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Welcome to Long Game Trading. I'm William Truit. Today we're exploring the personalities, unconventional ideas, and achievements of some of the most intriguing characters in financial history. The art of trading. Extraordinary people, extraordinary stories, a universe of possibilities. One thing that draws me to trading is the sheer number of ways people approach it.
Even after years of studying the markets and learning from successful traders, I still find approaches I've never considered. In some ways, it reminds me of the universe itself. Our galaxy contains hundreds of billions of stars. Beyond it lie billions of other galaxies, each holding mysteries we may never fully understand.
And every new discovery seems to reveal an even greater world waiting to be explored. That's what the world of trading feels like to me. Every approach opens another door. A strategy that makes perfect sense to one trader might be almost unrecognizable to another. And just when you think you understand how markets work, someone comes along with an entirely different way of looking at them.
There are traders who rely on sophisticated mathematical models and computers capable of analyzing large amounts of data. Others study human psychology, economic cycles, or the relationships between currencies and commodities. Some make hundreds of trades in a single day, while others patiently wait weeks or months for an opportunity worth pursuing.
But what interests me most isn't the technology, the strategies, or even the sums of money that sometimes change hands. It's the people, the personalities who have devoted their lives to understanding markets, often approaching the same problems from completely different directions. Some are brilliant mathematicians.
Others are instinctive speculators, independent thinkers, or unconventional characters whose lives could fill the pages of an adventure novel. Their stories are filled with major successes, painful failures, unexpected discoveries, and ideas that sometimes seem to contradict one another. I've spent years exploring different corners of this world.
From day trading and swing trading to options, futures, currencies, and automated systems. Along the way, I've discovered that my fascination with trading goes far beyond the possibility of making money. I love learning how these people think, what drives them, and how they develop their own ways of navigating the markets.
And much like the universe itself, the more I discover, the more I realize how much there is still left to explore. Trading is an art, not a single formula. Imagine putting 10 accomplished traders in a room and asking each of them to explain the secret of their success. You might get 10 completely different answers.
And what's interesting is that some of those answers might directly contradict one another. One trader might insist that predicting market direction is a waste of time, while another has built a successful career doing precisely that. Both could present convincing evidence that their approach works.
So, who's right? Perhaps both of them. That's part of what makes trading such an intriguing pursuit. There's no universally accepted formula for success, no single personality ideally suited to the profession, and certainly no shortage of people convinced they've figured it all out. Of course, the markets don't reward creativity simply for being creative.
An imaginative theory is worthless if it consistently loses money. Mathematics, probability, research, and risk management all have their place. But the art lies in how individuals bring these elements together. A trading method that works beautifully for one person might be disastrous for another. The difference isn't necessarily intelligence or dedication.
It may come down to temperament, patience, emotional resilience, or simply how someone sees the world. And perhaps that's what interests me most. Behind every successful trading career is a human being who somehow found a way to make sense of a complicated environment. Their methods may be fascinating, but the stories of how they developed those methods can be even better.
Some of those stories are so unusual that if they appeared in a novel, you might question whether the author had gone a little too far. Fortunately, they're real. Bill Lipshitz, the man who couldn't stop watching the markets. Imagine visiting someone's apartment and discovering that nearly every room contains a screen displaying live financial market prices.
There's one in the living room, another in the kitchen, one in the office, and another beside the bed so its owner can check currency prices in the middle of the night. And yes, there's even one in the bathroom, conveniently positioned at standing height. Welcome to the world of Bill Lipshitz. When author Jack Schwagger visited Lipshitz's apartment to interview him for the New Market Wizards, he discovered a man whose fascination with currency trading had become inseparable from his everyday life.
Lipshutz wasn't simply a hobbyist who enjoyed watching the markets. During the 1980s, he had become one of the most successful currency traders at Solomon Brothers, helping transform the firm's foreign exchange operation into a major force in global currency trading. But perhaps the most surprising thing about Lipshitz is how he got there.
