Kai Lenny Is Bright, Clear-Eyed, And Wonderfully Opinionated

In an insular industry, one that thrives on ego and bravado, Kai Lenny isn’t the person you’d expect him to be; the chiseled young Hawaiian has had to work his way in from the outside.

Over his relatively short career, Lenny has gone from paddle race and SUP wunderkind, to wind rider, to big wave hero, by following his heart and doing what enjoys.

While some might expect Lenny to be media trained and coy, when we get to talking he’s immediately gregarious and refreshingly candid, as he lays out the ostracism he suffered growing up on Maui as an alternative athlete, the sacrifices he makes to compete on the Big Wave Tour, dissatisfaction with prize money and judging criteria, and the balancing act of satisfying his non-endemic sponsors while fulfilling his desire to compete in the big wave realm.

Stab: You made your name as a stand-up paddler, windsurfer, and kite surfer. Now, you’ve got the foil deal going on; your status as big wave hero is solidified. But surfers are such weirdos, when it comes to anything but the standard shortboard. Did you ever catch any flack early in your career, when you were getting more well known outside of paddle racing?

Kai: Absolutely.

Growing up, I didn’t feel very comfortable at any of the surf breaks here on Maui. Just because I felt like such an outsider. I mean, I was acquaintances with all the surf kids. But I wasn’t a part of that group, really. I was definitely kind of on the outside of the fence.

It was what it was. I could’ve easily gotten in if I’d only surfed, but I was still preoccupied doing this other stuff. I wasn’t going to stop doing what I was doing because I wanted to fit in.

Every time I’d go out to any surf break… I used to surf every morning before school growing up but I just remember, every time I would be out there in the afternoon, when all the boys would come out they’d be like, “Oh, where’s your windsurf sail? You can’t stand-up paddle here,” all this stuff, even though I was just surfing.

Smart aleck comments, or whatever.

It all kind of changed when I started doing more big waves. Because at first it was like, “What’s this kid even trying to do out here? He’s a windsurfer. Blah blah blah.” Then I started getting waves, started getting bigger waves, then pretty quickly I found that the waves I was going for, the guys who were kinda haters, or whatever—they didn’t want them. And then they started respecting me because I was going on waves they didn’t want.

The last couple of years I finally feel like I can go anywhere here on Maui and not catch some sort of flack for anything.

Whereas, up until a couple years ago I never felt that comfortable at home. Which I think gave me an advantage because, mentally, I was always on my toes in a way. I had to prove myself.

“It all kind of changed when I started doing more big waves. Because at first it was like, “What’s this kid even trying to do out here? He’s a windsurfer. Blah blah blah.” Then I started getting waves, started getting bigger waves, then pretty quickly I found that the waves I was going for, the guys who were kinda haters, or whatever—they didn’t want them. And then they started respecting me because I was going on waves they didn’t want. It was that sort of thing.”

Photography

Heff/WSL

It all really comes down to playing in the ocean…

What I’ve noticed, the best surfers in the world all have appreciation for other sports. Because they can understand what it takes to be on a certain level in the ocean, and how different things can be. Most of the time it’s been people who maybe don’t surf all that great who are the most close-minded.

At the end of the day, the way I’ve kept true to what I do is just, you know, I only have one life to have fun. I want to be in the water all the time. All these sports are super fun, they pose different challenges. I’m not hurting or affecting anyone, so I’m gonna keep doing what I’m doing. Some of the experiences I’ve had, that are ingrained in my brain, I can’t imagine not experiencing them again. It’s just so much fun.

Do you think it helped your career, the fact that you had to forge a path outside of surfing?

Absolutely. Regardless of what people thought, I was sticking to my own guns, doing what I wanted to do. I just wanted to have fun, and it’s so windy here on Maui. My parents were surfers first, but also windsurfed, and they got me into both. And I really liked doing all that stuff. I could go to the outer reefs by myself. Have no one out. No crowds or anything.

And then I had all these opportunities through these alternative sports. I knew I always wanted to prove myself in surfing, to go to the North Shore, eventually. I was kind of carving my own path and I was following it wherever it went.

I knew that at some point it would kind of converge to where people would appreciate it.

One thing that I always wanted to do, that I still want to do, is to prove myself on the shortboard level. The core surfing level. Then still do all these other things and just be as well rounded as I possibly can.

I think transitioning from doing these alternative sports to big waves, and then continue to improve in really small waves as well… it’s kind of the opposite of what most people would ever do, you know? Like, usually you start small wave surfing, then big wave surfing, then you might do alternative stuff when you find success.

But now I’ve gone the opposite way and I’ve got all these amazing sponsors that aren’t within surfing. I’m still not really sponsored to surf big waves. It’s just what I do. And it’s kind of nice because, if I ever don’t want to go out, I don’t have to.

“Regardless of what people thought, I was sticking to my own guns, doing what I wanted to do. I just wanted to have fun.” – Kai Lenny

Photography

WSL/Heff

If you’re gonna go chase ‘QS points, you don’t think you’ll have a hard time finding motivation to paddle out in one foot onshore garbage?

