On the bike with Kai: Why big wave surfer Kai Lenny is stoked on cycling

(Pa’ia, Hawaii) – Kai Lenny has never done a cycling interview, and I have never sat down with a surfer. If it were December, we would not be shuttling our bikes from the beach through Maui’s upcountry to ride some of the empty roads on the island’s vast volcanic southern flank. But, it’s mid-May, and the huge waves that Lenny competes on have gone quiet for the summer, so we’re headed out with the bikes.

Part of me had hoped that we’d be riding over here, not driving. But I’ve been warned: Lenny hasn’t done any super long rides; in fact, he has yet to go up Haleakala on his bike.

As we kit up to ride, it’s as if he’s reading my mind.

“The thing about the bike is you enjoy the journey,” he says. “In the car, you’re just about getting there.”

Lenny, 28, was born and raised near Pa’ia on Maui’s rugged north shore. Rather than on the soccer field or in a youth cycling league, he became an athlete in the water. Lenny began surfing at four, windsurfing at six, stand up paddle surfing at seven, and kitesurfing at nine. He is currently the youngest inductee into the Surfers’ Hall of Fame and one of the boldest big wave surfers in the world.

In surfing, ‘big waves’ measure 20 feet or higher, and surfers are often towed in on a jet ski to access them. Last year, Lenny surfed his biggest wave yet: he caught Portugal’s famed Nazaré at 70 feet one October morning.

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I was surprised then, to see Lenny’s name on the list of Pinarello Scuderia athletes when the brand announced its ambassador team back in February. Why would a pro surfer, already indebted to dozens of sponsors and focused on riding — and surviving — the faces of gargantuan waves, take on another time commitment?

“When I get really passionate about stuff, I want to be a part of it as much as I can,” Lenny tells me. “I do love learning new things and being a beginner. It’s humbling. I think when you can learn something and make big gains, to learn how to learn again, it helps when you get back to the sport you’re a pro in.”

Learning how to ride

During the pandemic summer of 2020, Lenny not only learned how to get better on the bike, he learned how to use it to explore his own backyard. Where to find avocado trees pregnant with fruit and then cram them into his jersey pockets to take home. How to corner on the sweet tarmac descents that make road riding on Maui a dream. To realize just how sweetly the flowers scent the air.

“It was all time,” he says. “There were no cars on the road, and I went to places I’d never been on this island. I was born and raised here, and Donnie took me to places I didn’t know even existed. It made the island even more magical.”

Donnie is Donnie Arnoult, the founder and owner of Go Cycling Maui and Pa’ia’s Maui Cyclery bike shop. He’s also an inextricable link in the chain of events that got Lenny into cycling.

When Lenny was a preteen, even though Arnoult was nearly 20 years his senior, he became the young surfer’s cycling mentor. Arnoult was a friend of the family, a former pro, and had become the go-to guy for everything cycling-related on Maui. He was thus the perfect person to take young Kai out on endurance-building rides that would complement his training in the water.

They’ve been riding together ever since.

“I remember I got super into watching the Tour de France when I was younger, and it’s ‘cause I got my first Scott Addict from Donnie,” Lenny says. “It was during when Lance was in his heyday. My parents would watch it, and it was so cool to be able to watch it and then go ride. And to ride with someone who had been pro level like Donnie. We’d always do the Kahakuloa ride to Curley’s to get banana bread. That’s all I looked forward to, that banana bread.”

Lenny still has the Addict, and he still watches the Tour when he can. Now, he’s on the Pinarello Grevil although to be honest, he’s not taking up the allotted tire clearance with gravel-grinding knobbies. The road riding on Maui is just too good.

When the pandemic halted both Lenny’s usually-frenetic travel schedule and the influx of tourists to the islands, it resulted in more good-old-days riding with Arnoult. The 56-year old and a handful of pro surfers, including Lenny’s friend and fellow big-wave rider Ian Walsh, began a series of impromptu small group riders, heading mauka from the coast to explore the lesser-ridden upcountry roads between Haiku and Kula.

While Arnoult’s skills on the bike far exceeded those of the waterboys, and some of the rides were more about collecting avocados and fruit than putting in an effort, you don’t get a group of the world’s best surfers in a bunch and not expect them to make some waves.

“All my friends and I are super competitive,” Lenny says. “Donnie too. It’s fun because it started off as really cruisey, then it was like, ‘ok, who’s pushing up the hill now?’ No one talked about it, but everyone knew what was going on. It was almost like we were in our own little world.”

Pedal to paddle

According to Lenny, the professional surfing world does include bicycles.

“Most surfers spend a lot of time on stationary bikes,” he says. “Almost any pro surfer has a stationary bike at the house. At any major event, there’s a stationary bike set up.”

Lenny prefers to ride outside, and often spins along the coastline near his house to flush his legs after a session in the water. Cycling, he says, is as an important a recovery tool as a training one. However, he also points out a dynamic relationship between training on the bike and how it translates to surfing.

“What’s cool about riding here is that, in surfing when you’re put into a position on big waves, you’re committed to the situation you’re in, there’s no time out,” he says. “I think it’s good mental practice when you’re climbing up the mountain here, you’re not going to stop, especially when you’re riding with Donnie. It’s learning to love the hurt. I think there’s a translation there — it’s key to have endurance when you’re surfing all day.”

When Lenny rode with Arnoult as a teenager, his training was so surf-specific that the bike was purely a tool for building extra endurance. Now however, he’s found that riding provides other opportunities for physical and mental gains.

“Building up the legs is so important for surfing,” he says. “Going down a wave really fast, you’re absorbing all these bumps so your legs have to be like shocks. If your legs don’t get as tired, you can get back out there faster for the next wave.”

“Also — getting comfortable at high speeds. If you’re getting comfortable with speed going down a mountain when you’re in control of the bike it’s similar to how controlling a board would feel at high speeds in surfing.”

Lenny’s main competitive goals reside in big wave surfing, but his energy and stoke drive him to weave countless other activities into his day-to-day. Furthermore, the seasonal specificity of his sport (big waves break in the northern hemisphere during a short early-winter window) means that Lenny has time pursue his other passions with aplomb.

One of them is foil surfing, which, to the un-trained eye, resembles some sort of space-age version of the sport. In ‘foiling,’ the fins on the bottom of a traditional surfboard are replaced by a carbon fiber hydrofoil that allows the board to rise above the surface of the water. Because the board is above the water, the size and quality of the wave matters very little, ie. you can surf in basically any conditions.

Last year, when Lenny got skunked from his normal summer season due to the pandemic, he came up with a plan to marry foiling and riding.

“I wanted to ride on every single island and foil between them,” he says. “It was logistically kind of a nightmare and expensive. The reality is, I’ve really only ridden on Maui. I’ve ridden a little in other places but not with an intention. I have friends on other islands who have road bikes, so I thought it would be cool to link with them and connect the communities in between. It’s a long way, close to five hundred miles. The total between ocean legs and miles on the bike is 460 miles total, so we had nicknamed it the Hawaii 500.”

“As soon as you landed on the beach, you’d have to get on the bike,” he says. “No relaxing. Either always pedaling or always pumping. Pedal to pump. Pray for the downhills or a big swell. The joke was we’d all need wheelchairs on the way home.”

Initially, the goal was to get across each island as quickly as possible. To hop off boards on the eastern coasts and take the least challenging way west. However, as Lenny spent more time on the bike at home in Maui, he reconsidered. Why not tack on some big climbs or ride the more scenic roads?

Lenny’s Hawaii 500 has yet to happen, but when it does it will be the ultimate test of endurance, mental toughness, and leg strength — all things he’s become better at by being a beginner on the bike.