F*ck Your Hang-Ups

Kai Lenny will enjoy the ocean as he pleases.

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I should’ve known we’d end up at a trampoline park in Wailuku. While 28-year-old Kai Lenny may be considered the greatest crossover ocean athlete the world has ever known, he is constantly hovering above it. On a tow-board. On a kitesurf board. On a windsurf board. On a hydrofoil. He says he loves the ocean, but it is obvious that he loves to fly.

We pull up to a large warehouse with a sign on the front that reads “Ultimate Air Trampoline Park,” and I’m wondering if he’s got a nephew with a birthday that I’m unaware of. But I’m mistaken. This is a training session. We’re here to bounce, baby. Lenny introduces me to his “Air Awareness Coach,” Matt Christensen, a Red Bull project manager and a former head coach of the US Ski Team who led that team through three Winter Olympics.

Stock-car colorways and logo hits befitting full-race handling. As diverse and any-condition ready as Lenny’s quiver might look, rest assured that the bulk of the kit is designed for straight redlining. Photograph by Tom Servais.

There’s not a soul in the building. It’s off-hours, and someone in the back turns up Guns N’ Roses “Paradise City.” Lenny hands me a pair of grip-soled jump-socks and hops over to the expert mat. A giant foam-pit beckons in the distance, but I avert my eyes and follow his lead.

Lenny hits the trampoline and blasts off. It’s practice. He’s been doing backflips on hydrofoils lately. Backflips. And out at Jaws on a tow-board, he’s pretty much doing functional tube-to-flip-to-carve combos in 60-foot surf.

Recall that wind whipped, gigantic morning in November two years ago during the Jaws Big Wave Championships. On a swell that surged with such force that the waves moved boulders beneath the Peahi bluff lookout, the World Surf League’s Big Wave Commissioner had to call it. It was too big for the contest. Too windy. Too dangerous. Someone would drown. Jet skis and lifesaving sleds had already been taken and obliterated by rogue sets. The debris of the destruction floated in the whitewater at the base of the cliff. And the swell was still building.

While most competitors caught boats back to the safety of the harbor, a few surfers did not. Lenny switched from his 10-foot gun to a smaller tow-board, grabbed the handle of the rope, and nodded to his driver to whip him into whatever was deemed “unrideable.” With that, he proceeded to ride over a dozen waves with superhuman endurance—slinging  into behemoths, streaking across the rippled faces, dancing beneath falling guillotine peaks, air-dropping two stories down, capping waves off with corked backflips.

Sure, the event was called off, but the WSL kept the cameras running for the webcast. Lenny’s performance baffled the commentators who dubbed the following hour “The Kai Lenny Show.”

Lenny has surely benefited from Jaws sitting in his backyard, and having Laird Hamilton and Dave Kalama dragging him into its lineup before he was a teenager. But jumping over the ledge or tucking inside of a 40-footer? That’s just desire. Top photograph by Fred. Pompermayer. Bottom photograph by Erik Aeder.

As fate would have it, one of the commentators, Dave Kalama, was watching the evolution of what he, Laird Hamilton, and a half-dozen others had conceived over 25 years before at that very wave. Only it was rebooted. Progressed. Better. The contest resumed the following day in slightly less treacherous conditions, with Lenny placing runner-up to his childhood friend, and now four-time Jaws Championships winner, Billy Kemper.

“I honestly never looked at him as a major threat to me in paddle-surfing, mostly because he was into so many other types of wave riding,” Kemper would later say of Lenny. “And now he definitely is. He’s trained so hard and put so much effort into it that he’s now right there with the best in the world. It’s crazy.”

Back at the trampoline park, I watch as Lenny digs deep into the nylon mat and launches skyward, hanging inverted for a moment, and then back-arching through an Axl Rose growl. Through the blur I catch an unmistakable grin smeared across his face.


