MANAGING DIRECTOR, INVESTMENTS, THE OPTIMAL SERVICE GROUP OF WELLS FARGO ADVISORS, WILLIAMSBURG
Virginia Business //September 2, 2025//
MANAGING DIRECTOR, INVESTMENTS, THE OPTIMAL SERVICE GROUP OF WELLS FARGO ADVISORS, WILLIAMSBURG
Virginia Business //September 2, 2025//
Montgomery went to work at an investment firm in December 1975 — meaning he’s enjoying his 50th year in an industry for which he is ranked as Virginia’s top wealth management adviser on Forbes’ 2025 Best-in-State Wealth Advisors list, with $1.6 billion in assets under management by his team.
He credits the power of relationships and his alma mater, William & Mary, for his career success and staying power. “The trajectory of my life was determined, really, by lining up where I went to school,” Montgomery says.
A former captain of William & Mary’s football team, Montgomery was invited to the Philadelphia Eagles’ training camp after graduating with a degree in business administration but did not make the NFL team’s final cut.
Instead, Montgomery went to work in Lynchburg for an investment advisory firm managed by a William & Mary alum. After a few years, Montgomery was sent to open a new branch in Williamsburg that became The Optimal Service Group of Wells Fargo Advisors. Today, it has 13 associates. In 2019, Montgomery was inducted into Barron’s Advisor Hall of Fame.
Return to the full list of this category’s recipients.