He originally studied architecture at Cornell University. His introduction to serious trading came when his grandmother died and left him a portfolio of stocks worth approximately $12,000. Rather than pursuing a career designing buildings, he became increasingly absorbed in the financial markets. He studied companies, read financial publications, and spent countless hours watching stock prices.
Over roughly four to five years, he turned that original $12,000 into approximately $250,000. An impressive result for a young man still finding his way in the markets. Then in a matter of days, he lost virtually all of it. He had become convinced that the stock market was headed lower and accumulated a heavily leveraged position in put options.
When the market suddenly reversed, the account he'd spent years building was almost completely wiped out. For many people, that experience might have ended their trading ambitions. For Lipshutz, it became part of his education. By then, he had already joined Salomon Brothers, where he would go on to develop a successful career trading currencies.
His success wasn't built on an ability to predict every market movement. He understood the importance of relationships, liquidity, judgment, and recognizing when his own assumptions were wrong. And through it all, he remained utterly captivated by the markets. Schwagger also described Lipshutz as relaxed during their interviews.
Despite the monitors, the constant flow of information, and the large positions he sometimes managed, he didn't come across as a man overwhelmed by the activity surrounding him. He seemed completely at home in it. When Schweagger asked whether trading was still enjoyable after consuming so much of his life, Lipshutz's enthusiasm was unmistakable.
He described it as tremendous fun and said he would happily do it even without being paid. Here was a man operating at the highest levels of international currency trading, handling sums of money most of us can barely imagine. Yet his greatest enthusiasm seemed to come from the experience itself. I can't imagine wanting a market monitor in my bathroom, but I can certainly appreciate the fascination that would make someone put one there.
That combination of skill and sheer enjoyment is what makes Lipshutz memorable. For him, trading wasn't merely a profession or a means of accumulating wealth. It was an endlessly engaging pursuit that had captured his imagination, even when he was brushing his teeth. Jim Rogers, the investor who saw the whole world as an opportunity.
I just wait until there is money lying in the corner and all I have to do is go over there and pick it up. Of all the memorable observations I've encountered from legendary traders, that one from Jim Rogers has stayed with me more than almost any other. It sounds simple. Don't chase the markets. Don't feel compelled to trade every day.
Wait until an opportunity becomes so compelling that you can hardly imagine passing it up. Of course, recognizing those opportunities is considerably more difficult than Rogers makes it sound. But that philosophy helped shape one of the most successful investment careers on Wall Street. In 1973, Rogers joined forces with George Soros to establish the Quantum Fund, which went on to produce strong returns during the following decade.
What made Rogers unusual was the breadth of his thinking. He wasn't interested in finding a promising stock simply because its chart looked attractive. He wanted to understand the economic forces that could make an entire industry, commodity, currency, or country dramatically more valuable or less valuable over time.
His approach was fundamentally driven and often contrarian. Rogers studied supply and demand, government policies, political developments, and long-term economic trends. He looked for situations where the prevailing market price seemed completely disconnected from the underlying reality. If everyone was convinced an investment was worthless, he wanted to understand why.
If an asset had become wildly popular, he wanted to know whether the enthusiasm was justified. And he was perfectly willing to take the opposite side of a popular trade when his research convinced him the crowd had it wrong. Consider his approach to commodities. Rather than trying to predict tomorrow's price movement from a chart, Rogers might investigate whether years of low prices had discouraged production, whether inventories were shrinking, or whether rising demand was creating a shortage that the market hadn't yet recognized.
If the evidence was compelling and the price was attractive, he could establish a position and wait for the economic reality to become reflected in the market. Sometimes that meant holding investments for years. And sometimes it meant doing absolutely nothing. That last part is what I find especially appealing.
Rogers understood that the markets don't owe us a good opportunity every morning. He wasn't interested in trading simply for the satisfaction of being involved. In fact, he has often described himself as a poor short-term trader despite his success as an investor. Imagine that. A man who helped build one of the most successful investment funds of its era.
