Reggie Prevail Named to Inside Business 2026 Top Forty Under 40

NORFOLK, Va. — Oct. 26, 2026 — Reginald "Reggie" Prevail, a philanthropist, investor and futurist who advises founders and CEOs on growth strategy, has been named an Inside Business 2026 Top Forty Under 40 honoree. His profile, written by Hugh Lessig with a photo by Amanda MacDiarmid for Inside Business, was published today.

Prevail, 31, is Founder and CEO of Prevail Group LLC and leads Prevail Group and Prevail Ventures. A Norfolk native and a father, he has spent nearly his entire life in Hampton Roads. He serves on the boards of The Noblemen, the Sweet Pea Whitaker Foundation, YIG and Vaughn's Way, and he is a longtime volunteer and donor with Operation Smile. Through Prevail Foundation, he supports scholarships, youth development, innovation exposure and community initiatives focused on creating opportunities for the next generation.

Over the next five years, Prevail aims to create meaningful jobs, invest in and grow more companies, attract diverse talent and perspectives to the region, and help position Hampton Roads as a place where innovation and opportunity thrive.

His philosophy is "Win or win," the belief that every outcome teaches you something and moves you forward.

“I want to prove that you don't have to leave this region to build something with national or global impact.”

“Validate yourself today. Don't wait for anyone to tell you that you're enough.”

“Its people. All of its people.”

This year's honorees will be recognized on Friday, Oct. 30, from 5:30 to 8:30 p.m. at The Westin Virginia Beach Town Center, as Inside Business celebrates the 28th year of the program.