STREET DOGS: Regrets and joys of speculating

From Henry Hamon’s New York Stock Exchange Manual (1865): “Great gains usually alternate with great losses in this kind of business. One would think that jobbers would soon die of worry and anxiety, and often enough they are seen to be very ‘down in the mouth’. But nature is kind, and fits the back to the burden.”

“These are the men whose sole business is stock speculation,” wrote William W Fowler. “When they have once entered the street, they never leave it except in a pine box or a rosewood case, according to circumstances. If they lose money, they stay there to regain it, and if they make money, they stay there to make more. Constitutionally, and by temperament, they are speculators. Hear them talk, and you would suppose they lived on hope … those saddest words of tongue or pen, ‘It might have been’, enter largely into the thoughts and conversation of the speculator. If and but are the most frequent conjunctions in his vocabulary. His whole life is a series of regrets, and strange to say, these regrets are more often for what he might have made, but did not, than for what he actually lost.”

As if to confirm it, in his book, The Education of a Speculator, Victor Niederhoffer wrote: “During my trading career involving many hundreds of billions of dollars and at least 5,000 separate days of entering the fray, I have not had one satisfactory day. When I make money, I always want to kick myself for not being more aggressive. On those all-too-frequent occasions when I lose a dollar, every dollar hurts. And no matter how certain a particular speculation looks, there is always a good likelihood that it will go astray. Frequently, things are not what they seem. A deal that seems too good to be true is likely not to be true.”