A trip to Lenny’s garage is an intimate look into his psyche. He lifts up the carport-cum-watercraft-storage door to unveil the vehicles of his pursuits. I ask if I need to remove my shoes, even though it is a garage, before stepping into the temple. Although he doesn’t say no, his pause speaks volumes. That’s another thing I’ve learned about Lenny: He’s a clean freak. It’s evident in the order and quality of his equipment. The floor is spotless, as are his surfboards. On one side of the room are board racks with a row of two dozen surfboards of escalating lengths, all with the identical royal-blue-and-red-race-stripe paint jobs, sponsor decals placed in identical locations.

Above us hangs a Moth-class hydrofoil sailing dinghy and, next to it, more big-wave guns, racing paddleboards, stand-up paddleboards, and outrigger canoe amas. Below are shelves of tools, tightly rolled kitesurf and windsurf sails, life vests, coiled tow-ropes. On the other side of the wall is a row of tow and hydrofoil boards, all with Lenny’s signature colorway. Each craft looks like an aquatic race car. That’s also intentional, Lenny explains. He’s a diehard fan of Formula One racing and MotoGP. He has a fascination with speed, precision, and finely tuned, well, everything.

“I know there’s no such thing as perfection because of all the variables,” he says, “but what I love about the idea of precision is that, in order to be at my top level and become the best in the world at something, my whole ship needs to be tight before I step into the Thunderdome. That, and I hate clutter.”

He’s actually building a barn up the mountain, a watersports headquarters of sorts, to house all of his equipment and innovate new crafts. He says that ever since he was a kid, he’s been into designing wave-riding apparatus, fixated on how to make a good thing better. He shows me a surfboard with what appear to be micro-fins behind the regular ones, which act like diffusers on Formula One race cars. He explains how they increase a board’s performance by an umpteenth percentage.

On the way out of the garage, he excavates a canary-yellow orb from packaging peanuts in a box, cradling it in his hands like a soothsayer’s crystal ball. The gadget is actually a solar-powered marine buoy. Lenny plans to moor it at a secret wave of his choice, so he’ll know exactly when to hit it.

The precision stuff is cool and all, but beholding his arsenal of watercraft, what strikes me most about Lenny’s whole trip is his breadth of expertise. In short, while most pros need to put all their efforts into one discipline, Lenny’s won multiple races, world titles, and mega-events by claiming loyalty to none. It’s something that connects him to that catchall moniker and alienates him from any one tribe.

He motions me over to his truck and we’re off to grab a bite en route to Quatro International to speak with his shaper about a new design. Rolling into misty Haiku, every pickup truck seems to have some kind of windsurf or paddleboard hanging precariously from the bed. We order up two paniolo skillets at a coffee shop, and bump into Ian Walsh. The two talk about waves but mostly wind, like watermen normally do on Maui.

Tan, handsome, and articulate, Lenny is forthcoming and perpetually engaged. Comically, he grabs my recorder for emphasis when making a point. He is always “on,” a trait that dubious and bored surf journalists have weighed on cynically. No one can be that psyched, that pleasant, that perfect. Or can they?

Alas, no one can really tell me if Lenny’s Mr. Nice Guy schtick is an act. If he’s ever impatient, it seems, it’s with his father and manager, Martin. Regardless, the two appear to navigate that relationship beautifully, considering how badly it could go. But no, Lenny doesn’t booze, smoke, toke, or talk shit. If there’s any vice to be found, perhaps it’s his obsession with Taco Bell bean burritos. A self-proclaimed addict, he’s admitted to eating eight in one day, during a marathon session at Jaws. It’s also a free fucking country and that’s his gastrointestinal journey, not mine.

“I never really felt totally accepted by surfers, due to the fact that a lot of surfers didn’t think it was ‘core’ to branch out into other sports.”

