JOSEPH W. ‘JOE’ MONTGOMERY

Joe Montgomery started working at an investment firm in December 1975 — meaning he’s enjoying his 50th year in an industry in which he has received numerous accolades. 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.

Montgomery has repeatedly made Barron’s annual list of top wealth advisers in Virginia. In 2019, he was inducted into Barron’s Advisor Hall of Fame.

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, he went to Lynchburg to work for an investment advisory firm managed by a fellow William & Mary alum. After a few years, Montgomery was sent to open a branch in Williamsburg that became The Optimal Service Group of Wells Fargo Advisors. Today, it has 13 associates.

Montgomery has served on multiple boards in Virginia, including those leading William & Mary, Future of Hampton Roads and the Jamestown-Yorktown Foundation. He is a past vice chair of the Virginia Retirement System’s board of trustees and served on VRS’ investment advisory committee.