Downtime: Kiteboarding pulls Richmond businessmen together

Bruce Vanderbilt catches air on one of the Richmond group’s kiteboarding excursions. (Photos courtesy of Bruce Vanderbilt and Graham Gardner)

When Bruce Vanderbilt was in the midst of a multiyear sailing trip in the Caribbean, the local real estate investor didn’t expect to meet a fellow Richmonder along the way, let alone the future friend who’d bring him into a fraternity of kiteboarders.

Vanderbilt had just started taking lessons on how to kitesurf when he met Casey Cockerham, co-founder of Richmond rock climbing gym Peak Experiences, on a beach in the Grenadines.

An accomplished kiteboarder and adventure sports enthusiast, Cockerham showed Vanderbilt some air lifts and tricks before the two parted ways, and Vanderbilt was hooked.

“I got really into kiting at that point and became addicted. My entire sailing trip became kite destinations,” Vanderbilt said.

Vanderbilt picked up kiteboarding while on a yearslong sailing trip in the Caribbean.

Years later, the two ran into each other again at New Point Comfort, off Virginia’s Mathews County coast, and finally connected in Richmond, where Cockerham introduced him to Graham Gardner and Jeff Friend, two dental practitioners who have been kiting with Cockerham for years.

Soon enough, the four of them became a kiteboarding foursome, going on sporadic outings together and making regular trips to such kiteboarding hotspots as Cape Charles, Mathews County and North Carolina’s Outer Banks, where they do a “boys’ week” every year at Hatteras.

As Vanderbilt put it: “They let me into their crew.”

Gardner, an orthodontist at Gardner & La Rochelle Orthodontics, and Friend, a dentist at RVA Dental Care, had been going on adventures with Cockerham for years. Graham met him while he was in dental school in the mid-1990s, when Cockerham’s adventure sport of choice was kayaking.

“The A-team,” from left, Graham Gardner, Bruce Vanderbilt, Casey Cockerham and Jeff Friend.

“We started kayaking together, and I went off to do my orthodontics residency in New York for a couple years. I kept in touch with him and said, ‘I’m coming back to Richmond, and when I do, we’re going to start kayaking all the time,’” Gardner recalled.

“I get back in town and I’m like, ‘Alright, let’s go kayaking.’ And they’re saying, ‘Oh, we don’t really kayak as much anymore. We go kiteboarding.’”

Apprehensive at first, as the sport was new then and the gear not as safe as it is now, Gardner eventually gave it a go.

“I finally tried it and of course was immediately hooked,” he said. So hooked that he’s gotten his own place at Hatteras, after years of renting houses on their trips.

“I finally tried it and of course was immediately hooked,” said Gardner.

But the crew isn’t resigned to pre-planned annual trips. With Cockerham, they said, they’ve got to be ready to roll on short notice — or as Gardner put it, “chase wind.”

“Casey is constantly watching the wind,” Gardner said. “He knows exactly where it’s really good and where it’s going to be good. We don’t even watch the wind anymore because we don’t need to. It’s like we have an instant weather report coming to us.”

Gardner hanging loose.

Added Vanderbilt: “It’s like, get in the car at 3:30, 4 a.m., to be at the spot somewhere four hours away at the right time, to hike through a marsh. It’s all about strong, clean, consistent wind. It’s just a lot better for big jumps and a lot less risky.”

Unlike windsurfing, where a sail propels a surfer across the water, kiteboarding involves being pulled by a kite that’s attached to the rider via a harness. Kiters can skim across the water or get big-air jumps and perform tricks – a type of kiteboarding known as “freeride” or “freestyle.”

Other types of kiting include wave surfing or kitesurfing, where water is flat and can be shallow, and foil kiting, where a hydrofoil under the board lifts the rider above the water surface.

All in their 50s, the crew have each picked up their preferred kiting types, with Cockerham going big in freeride and freestyle, Friend preferring foil kiting, and Vanderbilt and Gardner falling somewhere in between.

