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The banker and the artist, Jeff and Wende Szyperski, find relaxation and inspiration at their Rappahannock River home.
Photo by Corey Miller
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Photo by Corey Miller
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Photo by Corey Miller
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The Szyperskis love spending time with their two rescue dogsRocket (pictured here) and Bella.
Photo by Corey Miller
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Jeff and Wende, September 21, 1983
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John and Edith Szyperski
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The Szyperski family in London
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Jeff, Wende with their children and two daughters-in-law at the ABA Convention
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Jeff delivering a speech at the ABA Convention
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Jeff having fun at the ABA Convention
Jeff and Wende Szyperski are wired for this. Whatever “this” might be in their lives.
Jeff is Chairman, CEO and President of Chesapeake Bank and heads its affiliates, Chesapeake Financial Shares and Chesapeake Wealth Management. He’s guided the company to recognition by American Banker as one of the 200 top community banks for 12 straight years and as one of the best workplaces in the country for seven consecutive years.
Chesapeake Bank has $930 million in total assets in 15 branches across the Northern Neck, Middle Peninsula, Williamsburg and Richmond. It traces its community banking history back to 1900 when it was founded in Irvington as Lancaster National Bank to serve isolated farmers and watermen plying their trades on and along the shores, rivers and inlets of Chesapeake Bay.
He’s a supportive husband of his wife, Wende Szyperski, and her fine art business and they have four adult children. Jeff is also a highly respected CEO who is navigating turbulent banking waters marked by consolidation, closure and evolving customer relationships.
Jeff champions both local communities and small businesses and sees Chesapeake Bank in the middle of it all. “I think community banks are perfectly situated to be the incubators of small business,” he said recently in an interview in which he was joined by Wende on the breeze-infused waterfront porch of their Rappahannock River home that’s undergoing extensive renovations.
While Jeff keeps community and small business at the forefront of his vision for Chesapeake Bank, it doesn’t mean he’s not thinking of bigger things for his company or himself. He’s influential and respected on the state, national and global banking scenes as a former chairman of the Virginia Bankers Association (VBA) and with his election
last October as 2018-19 Chairman of the American Bankers Association (ABA). The ABA is a banking trade organization that represents banks of all sizes and touts itself as the “united voice of America’s banks.” It acts in the interest of banks through its government lobbying efforts, offers professional development to its members and establishes industry standards and best practices.
Through his service in the VBA and ABA, Jeff has met and discussed banking issues with world political and financial leaders. In March 2017, Jeff was with bankers who met with President Donald J. Trump in the Oval Office to discuss relaxing federal regulations so people can more easily get business loans and mortgages through their local banks.
This past spring, he met French President Emmanuel Macron while attending the International Monetary Conference in Paris. On a global banking stage, the man who runs Chesapeake
Bank from Kilmarnock can make banking small talk—and banking big talk for that matter—at conferences with the largest banks in the world whose leaders hail from Tokyo, London, Singapore, Dubai and New York City. “At the end of the day,” Jeff Szyperski says, “the big bank CEOs are really dealing with the same things we are, like the attraction and retention of good employees, regulations and cybersecurity.”
A self-described computer nerd with a passion for technology—he fondly remembers his first “game-changer” Mac for work circa 1985—Jeff Szyperski brings a focused energy and, well, levity, to his job. While he has the personal connection thing down and endears himself to all 240 Chesapeake Bank employees by knowing their names, he’s also a CEO who will make you laugh and shake your head. Especially when he tours Chesapeake Bank offices around Christmas in his garish “holiday suit” that’s a patchwork of Santa hats, snowflakes, snowmen, reindeer and the like.
The artist in the family
At home, Jeff knows his place. Which means he doesn’t get anywhere near a sketch pad or canvas. He leaves that to Wende, who is easily the more talented of the two, at least when it comes to art. “I can’t even draw a stick figure,”
Jeff says. Wende Szyperski says her husband is an encourager. Sometimes he encourages her to go to an art workshop. Other times he encourages her by saying he’ll take care of dinner and for her to take her time as she’s trying—often futilely she says as she describes her painting process—to put the finishing touches on one of her pieces of art.
For Wende, art is a creative outlet that keeps her connected to the places, people and things she loves. She likes to focus on simple things or ordinary moments that bring her joy. She’ll paint barns, deer, osprey, crabs, boats, water, fire hydrants or whatever catches her eye and heart. She describes her painting as a spiritual experience that feeds her. It requires a lot of quiet time and slowing down. “You can’t hear things well spiritually if you don’t have your quiet time,” Wende says.
