Kai Lenny: Maui's Big-Wave Renaissance Man

Daniel Jenks

Hawaiian Kai Lenny has been a standout big-wave performer throughout this historic winter, culminating in a nomination for Surfline Men's Performance of the Year category at this year's Big Wave Awards.

Kai Lenny's Breakout Winter
Kai showed up at the first green call at the Eddie. He talked to the WSL broadcast about his big season in big surf.

The Maui born waterman developed his relationship with the ocean in his infancy. While he first learned to surf traditionally before pursuing anything else, his notoriety for riding a standard surfboard on the world's biggest waves is a rather new revelation for those who don't know Kai. He's a much bigger star in standup paddle, windsurfing, and kitesurfing circles. That said, Kai's rise to elite big-wave ranks was seemingly predetermined.

"He was born pretty much as the start of tow surfing," said his father, Martin Lenny. "Since Kai was little he's had this infatuation with the heroes of the sport. I remember when Kai was eight, Laird was renting a house down the street. For weeks he wanted to go down there and meet him. I said, 'Okay if you want to meet him you have to go knock on the door.' one day, Laird opens the door, and of course I don't know if Laird remembers this, but they come back and Laird waved to me. I asked Kai, 'What did you say to him?' He said he couldn't talk because he was too nervous. But he looked at me that day and said, 'Dad I'm going to be a big wave surfer one day.'"

Kai Lenny progressed rapidly earning his first sponsorship by Robby Naish at age 9. Photo: Darrell Wong. Kai developed quickly as an all-around athlete, but windsurfing became his first dedicated sport. He earned his first sponsor at age 9. Photo: Darrell Wong. - WSL / Darrell Wong

The island of Maui, however, often experiences high winds in the afternoons, right as a young Kai was finishing his school day. His desire to be in the water regardless of the conditions led him find his professional start in windsurfing and stand up paddling, receiving his first sponsorship by Robby Naish at age 9, a relationship that still exists today. He began competing in windsurfing competitions and ultimately made the choice to pursue his high school education online to focus on his calling as a professional waterman. Kai's desire to surf big waves, however, never waivered, despite his talent in windsurfing, stand up surfing and even kitesurfing.

Kai Lenny makes the drop during Round 1. In his first-ever appearance at a Big Wave Tour event, Kai made it all the way to the Semifinals. - WSL / Kelly Cestari

"He asked me when he was pretty young when he could go and surf Jaws," said Martin. "I told him it was up to him, but that [he was] going to have to get permission or a blessing from the guys-Laird (Hamilton) and Dave (Kalama) and Robby. And sure enough, when he was 16, at like 6:30 in the morning--I was up getting ready for work, and Kai looks me and asks if he can go surf Jaws, Dave had just called and asked if he wanted to go up and tow Jaws."

Kai Lenny's first day at Jaws with Dave Kalama on the ski. Photo by Erik Aeder. Kai then: His first tow session at Jaws was on a foilboard with Dave Kalama on the ski. Photo - Erik Aeder. - WSL / Erik Aeder

Though enough to make any parent a bit nervous, the day was a far cry from what we see Kai charging today. And who better than to trust with your child's life in big surf than longtime mentors and big wave legends Dave Kalama and Laird Hamilton?

"He's always been one to do his homework and earn his stripes before he moves forward. He's a little bit of throwback to the old school mentality. You had to prove yourself, you had to take your lumps, you had to show the more established guys that you deserved to be there. As with most everything he does, he not only did that, but he went way beyond," said longtime family friend and big wave mentor, Dave Kalama.

Kai Lenny
Kai now: Roughly seven years after his first tow-session at Jaws, Kai won the GoPro Challenge during the Pe'ahi Challenge.

"Laird and I were headed up there and I called him to see if he was into going and absolutely he was," said Kalama. "It was a good foiling day--just barely. We got him into a few. And he did great. You could tell there was some butterflies, but not too many."

Over the next seven years, Kai would develop himself into the man the world knows today and he's just getting started. "He still views himself as young and still in that mode of having to prove himself. But his self confidence is through the roof because of what he's accomplished and how he's surfing right now," said Kalama. "That means there's still a lot of growth potential, and that means he's still going to get A LOT better, which is kind of scary. I know Kai and how he's progressed, I've seen him go through these processes before. I really don't believe he views himself as one of ‘the guys' yet, which means he still thinks he can get a lot better and he will get a lot better. When he gets to that point where he considers himself one of the guys and isn't trying to earn his stripes, that's really going to be fun to watch."

Kai Lenny answered the call, has proven himself to giants of the sport and is ready for the next step, meet the winter wonder boy.

Kai Lenny got his start on a stand up at age 7. Photo: Martin Lenny Kai learned to surf, then windsurf, then stand up surf. Photo - Martin Lenny. - WSL / Martin Lenny

WSL: Tell us about your origins on a board, you surf, kite surf, stand-up. What's your go to equipment and where do your passions lie? Your website bio says SUP is your main sport is your journey changing?
I truly feel that I have become a product of my environment. I started off surfing when I was 4 years old on the south shore of Maui. I remember my first wave so vividly its as if it were yesterday! Still to this day I get the same rush I feel on a big wave out at Pe'ahi. I started windsurfing when I was 6, stand up paddling when I was 7, kitesurfing, tow-in surfing, and foil boarding when I was 9. Maui's conditions are constantly changing and offers world class conditions for all these sports. All I ever wanted to do was ride waves. It's awesome to do all these sports because they offer so many different perspectives.

