3 Traders You Probably Never Heard Of, and What Made Them Last
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By Spencer Li, CFTe · Last updated: 26 October 2026
Three traders worth studying that most people have never heard of are Tom Sosnoff, Bruce Kovner and Lewis Borsellino. None is famous for one giant trade. Each built a long career on a narrow skill. Sosnoff ran his trading like a business and built two companies out of it, Kovner traded his reading of the world economy for 28 years, and Borsellino made his name in a single futures pit. The habits they share can be copied on an ordinary account, even if their results cannot.
I first wrote about these three in 2016. This version keeps the people and the lessons, and every figure about them now comes from a source I could open and date.
Why do the famous trades teach the wrong lesson?
When most people think of a trader, they think of Nick Leeson, and for anyone in Singapore the story is close to home. In 1995, the 28-year-old fled Barings’ Singapore office leaving a note that said “I’m sorry”, and a secret file called Error Account 88888 showed he had lost £827m in the bank’s name. Barings, the City of London’s oldest merchant bank, collapsed. Leeson went to prison in Singapore.
Source: The Guardian
The obvious lesson is risk management. It is the right one. But there is a quieter problem with how trading fame works. The names everyone knows are mostly attached to one enormous trade, such as George Soros, still called the man who broke the Bank of England for a single bet against the British pound in 1992.
How many of you can recognize these faces? 😀
Source: philanthrophyroundtable.org, tastytrade.com
Stories like that leave beginners with a dangerous idea, which is that one big winner is all it takes to retire. Those trades were made with sums of money most of us will never trade. What carries over to a normal account is the boring part, steady and decent returns built to last, and that part can be learned.
Back in 2016 I put it this way: “Trading is not about getting a one-hit wonder. It’s a career decision, and requires as much commitment and passion as building a business.”
Who is Tom Sosnoff, and why does he trade like an entrepreneur?
Tom Sosnoff sharing option strategies on his daily financial show with his daughter
Source: Tastytrade
Tom Sosnoff spent more than 20 years as a market maker at the Chicago Board Options Exchange. A market maker quotes prices to buy and sell all day so that others can trade. His SIFMA profile says he was also one of the original traders in the S&P 100 index options pit.
He also wanted ordinary investors to trade options online, with proper tools, so he co-founded the thinkorswim trading platform. On 8 January 2009, TD Ameritrade announced it would buy thinkorswim in a deal valued at about $606 million, according to the press release it filed with the US Securities and Exchange Commission. In 2011 he founded the network now called tastylive, which teaches option trading in a live show every day, and the tastytrade brokerage followed six years later.
So what can a retail trader take from a man who sold a company? Mostly the way he thinks. In 2016 I wrote that “perhaps the reason why most traders fail is they fail to see themselves as entrepreneurs”, and Sosnoff’s career fits that line.
A business owner knows the odds of each decision, keeps the losing products small and puts more behind the ones that work. A good poker player does the same with every hand, and a trader can do the same with every setup. When a trader is right, they press the bet, and when they are wrong, they cut it quickly. Trading without a plan is as good as flipping a coin. With one, you can protect the account while it grows.
The other half is expertise. You have to know the tools and the lingo of your market cold. A forex trader feels the hand-over from the Asian session to Europe to New York. A seasoned price action trader can decide in a few seconds to stay out. That takes years.
You do not need a floor career to start thinking this way. My free 15-minute swing trader checklist is the daily routine I use myself.
Who is Bruce Kovner, and why did politics matter to his trading?
Bruce Kovner with his wife
Source: The Kovner Foundation
Bruce Kovner did not start in finance at all. According to his own biography, he studied government and economics at Harvard and finished the course work for a PhD in political science. He then spent a few years on political campaigns and in teaching before anyone showed him a market.
That changed in 1976. A family friend introduced him to the financial markets, and he spent more than a year studying currency, commodity and debt markets on his own. Then, in the line I find most relatable, he “borrowed $3,000 from his Master Charge account and began trading futures”. That is a credit card. Nobody should copy that part. It worked. He was later hired as a senior trader at Commodities Corporation, and in 1983 he set up Caxton Associates, one of the first modern macro hedge funds. He ran it as CEO for 28 years, until he retired in 2011.
Macro trading means taking positions based on the big picture, such as interest rates, growth and currencies, and his biography says he traded “based on his views of macroeconomic conditions”. As I read it on 26 October 2026, it also puts Caxton at $12 billion in assets, with “an average net annual return of over 21%” across his time there. My 2016 version of this post said 28% a year, every single year, and I cannot find a source for that, so it is gone. An average also says nothing about the worst year inside it.
The lens I find interesting is his training. Political science is the study of how governments and large groups make decisions, and a macro trader is betting on how those decisions turn out, such as what central banks will do next. Institutions express those views through price, by buying and selling in size. Few of us move hundreds of millions of dollars, but we can still see where the big money is leaning, which is all “the trend is your friend” really means.
Context matters more than any single signal. As I wrote in 2016, “just because you see a bearish candlestick pattern does not mean it’s a wise trade to short the market”. You have to see whether the surrounding price action supports the idea. And when Jack Schwager asked Kovner in Market Wizards where he put his stops, he replied, “Where they’re hard to get to.”
