The thrill of the ride
Kai Lenny, on break at home on Maui, can’t stay away from his office: the ocean
Maui’s Kai Lenny talks about his love for the ocean and his new passion for filmmaking
PAIA, MAUI >> It was Maui’s first south swell in two months, and Kai Lenny was loading the back of his matteblack 2017 Ford Raptor pickup truck with an assortment of ocean gear: longboards, short boards and even shorter boards with hydrofoil attachments.
“Every morning I wake up, it’s really boring if I’m not committed to going in the water,” said Lenny, who at age 24 has mastered a range of ocean sports like nobody before him.
“I mean it’s boring in the sense that I’d rather be in the water than on land. The only time I’m on land is to drive somewhere.”
On the last day of August, with West Maui reporting waist-high swells, Lenny was driving to Mala at the north end of Lahaina.
Enjoying a rare 11-day break at home in Paia, he was sitting atop the standings in the Association of Paddlesurf
Professionals World Tour and the World Surf League’s Big Wave Tour. He captured his biggest prize purse — $25,000 — with a stunning win at Puerto Escondido, Mexico, in July. It was his first competition on the big-wave circuit, adding to his list of accomplishments in windsurfing, kiteboarding and stand-up paddleboarding. Lenny said he gambled on the event, as it meant he would not be in Hawaii to defend his record-breaking SUP performance in last year’s 32-mile Molokai-2Oahu Paddleboard World Championships. “There’s always a sacrifice, but I think it was cool that I was able to win something I hadn’t done yet,” he said. “I try not to let others dictate what I do and just follow my passion and what I’m doing at the time.”
AS LENNY’S big truck sailed through Maui’s central isthmus, past acres of fallow sugar cane fields turned brown and brittle, he was eager to talk about perhaps the only activity that can keep him on land for any length of time: filmmaking.
This week brings the premiere of “Paradigm Lost,” a surf film he directed and produced with Johnny DeCesare. The hourlong movie debuts Friday at the Maui Arts & Cultural Center’s Castle Theater, followed by a screening Saturday at Turtle Bay Resort on Oahu. Lenny will be present for both. “I like the idea of how film can make you so inspired to do something. If you’re feeling tired and lazy, you can put on any movie and it stokes a fire within,” he said. “And I like storytelling.” The story Lenny tells in “Paradigm Lost” shows John John Florence, Kelly Slater, Clyde Aikau, Robby Naish and other top-flight watermen, including Lenny and his 20-year-old brother, Ridge, in action and philosophizing about what they do. “It’s a pretty simple message: What makes a surfer? Is it defined by the way you ride waves or what you ride? In this case it’s how you ride waves and not letting your equipment define you,” Lenny said.
RAISED BY ocean-loving parents on Maui’s north shore — the cradle of modern water sports and home to renowned windsurfing sites such as Kanaha and Hookipa and the monster Peahi surf break known as Jaws — Lenny was surfing at 4 and first came to notice as a windsurfing prodigy.
At age 9 he wrote to Naish, the sport’s godfather, seeking sponsorship. Naish offered support in exchange for a promise of good school grades and became one of Lenny’s mentors.
His coming of age coincided with the evolution of more extreme ocean sports such as kiteboarding and tow-in surfing and the explosion of stand-up paddling. “There’s always something I can be doing at a very high level,” Lenny said. “In the summer I can do downthe-coast runs on a canoe, paddleboard or kite- and windsurfing. In the wintertime when it gets big, all the outer reefs are breaking,” he said of the windward sites that lie just across the street from his childhood and current homes. “It’s like my own private area.”
WINDING along the pali section of Honoapiilani Highway, Lenny revealed that his biggest training issue is taking a step back to recuperate between grueling events. “After a giant race or surfing big waves, when I’m having a forcible rest day, a lot of times I can’t help myself and I’ll be working on equipment and getting things prepped for next session,” he said. The conversation stopped when the surf break known as Thousand Peaks came into view.
“Oh my gosh, there’s so much swell! I haven’t seen it like this in so long. This is insane. Whaaaat? That’s like the perfect foil wave.” Resisting the temptation to stop, Lenny continued toward Mala.
“A lot of times it’s just trying to make it through those days. You get so used to an adrenalin high and being on the edge of things that as soon as I’m not, it’s kind of difficult. It’s almost depressing.”
Forty-five minutes after leaving his house, Lenny steered his truck into a tight spot in the crowded dirt lot at Mala. His mother, Paula, a physician, and his girlfriend, Molly Payne, were waiting for him.
Lenny and Payne, whose older brother is professional surfer Dusty Payne, have been dating for three years. A slender blonde and confident surfer in her own right, Molly Payne designs the alola (“a life of leading adventure”) line of clutches sold at Sand People and other boutiques. “Typically in the job I do, it’s hard to have a girlfriend with all the traveling,” Lenny said. “But she’s grown up with a brother who’s a pro surfer and a family that’s all about surfing, so she really gets it.” The trio joined a dozen or so other surfers in the Mala lineup. Lenny carefully chose his waves, happy to share and shredding the long, rolling faces when it was his turn. Afterward the Lenny caravan headed back toward Thousand Peaks, but not before stopping for lunch at the roadside Leoda’s Kitchen and Pie Shop in Olowalu.