“There’s more power in that kite than like a 400-horsepower wakeboard boat,” said Vanderbilt, whose Richmond real estate holdings include the Ironclad Coffee building and Gallery5. “It’s an insane amount of power, and to be able to harness that is really an incredible feeling.”

Added Cockerham: “Graham and Bruce and I, we process dopamine a little different than I would say the average person does. We need our adrenaline fixes. Jeff doesn’t fit in that category; he’s much more rational and probably a bit more reasonable. He likes to live vicariously through us, and he’s still very good.”

Friend described his more cautious approach as correlating with his and Gardner’s day jobs working with teeth.

Gardner, left, and Friend on a moonlight ride.

“What G and I do is very different, but they’re pretty exacting. They’re little, teeny-tiny projects, very tedious, and it has to be done extraordinarily well, consistently, over and over again,” Friend said. “Kiteboarding is very specific too. You have to be able to do it well.”

Friend added, “I’m more risk-averse than these guys kiteboarding. I’m also probably more risk-averse than these guys in my performance at work as well. I’m pretty conservative in the things that I do. I think in some ways, if you love to be very detail-oriented and particular about things, kiteboarding is a good sport for you.”

Details are also what drives the rest of the crew, who use a kiteboarding platform called Woo to monitor their jump heights, angles and other details. The technology allows them to compare their performances to fellow kiteboarders around the world who use the same platform.

“I like the competition aspect of it,” Cockerham said. “You’re able to compete against 37,000 people around the world. Every day, everybody who is kiting that uses the Woo posts their stuff, and you get to see where you stand. I’ve got quite a few of the highest jumps in the world for that day, and consistently I’ve had 15 this year that were the highest jumps in the country. I like that aspect.”

While many kiteboarders are younger than them, the crew said most are about their age and some are years or even decades older, indicating the sport’s accessibility and advancement.

“We go with guys that are in their 60s and 70s. There was a guy in Hatteras, he was 91 taking his first lesson in kiteboarding,” Gardner said. “You can actually go out there and just ride it and have fun. There’s definitely a lot of younger people, but there’s also a lot of people that just like to go out and ride.”

“When I tell people I kiteboard, one of the things that they say is, ‘You must be so strong to hold a kite down.’ But the funny thing is you don’t really have to be very strong. It’s all your weight and a harness,” Gardner said.

“That’s why guys our age can do it,” Vanderbilt added, referring to the gear. “To jump, you have to have core strength.”

“It’s an insane amount of power, and to be able to harness that is really an incredible feeling.”

While they’ve met and often kite with many other kiters, Friend said their crew has become something special.

“We’ve all kited with a lot of people, but I think the four of us have depended a lot on each other in bad situations: lost boards, got launched, or kites out of control. I know with this crew that I’m in good hands,” Friend said. “This is definitely the A-team.”

For Cockerham, who has tailored his work life around being able to catch wind at a moment’s notice, the crew has resulted in solid friendships.

“The three of us have known each other for a long time, and Bruce has been the perfect addition to our crew,” he said. “There are a lot of kiters in Richmond, great people that we periodically kite with, but we’re the crew that we choose. It’s special.”

“We’ve all kited with a lot of people, but I think the four of us have depended a lot on each other in bad situations.”

Added Gardner: “Casey has set up his job in a way that if the wind is blowing, he can actually take advantage of it. He has done this on purpose.”

For Gardner, whose out-of-office pursuits include writing children’s books, the act of “chasing wind” and pursuing various interests are all about living life to the fullest.

“I just want to experience every part of life I possibly can,” he said. “I’m all about experiences, and I feel like someday I’m going to be in an old folks’ home and I’m not going to remember anything except a bunch of the cool things I did, and have my books to look at and go, ‘Really, I did that?’

The four friends on a pandemic-era outing.

“I’ve also had several people I’ve known that died, like, right after they retired,” he said. “They retired and died. I don’t want to retire and die. I certainly want to enjoy the journey. I want to experience as much of life as I can.”

This is the latest installment in our Downtime series, which focuses on business people’s pursuits outside of the office. If you, a coworker or someone you know around town has a unique way of passing time off the clock, submit suggestions to [email protected] For previous installments of Downtime, click here.

