A Shared Success Story: Chesapeake Bank Celebrates 125 Years with the Communities It Serves

There’s a humility in Tommy Kellum’s voice when he talks about his family business, W.E. Kellum Seafood. 

A business that’s five generations in the making. 

A business that from the humble shores of the Northern Neck ships 100,000 gallons of shucked oysters, along with several thousand boxes of half shell oysters, to 34 states each year. 

A business that more than 100 watermen across rural coastal Virginia sell their harvests to and that, during the busiest season of the year, scales up to 60 employees on-site of their processing operations, from interns and administrative staff to oyster shuckers and shippers.

But ask him about the people who got them there? That’s when the pride comes out. 

Strong. Thick. And with a genteel dash of southern hospitality.

He’ll tell you about the team. The customers. And his bank. 

Chesapeake Bank. 

“My great grandfather was an oyster producer, and he owned a general store,” Kellum said. “He dealt with the bank at that time. Then in 1948 my grandfather established a line of credit with the bank.”

They’ve been customers ever since. 

More than customers, in fact, Kellum said. 

“After five generations it becomes not so much a bank, but a partner,” Kellum said. “They financed the start of the business. Then they financed the second generation taking over. Then they financed the third generation taking over. This is more than just a bank to us. We would not be here without this bank.”

You likely would never hear that story directly from Chesapeake Bank. They, like Kellum, are far too humble for that.

“We were told once that we whisper when we should shout,” said Jeff Szyperski, Chesapeake Bank chairman, president and CEO.

This year, the bank’s 125th anniversary, you might hear them shout a little more. 

Shouting about being one of the last-standing bastions of true community banks, and why that’s so important in today’s economy that relies heavily on the health of small businesses to power employment across the nation.

Shouting about the unintended case study for success Chesapeake Bank has as part of its history, showcasing why it’s not just the right thing to do, but it’s also good business, to invest in building up community assets beyond the walls of the bank.

Shouting about investing, and sometimes taking a risk, on its people—the team members themselves and the customers they serve. 

And shouting about the milestone itself. 

One hundred and twenty-five years is a long time to be in business, and as Szyperski said, the hard work of the bank’s people to get here is worth shouting about.

Building the Bank

Officially speaking, Chesapeake Bank formed in April 1900 as the first national bank on the Northern Neck, then known as Lancaster National Bank.

With a modest $25,000 in investments cobbled together by local citizens themselves, the bank got off the ground primarily to support the watermen, fishermen and oystermen who worked in the region. 

In its opening years, the bank expanded to serve farmers and other businesses, too. 

Farmers—of the land and the water—are among the most resilient people. They have to be. 

The bank learned early on it had to be, too. 

In 1917, a fire in the village of Irvington took down the Lancaster National Bank building. 

Not a problem. The bank’s officers improvised and set up a tent nearby to continue offering services. 

Chesapeake Bank, renamed in the 1960s after Lancaster National Bank merged with the Chesapeake Banking Company, would go on to survive many more metaphorical fires.

The Great Depression, perhaps the hardest period in U.S. banking history, when roughly 9,000 banks failed between 1930 and 1933.

The shocks of the 1970s and early 1980s, when banks struggled under the pressure of high inflation and low growth.

The savings and loan crisis of the 1980s and 1990s, which was largely considered the biggest banking collapse since the Great Depression until the 2008 housing bubble burst. 

Why Not?

If the founding of Chesapeake Bank was the first act, the leadership of Douglas “Doug” Monroe headlines the second.

Monroe joined Chesapeake Bank in 1964. Despite being a native New Yorker, he knew the area, having spent childhood summers on a farm in Irvington. 

Following his military service to the U.S. Navy and completion of school at Washington and Lee, Purdue and the Rutgers University Stonier Graduate School of Banking, Monroe joined the Wachovia Bank family in North Carolina. 

Chesapeake Bank, technically still Lancaster at the time, recruited him in 1964.  

“He knew Irvington, he loved Irvington,” Szyperski said. 

The total assets of the bank when Monroe joined the team were just under $4 million. 

“To give you an idea of his legacy, we’re at $1.6 billion now,” Szyperski said. “He was a real innovator, an entrepreneur caught in a banker’s body, and did a lot of forward-thinking stuff for a little bank.”

