On Speculation

Meditations on a dirty word

— The Intelligent Investor (Chapter I), B.Graham

Gambling vs. Speculating

  1. There are two kinds of games in our universe: games where the odds are known and games where they are hidden.
  2. We know the exact odds at the casino table. You can figure it out with some math. Or…google.
  3. Playing with chance, “rolling the dice”, is not what makes you a gambler.
  4. Gambling is betting when these 3 things are true:
    a.) the odds are known,
    b.) the odds cannot be changed in your favor,
    c.) and — most importantly — those odds are not in your favor.
  5. Playing on the opposite side of a gambler is called being a business. The casino faces the same curtain of the unknown as you as the dice hurtle through the air.
  6. All a casino needs is a small advantage (i.e. 51% vs. your 49% ) to cross the line in the middle of the table — from “gambler” here, to “business” over there.
  7. You do not want to be a gambler. But if you can be a casino — by all means — roll dice for a living.
  8. Speculation, on the other hand, is betting in a game where the odds are hidden.
  9. In our everyday life, speculation is the game that the universe has forced us to play.

Be The Casino

  1. All games of probability have correct solutions.
  2. This is known as Expected Value. Multiply the prize by the odds of winning it. Multiply what you would lose by the odds of losing. Subtract the second from the first.
  3. If it’s positive, you have a positive expected outcome. You will know if you are the gambler or the businessman.
  4. Just because you made money on a bet doesn’t mean you made the correct bet. You should create space between the decision and the outcome and evaluate them independently.
  5. Of all things, this is the hardest — the mind revolts at this idea.
  6. The expected outcome of playing Lotto is to lose everything, anything, you bet. But it’s hard to tell the lotto winner he made the wrong decision when he bought his winning ticket.
  7. It bears repeating: in a game of probability, you can lose with a correct decision. And win with an incorrect one. But you should always bet the right way.
  8. Be careful of how you evaluate your decisions. Be the casino.


  1. Luck, then, is just the deviation from expected outcomes. However, in the end, time erodes good and bad luck. Time reveals the true expected outcome of the game. The gambler will not survive the waves of time, whereas the casino wants more of it.
  2. What are the expected outcomes of your decisions? Strive to be rational. Then prepare for luck. Be ready for deviations: seize moments of fortune when they do come. And protect your downside, always, so you can ride long into the future.

The Strange Case of the Lotto with Good Odds

  1. Low probability games are usually bad bets. Like Lotto and Powerball.
  2. However, a game can be both low probability and positive expected outcome at the same time.
  3. How? This can happen if the money at risk is very small, the prize is super high and if the odds to win are just high enough.
  4. It sounds like lotto — but it is worlds apart. The probability might be low, but the expected outcome is actually in your favor, unlike lotto. You crossed the thin line. The math worked.
  5. Imagine a game where you win mega-millions with a chance to win of 6%. A lotto with this setup would never exist in real life for obvious reasons, but if it did, then the advantage might actually be on your side — even though with a “94% chance of losing” it sure sounds like the odds are stacked against you.
  6. I would consider good venture bets to be of this nature: odds that sound “risky” — 1%, 5%, 10%…chance of winning, but have positive expected outcome in the end. (see: Black Swan Farming)
  7. This is especially true of contentious ideas — those good ideas that initially look like bad ones. The mainstream might dismiss a strange new idea completely; give it a 0% chance. But if you gain insight, the true odds could be “low…but high enough”. You wouldn’t go all in, but in these rare cases, a bet would be justified.
  8. To summarize: not all bets with big prizes are good. And not all bets with low odds are bad. Make sure to do the math!

A Game of Hidden Odds

  1. Games in which the odds are hidden can be tackled with the same strategies as games where the odds are known.
  2. Intelligent speculation then is making the same rational decisions, based on assumed odds. This is the art of speculation.****
  3. Still, the gambler is usually focused on possibility. Do the opposite: always bet on probability. Be on the side of positive expected outcome even if it’s based on assumed odds.
  4. Assumptions, about the odds, about how things are, are everything in this game. The calculation(logic) is easy. It’s the inputs that are hard.
  5. Logic is a sneaky trap, especially for thinkers. You can be lulled by the beauty of your own reasoning — which may be rock solid… except you started off with the wrong, many times unconscious, assumptions!
  6. Changes in starting assumptions are what start scientific revolutions. Paradigm shifts. They take time and usually involve a lot of resistance.
  7. Finding an incorrect assumption is like finding treasure — and the deeper, lower, and more widely accepted that incorrect assumption is, the bigger the reward.
  8. Investing is the art of finding incorrect assumptions. It is the art of finding opportunity by finding where you disagree with the world.
  9. Don’t just reason from first principles, challenge them too.

