Step into Kai Lenny’s home on Maui and one of the first things you’ll notice are the trophies. Ah, there’s so many! For example, there’s the iconic wood paddle for being named the 2013 SUP Race World Champion. Then there is the glistening, silver-colored trophy for earning the #1 overall Male Award at the 2013 SUP Awards. And of course, the 2017 Puerto Escondido Challenge Champion trophy, beautiful wood with a multi-colored Spanish skull, and so many more.
While staring at glistening proof of his accolades, it’s clear that Kai has one of the most diverse resumes in action sports. He’s not only a surfer who charges proper Jaws and he’s not only a kiteboarder and he’s not just a windsurfer, a SUP racer or prone paddler. While most 25-year-olds are getting comfortable in their first job, Kai is already a Champion in most of these disciplines.
Is there anything that could be more impressive? Well, as I found out, his attitude is equally – if not more – impressive. Though he has every reason not to be, Kai is one of the most humble and down to earth professional athletes you’ll talk story with. The 25-year-old Maui native, who has a strong build, an inviting white smile and brown eyes, does not let the trophies inflate his ego.
“Every morning I wake up, I look at my trophies and they inspire me to get in the gym and do the things that are difficult,” Kai told me. “The best things in life take a long time to get, and everything I’m going to do for the rest of the year and next year will be inspired by what I’ve done.”
These well deserved trophies aren’t only tools for motivation; they’re also pieces of metal and wood that encase memories of defining moments.
We’ve all, in some way, shape or form had one: that moment where you choose one path over another, or put your time and energy into one goal, and because of that, your trajectory years later in a career or geographically, is dramatically different. For Kai, a defining moment is “when my perspective shifts and I gain a confidence from it. How did my life change after those moments? Maybe it didn’t, but in between my two ears it did.”
After he completed an unprecedented mission this year – hydrofoiling interisland to attend multiple beach cleanups – I caught up with Kai to talk story about a few of his defining moments. He told a collection of defining stories dripping with saltwater and adrenaline, like being towed into waves at Jaws at 16 with Laird Hamilton and Dave Kalama and what it was like to be cheered “by your heroes” after winning the 2017 Puerto Escondido Challenge, all the while offering an honest and unfiltered look into the mind of today’s most celebrated waterman.
Age 4: Kai’s First Adrenaline-Fueled Wave Drop
“When I was 4, I had already started surfing on my very own,” Kai said. “So this defining moment happened at that age on the South Shore of Maui.” His parents went out to surf and some friends were watching young Kai on the beach. He snuck about 100 yards down the beach, taking an 8-foot board with him. “And by today’s standards, I was looking at a wave that was maybe waist high,” he said. “I paddled out, paddled for a wave and I could feel the wave sucking up, and then I dropped down to the bottom of the wave. I could feel the transition, and then I remember riding whitewater. It was the equivalent of surfing a giant paddle wave now at Mavericks or Jaws, and it was the start of my love for riding waves and riding big waves by myself.”
Age 6: An Introduction to Outer Reefs
Growing up on Maui, Kai spent time alongside watermen legends, like Robbie Naish, a World Champion in both kite and windsurfing. “I was surrounded by the best windsurfers on the planet, and at age 6, I was big enough and strong enough to hold up in a windsurf swell,” Kai said. “All of a sudden I had the power to sail half a mile out and dabble in waves that were out of my grasp before.”
Age 16: Equipment Troubleshooting with Laird Hamilton and Dave Kalama
When Laird Hamilton and Dave Kalama invite you to surf Jaws, no matter how scared you may be, you have to go. Or so says Kai, who got the call at age 16.