Openly acknowledging that short-term market timing wasn't his strength. Instead of trying to become good at everything, he concentrated on what he understood. There's another side to Rogers's personality that makes his story even more interesting. After retiring from active fund management at just 37, he decided to explore the world he'd spent so many years studying.
In 1990, he set off on a motorcycle journey that eventually took him across six continents and covered approximately 65,000 m. He wasn't simply looking for adventure. He wanted to see economies firsthand, talk to people, visit local markets, and understand how the world worked beyond the financial reports and economic statistics.
He later embarked on another journey, traveling through 116 countries in a specially modified Mercedes convertible. Those adventures eventually became books, including Investment Biker and Adventure Capitalist. I'm drawn to Rogers because his investment philosophy and his adventurous personality seem to come from the same source, an almost insatiable curiosity about how the world works.
He was willing to spend years investigating an opportunity, years waiting for it to develop, and then years traveling the world to see things for himself. And through it all, he demonstrated something that runs counter to the popular image of a successful trader. Sometimes the most profitable thing you can do is absolutely nothing.
Just wait for that pile of money in the corner. Ed Sakakota, the man who taught computers to trade. In the early 1970s, when most traders were still studying charts drawn on paper and placing orders by telephone, a young engineer named Ed Sakakota was doing something almost unheard of. He was teaching computers how to trade.
And we're not talking about the powerful desktop computers we take for granted today. Sakoto was working with room-sized mainframe computers using punched cards to test trading strategies against historical market prices. At a time when computer technology was still unfamiliar territory for much of Wall Street, he was exploring an idea that would eventually transform the financial markets.
What if a computer could identify profitable trading opportunities by following a consistent set of rules without being influenced by fear, greed, or the latest financial headlines. Sakakota had studied electrical engineering and management at MIT, but his interest in trading began with a frustrating experience in the silver market.
He believed silver prices should rise following a change in US government policy. The reasoning seemed perfectly sound by seeing silver went down. The experience left him questioning something fundamental. If the economic news was so favorable, why wasn't the market behaving as expected? Around that time, he encountered the work of Richard Donian, an early pioneer of systematic trend following.
Donian's research suggested that traders might profit by following established price trends rather than attempting to predict what markets should do next. Sakakota was intrigued enough to test the idea himself. He gained access to a brokerage firm's IBM mainframe computer on weekends and began running historical simulations of trading systems.
The results convinced him that relatively simple rules applied consistently could provide a profitable approach to the futures markets. He eventually developed one of the earliest commercial computerized trading systems for managing client money. But Sakoto wasn't trying to create a machine that could predict the future.
His approach was based on following trends, controlling losses, and allowing profitable positions room to develop. When a market moved in his favor, he wanted to participate. When it moved against him, he wanted to get out before a manageable loss became a disaster. The simplicity of that philosophy makes his results all the more astonishing.
In his original Market Wizards interview, Jack Schwagger reported that one account Sakakota managed had grown from an initial $5,000 in 1972 to more than $12.5 million in cumulative profits by mid 1988, even after substantial withdrawals. And he achieved those results without a trading floor full of analysts or an army of employees.
Yet, there's a fascinating contradiction in Sakakota's story. For someone who helped pioneer mechanical trading systems, he became deeply interested in the emotional and psychological forces that influence traders. He recognized that developing a profitable system was only part of the challenge. The person operating it still had to live with the consequences.
Imagine following a system that has just produced six losing trades in a row. The next signal appears and every instinct tells you to ignore it. Perhaps the system has stopped working. Perhaps you should wait for a little more confirmation. Or imagine holding a profitable position while watching thousands of dollars in unrealized gains disappear during a temporary pullback.
A computer doesn't experience anxiety or regret. The person responsible for the account certainly might. Sakakota came to believe that understanding those emotional responses was essential to long-term trading success. His interest eventually led him to develop the trading tribe, a community focused on exploring emotions, personal behavior, and the psychological challenges of trading.