Roots in entrepreneurship
Jeff has a genetic disposition to his business chops and entrepreneurial spirit, as well as his friendliness and sense of humor. His father, John Patrick Szyperski, was analytical,
but had a good sense of humor, as did his mother, Edith Szyperski, Jeff says.
His dad was bright and industrious, graduating from high school at 16 and college at 19 before entering the U.S. Navy and serving aboard the U.S.S. English, a destroyer escort, during World War II. John Szyperski served in the Navy from 1942 to 1958. In the Navy, he attended the Naval War College and earned a master’s in business administration from the University of Michigan.
After his Navy career, John Szyperski cemented his place in historical North Carolina business lore. Joined by business partner and fellow World War II veteran A.B.
Dusenbury, he opened the first McDonald’s in the Southeast in Greensboro, N.C., on September 30, 1959. The McDonald’s was at the intersection of Summit and Bessemer avenues and still stands today. McDonald’s had less than 500 stores nationwide then, and a burger went for 15 cents, fries were 10 cents and a chocolate or strawberry “milk shake” cost 20 cents.
John Szyperski and Dusenbury grew their franchise to more than 50 stores in Greensboro, Charlotte, High Point, Salisbury,
Durham and Raleigh. John Szyperski even graduated from the first class of Hamburger University in Chicago. John Szyperski died in 1999 at the age of 76, at the time married for 54 years to Edith, who died in 2011 at the age of 84.
Growing up in Greensboro as one of five Szyperski children, Jeff Szyperski liked tennis—one of his recent thrills was watching Roger Federer play at the French Open this year—and he enjoyed basketball, water skiing and snow skiing. In college at the University of North Carolina, he graduated in business and accounting.
Roots in the Northern Neck
Wende grew up in Lancaster County, living in White Stone and Irvington. She loved spending time with her four siblings exploring the local woods, waterways and neighborhoods— always on foot, bike, boat or horseback.
Jeff and Wende first met in high school at a dance. She attended St. Catherine’s School in Richmond and Jeff went to Woodberry Forest. Wende was two years behind Jeff at UNC, where she earned a bachelor’s in business administration. They dated in college and got married in 1985 when Jeff was a certified public accountant at a “Big 8” accounting firm in Raleigh. The Szyperskis loved Raleigh—“It still felt like a small town,” Wende says—but not so much Jeff’s job schedule because of the long hours.
Jeff recalls thinking, “There’s got to be something better than this.”
As it turned out, Wende had a line on a possible job in the banking industry. Doug Monroe, her father, was running Chesapeake Bank and was developing potential succession. Jeff decided it was worth a try.
“It was an opportunity,” Jeff says. “At the time I didn’t want to be a CPA for the rest of my life.”
Wende thought it would be a great place to raise a family.
In 1990, the Szyperskis and a young son made the move to the Northern Neck for Jeff’s job as assistant vice president of loan administration. There was just one little hitch.
“I was blissfully unaware I got into banking at the height of a recession,” Jeff says.
He learned tough lessons that would be valuable come ensuing recessions at the turn of the century in the dot com bubble burst and the Great Recession of the mid-aughts.
“We weren’t going to repeat mistakes of the past,” Jeff says. “We have had a relatively conservative posture on lending and didn’t participate in speculative lending.” He uses a baseball analogy to describe Chesapeake Bank’s mindset: “We never swing for the fence. We hit singles very well.”
Monroe helped Chesapeake enter into new services such as Chesapeake Payment Systems to help businesses nationwide process credit card payments. Jeff helped Chesapeake to further growth with some key employees. “It took a number of years for it to get profitable but now we’re profitable,” Jeff says.
A primary focus for Jeff in leading Chesapeake Bank is the company’s employees. He says he pays attention to employees, customers and shareholders, in that order. But employees are the critical link. He has an uncanny ability to put employees in places they’ll succeed.
“He can see the characteristics and the natural aptitudes they have that they would be really good at a position,” Wende says. “I’m always really amazed at that.” She turns to Jeff and says, “And then you’re good at coaching.”
Jeff sees good things ahead for Chesapeake Bank. He understands, especially from his own children, the “personless convenience” that’s come with the wired culture built around the Amazons, Googles, smartphones and online conveniences of today’s world.
While Jeff is in tune with the wired side of things, he knows employees are essential for success. “I’m optimistic,” Jeff says. “I think you’ll see community banks be able to accommodate that ‘personless convenience.’ People still need people at the end of the day. People are built for relationship.”
He notes that since he entered banking in 1990, the number of banks in the country has plummeted from about 15,500 to about 5,600 today. But Chesapeake Bank keeps expanding, most recently into Richmond.
“We’re one of the banks still standing,” he says. “And that’s a good place to be.”