From How to Win and How to Lose (1883) arguably the first trend-based market player arrives: “The shrewdest operator ever known on the London Stock Board was David Ricardo (1772–1823) who amassed an enormous fortune. In advice to a friend he sums up as the true secret of his success, the rule, every word of which is golden. ‘Keep down your losses – never let them get away from you. Let your profits take care of themselves.’”23
That precept is huge. Timeless. If you were to put Ricardo into language of modern day computer science 134 years later you would say, optimal stopping or win-stay, lose-shift or A/B testing. More clarification from 1883 keeps the focus on taking a loss: “Speculation is looked upon as being so much more risky than other avocations cause its results are more sudden and startling, though not one whit more disastrous. Statistics show that ninety-five out of one hundred men fail in mercantile life. The proportion is not greater among speculators: quicker action is obtained whether it be favorable or unfavorable, and it does not take five or ten years’ time to find that you are playing a losing game.”24
No one is saying that attitude comes naturally. From The Art of Investing (1888): “Then, in theory, it is so easy to win by speculation! To buy at a low figure and sell at a higher, or to sell at a high figure and afterward buy at a lower, seems such a simple operation! It almost looks as if you could go into Wall Street and pick up money from the sidewalks.”25
Intense study, practice, is the rock solid foundation. From Gold Bricks of Speculation (1904):
Speculation is inherent in the human constitution, and men have a legal and moral right to speculate, provided they do so reasonably, intelligently and at their own risks. Reasonable speculation is such speculation as cannot seriously or permanently affect the resources or position of the persons indulging in it. Intelligent speculation is such speculation as is indulged in only after a thorough investigation and study of the subject of the speculation. The professional speculator is in the market not for the purpose of either depressing or raising prices. He is as ready to make money on a rise as on a fall in prices. In either case he will try to ascertain what the probable tendency of the market is before he embarks in any undertaking. No speculator or clique of speculators in their senses would undertake to try to depress prices in the face of a rising market.26
From Investments and Speculation (1911) it’s easy to see free-market capitalism and less government as optimal:
Call it what you will, speculation will always be with us. Prudes may frown upon it, superficial thinkers may confuse it with the commonest forms of gambling, and sociologists may dream of the day when envy, ambition and covetousness will be a thing of the past and the human race can exist in peace without these human traits, but their agitations and outcries can no more check speculation than human ingenuity can devise a scheme to control the tides. What the blood is to the human body, speculation is to business. It is absolutely a necessary part of it. The only difference, if there is at all a difference, is in the form it assumes. What would business be without incentive? In fact incentive is all there is at the bottom of speculation. Men are willing to take risks to acquire wealth. They are willing to stake their capital upon opportunities, which appeal to their judgment. From the pioneer who heedlessly plunges into a trackless waste to find a new home with greater opportunities for the acquisition of wealth, to the modern capitalist, who, to control the trade in a given commodity, plans gigantic trusts, is a long line of speculators, as speculation is behind all their ambitions. The inventor who is, apparently, of all men the least of speculators, takes greatest speculative chances, for he uses up time and energy to shape his ideas into some form where they can be of practical use and should he fail has wasted them utterly and lost all. Illustration after illustration could be given to demonstrate how speculation in a greater of less degree enters into the material welfare of each individual. Without speculation no business could progress. It is the dynamic power behind every incentive to activity and progress. It is the desire for gain, which prompts the inception of every venture. If it is all that, then it can be readily seen how necessary speculation is. In fact, speculation in its highest form has shaped the course of history and often changed the map of the world. Intelligent speculation is no crime. It is not gambling. It is merely pitting human shrewdness against the uncertainties of the future. For that matter, life itself is a speculation in which ministers, prudes and agitators hope to avoid sickness and accident and live their allotted span of life. Between speculation and gambling there is as much difference as there is between night and day. Speculation commands the exercise of the greatest measure of acumen, where gambling trusts everything to luck and the turn of a card. Experience has demonstrated far too convincingly that wherever speculation has been leashed by the iron bonds of the law, the effect has been almost an immediate stoppage in the material progress of the country.27
And finally from Psychology of the Stock Market (1912), one year before the Federal Reserve System was established, the behavioral school comes into focus:
The psychological aspects of speculation may be considered from two points of view, equally important. One question is: “What effect do varying mental attitudes of the public have upon the course of prices?” “How is the character of the market influenced by psychological conditions?” A second consideration is: “How does the mental attitude of the individual trader affect his chances of success?” To what extent, and how, can he overcome the obstacles placed in his pathway by his own hopes and fears, his timidities and his obstinacies?28
This wisdom is clean, clear, and instantly true for those awake. These days, however, speculation is often positioned as a pejorative among the intelligentsia.