Certainly, his personality seems forged by the sea, à la his namesake, Kai. The child of California transplants who both moved to the North Shore of Maui to surf and windsurf, Lenny caught his first wave at 4 years old, a vivid sensation he admits he’s been trying to replicate his entire life. Apparently, before that milestone, his parents would leave him in a baby bouncer tied to a tree branch while they windsurfed near shore. By 6, he was windsurfing on his own and entering prone paddleboard races, and he’s currently a four-time Molokai 2 Oahu Championships winner and record holder. By 7, he was stand-up paddle surfing, and is presently an eight-time world champion in that particular discipline. By 9, he was kitesurfing, and became world runner-up in 2013. Around 10, he began tow-in surfing large waves, and then foiling, under the tutelage of tow-in godfathers Kalama and Hamilton. From tow-in surfing, he’s since joined in on paddling into big waves, placing runner-up on 2017/18 WSL Big Wave World Tour.

And yet Lenny wouldn’t choose one of his trades for all his efforts. It’s a major difference from the rest of the young talent pool on Maui, who mostly have followed the tried-and-often-untrue formula of going all-in on shortboards—NSSA to WQS to maybe, just maybe, the World Tour. Lenny instead stayed his own course, moving between the “tribes” within each discipline, even if one in particular wasn’t always so welcoming growing up.

Fifty-yard check-turns at Nazaré. Photograph by Helio Antonio.

“I never really felt totally accepted by surfers,” he admits. “I felt like an outsider, due to the fact that a lot of surfers didn’t think it was cool or ‘core’ to branch out into other sports. It was like, ‘Just surf or don’t surf at all.’ I’d get hazed, sort of bullied by the old guys. I was actually scared of going to my local break at Ho’okipa because of getting snapped at for SUPing. I realize now that it’s more their issue than mine, but at the time I thought there was something wrong with me. But what it taught me was that I’m really comfortable being alone and walking my own path. I always feel like people get too hung up on how we catch a big wave versus what it’s like riding big waves. But I always go back to my baseline, which is, first of all, I’m not riding big waves for anyone else. I just like riding big waves.”

Some of the surf brands even told him he needed to pick a side if he wanted to make a living. 

“I was like, ‘No. I’m going to prove them wrong and I’m going to exceed even my own expectations.’” 

Which, lots of world titles and some world records later, he did.

“He’s one of the true icons of his generation and that entire group on Maui,” says Hamilton. “Honestly, I think a lot of his multifaceted philosophy comes out of Maui. The nature of the conditions there is so wind-driven and -influenced, so you see a lot of creativity in the community. Kiting, foiling, windsurfing, all these things were birthed on Maui. It’s cool to see what he’s been able to do with each one.”

Still, I’m not entirely sold that he doesn’t have a favored child. I ask him if he had to choose between one, could he?

The picture of control at Maverick’s. Photograph by Fred Pompermayer.

“No,” he laughs. “Taking one away from me would be like taking away a finger. And I like all my fingers. Each one has a purpose. But I guess, my thumb is the most important, which I’d liken to getting barreled in big waves.”

Of course, lately, many of those barrels in big waves have been bagged via tow-rope. It’s a trend that purists hoped had died, but that Lenny is single-handedly reanimating at a whole new level. It’s also a subject of contention not lost on him.

“I had a tow session this year,” he says, “where I think I got 30 barrels, maybe more. I’ve never felt so comfortable big-wave surfing, because I was like, ‘On the next wave, I’m going to do this to get deeper or try this line in the barrel.’ It was what big-wave surfing is all about. I understand there are big-wave surfers whose goal is ‘the art of the hunt.’ But with towing, for me, it’s the art of the performance. It’s more about what you can do on the wave versus how you got onto the wave. I know tow surfing is definitely frowned upon by some core big-wave surfers. But there’s always got to be an enemy, right?”

He shrugs and scarfs down the rest of his eggs.

We pay for breakfast and walk next door to the old Pauwela Cannery, which now houses a number of craftsmen and surfboard makers, namely Quatro International, the world’s leading hub for windsurf, kitesurf, SUP, and foilboard design. Inside the shop, the hanging rows of windsurf boards, sails, deck pads, and fresh carbon fiber smell like a newborn robot.

“I always feel like people get too hung up on how we catch a big wave versus what it’s like riding big waves.”

