Wenner pointed to The New York Times as a useful comparison, in that the company built a great product, layered subscriptions on top, and can now treat advertising as a complement.
Of course, Chess.com also hopes to benefit from a broader cultural moment. The game stormed into the national zeitgeist during the pandemic, when lockdowns encouraged gameplay and the Netflix series The Queen’s Gambit added a dose of sex appeal. Since then, a string of high-profile cheating controversies, a Netflix documentary, and a forthcoming film with Boardwalk Hollywood Pictures have kept the game in the cultural conversation.
For Chess.com, the bet is that the same deliberateness that defined its product approach for nearly two decades can carry over to its ad business, that it can court Louis Vuitton without becoming a billboard. Whether that discipline holds as the revenue stakes rise is the open game.
