Reggie Prevail

Meet Reggie

GROWTH ADVISOR · FUTURIST · INVESTOR · PHILANTHROPIST

The Architecture of Impact

Reggie Prevail is a growth advisor and futurist, investor, and philanthropist who advises founders and CEOs on growth strategy and innovation.

Through the Prevail ecosystem, Reggie architects systems that multiply what matters. He is a growth advisor and allocator who identifies leverage points across capital, culture, and future literacy.

As the sole founder of 40X, Reggie built a platform dedicated to serving underestimated leaders. 40X teaches the literacies that traditional education skips and the systems that the wealthy inherit — equipping the next generation of founders, executives, and allocators to build the next century.

The 757 and Beyond

Deeply rooted in Norfolk, Virginia (the 757), Reggie's philanthropic and investment work begins at home but scales globally. The Prevail Foundation focuses on the quiet infrastructure that turns talent into trajectory: mentorship, youth programs, and long-term generational wealth building for families starting from scratch.

Through Prevail Ventures and Prevail Group, he brings capital and growth consulting to blue-collar businesses, healthcare, sports, and cutting-edge technology. The mandate is always the same: build what lasts, measure in decades, and invest where capital and strategy are scarce.

WIN OR WIN · Loss as leverage

WIN OR WIN is the framework. Loss is not the opposite of winning. Loss is the cost of winning. The work is choosing what to lose, when to lose it, and how to turn that loss into leverage. Builders who refuse the cost stay stuck. Builders who pay it move.

How to Lose

Reggie is also the author of How to Lose, a manual exploring the counter-intuitive architecture of winning and navigating failure.

Explore the book