“Success comes from knowing that you did your best to become the best that you are capable of becoming.” — John Wooden
Legendary UCLA men’s basketball coach and six-time national coach of the year John Wooden won 10 NCAA championships in 12 years, including an unprecedented seven in a row. His motivational words inspired a generation of athletes around the world.
Wooden preached the importance of character, humility and integrity. If he were still with us today, chances are he’d be a fan of Maui waterman Kai Lenny.
At 27, Lenny has already experienced more success than most will ever accomplish in a lifetime. You may have noticed there was no specific reference to what he’s been successful at, and there’s good reason. You see, like King Midas, everything Lenny touches turns to gold.
Lenny sees things through a much different lens.
“Emotionally, physically and spiritually, each event has marked a significant moment in my life,” says Lenny on the eve of the 2019 Jaws Big Wave Championships, held at Pe‘ahi, Maui. “We all evolve because we’re constantly learning. Each win and each championship has molded me, and win or lose, they all are really important to me. Eventually, they end up in the rearview mirror behind me because I’m always looking at what’s the next goal, what’s the next event, what’s the next adventure.”
Kai means “ocean” in Hawaiian, and he’s certainly lived up to his name. Thank goodness this young pioneer doesn’t need a business card to hand out to his network of contacts. Can you imagine what it would look like?
Seven-time world SUP champion. Surfing world champion. VICE KSP kiting world champion. Moloka‘i 2 O‘ahu foil world champion and world record holder. Moloka‘i to O‘ahu SUP world champion. 2019 Biggest Wave and Best Performance of the Year.
He’s also a hydrofoil surfer, racer and founder of Positively Kai Foundation — and that’s just a few of his many accomplishments.
“The titles are special, but the losses stick with me longer than the wins,” says Lenny. “After each event, I analyze and pick apart every wave. Each win takes years and sometimes a lifetime of preparation and training, but the win only lasts for 30 minutes or even 30 seconds. When the horn blows, there is a relief that comes over you, knowing you trained so hard for that 30 seconds.”
Born To Surf
Lenny’s journey to the top of the ocean world started when his parents, Martin and Paula, decided to move to Maui from California. The couple had two sons, and together they built their lives around the ocean and water sports.
“They were both drawn here for windsurfing. They came here and never left; it was their dream,” says Lenny. “My brother (Ridge) and I grew up only knowing this lifestyle. The ocean was our playground.
“I won the lottery of life being born here.”
While other Valley Isle youngsters were playing soccer or learning to ride a bike, Lenny was surfing before he was 5.
“I caught my first wave by myself when I was 4 years old, and when I did catch that wave and rode it out, I knew that’s what I wanted to do for the rest of my life.
I had my epiphany when I was 4 years old. No other options or failing that dream, what else would I do? It was in my head.”
Lenny was windsurfing at 6, stand-up paddling at 7, kite surfing at 9 and was sponsored before he turned 10. By the time he was 16, he was a familiar face at Pe‘ahi, Maui’s famed big-wave spot. He was a rising star in big surf who was driven to be the best.
“I have an unbridled drive in all I do, and I wanted to be the best growing up, no matter what I did,” says Lenny. “I do believe I have this natural talent, but I also have a natural drive within me to keep pushing myself. It was a perfect storm being born in the right place in the world on Maui, and I took full advantage of those opportunities.”
Making International Waves
Lenny burst on the international scene in 2012, when he captured the 2012 SUP World Race Champion title after winning the season’s finals of the first Standup World Series championship races at Turtle Bay Resort.
It was the start of an amazing run. In 2013, he was crowned SUP Race World Race Champion again and SUP Overall World Champion. In 2014, he finished fourth in the 32-mile M2O Paddleboard World Championships. The following year he came in second.
Since then, he’s won the WSL Big Wave Awards for Overall Performance and XXL Biggest Wave Award for an epic session at Pe‘ahi, and he surpassed his own record at the 23rd annual M2O Paddleboard World Championships, setting a 32-mile course hydrofoil record of 2 hours, 29 minutes and 38 seconds.
“I love the feeling of competing at my best — not beating people, but being the best I can be,” says Lenny. “I always felt like it took me longer to overcome challenges because I was almost too cautious. With each session, I build self-confidence, and I think fear is necessary because it allows you to take your performance to the next level. If you’re fearless, you don’t have that element.”
This summer, Lenny immortalized his hand and footprints in cement in front of Huntington Surf Sport in August, when he was inducted into the Surfers’ Hall of Fame.
“I have never seen myself amongst those legendary names; they’re equivalent to superheroes to me,” says Lenny, who was inducted into the Outrigger Duke Kahanamoku Foundation Hawai‘i Waterman Hall of Fame three weeks after his Surfers’ Hall of Fame induction at Huntington Beach. “Never in my wildest dreams did I think I would be in any hall of fame, let alone at this young age.
Maybe when I’m 60 and only if I played all my cards right! When they contacted me, I quickly said yes before they changed their minds.”
Lenny is already one of the most accomplished watermen the world has ever seen — yes, ever — and he’s only 27. But despite his phenomenal success, he remains grounded, humble and modest, understanding his place in Hawai‘i’s rich history of iconic watermen and women, including Rell Sunn, Eddie Aikau, Robby Naish, Laird Hamilton, Dave Kalama and Duke Kahanamoku.
“It is a complete honor; it still gives me chicken skin. I still believe I have to earn that honor and title. I honestly feel like I’m just getting started, and I’m not even at my prime yet,” he says.
A Giant In Giant Surf
At 5-foot-7 and 152 pounds, Lenny is by no means a hulking presence in the ocean. But make no mistake, his place in the lineup is always felt.
“At least the waves will always look bigger when I’m on them,” he says, laughing. “You know, I have no choice in the matter. I have to work with what I got and the best I’ve got. I rely on my technique and fine-tuning my equipment. To be honest, I feel like I grow a few inches when I’m on a big wave.”
Lenny may appear fearless in the ocean, but those who know him speak of his relentless work ethic and consider him a meticulous technician.
“I’m more scared of losing a big-wave contest than what a big wave can do to me,” reflects Lenny. “I’m not reckless. I’m very calculating. I’ve figured out how to apply my fear and make sure the reward outweighs the risk. Big waves are terrifying, incomparable to anything I’ve done. But my greatest fear is failing and quitting. That’s why I love competition.”
He showed that again, the morning after speaking with MidWeek, when he and 31 of the world’s elite men and women surfers competed in heart-stopping 50-foot surf in the Jaws Challenge at Pe‘ahi.
“Jaws is the pinnacle of big waves for me,” says Lenny. “It is a special place. It is my favorite wave on the planet. It is an incredible platform
and canvas — the wave I can’t ever see mastering.”
Lenny advanced to the final, but fell short to Maui’s Billy Kemper, who captured his fourth Jaws title. Now, Lenny’s focused on his next adventure.
His pursuit of his dreams requires him to be on the road eight months out of the year. He admits it’s tough being away from home, but understands the demanding schedule won’t last forever.
“The hardest part of my life is I can’t sit still,” he chuckles. “My life is very demanding, and I love it! But when I’m home, it’s family first. We always have dinner together. My parents came from very humbling beginnings and would always remind me and my brother, ‘Be humble, no one likes a big head.’ They taught us humility, and I never want to disappoint them. It’s who I am and will always be.”
Yes, Coach Wooden would have loved this young man.