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Creating coincidence: The importance of the Tribe connection

By Phoebe Brannock ’18 June 5, 2017

“She just…whomp! dropped the hammer on him,” Joe Montgomery ’74 finishes describing a conversation he had with Margaret Thatcher during his time as president of the William & Mary Alumni Association.

Montgomery is a natural storyteller, which is fortunate because he has collected many tales over his years as a Tribe football star, a financial advisor and a member of both the Alumni Association and the William & Mary Board of Visitors. A Southside accent that hints at his Lynchburg, Va., upbringing infuses calm and familiarity into his smooth timbre. These qualities dictate the rhythm of the conversation, which he punctuates with a few deliberate gestures. As he does, light glints off his silver cufflinks shaped like Superman’s shield. Montgomery has a quiet charisma, and anyone could sit and listen to him for hours.

From encounters with the greatest leaders of the 20th century to tailgate parties at William & Mary’s Homecoming, Montgomery has experienced life on a broad spectrum. He attributes this richness to a few individuals who have shaped his path.

“If you’re lucky enough in life to bump into one or two people who have an impact and sort of give you an opportunity and change the direction of what you might have done, you’re a very fortunate person,” Montgomery says. “I’m a very fortunate person, and I acknowledge that.”

Today, Montgomery is managing director of investments at Wells Fargo’s Optimal Service Group in Williamsburg. His services have landed him in Barron’s Hall of Fame (an award an advisor earns after 10 consecutive years of endorsements), on Forbes’ list of top financial advisors and on the Financial Times Top 400.

In addition to building the Optimal Service Group, Montgomery’s return to Williamsburg has enabled him to provide a few opportunities to William & Mary students and alumni.

Through internship offers, Montgomery provides young people with potential a chance to grow these skills and begin making life-enhancing connections.

“The intern thing is interesting because we’ve had a lot of kids over the years work for us,” Montgomery says. “Not necessarily that they were interested in finance, but sometimes it was just to give them another view of the world, and we’ve generally stayed in touch with a lot of them. I’m actually going up to one of their weddings here in a week or so.”

Montgomery’s enthusiasm for putting young people in opportunistic positions stems from a few of his own fortunate encounters. In 1970, Montgomery was leaning toward attending college and playing football at Virginia Tech when he bumped into Lou Holtz, William & Mary’s head football coach at the time. Rather, Holtz bumped into him.

“Coach Holtz was an incredible recruiter, a very persuasive individual. The great thing was, he turned out to be right about William & Mary, and in the long haul, going to William & Mary was one of the best decisions of my life,” says Montgomery of that critical encounter.

The William & Mary connection has held throughout his life.

“In Williamsburg, almost everybody has some connection back to the College,” Montgomery says as he rattles off an almost inexhaustible list of names of individuals who have interned for him or whom he brought onto his team. Montgomery’s hiring criteria, stems from Holtz’s recruiting criteria. Holtz taught Montgomery to surround himself with talented individuals with varied skill sets to contribute.

Between classes in the then-fledgling business school and playing center for the Tribe football team, Montgomery found time to prioritize friendships. He chose to live on-campus each of his four years, which enabled him to meet individuals outside of his graduating class. Montgomery attributes these friendships to the pure circumstance of “just being around.” After 45 years, they still keep in touch. 

“It’s kind of ironic when kids come out and talk about interviewing and what to do about jobs, etc.,” Montgomery chuckles. “Well, you’re talking to a guy who has never interviewed for a job. The truth of it is, I didn’t come here to play football, but I was geared up to play football after I graduated.”

In February of his senior year, Montgomery signed a contract to play for the Philadelphia Eagles. He shakes his head mirthfully when reflecting on the decisions he made as a 22-year-old.

“I assumed that I would be playing football because I had signed a contract to play football,” he says. “I spent nine weeks with the Eagles and got cut, spent a couple of days with the New York Jets and then I played for Charlotte in the World Football League the next year.”

William & Mary connections would surface again during Montgomery’s time in the league. When Montgomery wasn’t standing on the offensive line, he ran the door at a bar back in Lynchburg.

“A guy comes in, he’s having a drink, and he’s talking to the bartender who was a friend of mine,” Montgomery pulls out the story and unfolds it. “One thing leads to another; they’re talking about football. My friend, Mickey, he says something about ‘Hey, I got a friend who played at William & Mary.’ And the guy, he says, ‘Ah, you know Joe Montgomery? I saw him play. I’d like to meet him when he’s back in town.’ That’s the guy who ultimately hired me into this business. If I hadn’t gone to William & Mary, that guy wouldn’t have blinked.”

Montgomery drove back to Lynchburg to meet with the man who had asked about him over a drink, Larry Phillips ’55, the manager of the Wheat First Securities office in Lynchburg. Thinking that he would play football for another year, Montgomery was not looking for a new career at the time; he was simply seeking connections. The chance meeting and some adamant persuasion on the part of Phillips landed Montgomery in the investment business. A few years later, Phillips requested that Montgomery return to his college town to open another Wheat First office.

Williamsburg has not topped the list of preferred cities for young urban professionals since its final days as Virginia’s capital in the 1770s. Montgomery initially did not feel much excitement to conduct business in between costumed interpreters and TWAMPS, but Phillips put Montgomery’s mind at ease. The two had already done bond work for an area hospital, so they visited and started to create networks. Montgomery also read the Williamsburg prospectus for potential growth.

“When I came back, I realized, ‘okay, you can’t go back and hang around at the fraternity house,’ but here’s what the upside is: Just kind of broaden your horizons by taking the time to look at it and study it. As it turns out, this has been a big growth area. It’s perfect for what we do, and we run an international business out of here,” Montgomery explains.

With clients on the West Coast, South Africa and Bermuda, Montgomery has created a substantial network. Partners in the firm travel across the country and across the world each week to provide clients with a comprehensive approach to investing and financial planning. Over the years, Montgomery has remained a constant in the business as he has navigated bank buyouts and the inevitable name changes that accompany them.

“No change for me, other than a whole bunch of business cards,” Montgomery smiles. “That’s kind of funny, but it’s also part of something a little different: We’re pretty unique in that we’ve had a lot of continuity. We’ve been the same; people count on us.”

Montgomery particularly enjoys staying connected through what he describes as a “six degrees of Kevin Bacon kind of party,” where people who know a friend-of-a-friend and show up to enjoy barbeque catered by a North Carolina company.

The Optimal Service Group has hosted a Homecoming tailgate adjacent to the Alumni House since 1985 when Montgomery and his friend, the late Russ Brown ’74, started the tradition. Alumni of all ages bring their families to gather and celebrate existing William & Mary connections while creating new ones.

“That’s just special about William & Mary. Part of it has to do with size,” says Montgomery. “The Board of Visitors and the president work very hard to maintain that intimacy that is unique for a state school, which is very unusual. It means we all have to step up and do what we can, both time and other things, to support it because we don’t have 200,000 alumni. It’s important for everybody to think about how they can be a part of it.”