Revisiting the Conversation: You Don't Win the Game in One Move

Earlier this year, Ashley Lynn Priore sat down with CanvasRebel to discuss entrepreneurship, leadership, and the evolution of Queenside Ventures.

One idea surfaced throughout the conversation: Success is rarely built in a single move. For Ashley, that lesson comes directly from chess.

As both a competitive player and strategist, she has spent years studying how positions develop. Chess teaches players to think beyond immediate outcomes and focus instead on creating stronger positions over time. The same principle applies to leadership, business, and long-term growth.

From Chess Programs to Queenside Ventures

During the conversation, Ashley reflected on the early days of her work.

What eventually became Queens Gambit and Queenside Ventures did not begin with a detailed roadmap or long-term business plan. It began with a question:

Why weren't more girls being introduced to chess?

That question led Ashley to begin teaching chess in libraries, schools, and community spaces throughout Pittsburgh. As the programs grew, so did the realization that chess was teaching far more than the game itself.

Students were building confidence. They were learning how to make decisions. They were becoming more comfortable navigating uncertainty and thinking ahead.

Over time, educators, leaders, and organizations began asking a different question: Could these same lessons apply beyond the classroom?

The answer became Queenside Ventures.

Building Position

One of the strongest ideas from the CanvasRebel conversation was the concept of building position.

In chess, players rarely win because of a single brilliant move. More often, success comes from a series of intentional decisions that gradually improve the position.

Leadership follows a similar pattern.

The strongest organizations are built through relationships, consistency, communication, and strategic decision-making over time.

The strongest careers are often shaped by conversations, opportunities, and experiences that may seem small in the moment but become significant later.

As Ashley shared in the interview, "Chess teaches you that you don't win the game in one move. You build your position over time."

That philosophy continues to guide the work of both Queens Gambit and Queenside Ventures today.

Strategy as a Long Game

The CanvasRebel conversation also explored a broader leadership lesson. Many people view strategy as finding the perfect answer. Chess suggests something different. Strategy is often about creating better options.

It is about understanding the position, recognizing patterns, and making decisions that strengthen what comes next.

That mindset remains central to Queenside Ventures' work with executives, entrepreneurs, athletes, and organizations.

Because whether you're leading a company, building a career, or navigating change, the principle remains the same:

You don't win the game in one move. You build your position over time.