Then it was on to Ukumehame for a foiling session. “Oh, yeah, look at that. It’s pumping,” Lenny said as he pulled off the highway.
ASKED if he had to pick one sport above the others, Lenny replied it would be like choosing which finger to cut off: “They all serve a purpose.”
“I consider all the sports I do not so much sports, but disciplines of surfing. My favorite thing in the world to do is ride waves. So at the end of the day, I just wanna ride waves; it’s the equipment for the conditions that defines what I’m going to do.”
He compared it to ice cream: “Some people like chocolate more than they like strawberry. It’s the same with surfing. I just happen to like all the flavors.” Lenny might not want to name a favorite, but it was obvious hydrofoiling — on a kiteboard, surfboard or SUP board — is his flavor of the moment.
At Ukumehame, Lenny pulled a 44-inch Naish foilboard from the back of his truck and attached a 3-footlong wing assembly before heading out far left of the lineup. He picked a small, formless bump and took off, rising above the surface, gliding like a magic carpet. Lenny was still standing when the ride ended and he pivoted into a U-turn, pumping with his legs to propel the board back out to repeat the cycle. It was a startling sight. Aside from the high-performance aspects of foiling, Lenny said he likes that he doesn’t get in the way of other surfers in overcrowded breaks.
“The true benefit is that it allows you to ride something out of nothing — the unridable is ridable — and there’s something neat about that.”
DESPITE his globe-trotting exploits, Lenny remains remarkably genuine and unjaded. He still lives with his parents in a one-bedroom apartment above the garage of the family home in a quiet neighborhood.
His parents, Martin and Paula Lenny, said they were wary of the pitfalls of raising a precocious “child star” and committed to his education, even after he began home schooling at age 15 to accommodate his burgeoning career.
Naish remains a main sponsor, along with Tag Heuer, Hurley, GoPro and Red Bull, which signed Lenny at age 12; he is also featured in TV commercials for First Hawaiian Bank. These sponsorships provide the bulk of his income and fund his expenses. He doesn’t drink alcohol or most anything else except water, and most nights he’s in bed by 9. As for nutrition, Lenny prefers the fresh, healthful food easily found on Maui but also scarfs down bean-and-cheese burritos at Taco Bell to fuel his lean 5-foot-7, 154-pound body. A typical breakfast at home includes four eggs, avocado, cheese, ketchup and Tabasco in burrito form to eat on the run — a consistent theme in Lenny’s single-minded pursuit of his ocean obsessions.
“No matter how early I wake up, I’m in a rush because I can always be there a little quicker,” he said.
BACK AT Ukumehame, Lenny came ashore after an hour in the water and reluctantly stowed his gear. Five days later he was off to attend a surf expo in Orlando, Fla., as Hurricane Irma threatened.
So far this year, Lenny figures he’s circumnavigated the globe six or seven times for competitions and promotional appearances. He said he hadn’t been home more than a week at a time since April.
With the winter season approaching, he’ll be spending more time in the islands, flying back and forth between Maui and Oahu as the surf dictates.
In February, Lenny won the Sunset Beach Pro SUP surfing championship for the fifth time, but his heart belongs to Jaws.
“It’s perfect as a small wave, but it’s giant. Jaws just seems to be groomed unlike any place on Earth for wave-riding,” he said. Lenny’s father likes to tell the story of how when Kai was 8, he would hold hands with younger brother Ridge and walk to his hero Laird Hamilton’s house in their neighborhood and knock on the door hoping to meet the big-wave pioneer. When they finally caught Hamilton at home, Kai declared he was going to ride Jaws one day.
In the years that followed, Lenny fell under the tutelage of Hamilton and fellow bigwave star Dave Kalama. When he was 16 they judged him ready to take on Jaws, and Lenny challenged 25foot faces on a foilboard his first time out.
“Jaws takes precedence over everything,” he said. “I’ve had the opportunities to go on dream trips and chum it up with celebrities, but as soon as I hear Jaws is going, I’m like, ‘Yo, forget that.’
“People say, ‘You could’ve hung out with Tom Brady and Cristiano Ronaldo and all these famous stars,’ but I’m like, ‘I didn’t get into this to hang out with people — unless they’re out at Jaws.’” Jaws is next up on the WSL Big Wave Tour, with the Pe‘ahi Challenge holding period starting Oct. 15. Lenny will be waiting for the call.
A stand-out foilboarder, Lenny assembles his gear before hitting the waves at Ukumehame. At left, a 10-year-old Lenny rides an early hydrofoil board outfitted with snowboard boots at Outer Sprecks, Maui. At top, a custom board by Gerry Lopez and the green jersey he wore while winning a recent bigwave surfing contest in Puerto Escondido, Mexico, are displayed in Lenny’s bedroom.