JASON MCCLAIN is a globally recognized entrepreneur, serial entrepreneur boasting over three decades of experience empowering leaders and teams to thrive through change, acclaimed author, and impactful keynote speaker. He is an expert on resilience, focus, and strategic decision-making, drawing from a 30-year career that includes founding and successfully exiting over a dozen companies in the digital landscape.

A Private Pilot, mentor, and business coach, he takes his lifetime of achievements and delivers a message of resilience that is actionable. Built on a foundation of founding and successfully starting and selling over a dozen companies, developing a high-end luxury wine brand, McClain Cellars, a Recording Studio, and a Software Platform, McClain knows the journey of the business owner and entrepreneur firsthand. Having started over 100 companies, failing at most and yet selling over a dozen over the past 30 years, he is a testimony of strength and belief.

His philosophy, “Your perceived limitations are often the source of your greatest strengths,” stems from his own life journey, which required him to adapt and innovate after being born with a physical difference. Jason’s unique and battle-tested insights are codified in his books, Pivot to Profit: Turning Failures into Fuel (featuring the R.I.S.E. System) and Island of One: Born Different. Built to Thrive (featuring the C.O.M.P.A.S.S. System). He has spoken for major organizations including Disney, CBS, ABC, and Pepsi, delivering practical strategies that equip audiences with a growth mindset and a blueprint for overcoming professional and personal adversity.

Born with a unique physical difference—without fingers on his left hand—Jason was relentlessly forced to “adapt and overcome” a world not designed for him. This constant need to innovate—whether teaching himself to play guitar, learning to fly an airplane, or building a successful career after periods of homelessness—cultivated an unparalleled resilience that became the foundation of his entrepreneurial success.

Jason’s career spans over three decades, during which he has founded and successfully divested over a dozen companies across various sectors, demonstrating his expertise in navigating the digital landscape. This journey was not without major setbacks; he openly shares the profound lessons learned from surviving corporate embezzlement and two business failures. These challenges forced him to codify his strategies for managing risk, improving decision velocity, and building resilient businesses.

His actionable philosophies are detailed in his acclaimed books:

Pivot to Profit: Turning Failures into Fuel: Teaches the R.I.S.E. System (Reckon, Identify, Strategize, Execute)—a tactical blueprint for turning any crisis into a profitable opportunity.

Island of One: Born Different. Built to Thrive: Teaches the C.O.M.P.A.S.S. System (Clarity, Ownership, Manage, Perspective, Acknowledge, Satisfy, Strengthen)—a psychological framework for finding inner clarity and confidence.

Beyond the stage, Jason is the owner of McClain Cellars, a luxury wine brand, which itself was founded using his R.I.S.E. principles, pivoting from a volatile market model to include a scalable virtual winery program.

As a highly sought-after speaker, Jason delivers high-impact keynotes globally, helping organizations like Disney, Pepsi, CBS, and ABC build a culture of genuine resilience, strategic agility, and holistic success. He lives in California with his wife, Sofia, and their three daughters, who he credits as the unwavering source of his purpose.