“Boy Wonder”, “Boy Plunger” and the “Great Bear of Wall St.” are a few of the monikers Jesse Livermore was known by.

Livermore was immortalized in the trading classic Reminiscences of a Stock Operator by Edwin Lefevre — a book your author has read countless times over the years and still pulls new wisdom from with each revisit.

Jesse Livermore Reminiscences of a Stock Operator

Reminiscences has stood the test of time because it, more than any other book, explains the fundamental truths that lie at the heart of successful speculation. It’s no doubt a reflection of Livermore’s deep and intimate understanding of this great game.

One of the ironies I’ve learned through years of dissecting the habits and practices of top traders like Livermore is that there is nothing special to what they do. I’m not implying that what they’re able to do isn’t impressive; of course it is. I simply mean that they have no special or secret knowledge or ability that’s unique to them.

[drizzle]Most people start out in this game looking for that “thing”; whether it be a special insight or indicator or strategy or whatever, that will show them how to win. They think if they can just find the secrets to what make the greats great, then they’ll be set. But in reality… if there’s any secret at all, it’s that there is no secret.

All of the important truths that a speculator needs to understand were plainly communicated by Jesse Livermore over 75 years ago.

Does that mean you can read Reminiscences… and instantly become a great trader? Well, let me ask you this: can you read the classic Ben Hogan’s Five Lessons on golf and go out and play scratch golf? Of course not! And that’s because both books have all the foundational knowledge you need to succeed but they don’t supply the practice that ingrains the lessons and transforms that knowledge into wisdom.

Here’s how Jesse Livermore put it, “The training of a stock trader is like a medical education. The physician has to spend long years learning anatomy, physiology, materia medica and collateral subjects by the dozen. He learns the theory and then proceeds to devote his life to the practice.”

The practice is the hard part. It takes time and a Herculean effort. Blisters and portfolio losses. There are no short-cuts. But practice without knowledge is wasted effort. It’s like trying to run on your hands because nobody ever told you to use your feet.

So with that, here’s the knowledge (with some commentary by me), as given by Livermore many years ago. What you do with it is up to you but I suggest you try running with your feet.

Jesse Livermore – Learn How to Lose

An old broker once said to me: ‘If I am walking along a railroad track and I see a train coming toward me at sixty miles an hour, do I keep on walking on the ties? Friend, I sidestep. And I do not even pat myself on the back for being so wise and prudent.’

To be a great trader you have to be a great loser. Sounds like a contradiction right? Well it isn’t. The fact is, great traders will typically have more losing trades than profitable ones. They’ll spend more time in an equity drawdown than at new highs. Some of this is due to the natural 90/10 distributions of markets (Pareto’s Law), but much of it is actually by design.

Mark Spitznagel wrote in The Dao of Capital that the most valuable lesson he learned from his Chicago trading pit mentor, Everett Klipp, was that “you’ve got to love to lose money.” If you love to take small losses then you’ll never take a large one. That’s important because it’s the large ones that’ll kill ya’.

Humans are naturally averse to losing (obvious statement). Our psychological programming attaches a lot of nonsensical meaning to taking losses in the market. We are evolutionarily wired to be bad emotional traders. The key is to invert this instinctual response and learn to “love to lose”. Jesse Livermore talks about this inversion:

Losing money is the least of my troubles. A loss never bothers me after I take it. I forget it overnight. But being wrong — not taking the loss — that is what does damage to the pocketbook and to the soul.

And here’s a simple and yet KEY… KEY fundamental truth to good trading: never add to your losers, sell what shows you a loss, and let run what shows you a profit.

Of all speculative blunders there are few worse than trying to average a losing game. My cotton deal proved it to the hilt a little later. Always sell what shows you a loss and keep what shows you a profit. That was so obviously the wise thing to do and was so well known to me that even now I marvel at myself for doing the reverse.

This lesson was important enough that Paul Tudor Jones had it plastered on the wall right above his desk.

Livermore’s occasional failure to follow this rule is what led to the multiple blowups he experienced throughout his career. He lost when he failed to follow his advice that it’s “foolhardy to make a second trade, if your first trade shows you a loss. Never average losses. Let this thought be written indelibly upon your mind.”

Jesse Livermore learned the hard way that our natural instincts must be flipped.

Instead of hoping he must fear and instead of fearing he must hope. He must fear that his loss may develop into a much bigger loss, and hope that his profit may become a big profit.

The Importance of Understanding General Conditions

I still had much to learn but I knew what to do. No more floundering, no more half-right methods. Tape reading was an important part of the game; so was beginning at the right time; so was sticking to your position. But my greatest discovery was that a man must study general conditions, to size them so as to be able to anticipate probabilities.

Not many people realize this, but Livermore was the original “global macro” guy. His “greatest discovery” was the importance of macro — or what he called “general conditions”.

He had the same realization that hedge fund manager Steve Cohen had decades later, which is “that 40 percent of a stock’s price movement is due to the market, 30 percent to the sector, and only 30 percent to the stock itself.”

After Livermore made this discovery he said “I began to think of basic conditions instead of individual stocks. I promoted myself to a higher grade in the hard school of speculation. It was a long and difficult step to take.”

This revelation completely changed the way he approached markets and trading. While everybody was piking around, losing money playing the “stock picking” game, Livermore was studying general conditions. He now understood the simple fundamental truth that you want to be long in a bull market and short in a bear market.

I think it was a long step forward in my trading education when I realized at last that when old Mr. Partridge kept on telling the other customers, ‘Well, you

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