During the session, which was Kai’s introduction to Jaws, the waves were 12-15 foot Hawaiian. He was riding a hydrofoil in snowboard boots. “I recall being so terrified,” he said. “I hadn’t used snowboard boots all winter, and the saltwater had eaten the insoles. Dave threw me the rope, and I stood up and the soles fell off. I lifted the boot and you could see my foot! Dave had that look of ‘we made a mistake’, a sort of disappointment. But it was the equipment, not me. Dave saw that, cracked up and gave me his boots – they were huge, like size 11 – and my feet were only size 8 at the time. I was basically swimming in them. I remember catching a wave, and I was so deep and the wave closed out on me… I was hanging on for dear life and made it to the outside.“
Age 17: Proving Himself in the “Big Leagues”
Kai admits that the transition from a child star to a professional athlete can produce anxiety. “I was so nervous since I had already been getting attention for windsurfing, kitesurfing and standup paddleboarding,” he said. “I hadn’t proved myself in the big leagues yet.” So Kai entered the 2010 Sunset Beach SUP Pro feeling butterflies: “I was intimidated by all these Hawaiian professional surfers.”
The time he had spent around legends of the sport, like Naish, Hamilton and Kalama then began to pay dividends. He advanced heat after heat, eventually winning the contest. “That was a huge deal,” he said. “I somehow pulled it off and won, and it gave me the confidence to compete on a Pro level not only in stand up, but also in other sports.”
His confidence, combined with his skill, resulted in more hardware: Kai would win 7 World Titles between SUP racing and SUP wave riding in the years to come. “I had goals of being a World Champion athlete, goals that I had dreamed of achieving because the people I was surrounded by on Maui were World Champions in one sport or the other,” Kai said. “Those were some defining times.”
Ages 17-19: Entering the Big Wave Arena
Kai’s first paddle session at Jaws took place in 2010. But he didn’t have a normal gun, so he entered the lineup on a stand up paddleboard gun. “The wave was so steep and terrifying I made it by the skin of my teeth,” Kai said.
Two years later, he started paddling for waves the sizes of 3-5 story buildings with appropriate equipment: a traditional gun. “I remember catching a couple waves and it was something I had never done before,” he said.
The following year, he was awarded an alternate spot for the Quiksilver In Memory of Eddie Aikau. “I think I was second to last,” he said. “I had to start somewhere right?” For Kai, being mentioned among the world’s elite big wave surfers in a contest that was named after his hero was a defining moment.
“Eddie was my hero growing up, even though he died well before I was born,” Kai said. “At my elementary school, we had ‘famous people day’ and I dressed up like Eddie two years in a row. I would bring my surfboard to class and wear a wetsuit as part of the act. Back then, kid’s surfboards were just really small shortboards, and the board I brought to school had red rails and a couple stickers on it of the companies I liked. I conducted a detailed report on Eddie, where I pulled information from research online, and talked to some of the Maui locals who knew him. So being named an alternate in 2013 and attending the opening ceremony was special because I was that much closer to his legend.”
The following year, Kai was one alternate slot higher, and his goal is to continue a methodical climb up the list. “Up until now, I’ve gone up 3 or 4 spots,” he said. “That’s pretty special.”
Age 22: Reintroducing Hydrofoil surfing
Kai’s previous memories with hydrofoil surfing included a jet ski, snowboard boots, and having the sole fall out while Jaws was exploding into mountains of whitewater nearby. But one day, he had an idea that developed into a mission: why can’t anyone ride the hydrofoil on small waves instead of just big waves?
“When I had the idea, I was doing a ton of paddling both downwind canoes and stand up paddleboards, and I wanted to harness those open ocean swells,” he said. Kai helped design a special foil for a SUP, and then translated that foil to a much smaller board.
Ask him what it feels like, and he’ll say “flying” and “snowboarding powder”. Kai noted that most of the world doesn’t have premier waves, and that the foil was “the great equalizer. The worse the waves, the better it felt. My only regret is that I didn’t do it sooner, because it’s opened up surf spots that are uncrowded. There’s epic waves everywhere now.”
This instilled even more confidence in Kai. “It was groundbreaking for me because it gave me confidence to believe in my ideas and approaches and not second guess myself,” he said.
Age 23: An Undisputed Win at the “Channel of Bones”
Known as the Channel of Bones, the Ka’iwi Channel is a treacherous 26-mile expanse of ocean that separates the islands of Molokai and Oahu. This is the setting for the Molokai 2 Oahu Paddleboard World Championships, an annual 32-mile grueling race that first began in the mid 1990s.