Under his leadership, the bank introduced many new banking initiatives, including the “Boat-n-Bank,” the nation’s first bank branch on a boat designed to serve the community’s watermen. 

“He was always looking for that next ‘permissible banking activity’ that could serve the community, as the banking vernacular goes,” Szyperski said. “He was always asking ‘why not?’ If you told him something couldn’t be done, he would find a way to do it. He saw it as a challenge.”

That mindset pushed him both at work and in service beyond the bank. 

Just read the biggest section in his 2023 obituary. 

Founding board member of Chesapeake Academy. Founding board member of Rappahannock Westminster-Canterbury and Virginia Quality Life, Inc., which focused the effort to establish a permanent campus for the Northern Neck YMCA, the Northern Neck-Middlesex Free Health Clinic, River Counties Chapter of the Red Cross and RGH Rehabilitation Services and Sports Medicine Center. Chairman of the Board of Rappahannock General Hospital. Recipient of the River Counties Chapter of the American Red Cross “Community Hero” award. 

It goes on and on. 

That “why not” mentality is woven through all that work, Szyperski said.

A feasibility study said the community was too small for a hospital. Monroe was part of a group that said we’re going to do it anyway and thus Rappahannock General Hospital was born. 

Another feasibility study said the community population wouldn’t support a long-term care community. Monroe was part of a group that built it anyway and today Rappahannock Westminster- Canterbury is the third-largest employer in the region. 

When Monroe moved to Irvington with his young family, the public schools said there were not enough books for his son. So Monroe and two other families started their own school, which today is Chesapeake Academy. 

Before Monroe got involved in philanthropy in the region, the biggest fundraiser to date in Lancaster County had raised $1.5 million. Efforts to raise funds to establish the Northern Neck YMCA came in at nearly $15 million. 

And Monroe, and Chesapeake Bank, was part of that, too.

Servant Leadership

By the late 1980s, Monroe knew he needed to start thinking about a succession plan. 

This presented Szyperski an opportunity to change careers from being a CPA and enter the changing banking industry.

Szyperski arrived in 1990.

Remember the note about resilience and the savings and loan crises of the 1990s? Szyperski arrived right in the middle of that. 

“That was a very difficult time for the bank,” Szyperski said. “I saw what bad looked like and knew early on we had to learn from that.” 

Admittedly, Szyperski had no formal banking experience before coming on. 

He spent the first five years as a student, on the job and in a classroom at the Graduate School of Banking at Louisiana State University. He won’t shout this fact, but he graduated first in his class there.

Szyperski started out in the loan administration department, the epicenter of all the problems of the 1990s, then moved into working in commercial lending and finally was named bank president in 2003.  

If Monroe was the innovator, Szyperski was the culture champion. 

“I Dare You to Care: Using Emotional Intelligence to Inspire, Influence, and Achieve Remarkable Growth” sits front and center on his office bookshelf. 

“When I came to the bank there wasn’t a real defined sense of culture,” Szyperski said, not as a criticism, more as a realization of how he could build on Monroe’s legacy. 

So Szyperski started looking at the bank’s people, working to find ways to help his team grow from within. 

Creating and cultivating culture is a slow drip, Szyperski said. It takes time. 

And it takes commitment to people, in- and outside of the bank.

Step two was building on the civic investment in community that Monroe laid the groundwork for. 

“The fact that people see us as a community leader makes people want to do business with us,” Szyperski said. “It’s good business to be a community leader. It’s not why we do it, but it does help.”

Combining that with the investment in people creates the secret sauce. 

“We have a dual mandate,” Szyperski said, to “provide a good solid return to our shareholders and support our communities. Those two can, and have to be, done at the same time. We cease to be a good community partner when we cease to be profitable to our shareholders. I love leading with civic, but not to the detriment of what’s fueling the engine. You have to give oxygen to the organization if you want the organization to produce.”

A Case for Community Banks

When Szyperski got into banking, there were about 15,990 banks across the county. Today there are about 4,600, primarily due to mergers. 

“Think about that,” Szyperski said. “Two-thirds of the industry has gone away since I’ve been a banker. And that’s continuing.”

Of the 4,600 banks in the country, 118 account for 85% of the assets in the banking system. The other 4,400 have the remaining 15%. Those are the community banks. 

“Yet that 15% accounts for 38% of all small business lending,” Szyperski said, citing Federal Reserve numbers. 