**** I view all forms of investing as speculation — even the most conservative kinds. I disagree with Graham slightly: I believe Value Investing is a form of grounded speculation, based on clear, common sense assumptions. As you have probably gathered, I do not attach any bad connotations to the word speculation by my personal definition.

The Aperiodic, Infinite Sequence

  1. What do we mean by “hidden” odds? At the casino table, you only need to assume one thing to be able to calculate the odds precisely: that the dice are fair.
  2. On the other hand, calculating the odds that “Company XYZ will meet earning estimates next year” requires assumptions about the decisions of management and competitors, the strength of foreign and domestic economies, the actions of the Fed, breakthroughs in technology…. a whole lot of assumptions that stack up.
  3. We can simplify the casino table as a “closed” system that needs very few assumptions — whereas a complex bet in the markets involves many, many assumptions that are hard to simplify (ex: free will). It is an “open” non-linear system: we can estimate the odds, but they will always be opinions, not mathematical truths. The odds will be hidden.
  4. Just because you have done your meticulous analysis on a stock, industry, economy … doesn’t mean you have left the realm of speculation. Unfortunately: you are still speculating. You may have felt the odds, but you will never truly see them.
  5. Imagine reaching into a bag of colored stones. You draw one stone. It’s red. 🔴 The next one…. White. ⚪️
  6. After drawing out a few, 🔴🔴🔴⚪️🔴🔴🔴⚪️🔴🔴🔴🔴…we could make some educated guesses about the odds of this bag. You might reason— after drawing out a lot of reds — that the bag probably contains mostly reds.
  7. After drawing out a hundred, a thousand, a million…of these stones, you might get very confident and bold in your analysis. But we will never know what the true distribution of the colors were inside the bag until the final stone is drawn. The final stone tells all.
  8. Now consider: time hides an eternity of “stones” in the dark…
  9. It is critical that you account for this immovable curtain. In a card game where expected outcome is on your side, you can simply protect yourself from (bad) luck by being well capitalized.
  10. But in a game of hidden odds, you must increase this moat and also protect yourself from being absolutely wrong about those odds in the first place.

Predictions vs. Forecasts

  1. Predictions sell. TV pundits earn their money from making confident calls. Tarot card readers, too. They sound bold, certain, authoritative. Like a true expert!
  2. Forecasts, on the other hand, are almost never 100% confident. They speak in probabilities. They sound uncertain. And they shift over time. Forecasts are what weather scientists do. Be a weather forecaster.
  3. It is not about how often you change your mind — but rather, why you do it.
  4. Time is like a fog: you can see the rough shapes ahead but the objects get clearer as you approach. Steer your ship accordingly. If you vigilantly look for information to change your mind and look at the right things however — paradoxically, you will likely find that you change your mind less.
  5. The price dropped 3 seconds ago. Should you sell? Now it is up. Should you buy? Did the above say something meaningful about the future? This is not to say that price itself cannot affect reality (see Reflexivity). But be clear about the causal chain behind your prediction.
  6. Couch and hedge your predictions with caveats. Be “wishy washy”.**
  7. Always say: “I predict X…but only if...” This does two things. First, it reveals the equation you are using. And second, it forces you to reveal your assumptions.***
  8. If you are aware of both your assumptions and your equations, then you can evaluate and improve them. Predicting without this is like writing down an answer to a math problem without showing the work. You learn nothing from a random answer, even if it happens to be correct. Show the work and let the world teach you.
  9. “He called AMZN’s 10X ten years ago, here’s what he’s saying now about XYZ!”… are qualifiers that should hold little weight. Do not invest by authority — never blindly copy, even from the most revered legends of your field. Listen, but decide via reasoning. Do your own work and see if you reach the same conclusions.
  10. Do not attach your calls about the future to your ego. It is not just a matter of humility, it is a matter of your survival!

** Howard Marks’ memos at Oaktree are a great example. Infuriating to read if you are looking for bold, clear predictions about the future. But sharp. I would recommend subscribing to his newsletter.

