Entrepreneur • Investor • Author • Philanthropist • Advisor
Empowering Leaders to Build the Future of Business and Community
As Founder of Prevail Group, Reggie advises and invests in visionary businesses redefining their industries and communities. In partnership with Singularity, he helps global brands and family offices navigate the future with strategy, innovation, and purpose.


Entrepreneur • Investor • Author • Philanthropist • Advisor
Empowering Leaders to Build the Future of Business and Community
As Founder of Prevail Group, Reggie advises and invests in visionary businesses redefining their industries and communities. In partnership with Singularity, he helps global brands and family offices navigate the future with strategy, innovation, and purpose.
About Reggie Prevail
Building Businesses. Creating Impact. Inspiring Growth.
What’s up — I’m Reggie Prevail, a Virginia native born in Norfolk, VA.
I’m the Founder of Prevail Group, where I lead business transformation, culture building, and growth strategy through sales and smart technology implementation. I invest in companies through Prevail Ventures, focusing on businesses across the 757 while also backing select opportunities internationally. And I invest in people through the Prevail Foundation, supporting youth, community programs, and pathways that elevate the next generation.
Every project I take on — whether in business or philanthropy — is driven by one simple belief: we all have the power to prevail.

• Book Sneak Peek
How to lose: shifting the mindset, redefining the meaning of loss
“How to Lose” by Reggie Prevail is not your typical success book. Instead of teaching you how to win, it reshapes the entire conversation by showing why losing, letting go, failing forward, and releasing what doesn’t serve you is the most powerful path to growth. It’s bold, counterintuitive, and refreshingly honest.
This book challenges the traditional “win at all costs” mindset and introduces a new way of thinking, you win because you learn how to lose. With sharp insights and a clean, no fluff style, Reggie gives readers a mindset shift that feels both freeing and motivating. If you’re ready for a perspective that disrupts the norm, this book is your starting point
How I Help Leaders and Businesses Prevail
Strategic Guidance. Meaningful Investment. Lasting Impact.
Advisory & Investment
Partnering with founders and executives to develop growth strategies, attract investors, and scale their businesses with purpose.
Speaking Engagements
Inspiring audiences with insights on leadership, innovation, entrepreneurship, and community impact.
Growth COnsulting
Guiding entrepreneurs from concept to execution through strategic planning, project management, and mentorship.
Philanthropic Initiatives
Collaborating with organizations and community leaders to create programs that drive sustainable change.
• TESTIMONIALS
What people are saying
“Reggie has a rare ability to see both vision and execution. His guidance helped our startup secure funding and build a solid foundation for growth.”
— Marcus T., Founder, Elevate Tech Solutions
“Working with Reggie changed the way I approach leadership. His insight and mentorship brought clarity to both my business and personal goals.”
— Tanya R., CEO, Urban Legacy Group
• INSIGHTS
Ideas to Help You Prevail



Win or Win.
A mindset. A movement. A way to prevail.



• WORK WITH REGGIE
Ready to Prevail in Every Area of Your Life and Business?
Let’s work together to turn your vision into action.
How I Help Leaders and Businesses Prevail
Strategic Guidance. Meaningful Investment. Lasting Impact.
Advisory & Investment
Partnering with founders and executives to develop growth strategies, attract investors, and scale their businesses with purpose.
Speaking Engagements
Inspiring audiences with insights on leadership, innovation, entrepreneurship, and community impact.
Small Business Development
Guiding entrepreneurs from concept to execution through strategic planning, project management, and mentorship.
Philanthropic Initiatives
Collaborating with organizations and community leaders to create programs that drive sustainable change.


