracing simplicity, reducing risk, and acting decisively when opportunities arise.

    The Dhandho Investor offers not just a roadmap for investing but also a philosophy for navigating uncertainty in business and life. Its timeless lessons resonate for anyone seeking to grow wealth sustainably and wisely.

    The Dhandho Investor: A Low-Risk Path to High Returns

    Mohnish Pabrai’s The Dhandho Investor offers a compelling and practical framework for building wealth through low-risk, high-return investments. Inspired by the entrepreneurial spirit of the Patel community and the investment wisdom of Warren Buffett and Charlie Munger, Pabrai distills principles that challenge traditional notions of risk and return. Here’s an in-depth look at the Dhandho philosophy and its application.

    The Dhandho Philosophy

    The Gujarati term “Dhandho” translates to “business” and signifies endeavors that create wealth with minimal risk. Pabrai flips the traditional idea that high returns require high risk. Instead, the Dhandho framework focuses on reducing downside risk while maximizing upside potential. It is a disciplined, pragmatic approach to investing and entrepreneurship.

    Nine Core Principles of the Dhandho Framework

    1. Buy Existing Businesses
      Avoid the risks of startups by acquiring or investing in established businesses with a proven track record and stable cash flows. In public markets, you can own fractions of such businesses without running them yourself.
    2. Invest in Simple, Predictable Businesses
      Simple businesses are easier to understand and analyze. Focus on industries with enduring demand and slow change, such as motels, consumer goods, or basic services.
    3. Target Distressed Businesses or Industries
      Look for businesses experiencing temporary setbacks or industries undergoing downturns. Distressed assets often sell at a significant discount, creating opportunities for outsized returns.
    4. Seek Durable Competitive Advantages (Moats)
      Invest in companies with lasting advantages, such as brand strength, cost leadership, or regulatory barriers. Durable moats ensure that a business can fend off competition and sustain profitability.
    5. Make Few, Big, Infrequent Bets
      Concentrated bets on high-conviction opportunities yield better returns than spreading investments thin. Use tools like the Kelly Criterion to determine optimal bet sizes.
    6. Exploit Arbitrage Opportunities
      Take advantage of price disparities or inefficiencies, such as undervalued stocks, geographic advantages, or business model quirks, to secure low-risk, high-reward outcomes.
    7. Ensure a Margin of Safety
      Purchase assets significantly below their intrinsic value. This cushion protects against downside risk even if things don’t go as planned.
    8. Embrace Low-Risk, High-Uncertainty Investments
      Investments with uncertain outcomes but limited downside risk often offer the best opportunities for substantial returns.
    9. Copy Proven Ideas Instead of Innovating
      Innovation can be risky. Copying successful models and adapting them reduces risk and increases the likelihood of success.

    Case Studies: Dhandho in Action

    The Patel Motel Model

    The Patel community in the U.S. demonstrated the Dhandho mindset by buying distressed motels, cutting costs with family labor, and reinvesting profits. This low-risk, high-return strategy helped them dominate the motel industry.

    Lakshmi Mittal and Steel Arbitrage

    Lakshmi Mittal turned a small steel mill into a global empire by buying distressed mills at steep discounts. His ability to streamline operations and scale created immense value from challenging industries.

    Warren Buffett’s Bet on American Express

    In the 1960s, Buffett invested 40% of his portfolio in American Express during the “salad oil scandal,” when its stock was halved. He recognized that its core business was unaffected and reaped significant returns when the market corrected.

    Richard Branson’s Virgin Empire

    Branson’s ventures, like Virgin Atlantic, exemplify creative arbitrage. By leasing planes and leveraging partnerships, he minimized downside risk while capitalizing on unmet market needs.

    Applying the Dhandho Framework to Investing

    Intrinsic Value and Margin of Safety

    Estimate the intrinsic value of a business using discounted cash flow (DCF) analysis. Only invest when the stock trades at a significant discount to this value, ensuring a margin of safety.

    Finding Opportunities

    Identify distressed businesses or industries through:

    • News and market reports.
    • Value-focused investor filings (e.g., Warren Buffett, Seth Klarman).
    • Resources like Value Investors Club or Joel Greenblatt’s Magic Formula Investing.

    Portfolio Management

    Maintain a concentrated portfolio of a few high-conviction bets. This approach mitigates dilution of returns and allows for meaningful gains when bets succeed.

    Mindset for Dhandho Investing

    1. Think Probabilistically
      Treat investing like betting on favorable odds. Use probabilities to assess risks and returns, ensuring that potential upside far outweighs downside.
    2. Be Patient and Disciplined
      Wait for rare opportunities where the odds are overwhelmingly in your favor. Avoid emotional reactions to market fluctuations.
    3. Focus on Simplicity
      Stick to businesses you can fully understand. Complexity increases the likelihood of mistakes.

    Closing Wisdom: The Dhandho Edge

    The Dhandho framework is a powerful tool for building wealth by minimizing risk while maximizing returns. By focusing on undervalued assets, leveraging durable competitive advantages, and exercising patience and discipline, investors can achieve outsized success. As Pabrai emphasizes, the key lies in embracing simplicity, reducing risk, and acting decisively when opportunities arise.

    The Dhandho Investor offers not just a roadmap for investing but also a philosophy for navigating uncertainty in business and life. Its timeless lessons resonate for anyone seeking to grow wealth sustainably and wisely.