Bruce Vanderbilt catches air on one of the Richmond group’s kiteboarding excursions. (Photos courtesy of Bruce Vanderbilt and Graham Gardner)

When Bruce Vanderbilt was in the midst of a multiyear sailing trip in the Caribbean, the local real estate investor didn’t expect to meet a fellow Richmonder along the way, let alone the future friend who’d bring him into a fraternity of kiteboarders.

Vanderbilt had just started taking lessons on how to kitesurf when he met Casey Cockerham, co-founder of Richmond rock climbing gym Peak Experiences, on a beach in the Grenadines.

An accomplished kiteboarder and adventure sports enthusiast, Cockerham showed Vanderbilt some air lifts and tricks before the two parted ways, and Vanderbilt was hooked.

“I got really into kiting at that point and became addicted. My entire sailing trip became kite destinations,” Vanderbilt said.

Vanderbilt picked up kiteboarding while on a yearslong sailing trip in the Caribbean.

Years later, the two ran into each other again at New Point Comfort, off Virginia’s Mathews County coast, and finally connected in Richmond, where Cockerham introduced him to Graham Gardner and Jeff Friend, two dental practitioners who have been kiting with Cockerham for years.

Soon enough, the four of them became a kiteboarding foursome, going on sporadic outings together and making regular trips to such kiteboarding hotspots as Cape Charles, Mathews County and North Carolina’s Outer Banks, where they do a “boys’ week” every year at Hatteras.

As Vanderbilt put it: “They let me into their crew.”

Gardner, an orthodontist at Gardner & La Rochelle Orthodontics, and Friend, a dentist at RVA Dental Care, had been going on adventures with Cockerham for years. Graham met him while he was in dental school in the mid-1990s, when Cockerham’s adventure sport of choice was kayaking.

“The A-team,” from left, Graham Gardner, Bruce Vanderbilt, Casey Cockerham and Jeff Friend.

“We started kayaking together, and I went off to do my orthodontics residency in New York for a couple years. I kept in touch with him and said, ‘I’m coming back to Richmond, and when I do, we’re going to start kayaking all the time,’” Gardner recalled.

“I get back in town and I’m like, ‘Alright, let’s go kayaking.’ And they’re saying, ‘Oh, we don’t really kayak as much anymore. We go kiteboarding.’”

Apprehensive at first, as the sport was new then and the gear not as safe as it is now, Gardner eventually gave it a go.

“I finally tried it and of course was immediately hooked,” he said. So hooked that he’s gotten his own place at Hatteras, after years of renting houses on their trips.

“I finally tried it and of course was immediately hooked,” said Gardner.

But the crew isn’t resigned to pre-planned annual trips. With Cockerham, they said, they’ve got to be ready to roll on short notice — or as Gardner put it, “chase wind.”

“Casey is constantly watching the wind,” Gardner said. “He knows exactly where it’s really good and where it’s going to be good. We don’t even watch the wind anymore because we don’t need to. It’s like we have an instant weather report coming to us.”

Gardner hanging loose.

Added Vanderbilt: “It’s like, get in the car at 3:30, 4 a.m., to be at the spot somewhere four hours away at the right time, to hike through a marsh. It’s all about strong, clean, consistent wind. It’s just a lot better for big jumps and a lot less risky.”

Unlike windsurfing, where a sail propels a surfer across the water, kiteboarding involves being pulled by a kite that’s attached to the rider via a harness. Kiters can skim across the water or get big-air jumps and perform tricks – a type of kiteboarding known as “freeride” or “freestyle.”

Other types of kiting include wave surfing or kitesurfing, where water is flat and can be shallow, and foil kiting, where a hydrofoil under the board lifts the rider above the water surface.

All in their 50s, the crew have each picked up their preferred kiting types, with Cockerham going big in freeride and freestyle, Friend preferring foil kiting, and Vanderbilt and Gardner falling somewhere in between.

“There’s more power in that kite than like a 400-horsepower wakeboard boat,” said Vanderbilt, whose Richmond real estate holdings include the Ironclad Coffee building and Gallery5. “It’s an insane amount of power, and to be able to harness that is really an incredible feeling.”

