About ROOKS

Strategy for how you think, prepare, and perform.

ROOKS Ventures is a lifestyle brand built on the principles of chess—strategic thinking, disciplined action, and long-term vision.

BUILT ON THE PRINCIPLES OF STRATEGY

Chess teaches you to assess the position before you move. To understand the objective. To recognize that every decision changes what becomes possible next.

ROOKS takes those principles beyond the board—into health, mindset, performance, business, and everyday decision-making. The goal is not perfection. It is learning to think more clearly, prepare deliberately, and make better moves over time.

HEALTH

Support the foundation.

ONE PHILOSOPHY. MULTIPLE ARENAS.

ROOKS applies the same strategic mindset across four interconnected areas.

Through products, media, and experiences, ROOKS is building an ecosystem designed around the way people think, prepare, and perform.

MINDSET

Strengthen how you think.

STRATEGY

Understand the position.

PERFORMANCE

Execute with purpose.

BUILT FROM EXPERIENCE

Medicine. Military Leadership. Business. Systems.

ROOKS grew from a simple observation: the principles that improve performance in one arena often carry into another.

Founder James Gray’s experience across medicine, military leadership, business, and systems improvement revealed a common thread—whether the challenge involves health, an organization, or a high-stakes decision, better outcomes begin with understanding the position before taking action.

ROOKS brings those lessons together around one idea: think strategically, prepare deliberately, and move with purpose.

A BROADER ROOKS VISION

ROOKS is ultimately about more than products. It is about creating environments—physical and digital—where strategy, learning, health, performance, and meaningful connection can come together.

That broader ecosystem also includes ROOKS Chess Cafe, a separate nonprofit initiative focused on community, chess, conversation, and connection. ROOKS Ventures and ROOKS Chess Cafe are distinct organizations that share a belief in thoughtful engagement, lifelong learning, and purposeful community.

LEARN ABOUT ROOKS CHESS CAFE →