Becoming A Winner

There are two aspects to becoming a winner: the attainment of mastery and the belief that one can win and succeed. You can win without mastery but that is unrepeatable luck. Being a winner is the combination of mastery and self belief.

I have discussed the attainment of mastery in a previous blog post on long term thinking (“Long Term Thinking: The Key To Mastery”, May 8, 2025). In contrast to The Dabbler and The Obsessive, The Master takes a long term approach to his craft, honing his skill over time, showing up consistently through ups and down. He doesn’t try to accomplish his goal too fast like the Obsessive and he doesn’t expect constant and continuous improvement like The Dabbler. He simply shows up, day after day, to do the work. Many mistakes will be made and lessons learned. Over a long period of time, this mentality results in mastery.

But winning, in addition to mastery, requires self belief. While many have skill, only a few reach the very pinnacle of success, winning repeatedly for high stakes. In order to win, one must believe that one can win. The best generator of this belief is to have actually won before. There is a cliche about “acting like you’ve been there before”. But having actually won before provides evidence to ground one’s belief that one can do it again. Further, the more times one has won, the higher the self belief that one can do it again. That’s why the first big win is frequently so treacherous and so meaningful.

In my own case, I have won a number of poker tournaments over the last couple of years, including chopping the Bay 101 Last Saturday $1000 three times (April 2024 (~$16,000), April 2025 (~$16,000), January 2026 ($29,000)) and winning the WSOP Monster Stack at Thunder Valley in October 2024 ($31,000).

These wins, combined with the mastery earned from honing my game over the last twenty years, have led me to enter tournaments with the self belief that I can win, to play like I have a strong chance from the beginning and to maintain that belief as I run deep given the knowledge that I’ve done it before. In other words, winning has begat winning.

In the stock market, I started to win in a big way for the first time in 2025 – and it has continued so far into 2026. As detailed in my 2025 Letter, the turning point was reading a quote in Jack Schwager’s Little Green Book of Market Wizards in November 2024: “Do more of what’s working and less of what’s not.”

One consequence of reading that sentence and the subsequent analysis it led to was the creation of a spreadsheet containing all of my positions, their current size and value and my cost basis, which I monitor regularly. If a position isn’t working for too long, I start to scrutinize it and wonder if I’ve made a mistake or what the problem might be. I go deeper and sometimes make an adjustment when appropriate. If something is moving hard against me, especially on the short side, I cut my losses much more quickly than I used to. This keeps my portfolio filled with positions that are working or that I expect to work in the near future.

The larger point is that the mastery I developed over 25 years of work and learning combined with my recent success has created a humble confidence that I can continue to succeed while flaming the hunger of my ambition to do so after years of painful failure. The end result is a mentality where I expect to win which begets more winning.

I have often thought that Michael Jordan’s game winner in the 1982 NCAA Championship Game as a freshman was the crucial moment in the great champion he ultimately became. Hitting such a big shot at such a young age must have given rise to enormous self belief that he could do it again and was destined for great things.

Similarly, it was once thought that no human being could run the mile in under 4-minutes. But after Roger Bannister broke the 4-minute barrier in 1954, many others did so in short order as well. This suggests that the limit was not physical but psychological. Once Bannister did it, others thought in effect: “If he can do it, I can too.”

In psychology there is something known as The Pygmalion Effect: self belief and self doubt are often self fulfilling prophecies. As Henry Ford said: “If you think you can or think you can’t, you’re probably right.” In conjunction with mastery, strong self belief is a powerful formula for performing at a high level.