The Book On High-Stakes Thinking

David Webb is a seasoned entrepreneur and business leader with more than three decades of experience at the intersection of technology, finance, and services. As the founder and CEO of multiple ventures-some celebrated successes and some hard-learned failures-he has cultivated a reputation for turning complexity into clarity, driving growth, and leading organizations through periods of both turbulence and transformation. His career has been defined by a willingness to take calculated risks, embrace innovation, and pursue opportunities others often overlook. David's debut book, Life Unscripted: What You Should Have Learned in High School, distilled years of professional and personal experience into a practical guide for navigating the overlooked realities of adulthood. His second, The Book On Risk Management in Payments, marked a decisive step into specialized territory, tackling one of the most pressing challenges in global commerce: how to anticipate threats, safeguard trust, and manage risk in a world where money moves faster than regulation. With his third book, The Book On Strategic Obsession: How to Turn Long-Term Thinking Into a Competitive Weapon, David advanced his mission further by exploring the discipline of sustained, long-horizon thinking as a defining advantage in leadership and strategy. Drawing from decades at the intersection of leadership, risk, and relentless execution, he reframed strategy not as a static plan on paper, but as an enduring obsession that separates fleeting achievements from lasting success. His fourth book, The Book On High-Stakes Thinking: How to Make Decisions That Actually Matter, pushes into even more urgent terrain-the art of thinking clearly when the consequences are severe. Here, David dissects how individuals and organizations can cultivate mental frameworks that withstand pressure, avoid cognitive traps, and transform decisive moments into defining victories. It is a work that combines psychological insight with practical execution, written for those who cannot afford to think small when the stakes are anything but. Beyond writing and business, David remains committed to mentoring entrepreneurs and contributing to community initiatives that promote education, resilience, and personal growth. Whether in boardrooms, classrooms, or in print, his work reflects a consistent theme: empowering others to think critically, act decisively, and build systems that endure.