At Collision Conference 2024 in Toronto, Alex Leibow, VP of Content & Media at Chess.com, and Levy “GothamChess” Rozman, International Master and one of the world’s most recognizable chess creators, sat down with journalist Jade Scipioni for a conversation about the future of chess, content and media. What emerged was something much bigger than a discussion about a board game. It was a conversation about building audiences, embracing failure, recognizing opportunity, creating through uncertainty and knowing when to make your next move.
Be Ready Before the Moment Arrives
Speaking at Collision, Leibow said Chess.com had reached 175 million members at that point, roughly four times its January 2020 membership. He said a “healthy share” of that growth came from The Queen’s Gambit, despite Chess.com having no involvement in creating the show. The important word is not necessarily “growth.” It is ready.
Businesses often spend enormous amounts of energy trying to predict the next big thing. They want to know which technology will take off, which platform will dominate, which consumer behavior will change and where the next audience will come from. But Chess.com’s experience suggests another approach: build something valuable before the moment arrives, then be prepared when circumstances outside your control create a surge of interest. You cannot manufacture every cultural moment. Sometimes another company, creator, filmmaker or cultural event creates the wave. What you can control is whether your organization is prepared to respond when that wave reaches you.
Chess.com had already built the platform, community and infrastructure. When interest in chess accelerated, there was somewhere for that interest to go. That is more than luck. It is positioning.
Expertise Has Become Entertainment
For a long time, expertise lived behind institutions. You went to a classroom to learn, bought a book, watched television or read a newspaper. The internet changed that distribution model, allowing experts to build audiences directly and turn specialized knowledge into something people can discover, follow and share. That is one of the reasons Rozman’s rise as GothamChess is so interesting. His subject is extraordinarily complex, yet his content has helped make chess accessible to audiences well beyond serious tournament players. The challenge is not simply understanding chess; it is translating that knowledge into stories, explanations and entertainment that people actually want to consume.
The lesson extends far beyond the game. A lawyer can know the law. A scientist can know the science. An entrepreneur can understand a market. A financial professional can understand an industry. But expertise alone does not automatically create attention. In the creator economy, the ability to communicate knowledge in a compelling way can be almost as important as the knowledge itself. This is one of the defining characteristics of modern media: the expert is increasingly becoming the publisher, broadcaster and personality at the same time. The person who can make a complicated subject understandable – and make people care about it — can build an audience without waiting for a traditional media institution to give them permission. Knowledge creates value. Storytelling creates attention. Together, they can create an audience.
You Don’t Have to Be Good to Begin
One of the most uncomfortable truths about creating anything is that the beginning is rarely impressive. Your first video may be awkward. Your first article may receive almost no attention. Your first business may be small. Your first presentation may be something you would rather not watch again six months later. That is normal.
The internet has a way of hiding the beginning. We see the creator with millions of followers, not the years of work that came before the audience arrived. We see the successful company, not the early version operating with a handful of people and limited resources. We see the finished product, not the experiments that failed along the way. But every successful body of work has a first piece. The point is not to start impressive. The point is to start and become better through repetition. That may be one of the most useful lessons for anyone building a company, a personal brand, a creative career or simply a new skill. The first version is supposed to be a beginning, not a masterpiece.
Learning How to Lose
There is another lesson chess teaches particularly well: how to lose. During the Collision conversation, Leibow spoke about his young son learning chess. For a child, the game offers an unusually direct introduction to failure. You make a move, your opponent makes a better move, and sometimes you lose. Then you play again. The board does not care about your intentions. It does not care how confident you were before the game or how much you wanted to win. It simply shows you what happened.
That can be a powerful lesson for adults, too. A failed pitch is information. A rejected application is information. A product that does not sell is information. A piece of content that nobody watches is information. None of those outcomes automatically defines you. They tell you something about the position you are in. The question is what you do with that information. In a culture that often celebrates winning while hiding failure, learning how to lose may be one of the most valuable skills chess has to offer.
Your Weaknesses Are Not Your Ceiling
Chess players study their mistakes because ignoring them does not make them disappear. Improvement begins with identifying the weaknesses that are holding you back and understanding what needs to change. Rozman’s own coaching philosophy reflects that approach. In a Chess.com interview about his coaching, he described his method as first identifying a student’s strengths and weaknesses and then developing a practical, individualized study plan. He compared the process to a barrel with holes in it: adding more knowledge does little good if the underlying weaknesses remain.
The same principle applies to business. You do not need to know everything. You need to know what you do not know. That might mean hiring someone with a skill you do not have. It might mean finding a mentor, working with a coach or listening to criticism you would rather not hear. The objective is not to eliminate every weakness overnight. It is to understand where improvement is needed and create a deliberate path toward it. Growth often begins with a difficult sentence: “I’m not good at this yet.” The word yet matters because a weakness is not necessarily a permanent identity. It can be a starting point.
The Queen’s Gambit Changed the Conversation
The Queen’s Gambit phenomenon is particularly revealing because Chess.com did not create it. Leibow said at Collision that the series had been “huge” for Chess.com and that the company saw the impact an exceptional show could have on its growth. He also discussed Chess.com’s interest in being involved in future storytelling around chess. That represents an interesting evolution. A company built around an ancient board game was now thinking not only about how people play chess, but also about how people encounter the game through stories and entertainment.
That is increasingly how modern categories are built. A documentary can change how people understand an industry. A television series can make an obscure subject culturally relevant. A creator can introduce millions of people to a product they had never considered. A podcast can turn a technical subject into a mainstream conversation. Culture can create demand in ways traditional advertising cannot. And when that happens, the companies already positioned around the category have an opportunity — provided they are ready.
Enjoy the Process, Not Just the Outcome
There is a final lesson running underneath the entire conversation. The danger of focusing only on winning is that you can miss the game itself. The same is true in business and life. If every project is judged only by its final result, the process becomes something to endure rather than something to learn from. Building anything meaningful takes time. There will be experiments that fail, ideas that change, unexpected opportunities, wrong turns and long stretches when nobody is watching. There may be periods when the work seems to produce very little visible progress. That does not necessarily mean nothing is happening. Skills are being developed. Judgment is improving. Relationships are forming. Experience is accumulating. The next opportunity may be getting closer without announcing itself. The people who can keep learning through those stages have something that cannot be measured by a single viral moment: they are still playing.
You Don’t Need to See the Whole Board
Chess does not require you to know exactly how the game will end before you make your next move. You study the position, consider the possibilities, make a decision and then respond to what happens next.
That is not a bad model for modern life. No entrepreneur knows exactly what the market will look like five years from now. No creator knows which piece of content will become the one that changes everything. No professional knows every turn a career will take. Even the best plans are built on incomplete information. We make decisions with what we know. Then the circumstances change. We learn. We adjust. We make another decision. That may be the real lesson hidden inside the chessboard. The future cannot always be predicted. The next move can still be considered.
Build before the moment arrives. Learn from the losses. Understand your weaknesses. Tell better stories. Stay true to your voice. And when the opportunity appears, recognize it. Because sometimes the most important move is not the one that wins the game. It is the one that puts you in a better position for the move that comes next.
You do not have to see the entire board. You just have to make the next move.