And then there's his unconventional personality. Sakakota even recorded a humorous musical performance called the whipssaw song using music to communicate his trading principles. It's not every day you encounter a legendary futures trader who also sings about cutting losses and following trends. What interests me most about Sakakota is that he approached trading from two seemingly opposite directions.
He used mathematics and computers to remove emotional decisionmaking from the trading process, yet devoted considerable attention to understanding the emotions of the people making those decisions. Perhaps he recognized something that remains true regardless of how sophisticated our technology becomes.
You can program a computer to follow trading rules. Getting a human being to follow them is another matter entirely. Richard Dennis, the trader who believed great traders could be made. Picture a teenage boy standing at the edge of a crowded Chicago commodities exchange, watching traders shout orders and wave their arms in a frantic competition to buy and sell futures contracts.
The boy desperately wants to join them. There's just one problem. He's too young. In the late 1960s, Richard Dennis was only 17 years old, and exchange rules required traders to be at least 21. But Dennis wasn't about to let a technicality keep him from the markets. He persuaded his father, a Chicago city employee, to enter the trading pit on his behalf.
Young Richard would communicate his trading instructions from the sidelines while his father executed the orders. Imagine being that father taking trading instructions from your teenage son while surrounded by professional commodity traders. And what's interesting is that the boy would eventually become one of the most successful traders in the history of the Chicago futures markets.
Dennis didn't come from a wealthy Wall Street family. He grew up on Chicago's Southside and began working as a runner at the Chicago Merkantile Exchange, earning just $160 an hour. He was fascinated by the markets, but his early trading education wasn't exactly painless. He made plenty of mistakes and suffered losses that might have discouraged someone with less determination.
In 1970, he borrowed $1,600 from his family, spent $1,200 purchasing a seat at the Mid America Commodity Exchange, and began trading with the remaining $400. Within a few years, that modest stake had grown into a substantial fortune. By his mid20s, Dennis was a millionaire, and his success would eventually earn him the nickname Prince of the Pit.
His trading philosophy was based on an idea that sounds almost too simple to be effective. Follow the trend. Dennis wasn't focused on predicting what a commodity should be worth based on economic forecasts. He believed that price movements themselves could reveal opportunities. When a market broke out of an established trading range and began moving strongly in one direction, he wanted to participate.
If the move continued, he stayed with it. If the market reversed, he accepted the loss and moved on. He understood that many trades would fail, but a relatively small number of powerful trends could produce enough profits to more than compensate for those losses. It required patience, discipline, and a willingness to be wrong repeatedly without abandoning the approach.
and Dennis became convinced that these abilities could be learned. His friend and fellow trader William Eckhart disagreed. Ehart believed that exceptional trading success depended on natural ability while Dennis argued that the necessary skills could be taught. Eventually, Dennis proposed an experiment to settle the argument.
In 1983, he began recruiting aspiring traders through newspaper advertisements. Applicants came from a wide variety of backgrounds, and many had little or no professional trading experience. Dennis and Ehart taught the recruits a systematic approach to futures trading, including rules for entering positions, exiting trades, managing risk, and determining position sizes.
After a brief training period, Dennis gave them real money to trade. He called them the turtles, reportedly inspired by a visit to a turtle breeding operation in Singapore, where he joked that traders could be grown in much the same way. The results gave Dennis plenty to talk about. Several turtles went on to become highly successful traders, demonstrating that people without years of professional market experience could learn and apply a systematic trading approach.
Not every participant achieved the same results, and Dennis himself would later experience substantial trading losses. His career was hardly an uninterrupted march toward greater wealth. But that's part of what makes his story so compelling. Richard Dennis began as a teenager who wasn't even old enough to enter the trading pit as a trader, persuaded his father to execute orders on his behalf, and eventually accumulated a fortune in the very markets he once watched from the sidelines.
Then, having achieved success himself, he set out to prove that other people could learn to do it, too. And some of them did. Jack Schwagger, the man who introduced us to the Wizards. Imagine being able to sit down with some of the world's most successful traders and ask them just about anything. How did you get started?