Added Cockerham: “Graham and Bruce and I, we process dopamine a little different than I would say the average person does. We need our adrenaline fixes. Jeff doesn’t fit in that category; he’s much more rational and probably a bit more reasonable. He likes to live vicariously through us, and he’s still very good.”

Friend described his more cautious approach as correlating with his and Gardner’s day jobs working with teeth.

Gardner, left, and Friend on a moonlight ride.

“What G and I do is very different, but they’re pretty exacting. They’re little, teeny-tiny projects, very tedious, and it has to be done extraordinarily well, consistently, over and over again,” Friend said. “Kiteboarding is very specific too. You have to be able to do it well.”

Friend added, “I’m more risk-averse than these guys kiteboarding. I’m also probably more risk-averse than these guys in my performance at work as well. I’m pretty conservative in the things that I do. I think in some ways, if you love to be very detail-oriented and particular about things, kiteboarding is a good sport for you.”

Details are also what drives the rest of the crew, who use a kiteboarding platform called Woo to monitor their jump heights, angles and other details. The technology allows them to compare their performances to fellow kiteboarders around the world who use the same platform.

“I like the competition aspect of it,” Cockerham said. “You’re able to compete against 37,000 people around the world. Every day, everybody who is kiting that uses the Woo posts their stuff, and you get to see where you stand. I’ve got quite a few of the highest jumps in the world for that day, and consistently I’ve had 15 this year that were the highest jumps in the country. I like that aspect.”

While many kiteboarders are younger than them, the crew said most are about their age and some are years or even decades older, indicating the sport’s accessibility and advancement.

“We go with guys that are in their 60s and 70s. There was a guy in Hatteras, he was 91 taking his first lesson in kiteboarding,” Gardner said. “You can actually go out there and just ride it and have fun. There’s definitely a lot of younger people, but there’s also a lot of people that just like to go out and ride.”

“When I tell people I kiteboard, one of the things that they say is, ‘You must be so strong to hold a kite down.’ But the funny thing is you don’t really have to be very strong. It’s all your weight and a harness,” Gardner said.

“That’s why guys our age can do it,” Vanderbilt added, referring to the gear. “To jump, you have to have core strength.”

“It’s an insane amount of power, and to be able to harness that is really an incredible feeling.”

While they’ve met and often kite with many other kiters, Friend said their crew has become something special.

“We’ve all kited with a lot of people, but I think the four of us have depended a lot on each other in bad situations: lost boards, got launched, or kites out of control. I know with this crew that I’m in good hands,” Friend said. “This is definitely the A-team.”

For Cockerham, who has tailored his work life around being able to catch wind at a moment’s notice, the crew has resulted in solid friendships.

“The three of us have known each other for a long time, and Bruce has been the perfect addition to our crew,” he said. “There are a lot of kiters in Richmond, great people that we periodically kite with, but we’re the crew that we choose. It’s special.”

“We’ve all kited with a lot of people, but I think the four of us have depended a lot on each other in bad situations.”

Added Gardner: “Casey has set up his job in a way that if the wind is blowing, he can actually take advantage of it. He has done this on purpose.”

For Gardner, whose out-of-office pursuits include writing children’s books, the act of “chasing wind” and pursuing various interests are all about living life to the fullest.

“I just want to experience every part of life I possibly can,” he said. “I’m all about experiences, and I feel like someday I’m going to be in an old folks’ home and I’m not going to remember anything except a bunch of the cool things I did, and have my books to look at and go, ‘Really, I did that?’

The four friends on a pandemic-era outing.

“I’ve also had several people I’ve known that died, like, right after they retired,” he said. “They retired and died. I don’t want to retire and die. I certainly want to enjoy the journey. I want to experience as much of life as I can.”

This is the latest installment in our Downtime series, which focuses on business people’s pursuits outside of the office. If you, a coworker or someone you know around town has a unique way of passing time off the clock, submit suggestions to [email protected] For previous installments of Downtime, click here.

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