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

    Diverging Paths: Marks and Buffett's Contrasting Investment Philosophies

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

    Risk Management

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

    Investment Philosophy

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

    Investment Universe

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

    Communication Style

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

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

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

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

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

    Intrinsic Value: The North Star of Investing

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

    Long-Term Orientation: The Antidote to Short-Termism

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

    Tuning Out Market Noise: The Path to Rationality

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

    Margin of Safety: The Investor’s Fortress

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

    Circle of Competence: Knowing Your Limits

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

    Temperament and Discipline: The Investor’s Emotional Rudder

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

    Prioritizing Loss Avoidance: The Foundation of Winning

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

    The Importance of Management: The Human Element

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

    Opportunistic Investing: Seizing the Right Moment

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

    Financial Strength and Conservatism: The Bedrock of Stability

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

    Skepticism of Forecasts: Embracing the Unknown

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

    Value Investing Philosophy: The Time-Tested Path

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

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

  • Planning for Sequence of Return Risk

    Planning for Sequence of Return Risk

    Sequence of return risk is an important factor to consider when planning for retirement. It is the risk of a downturn in the stock market or other investments at the beginning of your retirement. This can result in a lower-than-expected return on investment, which can make it difficult to meet your retirement goals.

    Fortunately, there are strategies you can use to mitigate sequence of return risk. The most important is to start saving early in life. This provides more time for your investments to compound and helps minimize the chances of a downturn occurring in the first few years of your retirement.

    Another important strategy is to diversify your investments. This means having a mix of stocks, bonds, and other investments in your portfolio. Having a mix of investments reduces the risk associated with any one type of investment, and can help minimize the effects of a downturn in the stock market.

    Additionally, you should consider investing in annuities. Annuities are a type of insurance that provide a guaranteed income in retirement, regardless of market conditions. This can provide a measure of security, as it ensures that you’ll have a steady income stream even if the stock market takes a downturn.

    It’s important to stay informed about current market conditions. This helps you stay aware of potential threats to your retirement income and gives you the opportunity to make adjustments to your portfolio if necessary.

    By taking these steps, you can plan for sequence of return risk and ensure that your retirement savings will last for many years to come.

  • 50 Ways to Grow Your Wealth and Minimize Risk

    1. Understand personal finance and investing inside and out.
    2. Create a financial plan with specific goals.
    3. Save and invest a significant amount of your income.
    4. Diversify your investments to spread out risk.
    5. Educate yourself about different investment opportunities and pick those that align with your goals and risk tolerance.
    6. Take calculated risks when it makes sense.
    7. Stay disciplined and avoid emotional or impulsive decision making.
    8. Monitor and review your investments regularly.
    9. Consider getting professional advice from a financial advisor or planner.
    10. Be patient and consistent in pursuing your financial goals.
    11. Start or invest in a business.
    12. Take advantage of tax-advantaged investment opportunities.
    13. Get more education or training to increase your earning potential.
    14. Cut unnecessary expenses and prioritize spending on things that will help you achieve your goals.
    15. Develop a strong work ethic and focus on constantly improving in your career.
    16. Network and build relationships with successful and influential people.
    17. Stay up to date on market trends and developments.
    18. Explore alternative investment opportunities, such as real estate, commodities, or collectibles.
    19. Use leverage, such as borrowing money or using options, cautiously and with a clear understanding of the potential risks and rewards.
    20. Develop and maintain a positive attitude and mindset.
    21. Take care of your health and well-being to ensure that you can continue working towards your goals.
    22. Stay organized and keep track of your finances.
    23. Use technology and tools to help manage your finances and investments.
    24. Develop strong communication and negotiation skills.
    25. Find mentors who can provide guidance and support.
    26. Learn from your mistakes and adapt your approach as needed.
    27. Stay focused and avoid distractions.
    28. Be persistent and don’t give up in the face of challenges or setbacks.
    29. Invest in yourself, such as through personal development or additional education.
    30. Thoroughly research and evaluate investment opportunities before making a decision.
    31. Don’t put all your eggs in one basket; diversify across different asset classes and industries.
    32. Be aware of and avoid investment scams and other fraudulent activities.
    33. Don’t let fear or greed guide your investment decisions.
    34. Use stop-loss orders to minimize potential losses on your investments.
    35. Consider the long-term potential of an investment, rather than just focusing on short-term gains.
    36. Be willing to take a calculated risk in order to potentially earn higher returns.
    37. Be proactive and take action to achieve your goals, rather than waiting for opportunities to come to you.
    38. Invest in undervalued assets that have the potential for long-term growth.
    39. Don’t be afraid to ask for help or advice when you need it.
    40. Educate yourself about the risks and rewards of different investment strategies.
    41. Keep a close eye on the market and be prepared to make changes to your investment portfolio as needed.
    42. Don’t be afraid to take a break and reassess your strategy if you’re not seeing the results you want.
    43. Invest in assets that provide a steady stream of income, such as rental properties or dividend-paying stocks.
    44. Be open to new ideas and approaches, and be willing to try new things.
    45. Don’t be afraid to cut your losses if an investment isn’t performing as expected.
    46. Be willing to take on some level of risk in order to potentially maximize returns.
    47. Seek out new opportunities and take on new challenges.
    48. Be proactive in managing and reducing your debt.
    49. Adapt to changes in the market and in your personal circumstances.
    50. Continuously educate yourself and stay up to date on the latest developments in the world of finance and investing.