Kai Lenny on Joining Pro Cycling Team, Cross-Training With Underground Road Bike Crew of Hawaii Pro Surfers

Kai Lenny cycling
Brian Solano courtesy Pinerello

With the pandemic’s end closer in sight for the U.S., many among us are taking stock of all that we’ve accomplished in the past 15 months with disrupted schedules and less travel. Yes, you watched all of Yellowstone. You learned how to make sourdough. Maybe you got the calves you always wanted? Did you at least clean the garage?

Well, what does a guy like Kai Lenny do? How does a guy who already owned the windsurfing and paddle racing scenes—that is, before he pioneered foiling, helped reshape big-wave tow surfing, then every once in a while, make some heats in World Surf League events—spend that down time?

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To start, Lenny, like most of us, was limited by international travel restrictions. Unlike most of us, he had the South Pacific Ocean to work and play in. But interestingly enough, Lenny looked to the land this time for his next jolt of excitement. He started riding a road bike.

And of course, in case you’ve dedicated your life to cycling…he’s already better than you.

“During the pandemic summer, we started riding like three days a week because I was here,” Lenny says. “A local group of my friends who are also pro surfers started getting really competitive. We came up with ways to push each other. It served as a great crossover to serve our goals and ambitions on the water.”

Of course, the conditions dictated their days. When the ocean called for it, Lenny was riding wind or wave. There was mountain biking. He upped his gym workouts to twice a day, four days a week. And he started dialing in the 8-foot halfpipe in his yard, which has a special harness that mitigates injury for board-awareness training.

Lenny Cycling
Brian Solano courtesy Pinerello

But the road biking is what became his new focus, riding with the likes of big-wave charger Ian Walsh, WQS competitor Ian Gentile, the legendary Buzzy Kerbox’s son Kody Kerbox, and other special waterman appearances.

John John and Nathan Florence are really into road biking as well on Oahu. It’s fun having that surf community into it. With different apps, we can stay competitive with each other.

And now Lenny is actually part of the first U.S. Team for Pinarello, the storied Italian bicycle brand. They’re calling the ambassador program ‘Scuderia,’ an Italian term for team.

Lenny is just one member of the Scuderia. The rest of the squad is also interesting and diverse, including BMX star Jamie Bestwick, ski mountaineer Meredith Edwards as well as Amity Rockwell, Mari Holden, Adam Roberge and Jess Cerra, from all across the cycling world.

Lenny has always been familiar with the culture.

“Cycling has been in the family since my mom was a pro bike racer and won numerous state titles in Oregon and competed all over the country,” says Lenny. (Incidentally, mom Paula Lenny was also an Occupational Medicine Specialist—full family of overachievers.)

Lenny remembers stories of how she would attack on the hill climbs of a race.

“That was always my inspiration out on the water,” he says. “When conditions are most challenging, that’s when you attack.”

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Kai Lenny Jaws Maui
Lenny surfing Jaws in Maui, February 2020 Brady Lawrence / Red Bull Content Pool

Lenny got into cycling when he was 12.

“It’s served as a great training tool,” he explains. “Whether it’s for recovery, actually building my lunch capacity for big waves or getting better leg endurance, that was always my goal.”

Lenny is pedaling Pinarello’s Grevil, the SRAM AXS force build. He credits a big piece of all this to Donny Arnoult, an elite road and mountain bike racer who moved to Maui in 1999, started a bike tour company and opened Maui Cyclery. He has always been a resource for Lenny and taken him on rides through the years.

“The thing that always keeps me interested on Maui is that I was able to ride so many different conditions—from climbing 10,000 feet to the top of Haleakalā, our biggest volcano on Maui, to coastal rides, jungle, gravel, pretty much anything you can ever want on this island in the Pacific,” Lenny explains.

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He talks about riding the Skyline, up the national park across the mountain toward the South Shore with many of the other islands visible on a clear day where the airplanes are actually below them, taking off and landing.

Lenny never expected to be working with a bike company.

“But now that I’m getting involved with the Scuderia Pinarello, it’s just a greater motivator to get out on the bike,” he says. “Any time I spend on land I want to be in the saddle, doing something that moves me toward my goals on the water—with people I can be competitive with, my friends who are pro athletes and Donny, who has been a huge motivator here for the cycling community.”

Last summer’s riding was limited to Maui but with restrictions lifting, this year, Lenny is eyeing up a new challenge nicknamed The Hawaii 500.

“It starts from the far side of the Big Island of Hawaii, which is the farthest east and you ride west, then jump on a hydrofoil and foil across the channel, ride a bike across Maui, and do every single island until you wind up on the most west end of Kauai. It’s probably like 460 miles. We’re just waiting for all the islands to open up. Hopefully things kind of reset.”

Bear in mind, this would not be on a standup-paddle foil but a “surf foil” where you pump the board and ride open ocean swell, ideally not falling at all.

“It’s condition dependent,” he notes. “It won’t be perfect on every leg but it will be quite the adventure.”

It always is with this guy.

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