Who is Lewis Borsellino, and why go deep on one market?
Borsellino trading in the pits as a young man.
Source: Tastytrade
Lewis Borsellino’s trading career started over a game of racquetball. In an interview with Stocks & Commodities on 21 April 1999, he said he asked a trader he played with whether he could open an account to trade gold futures. The trader told him to come down to the exchange first, because he did not know what he was doing and would just be throwing his money away. So he went.
“The moment I walked out on the trading floor, though, I thought it was the greatest thing I ever saw in my life,” he said. He went on to work as a runner, a clerk, a broker, an independent trader and a fund manager, and he made his name in the S&P 500 futures pit at the Chicago Mercantile Exchange. The publisher’s note on his 1999 book, The Day Trader: From the Pit to the PC, gives his career at that point as 18 years.
That is the lesson I took from him. Get very, very good at one thing. Many traders keep adding indicators, hoping the next one will turn them into a trader. It rarely does. In 2016 I wrote that what works is to “be very good at at most 1 or 2 indicators, or simply trade with no indicators”. If you are not sure which tools belong on a chart, my guide to the 3 types of technical analysis sorts them.
Some traders specialise in a market and some in a method, so in the proprietary trading world, some read only the order book and never look at a chart, while others work on portfolio allocation. I went the market-wide way, with one set of rules that I apply across stocks, forex, commodities and crypto. The principle holds either way. Pick something. Then go deep.
The title of his book tells the rest of the story. The pits were going electronic, and From the Pit to the PC says where he went next.
Did these traders just get lucky?
In June 2023, a trader on Reddit’s r/trading asked whether the Market Wizards were mostly survivorship bias. They wrote that “most of these guys here were just cowboys who got lucky”.
It is a fair challenge. Some of it is true. We only hear about traders who survived, and the ones who blew up quietly disappear from the books, and Leeson himself shows how convincing a lucky streak can look. As at 1993, he had made £10m for Barings, 10% of the bank’s profits that year, and on that record he looked like a star. Two years later the bank was gone.
What separates luck from skill is time and the number of decisions. One trade proves very little. So does one great year. Twenty-eight years running a fund through very different markets is much harder to fluke, which is also why I tell students to judge a method across 100 to 200 trades, never on a handful of wins. The habit behind it is unglamorous position sizing. In my weekly outlook on 18 March 2026, talking about one of our open trades that was moving around a lot, I said “we need to position size correctly”. It is the opposite of the one big bet.
What does trading as a career really take?
Source: Goalcast
Many traders stay frustrated because they never change their behaviour, so they take many, many trades without asking the right people or looking for the right guidance, and they repeat the same mistakes. The regret piles up with the losses. If you do what you always do, you get what you always got.
All three of these traders changed what they did when the world changed around them. Sosnoff went from the floor to building software, Kovner left academia for a market he had studied for a year, and Borsellino followed the business from the pit to the screen.
Whether you trade on the side or are thinking about it as a career, it takes time, real expertise, patience and some street smarts. None of it arrives in one trade, and the fear and greed of the first few years tend to be the real tuition. Keeping the work small and daily helps, and the free 15-minute swing trader checklist is the routine I run.
FAQ
Who are the three traders in this post?
Tom Sosnoff, a former options market maker who co-founded thinkorswim and founded the tastylive network. Bruce Kovner, who founded the macro hedge fund Caxton Associates and ran it for 28 years. And Lewis Borsellino, an S&P 500 futures pit trader at the Chicago Mercantile Exchange.
What do long-lasting traders have in common?
Deep expertise in a narrow area, a defined way of trading they trust in different market conditions, and a habit of reviewing and adjusting their own results over many years. None of the three relied on one huge winner.
Is it better to specialise in one market or trade many?
Either can work. Borsellino specialised in one market, while others specialise in one method and apply it across markets. What fails is constant switching, because you never stay long enough to get good at anything.
Did Bruce Kovner really start with borrowed money?
Yes. His own biography says he borrowed $3,000 from his Master Charge account, a credit card, and began trading futures after more than a year of study. It is a story, not a method to copy.
Do you need a huge account to learn from these traders?
No. The habits are what transfer: running trading like a business, understanding what moves the market, sizing positions carefully and getting very good at one thing.
Which of the three is closest to how you trade, the entrepreneur, the macro thinker or the specialist? Let me know in the comments.
If you want to build these habits in order, start with my free trading guides. The guide to money and risk management covers sizing, and the one on trading psychology covers the patience.
And if you want one small routine instead of one big trade, grab the free 15-minute swing trader checklist.
About the author. Spencer Li is The 15-Minute Trader and the founder of Synapse Trading. He is a Certified Financial Technician (CFTe) with 15+ years of trading, run from 70+ countries. He holds a B.Acc and B.BM from SMU. Every trade he takes is public, dated, losses left in. He teaches rules-based swing trading in 15 minutes a day, one system for any market.
Education, not financial advice. Synapse Trading is not licensed by MAS to advise on investment products. Trading carries risk of loss, and past performance is not indicative of future results.
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Educational content only, not personalised financial advice. Trading carries risk, including loss of capital. Past performance is not indicative of future results. Synapse Trading is not licensed or regulated by MAS.