No! I love surfing one foot onshore garbage. It’s so much fun.

The only time I think I’d get annoyed, competing full time on the ‘QS, is with all the waiting. Because you can do, like, two weeks of not even surfing. Just waiting for waves to dribble in.

But I’ve always felt that’s the most challenging thing in surfing, for me. Small waves. Having the fast twitch muscles to get going and do airs and turns. It’s its own challenge.

With social media, and the ability to package yourself instead of relying on brands or other platforms, how do you manage your career?

Social media has been really good for alternative athletes. It creates value to those non-endemic brands. Like the Tag Heuers. Even Red Bull, in a way.

Nowadays, if you don’t post something, it’s like it didn’t happen. It’s the weirdest thing. I remember, a couple posts ago, I put something up and someone was accusing me, like, “Do you ever just surf on your own?”

And I remember thinking, “God, 95% of the time someone’s not filming. But you wouldn’t know that because I’m not telling you that.” It’s the most bizarre thing.

I have been working with people since I was twelve years old through these other sports, filming, and just this last year have been focusing on collecting more footage. Actually having someone with me at all times. 

It’s a pain in the ass getting pretty much anywhere from Hawaii, and you travel with a massive amount of gear. How do you handle logistics?

My dad has always helped manage me, and through the years I’ve gained enough connections everywhere that I kinda know someone everywhere I’m going. Which is awesome. I have a good network.

But the majority of the time, I’m traveling by myself.

That’s got to be a challenge sometimes, though? I mean, you don’t travel light.

What I’ve learned is how to pack everything meticulously, so nothing is too heavy. I always feel like I can move all my equipment in one go, if I have to. If I’m in a tight position, I can physically maneuver five board bags all at once, with a few carts.

At times it’s stressful, but what I’ve realized about these huge board bags—it’s kind of a blessing in disguise because no one is going to touch them. You can leave them somewhere, go get a rental car, and come back and they’ll still be there.

Because even in these third world countries people are like, “What the hell am I gonna do with that thing?”

Granted, that’s not the ideal situation. But you do get times when push comes to shove and you have to adapt.

But I have to bring everything everywhere, because every time I leave something behind, I wish I had it. And I hate that feeling. So I’m willing to battle to bring it.

Sometimes airlines don’t like it, but I’ve found you’re better off traveling far, far, distances with airlines with more board bags than less. Typically, they either get annoyed with you, or feel bad, and let you on. And a lot of time they’ll charge you the same for one small board bag as four big boards bags.

There are those times they want to charge you four grand, but most of the time they just want to get you out of there.

“One thing that I always wanted to do, that I still want to do, is to prove myself on the shortboard level. The core surfing level. Then still do all these other things and just be as well rounded as I possibly can.” – Kail Lenny

Photography

WSL/Heff

Speaking of travel costs, you won $3000 for equal seventh at Nazare, and getting there ain’t cheap last-minute. Hell, an inter-island flight runs $400. How much are you spending to compete?

First place in a Big Wave World Tour event is twenty five grand. Second place is, I believe, sixteen.

And I’m pretty grateful for that. Because a lot of the other sports I’ve come from, winning an event is, like, four grand. It’s not that much.

That being said, I think the fact that the Big Wave Tour events typically have the biggest viewership of any surf event in the world, and the fact the we only have three events per year, which isn’t a lot for a lot of these big wave surfers that only compete in that discipline, it’s kinda funny that, over the years, the prize money has dwindled.

There was more money in big wave surfing in the late-90’s than now. Which is kind of bizarre. The XXL awards is losing money this upcoming year.

By no means am I whining about anything, because I’m coming from a place where twenty five grand is a lot better than four. But the thing is, you risk your life and maybe you don’t even make your first heat—anything can happen. And then you don’t make enough money to even cover a one-way ticket to get to these events.

Usually the time these events run is in the Winter, which is holiday season, so ticket prices are super gnarly to begin with. Let alone last-minute.

Then, most people might bring one or two board bags. I bring three. Because, of course, I have to take a tow board and I have to take a foil. That right there is six hundred, at best, each way. Sometimes it’s seven or eight hundred. Then you have to rent a car, and last minute accommodations…

And for a lot of people these events are a million miles away. To get to Nazare is so gnarly for us in Hawaii. We have to leave here before they call it ‘green light.’ Because if we don’t, we’ll show up the day before [the event], in the afternoon. And to be jet-lagged after traveling for thirty six hours, then go huck it on some fifty footers, is not fun.

A lot of these guys on the tour have normal jobs, and I know there’s a couple guys that do hard labor construction work, and build up all this money, just to blow it all during the winter on equipment and travel.

Everything adds up. Three grand does not cover it. I’ll put it that way.

I don’t think anyone is really coming out of the Tour events making money. Maybe some people are making a little bit, but it’s not much. A little drop in the bucket.

The WSL does provide some accommodations, but they’re not typically very desirable. And you want to get a good night’s rest before going out into giant surf.

“There was more money in big wave surfing in the late-90’s than now… I don’t think anyone is really coming out of the Tour events making money. Maybe some people are making a little bit, but it’s not much. A little drop in the bucket.”