Why does that matter, especially in a rural community?

Because that’s who it hurts, he said. Rural communities. 

“Community banks are significant drivers of the American economy,” according to the American Bankers Association. “They are the biggest lenders to America’s agricultural community, and as small businesses themselves, they are particularly active in small business lending.”

Community banks, the American Bankers Association reported in 2024, hold more than $2.31 trillion in loans for local communities and more than $4.5 million small-dollar loans for business totaling nearly $325 billion. 

“It’s very important to have community banks in a rural community,” said William “Bill” Lee, who became a customer in 1973. Lee retired from a career with Verizon and currently is serving his fourth term as a member of the Lancaster County Board of Supervisors. 

“The top leaders of the bank understand the community, our community,” Lee said. “This community bank, Chesapeake Bank, is very important for the businesses in this area and keeping them going.”

The Kellum family experienced that firsthand, not just in the loans approved through Chesapeake Bank to finance the generational share of the business, but also through day-to-day operations.

There’s not an oyster industry credit and banking checklist, Kellum will tell you. 

“A specialized industry like our requires understanding,” Kellum said. Chesapeake Bank “knows what our business does, how it operates and can react to needs at a local level. They were able to lend us money based on their understanding of our industry. Without that they wouldn’t have been able to make informed decisions.”

One of the Cs of credit, Szyperski said, is character. 

“Banking regulation tries to drive you into cookie-cutter ways of approval,” Szyperski said. “But you can’t make everything a formula, especially when it involves small business. Community banks are good at judging character and making things happen, making people successful,” Szyperski said. 

Szyperski is as passionate about the power of community banks as he is the importance of culture within the walls of the bank. 

“Small business lending accounts for half of all new job creation in the U.S.,” he said. “If small business suffers, job creation in our country suffers. Job creation in our region suffers.”

Virginia is home to countless small businesses that Chesapeake Bank has bet on, helped cheerlead as they rode waves of success and supported when they needed a little extra help. 

Like Pete Henderson of Henderson, Inc. 

Based in Williamsburg, Virginia, Henderson calls his company simply “our family construction business.” And they are. A family construction business that builds some of the most iconic properties in Virginia, including roller coasters. 

“We have decades of work we’ve done together with Chesapeake Bank,” Henderson said. “What attracts us to Chesapeake and what attracts Chesapeake to us is similar values.”

Honesty, community and integrity being some of those. 

“It’s one thing to say you’re a community bank, but it’s another to actually act like a community bank,” Henderson said. “Chesapeake Bank has helped me during the good times and the bad times and the good times again.”

Or take Brent and Becky’s Bulbs, a Gloucester-based internationally acclaimed bulb supplier with endorsements from the likes of Martha Stewart herself.

“Every time I [go] into Chesapeake Bank they ask me is there anything we can do to serve you better,” Becky Heath said. “When I’ve had an idea, they try to accommodate.”

Like the time, decades ago, when she wanted to figure out how to wire money from her own desk. The big banks in town wouldn’t allow it. Chesapeake Bank helped find a way. 

“That’s when I realized what customer service really is,” Heath said. “They have just always bent over backwards to make things faster, easier. That’s important in business.”

Plus, “it’s just the best feeling to know that someone knows who you are when you walk in the door,” Heath said. “Really knows you.” 

The Bank Beyond the Anniversary

If Szyperski were to write the story of Chesapeake Bank, chances are there would be far less quotes from him in it. 

“Organizations that succeed are not the ones with the single visionary CEO,” Szyperski said. “The ones that succeed are the ones who have the right people on the bus.”

Or in the case of Chesapeake Bank, on the duck boat. 

The stories of those right people, sitting in the right seats, are what got Chesapeake Bank from 1900 to 2025, he said. 

“With the right people, you figure out where the bus needs to go,” he said. 

The thing about people, though, is that when Szyperski talks about them, he’s talking about his team. His shareholders. The residents in the community they serve. Customers. Business owners. 

“When I think about Chesapeake Bank, I think of the environment they have created in the community with people, with businesses, with nonprofit groups,” said Lee.

“It’s impressive how many resources they have poured into the community,” he said. “They play a big role in our community. That stands out more to me than anything.”

Chesapeake Bank, Lee said, “definitely goes beyond being just a bank.”

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To learn more about Chesapeake Bank, go to www.ches.bank.