It was 30 seconds. Thirty seconds that Kai Lenny was held underwater, 30 seconds that ticked by after he wiped out on a 50- foot monstrosity at Pe‘ahi, also known as Jaws, Maui’s infamous big-wave surf break. Moments before, the surfer bottom-turned into a barrel the size of a house—the biggest he’s ever ridden. Then it closed in on him, the weight of millions of tons of water pressing down on him.
“I got absolutely destroyed,” Kai recalls. “It’s like you’re watching a movie. You can’t save the character in the film. You can just sit there and watch from your seat. … But as I was underwater, I just couldn’t get out of my head the amazing view I had. Bar-none it was the happiest I’ve ever been when I came up, and I just wish I could experience it again soon.”
The 22-year-old, who excels at surf sports of all kinds (he’s a six-time standup paddle world champ, and is versed in kiteboarding, windsurfing, and foilboarding, among others), has an uncanny ability to see the good in all things. Recalling another massive wipeout at Jaws when he was dragged underwater for the length of two football fields and his foot was nearly cut in half after his surfboard fin tomahawked through his toes, he’s still stoked: “That was also a really good experience,” he says, “because I know I can survive it.”
Such positivity has defined Kai since he was a kid doing his best to make the most of every moment. His parents, Martin and Paula, are avid windsurfers from California. The couple, who vacationed on Maui decades ago and never left, made a pact that they would not change their lifestyles after Kai and his younger brother, Ridge, were born. “We would go to the beach every chance we could,” Kai’s father, Martin, says. “[Kai] was kinda doomed. … We had a little crib in the van that we’d put out on the beach. Then we’d go surfing, and then later in the afternoon, it’d get windy, so we’d go windsurfing.”
The young Kai reasoned he could either sit on the beach and “get sandblasted,” or he could go out into the water. So he paddled out, and at 4 years old caught his first wave with the longboard his parents had left for him on the beach. This was on a small inside break at a spot called Thousand Peaks on Maui’s west shore. “Down the beach, I saw this little perfect wave,” he recalls. “I just remember dropping in for what felt like forever. … It was probably pretty small, like ankle-high, but it felt like it was a huge drop—I mean at 4 years old, you’re not even three feet tall—and I knew exactly what I wanted to do with the rest of my life.”
Since then, Kai has done just that, exploding onto the crossover boardsports scene with unparalleled dynamism. The multi-dimensional athlete, who’s been sponsored by Maui-based surf company Naish since he was 9 and Red Bull since he was 11, has been around the world and back. Standup paddling has taken him across a lake in Germany, through rapids in Colorado, and down the face of perfect waves in Fiji. He bet his kiteboard could win against a $15 million dollar yacht, racing Oracle Team USA down the San Francisco Bay. He even scaled mountains in Patagonia with Navy SEALs, crossing glacial lakes and clearing crevasses, in order to push the limits of his training.
But it’s Hawai‘i he returns to. “It’s the one place where I can really breathe,” says Kai, who, even as he says this, is preparing for trips to Bermuda, Japan, and Oregon for competitions and training. Despite his busy schedule, Kai makes time for the foundation he created in 2015, Positively Kai, which provides grants to nonprofits for improving ocean awareness and youth development. “The purpose is to really open kids’ minds to their potential future, and to show them that they can make anything of their life,” Kai says. “It’s not necessarily about becoming a professional surfer, it’s teaching kids life lessons through surfing—and the ocean will teach you all life lessons.”
Just one day after placing second overall in the Moloka‘i 2 O‘ahu Paddleboard World Championships—a grueling 32- mile channel crossing considered one of the world’s most prestigious paddleboard races—Kai was back in the water to host an ocean-safety surf clinic with Duane DeSoto’s nonprofit, Nā Kama Kai, which empowers youth through ocean-based programs. He also donated $10,000 to it.
Like the kids who partook in the clinic, Kai sees himself as a perpetual student, even as a seasoned pro. “The time you stop getting better at something is when you forget how to learn,” Kai says. “I’m just going to keep putting my paddle in front of me. I’m going to try and get closer to that island. There’s no better feeling than when you’re coming into the home stretch and you’re like, I made it. Or, I’m making it.”