Master of the Oceans: Kai Lenny

Kai Lenny is a watersports prodigy. Big wave surfing, windsurfing, kite surfing, stand-up paddling – he’s one of the best in the world in each of these disciplines. But in 2020, even the wunderkind of the waves had to reinvent himself.
Text Christine Yu
Photo Fred Pompermayer

Kai Lenny says he’s searching for pure entertainment. But since the pandemic scratched his plans for 2020, he’s had to settle for adventure closer at hand. Yes, it took a global pandemic to finally slow Kai Lenny down.

Even just talking on the phone, his infectious energy pours across the line and you know that he doesn’t like to sit still. After all, this is the same guy whose parents used to take him to the beach every day as a toddler to tire him out so he would sleep through the night. He’s used to jetting off on a plane every week or two. “It’s the longest stretch I’ve been home probably since I was twelve or something,” he says.

That’s how he ended up sailing across the Kauai Channel on a foiling catamaran with two-time World Surf League champion John John Florence in July. “We were just on the phone talking, like, ‘Hey, we should do something fun. What if we sailed your foiling boat from Oahu to Kauai? Let’s do it!’” Lenny says.

A week later they pushed off from Oahu on Florence’s Flying Phantom. It looks like a spaceship; the foil extends down from the bright-red hulls, lifting up the boat and allowing it to rocket across the surface of the water. Lenny and Florence dangled off the side somewhat precariously. Nine hours later they arrived in Hanalei, Kauai. When asked about the crossing, Lenny says in his trademark stoked tone, “It was so much fun.”

But it was more than just the challenge of crossing the channel that excited Lenny. It was the spontaneity of it all. Normally it would take a year or more to pull off something like this.

But it was more than just the challenge of crossing the channel that excited Lenny. It was the spontaneity of it all. Normally it would take a year or more to pull off something like this. Lenny and Florence (and their people) would have to coordinate their schedules. Between contests, sponsorship obligations and other projects, the chances of finding an overlapping day or two when they’d both be home in Hawaii would be nearly impossible, not to mention a lot of hassle. But with both of their lives on hold, Lenny and Florence are free to do whatever they want in the interim.

This spontaneity is a major contrast to how Lenny typically leads his meticulously focused life chasing big projects and big goals. “He has this incredible can-do attitude – I can do that, I’m going to do that – when everyone is like, ‘You’re crazy, man. You’re out of your mind,’” says Johnny Decesare, founder of Poor Boyz Productions, who’s been filming the watersports prodigy since he was eleven years old.

“We were just on the phone talking, like, ‘Hey, we should do something fun. What if we sailed your foiling boat from Oahu to Kauai? Let’s do it!’”

Kai Lenny

And Lenny had ambitious plans for 2020: travel with his friends to chase gigantic waves on every big swell around the world, while also giving it his all on the competitive circuit. “Literally, as soon as I really committed to it, it was like the whole world came to a standstill,” he says.

While his goals are on hold (for now), his latest project, Life of Kai, which launches in November, offers a glimpse at some of the innovative and mind-boggling things the pro athlete has been up to and is capable of. His other web series, Positively Kai and 20@20, which debuted this summer, highlight Lenny’s fun adventures and insane, physics-defying antics at home and abroad. Life of Kai, on the other hand, delves into what it really takes to be Kai Lenny.

Credit: Brian Bielmann

“Literally, as soon as I really committed to it, it was like the whole world came to a standstill.”

Kai Lenny

“I think people see a general vision of most pro athletes, myself included, that you just go out and do this,” Lenny says. “I really wanted to capture what I have to go through – the good, the bad, the tough moments, everything that leads me to my best times, whether on top of the podium or riding the biggest wave of my life.” He wants to inspire people, too. “How much dedication are you willing to put toward something and how much passion is fueling that fire? That unrelenting determination has been the magic behind me. Hopefully, I inspire kids to follow their passion and think, ‘If he can do it, I can do it,’” he says.

The series was shot in the fall and winter of 2019/2020 and follows Lenny through an abbreviated big-wave season. Sure, you get to see how Lenny preps his body and mind to surf massive conditions (and survive mighty wipeouts) at surf survival training camp and how he puts those tools into action as he competes in the Jaws Big Wave Championships in December and the Nazaré Tow Surfing Challenge in February. But the series also gives you a better sense of who Lenny is and his approach – as someone who’s constantly learning, innovating and is always ten steps ahead of everyone else. You’ll see how he adapts to different situations, whether it’s equipment or technology failures or fickle weather systems and how he refines his surfboards and hydrofoils. Life of Kai really is just the life of Kai.

Credit: Fred Pompermayer

"Hopefully, I inspire kids to follow their passion and think, ‘If he can do it, I can do it,’”

Kai Lenny

By now you probably know the story. Kai Lenny is the wunderkind whose parents moved to Maui to windsurf. He was a prodigious young windsurfer himself – a tiny kid flying high above the waves at Hookipa Beach Park who used to sew mini sails and kites during circle time at his Montessori school. His mentors include Laird Hamilton, Dave Kalama, Robby Naish and other famous pioneers who were literally inventing new ocean sports in his backyard. It rubbed off on Lenny. He’s a stand-up paddle world champion many times over (winning his first title at age eighteen), winner of the grueling Molokai 2 Oahu Paddleboard World Championships and one of the most dominant wind and kitesurfers in the world. Yes, he surfs, too. He’s a fearless big-wave rider who can also kick some impressive aerials on a shortboard.

Lenny isn’t just a good athlete. He’s a gifted waterman. He has a keen vision of the ocean and looks at it differently than most people. “He sees the sea surface and what’s under the sea surface and uses that energy,” says Decesare. In big waves, Decesare says that Lenny’s mind is like a calculator, putting aside fear to work out different variables and factors. This gives him the confidence to perform in conditions that would make normal humans blanch.

It took a while for Lenny to gain the respect of his peers and it was his big wave surfing that helped him prove himself. Lenny has surfed the massive waves at Peahi, the famed Maui break also known as Jaws, on every type of board since he was sixteen years old. He’s able to perform so well precisely because of his windsurfing and kitesurfing background. People started to take notice, especially as Lenny began to focus more on surfing.

Read the whole story about Kai Lenny in rampstyle #21


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