“I had been paddling the Molokai 2 Oahu Paddleboard World Championships on a prone paddleboard and an SUP since I was 12-years-old,” Kai said with a casual tone. “In 2015, I had won the Stock division and broke the record, but I had never won the Unlimited division, and that was a goal a long time coming. Amongst peers and legends, it was a really big deal to win that event and that it felt like something I had to do to be on the level of the greats before me.”
In 2016, Kai stepped onto that level, breaking a new record along with being the first across the finish line. He did it in 4 hours, 7 minutes and 41 seconds.
Age 24: An Interisland Cleanup Campaign via Hydrofoiling
His next defining moment was a product of his familiarity with the Ka’iwi Channel and his desire to give back to the Hawaiian community.
“I wanted to give back to the islands, because it’s these islands that have made me who I am,” he said. “I was also wondering how could I bring awareness to such a problem like ocean plastics, and there’s no better way than doing a cleanup on all the islands.”
Partnering with Sustainable Coastlines and Redbull, Kai embarked on a statewide beach cleanup, and instead of venturing to each island via air, he decided to travel by hydrofoil. “The whole idea was to use hydrofoil as vehicle for awareness for beach cleanups on each island,” he said.
Surfing alongside escort boats, he hydrofoiled from the Big Island to Maui in just over 4 hours, and broke his own record – set at the Molokai 2 Oahu Paddleboard World Championships – by 45 minutes from Molokai to Oahu. “That was a cool accomplishment,” he said. “I was just in boardshorts from the Big Island to Maui, feeling so free, a freedom I had never tasted. Here I was – surfing – going up to 20 mph across the ocean and it felt like I was on a perfect wave but I was in the middle of nowhere,” he said.
“The distance was intimidating, but at the same time, I was having so much fun,” he continued. “Along the way, I was inspired and humbled by what I was learning from Sustainable Coastlines and Five Gyres. As a professional athlete, you have to make it about yourself to be the best there is, and you have to be a little selfish. That goes against my upbringing. I was always taught to give back as much as I can, and this felt like I was giving back to the people and the islands.”
Age 24: Dethroning his Heroes in Dramatic Fashion at the Puerto Escondido Challenge
Kai was “disappointed” after his rookie year on the Big Wave World Tour in 2016: “Competing in big waves is another ball of wax. The first time I surfed places like Nazare and Puerto Escondido were on the Tour. And there’s so many good big wave riders, so I was wondering to myself if I was capable of holding my own,” Kai said.
Before the 2017 Puerto Escondido Challenge was set to run in his second year on Tour, Kai had a choice to make. He had been training all summer for the Molokai 2 Oahu Paddleboard World Championships, and the two events fell within the same window. On one hand, Kai was the defending champion in Hawaii, but on the other, Puerto was expected to be pumping and he had committed himself entirely to the Tour.
“Choosing Puerto was the best decision I could have made,” Kai said. “I didn’t think I was going to go down there and win. There was actually more of a chance of me winning the race.”
After touching down in Mexico in late July of this year, Kai decided to take a different approach mentally. “I let go and wasn’t afraid to go after it,” he said. “I wasn’t trying to say I have to win this or I have to do really good in this. Heat by heat and wave by wave, if I did well, I was stoked. Because I was having so much fun and enjoying those waves, by the time the Final came, I realized hey I can win this thing.”
With three and a half minutes left in the Final, Kai paddled into a bomb and stood tall in a massive barrel, earning a 8.60 from the judges. Three minutes later, he was the Champion.
“I didn’t know I won the event,” Kai said. “I was claiming that wave because up to that point, I was getting so pounded I claimed because I finally made a wave!”
After paddling in, Hawaiian cohorts Makua Rothman and Nathan Florence carried him up the beach into the competitors area. “All these legends and my heroes were there clapping for me and I remember thinking ‘is this really happening right now? Wow’! On a personal level, it solidified that feeling that I was meant to be there. And that I earned it,” Kai said. “Even if you surf big waves, it takes a special level to be near guys like Shane Dorian and other legends. You grow up watching these guys, and then you wonder if you can hang with them in the same arena. It was fulfilling to be on that stage, having earned it the hard way. It gave me a lot of excitement and inspiration for the events to follow – I have nothing to lose and everything to gain.”