Colin Field is an outdoor adventure photographer, writer and editor, based near Collingwood, Ontario.

Blast From the Past: Kai Lenny

Back in my days as associate editor at Windsport magazine I was fortunate enough to interview a young windsurfer by the name of Kai Lenny. He was just a grom at the time, but it was clear big things were in store. And if you’ve seen any of the Positively Kai episodes you know he’s now one of the world’s best watermen. Here’s a story I wrote about a little kid with a dream back in 2004.
Photos by Julia Schweiger.

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Being a waterman takes an open mind and a variety of skill sets. With worlds of wisdom gained through years of experience, the term waterman usually applies to guys who have been around for years. The obvious names are Laird Hamilton, Robby Naish and Dave Kalama.

So, learning that 12-year-old Kai Lenny’s website is hawaiianwaterman.com, one can’t help but think that maybe Lenny is jumping the gun a bit. That is until you see shots of him airborne on a windsurfer, perched atop a foil board, or tow-surfing double-overhead waves. The boy’s got skills. And considering that his middle name is actually Waterman (his great-grandmother’s last name), the title of his website is spot on. So the next time you hear the term waterman, try not thinking about the old guys. Think about the next generation.

Lenny started windsurfing at the age of six but says he “got serious about it” when he was eight.

“In the beginning it was hard because the gear wasn’t made for my size yet,” he says. “At first my sail was a piece of sail material with a sleeve sewed on and a clew hole. Then the kids’ sails got way better. They started making them like grown-up sails but lighter.”

Through his Naish sponsorship and his friendship with Naish team manager Michi Schweiger, Lenny has not only watched kids’ gear improve, he’s helped influence the movement.

“Kai has done a lot for the development of kids’ gear. He basically gives the main part of the input,” says Schweiger. “Together with him, we had the chance to figure out stance distances, board sizes, board shapes and rigs. This gear gives kids a chance to experience the sport and get better.”

Counting the obvious watermen—Hamilton, Naish, Kalama—and others as friends of the family has been a huge influence on Lenny. And with a father whose goal is to get on the water every day, a mother who loves to participate, and a younger brother nipping at his heels, one can’t help but feel a tinge of jealousy at such a childhood.

“One of my friends jokes that when he dies he wants to come back as one of my kids,” says Kai’s father, Martin Lenny.

While the future is always uncertain, Kai’s is wide open. The open-mindedness that his role models have displayed has given the grom a positive outlook on life. And his willingness to try new things means his skill sets will continue to grow.

“He already displays the versatility that part of our own generation missed out on,” says Schweiger. “There are certain conditions where you can do things other than windsurfing, like surfing, tow-surfing, paddle-boarding. A while ago it was, ‘I’m a windsurfer’ [or] ‘I’m a surfer.’ This trend definitely goes away from that. For that reason I would say that he is a young waterman—he feels comfortable in all environments, and, most importantly, he has fun with
whatever he does.”

While the average American kid can only dream about the life Kai is leading, he realizes he’s lucky to live on Maui, surrounded by some of the greatest watermen of all time. And when he isn’t on the water, he manages to keep himself busy.

“I work on making movies, and I design sails and kites with old pieces of sail material and kite material,” Kai says. “I like to windskate and skateboard, and I like to watch surf and windsurf movies.”

With Kai’s image appearing more frequently in the watersports media, he is becoming not only a role model to the younger generation but an influence on parents as well. The new kids’ gear makes it easier than ever for parents to share the stoke with their children.

Kai’s example shows that windsurfing is a healthy and positive addiction. And when asked about advice for kids his age, Kai shows all the
wisdom of a veteran waterman.
“Go out there and have fun,” he advises. “And don’t give up.”

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