WSL: What was it like growing up on Maui? Tell us about your upbringing.
My parents are avid ocean people, they do all the sports that I do now. When I was growing up I had no choice I was going to the beach and I could either get sand blasted in the face (since Maui's so windy) or I could get on the water. Some days it would be surf days, other days might be a wind sport kind of day. It also helped that I have known Robby Naish, Dave Kalama, Laird Hamilton, Rush Randle and a bunch of other legendary waterman like uncles. They brought me under they're wing and inspired me to do everything. They also inspired me to want to surf the holy grail of Maui surfing, Pe'ahi.

Lenny at Pe'ahi
Kai had an incredible performance at the Pe'ahi Challenge. For a guy on the cusp of becoming a ‘rookie' as Dave Kalama says, he looked pretty veteran in Round 1 of the event.

WSL: You and a lot of the other guys from Maui have grown up surfing Jaws. Tell us about Jaws as a proving ground for big wave surfers on your island.
Some of my earliest memories are of being on the cliff at Peahi and watching my heroes surf unimaginable size waves. My entire life I have been obsessed and have wanted to surf that wave. I'm sure the same could be said with the rest of the Maui boys since this jewel was right in our backyard. When I finally did get my chance to go out there, my first experience was on a foilboard with Laird and Dave when I was 16. After that I windsurfed, kitesurfed, tow-in surfed out there. Right when I started to get comfortable with all these sports, Shane Dorian showed up, and blew the door wide open for paddle surfing at Pe'ahi. My first paddle session at Pe'ahi was in March 2010 when Shane caught his crazy one, I caught one on my SUP and remembered thinking, OMG, what have I got myself into! I got a 10' surfing gun in 2011 and from that point on I have taken baby steps to go deeper, to get better in bigger waves. My goal is to surf out there for 30 years, I can't wait to see what I experience in that time span!

Kai Lenny at Jaws, Maui, Hawaii on January 15, 2016 (D). Photo by An entry into the 2016 Paddle Award category. Kai's earning his stripes on a surfboard, but he'll never give up his other interests. Here he is at Jaws, on January 15, 2016 by paddle and all. This photo is an entry into the 2016 Paddle Award category. - WSL / JOHANN MEYA

WSL: Tell us about your first time surfing the big stuff. Age? Where was it? Who was there and how did it go?
My first session ever was when I was 16 years old, but the biggest day came the following winter out at Pe'ahi in 2009 when the last Eddie ran. I remember vividly going out to Pe'ahi with Laird and Dave and their crew. I got towed into a ton of big waves but my most memorable wave was one Dave Kalama towed me on to on the left. I felt great until I rode it way to far because I was having so much fun and ended up getting closed out on. It's so funny, I totally thought I was going to die! I opened my eyes and saw these crazy under water clouds. I remember when I surfaced I started laughing because I was still living! Then Dave whipped by me and said, "I'm gonna grab your board." Then the Walsh twins scooped me up and brought me to the channel. I was addicted, my nerves calmed knowing I could actually handle a beating out there.

WSL: Who are your biggest influences and mentors? What kinds of advice have they offered you over the years?
My influencers and mentors are a wide range a exceptional human beings. When I was first getting started there were those who believed in me enough to help me along the road. Laird, Dave, and Robby were always mentoring me in all my sports and especially Pe'ahi. I'm lucky to have spent the time with them in my early years of big wave surfing. It's been really cool to have guys like Shane Dorian, Ian Walsh showing by example how to paddle giant surf. They've always been so nice to me and when I was just getting paddling, offered some incredible advice. I also get so much inspiration from the Maui Crew Albee, Billy Kemper, the Walsh twins, they are charging out there. I am also very grateful to have Victor Lopez and Darrick Doerner giving me advice.

Kai Lenny and his early windsurfing days. Photo: Martin Lenny Kai got an early start in all things ocean. Photo - Martin Lenny. - WSL / Martin Lenny

WSL: With the amount of big wave days this winter you've had a chance to shine. Where do you go from here? What are your goals when it comes to riding big waves?
Five years ago there is no way I could have ever imagined the waves I'm riding and the waves I've ridden. This winter alone I feel like I have learned as much as the past three seasons combined. This El Nino winter has been the ultimate blessing! Before every swell I think about the waves I want to ride and how I want to ride them. It's the mental process that has helped me overcome certain fears and scenarios that I've already played out in my head before they even occur. I'm taking baby steps just like all my heroes have told me to do. My current vision of the future is to be riding smaller boards so that I can do turns and negotiate longer barrels.

WSL: Tell us about some of your challenges (life or surfing). What have you overcome to get to where you're at and what does that mean to you?
I have always been a perfectionist so I'm always looking for ways to improve and step up my ability. I think most of all it's about improving myself as a whole. If I look back a month from now I want to be able to say to myself that the person I am now is way better than that person I was. When I was younger my biggest challenge was to prove that I could do all the sports and I didn't have to choose one. I still can't imagine having to choose one sport, they are all so much fun why would I want to stop!

Kai Lenny at Maverick's, California on February 4, 2016. Photo by Frank Quirarte. An entry into the 2016 Paddle Award category. Kai travelled to Maverick's this winter to begin challenging himself in colder climates. The extra weight of a wetsuit didn't appear to slow him down. This photo on February 4, 2016 by Frank Quirarte is another entry into the 2016 Paddle Award. - WSL / Frank Quirarte

WSL: Tell us about your worst wipeout and how you managed it in the moment and after.
One that sticks out most from this year--I remember taking off on a wave and being way too deep. In the position I was, I thought I was going to set up for the biggest barrel my life. But the top of the wave started crumbling and I was so high on the way I didn't have time to get down the face so I literally had no option but to jump off my board. The wave blew me up so hard it inflated my entire wetsuit with water and put my ripcords for my inflation vest into my wetsuit. My board broke into three separate pieces and I got cemented onto the bottom of the reef in a squat stance. In total I was down for about 45 seconds and it ended up being a two-wave hold down. Nice to know that I can handle it!