What was your biggest mistake? What separates a great trader from an average one? And perhaps most interesting of all, what goes through your mind when millions of dollars are at stake? That's essentially what Jack Schwagger set out to do. And in 1989, he published a book that would become one of the most celebrated works in trading literature, Market Wizards.
Schwagger was already an experienced market analyst and author. But he had become fascinated by a question that couldn't be answered simply by studying price charts or economic reports. What made exceptional traders exceptional? He began interviewing people who had achieved strong results in the financial markets.
Some were futures traders. Others specialized in stocks, currencies, or entirely different approaches to speculation. Among the people he interviewed were Ed Sakakota, Richard Dennis, and Bill Lipchitz, whose stories we've just explored. But Schwagger wasn't simply collecting success stories. He wanted to understand how these people thought, how they handled losing money, how they developed their methods, and what their experiences could teach the rest of us.
And he knew how to ask questions that brought out the person behind the trading record. Rather than trying to reconcile their conflicting ideas into a single formula, Schwagger let each trader tell the story in his own way. The result was a collection of conversations as revealing about human nature as they were about financial markets.
That's what makes the book so enjoyable. You aren't just learning about trading strategies. You're meeting the people who developed them. Schwagger went on to publish the new market wizards, stock market wizards, hedge fund market wizards, and unknown market wizards, continuing his exploration of exceptional traders across different generations and markets.
If you've never read the market wizards books, I can't recommend them highly enough. They're books I would suggest to anyone interested in trading, regardless of whether they ever intend to place a trade. Not because they'll hand you a guaranteed formula for making money, but because they'll introduce you to some interesting people and give you a glimpse into the way they see the world.
And once you've met a few of these characters, you may find yourself wanting to meet a few more. A lifetime of discovery. What stays with me about Jack Schwagger isn't only what he learned from the traders he interviewed. It's how much he seems to enjoy learning it. You can hear that enthusiasm in his interviews and speaking engagements.
His excitement about the markets and the people in them is contagious. I remember watching him speak and being struck by how much he reminded me of my father. Not because they shared the same interests, but because they shared the same enthusiasm for life. My father was fascinated by all sorts of things.
aviation, electronics, computers, wilderness survival, music, and whatever else happened to capture his imagination. Growing up, our home seemed to be filled with a constant sense of excitement and discovery. There was always something interesting happening, something being built, something being learned, or some new adventure being contemplated.
As a child, I assumed every home was like that. Only much later did I realize how much of that atmosphere came from my father and how deeply his enthusiasm had shaped my own life. He gave me something far more valuable than an interest in any one subject. He gave me a sense of wonder about the world.
And when I watched Jack Schwagger speaking with such obvious delight about traders and markets, I recognized that same quality. There's something infectious about meeting someone who has never lost the excitement of discovering something new. And that brings me to something else. That sense of curiosity isn't limited to the three of us.
We live on a planet with more than 8 billion people. And among them are countless dreamers, inventors, musicians, gardeners, photographers, pilots, scientists, collectors, and people pursuing interests. the rest of us might never even think about. Some are recognized as masters of their craft. Others spend their entire lives learning and experimenting without ever attracting an audience.
But the excitement is no less real. Somewhere, someone is restoring an old airplane. Someone else is learning their first three chords on a guitar. Another person is staring through a telescope trying to understand something about the universe. And somewhere a new trader is watching a price chart, fascinated by the possibilities unfolding on the screen.
Different passions, different dreams, the same human curiosity. And trading is one of those passions. like music, painting or any other art. It offers a lifetime of learning, experimentation, frustration, discovery, and the occasional moment when everything seems to come together. There may be rules to learn and techniques to master, but no two people will ever approach it in exactly the same way.
That's what keeps me coming back to trading. It isn't simply a way to make money. It's an art. I'm William Truit and this has been Long Game Trading. Thanks for listening. Respect yourself. Respect your money. This episode is provided for educational andformational purposes only. Nothing discussed constitutes personalized investment advice. Trading involves risk, including the potential loss of capital.
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