I follow Lenny to another room where he has a few giant racing paddleboards stashed upright, his remote office of sorts where he spent time editing his 2017 biopic, Paradigm Lost. He introduces me to Keith Teboul, his main board-maker, and the two look at a monitor in the showroom, tweaking digital dimensions on a new foilboard. It’s Lenny who has often been credited for spearheading the genre’s modern resurgence. His accomplishments have been groundbreaking, namely his 2017 Molokai 2 Oahu Race win where he hovered the 32 miles downwind in a blistering 2 hours and 52 minutes without getting his toes wet. He’s won the race on a foil every year since.

“Foiling…it’s the closest way to feeling like a bird—or like flying—that you could possibly do for the price. Do you want to check it out?”


The whole foiling thing has always confused me. Are you supposed to do it in good waves or shitty ones? I can never get a straight answer from foilers on that and, for the most part, only see it performed in the latter.

Pulling up to Kahului Harbor, one of the island’s foiling hubs, we watch men, women, and children levitating over the sea. They paddle disc-like, rockerless craft into mushy, waist-high rollers inside of the breakwater, quickly activating the underwater wings into a bizarre hover. Indeed, it’s a sight for sore eyes, their zipping to-and-fro at speeds doubling, if not tripling, what a surfer would ride out here on a normal board. Like seabirds flying low over the surface, they cast silent shadows, their dark twins following with every maneuver.

It is notoriously difficult to learn to foil as a beginner, and surfing experience doesn’t necessarily put you on the fast track to success. Even articulating the sensation of foiling gathers a hodgepodge of information ranging from snowboarding in deep powder to slacklining in Ugg boots. Most, however, will unanimously compare it to flight.

“You’re flying, simple as that,” says Kalama, who helped develop modern foils in the 1990s. “Maybe you’re not flying high—more like 2 to 3 feet above the water—but that doesn’t negate that sensation of flight. There’s a freedom and speed and lack of friction foiling gives you that is so attractive.”

As we watch in silence, I can feel Lenny sensing my hang-ups. The waves just look so…bad. 

Making maxing Cloudbreak his personal oyster. Photograph by Scott Stinton / Red Bull Content Pool.

“It’s interesting, because when you’re on the shore, you look at this board, and you’re like, ‘This is so crazy.’ Most surfers get turned away from it, because it just looks like a lot,” he says. “But then you get in the water, and everything on the foil has a function for performance, working harmoniously together, every part helping the foil execute.”

Maybe I’m looking at it all wrong. Maybe the waves-first approach is incorrect. I remember something Hamilton said months earlier: “Foiling actually becomes four-dimensional with that ability to rise and fall while turning, as opposed to surfing where you’re usually stuck to the wave.”

I kind of like being stuck to the wave, though. But what’s certain is that much of foiling’s popularity and sheer accessibility is thanks to Kai Lenny.

It’s not like he or Hamilton invented the tech. As far as origins go, the first prototype of a hydrofoil was designed about 120 years ago to lift a boat out of the water while in motion, reducing hull drag. After some early development by inventors like Alexander Graham Bell, foils were incorporated into record-setting speedboats in the early 1900s, and later used on passenger and military craft. It wasn’t until about 25 years ago, though, that Maui’s Strapped Crew started attaching hydrofoils to surfboards and using them to ride big ocean swells not far from where Lenny and I are now sitting.

“Being scared is the healthiest thing in the world, because it puts me in a state of focus. It cuts away all the bullshit.”

Getting the idea from an invention for water skiing called the “Air Chair” (a hydrofoil mounted beneath a small chair with a seatbelt, towed behind a boat), the crew—consisting of Hamilton, Kalama, Mark Angulo, Pete Cabrinha, Darrick Doerner, Brett Lickle, Rush Randle, and Mike Waltze—modified the craft, fashioning crude aluminum snowboard boots and bindings so they could stand upright. They began towing each other into bigger and bigger waves, quickly realizing how the foil allowed them to literally slice through surface chop far more smoothly than the rail of a normal surfboard. They’d even bring a 10-year-old Lenny along with them to get in on the action.