*** There is also the case for non-predictive approach to life. See Taleb’s Anti-fragile.

The Predictability of Hydrodynamic Flow

Broad Strokes and Truisms

  1. It is sometimes easier to predict what is bigger and far out in the future than something small, in the coming moment. The tides are easier to predict than the ripples.
  2. There are many things that change in this world. But it is more important to find what probably won’t, and then reason from that.
  3. To revisit and rephrase an earlier definition: Investing is the art of finding what is inevitable, but still contentious.
  4. There are things that people surprisingly continue to underestimate. The sheer magnitude of exponential growth. The value of intangible things vs. things you can touch.
  5. An example of a tide is the idea of “Bits vs. Atoms”, crystallized in the seminal 1995 book “Being Digital” by the founder of the MIT Media Lab, Nicholas Negroponte (and summarized brilliantly here). These are big, lasting changes that underly civilization. Note: like all things, this too can change, reverse, or die. But the tide moves slower, and the turns are easier to catch.
  6. Be careful of time tested “knowledge”. Many are still speculations in disguise and should be treated with the same caveats.
  7. For example, there is no law in physics that says the S&P500 will return 7% in the future.
  8. This is not to say that this is an unreasonable assumption to make. But be sure you know how we got to that piece of knowledge. And always be prepared when the assumptions or equations beneath it change.
  9. “Apples will continue to fall from trees in the future because it has always done so in the past” is different from saying “Apples fall because of a principle called gravity…”. It is a different kind of “knowing”.
  10. Both kinds of knowing are important but always seek to also learn the second kind. And always question how you “know”.*

*Induction is the art of forming assumptions based on prior experience. Deduction is the art of performing correct logic on top of those assumptions. As mere mortals, we need to perform both to make sense of the world.

circa 1956

The History of the Future

  1. When speculating about the future, you should to not just look at history: what happened at each point in time.
  2. You should also look at the “history of the future”: what people thought would happen next at each point in time.
  3. Our predictions form a parallel timeline to actual events. The “future”, as it exists in our heads, and how it emerges in culture, has an evolution, a trajectory and a pattern just like the real events themselves.
  4. It’s a good exercise read up on old breaking news articls and books that have met their expiry date. Books about the impending Y2K bug. Movies and Scifi written in the 50's about the very futuristic year 2010.
  5. It’s especially informative to look at how our past selves reacted to new technologies. Examples like this, this and my favorite this. Unlike forecasts being made today, we can evaluate these ways of thinking with full clarity thanks to the power of hindsight.
  6. It is tempting (and a bit fun) to laugh at older, bad predictions. Instead, recognize that we are in the same boat. Someday our movies, our books, and what is said on TV will be viewed in the same way. View them with humility: dissect the equations they used. Try and see which key assumptions they got wrong. Is there a pattern?
  7. You will begin to see differences in how people extrapolate into the future. Compare the consensus with the outliers. What did people like Jobs or Bezos ignore about the present? Try and see with their eyes as they stood at the edge. It’s ‘85 and nobody is using a mouse. It’s ‘95 and shopping over the internet is a pain. It’s 2017. And we are looking with 2017 eyes…
Seeing with 1995 eyes: “But there’s a difference!”. Note what Bill pays attention to vs. Letterman and the audience.

Jobs: The most compelling reason for most people to buy a computer for the home will be to link it into a nationwide communications network. We’re just in the beginning stages of what will be a truly remarkable breakthrough for most people — as remarkable as the telephone.

Playboy: Specifically, what kind of breakthrough are you talking about?

Jobs: I can only begin to speculate. We see that a lot in our industry: You don’t know exactly what’s going to result, but you know it’s something very big and very good.

1985 Playboy Interview: Steve Jobs

The Final word: All-in, usually isn’t

In a poker game, when you go “all-in”, you never actually are. “All-in”, in the truest sense, would mean selling the house and kids!

It’s possible to make bold bets and yet live to see another day. Companies need to make risky but smartly contained bets in order to survive (see Google X, Bell Labs, Loonshots and moonshots, and R&D in general…).

“When starting SpaceX I thought the odds of success were less than 10%, and I just accepted that I would probably just lose everything. But that maybe we would make some progress. If we could just move the ball forward, even if we died some other company could pick up the baton and keep moving it forward. So that would still do some good.”

The games we play are sub games, of sub games, of sub games… There is always one game larger. There will always be one bigger “why”. And in the largest game of all where the prizes are priceless, those crazy risks you take might not be crazy after all.

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