While this was fun for a while, the foil’s popularity truly caught fire with the global kitesurfing community. Kitesurfers the world over began to mount foils to the bottoms of their boards, which jumpstarted foil companies to mass-produce them, with most constructed out of carbon fiber composites. Alex Aguera, a professional kiter and designer on Maui, is credited with developing the modern profile, which is still the standard.

But it wasn’t until just a few years ago that Lenny popularized the foil’s untapped potential by riding them mounted to smaller SUPs and shortboards. Users could paddle into a wave without the assistance of a kite or sail, jumpstarting the foilboarding craze of today.

Lenny being Lenny, it didn’t stop there. Currently taking the foil to exploratory frontiers, he recently won the renowned Maui 2 Molokai Challenge race on an SUP foil in a blistering 2 hours and 17 seconds. For some perspective, that’s about an hour faster than what was previously accomplished without a foil.

“There’s no drag,” Lenny explains. “It’s pure speed, no resistance. It eliminates surface tension, so you can get going at about 25 mph pretty easily. A foil has got to be the fastest craft on the water, even faster than some sailboats. It feels like floating on a cloud. You don’t feel the chop, everything is quiet and smooth. It kind of defies your own imagination, because you can’t really see what’s lifting you out of the water. It’s sci-fi.”

Photograph by Marc Chambers.

The flight parallel isn’t too far off. The mechanics behind a hydrofoil are similar an airplane, only the physics happen underwater. The foil’s front and rear wings, literally connected to a tube called the “fuselage,” act as surfaces to create lift, much like a plane’s wings. As the prone or SUP board above the foil gains momentum with a swell, the foil lifts the board off the water, decreasing drag and allowing greater speed, simultaneously maintaining (if not generating) momentum.

But like most surfing-adjacent watersports, foiling, while enjoyed by the likes of John John Florence, Ian Walsh, and Jamie O’Brien (JOB and Lenny have foiled Third Reef Pipeline together), is still polarizing in the surfing community.

I repeat the question: “Good waves or shitty ones?”

“Listen. While you might need all the elements like wind, swell, and tides to align for a good surfing session, on a foil, you really don’t need any of that to have an amazing time. For me, if the waves are giant, I have my guns. But on the other side of the spectrum, I have my foil for the world’s smallest waves. You want to go fly for real?” 

Hell yes, I do. 

Christensen counts Lenny down and sets up an iPhone for playback, drilling him on backflips and Cork 7 twists, techniques that Lenny’s mastering for maneuvers on his arsenal of wavecraft.

Bounced-out and thoroughly winded, Lenny gets a call from his shaper, Keith. They’ve got a windsurfing session scheduled in a half-hour to try out some new designs. We hop out of the park and jump back in the truck, and Lenny drops me off en route, practically foaming at the mouth to get back in the sea. I ask him about this obvious, albeit healthy addiction. That, and whether his golden smile masks any fear when it’s serious out there.

“For me, it’s like the ocean is a battery pack,” he replies. “I get energy from being in the water, and when I’m not, I don’t have that same spark. Being scared, I feel, is the healthy thing in the world, because it puts me in a state of focus. It cuts away all that bullshit that’s floating in the air, the stuff that doesn’t really matter at the end of the day. It reveals what is truly important.”

I ask Lenny if there will ever be a day he finally switches his efforts to land. Racing cars, perhaps? He’s gushed over his fallen idol, Ayrton Senna, multiple times. Is piloting a jet plane in the cards? A spaceship, maybe?

“I think what makes me immune to getting burned out is my obsession with variety,” he says. “When I start to get jaded with one thing, I just go to the next thing I do in the ocean. Plus, I don’t know how you can ever get bored riding a really big wave. I think that I’ve positioned myself to never get jaded. To me, it’s endless. There’s always some new way to ride water.”

As far removed from the “core” as his activities may seem, critics find themselves in a difficult position when Lenny is toying with 60-foot waves. Photograph by Mike Coots.