Photography

WSL/Justes

When you say that the accommodations aren’t desirable, what do you mean?

They’re, typically really small. So you don’t have space for equipment. And everything is put together so last minute…

It can help with the budget of the trip, but I feel like, if you’re going to surf big waves, you want to have a nice bed. You want to always have warm water. You want to have a good restaurant nearby if you don’t have a rental car. If you’re gonna put yourself in a gladiator pit you want to stay somewhere that’s nicer.

When we had it in Puerto, that was the gnarliest. One of the rooms I got down there was so gnarly. There was rat shit on the walls, the sheets were dirty, there were dead cockroaches in the corner of the room. I was baffled.

I went walking through the town looking for anywhere else that had space. I somehow lucked into the most expensive place there, because I was, like, “I am not staying there for four days with rat shit on the walls.”

Your entire career revolves around promoting yourself, traveling all over to do rad stuff. But the Tour, even though there’s only three events, has a seven-month window. That has to make it difficult to plan things.

Oh man, I can’t even tell you how many times I’ve had to cancel unbelievable opportunities to compete on the Big Wave Tour. It gives you minor anxiety because, what people don’t see, is that the events almost get called on, like, every other week.

But then they’re like, “Oh, no, no, no. We’re not gonna run it. It doesn’t look good. We’re not gonna do it.”

But up until that point they’re, like, “Okay, get ready.”

So you’re getting your accommodations ready. You’re booking flights. Just to make sure you have a flight. Getting your board bags ready.

Then, “Okay, we’re off. We’re off.”

It’s this kind of roller coaster all winter.

I mean, I love competing in big waves. I love being able to go to these places and surf with only five guys. That is awesome. Because everything is pretty crowded nowadays. But, by the time it runs, you’ve already gone through the highs and lows seven times to get there.

Nothing is worse than from now until March, because you’ve already surfed big waves for the last two or three months and they’ve almost called a big wave event on a million times and you’re like, “Oh my god, run this thing thing already.”

“It’s this kind of roller coaster all winter… I mean, I love competing in big waves. I love being able to go to these places and surf with only five guys. That is awesome. Because everything is pretty crowded nowadays. But, by the time it runs, you’ve already gone through the highs and lows seven times to get there.” – Kai Lenny

Photography

WSL/Keoki

Does it cause problems with your sponsors? You’ve said you’re not really sponsored for big wave surfing, and you have other things to do… does it fuck with your obligations?

I’ve always been able to work it into my sponsorship deals that, if one of the three events come up, it takes priority. And all my sponsors understand that. But I don’t think they expect it to happen that often. Nine out of ten times I have to call one of my sponsors and be like, “Hey, I’m not going to be able to make it. I can’t make this obligation because there’s this Big Wave Tour event and that’s what I want to do.”

But some of the non-endemic sponsors I have, and opportunities they provide, meeting and taking people on the water and doing really crazy things with really relevant people, big athletes or whatever… I’ve had to say no to some pretty crazy things. 

I’ve thought about it at the time. Like, “Nobody in their right mind would have said ‘no’ to this. Going on this huge yacht in the Caribbean and living the dream. Getting to do something with Cristiano Ronaldo or Tom Brady…”

But I always know I’m making the right decision because I wouldn’t be getting those opportunities if I didn’t focus on what I love to do and follow it with the truest passion. And big waves have brought me a lot of success because people love to see images of big waves.

All those opportunities, I’ll get another crack at them some day. And if not, so be it.

At what point does it stop making sense for you to compete? There’s nothing to stop stop you from chasing swells and getting footage, and putting out viral footage that a billion people see while having nothing to do with the WSL.

I love competing and I’m so lucky that a lot of my other sports cover my passion for riding big waves. What I think most people don’t understand is that big wave surfing is so expensive, even on just a normal swell.

I’m dropping thousands and thousands of dollars per swell out at Jaws. Because I need to get a boat, I need to have drivers for my jet skis. I need to make sure the jet skis are tuned up by the mechanic. I’m flying a photographer or a videographer out. Just the whole machine is so big sometimes.

The event itself is the same thing. It costs a ton of money to do. Most of the time it can cost more money to compete than you’ll actually make from it. You won’t even break even.

At Jaws we always get our own boats, and we always have our own jet skis. Just in case. You want to be prepared in that environment.

There’s been a lot of tension behind the scenes with the Big Wave World Tour, because there’s a few things everyone is trying to work out. Certain obstacles to work over.

If things don’t shape up I’m sure people will not do the Tour. But as long as the Tour is, hopefully, providing everyone a good platform to get noticed or seen, or get a paycheck, they’re gonna keep doing it.

For me, competing in big wave surfing is just a passion. I always have a goal to win and I feel like competing, in itself, has allowed me to perform at a higher level. Because when you throw on that heat jersey the competitiveness kicks in, everyone is watching, and you feel inspired to go a little bit bigger than maybe you would have on your own. I love that part.

“I’m dropping thousands and thousands of dollars per swell out at Jaws. Because I need to get a boat, I need to have drivers for my jet skis. I need to make sure the jet skis are tuned up by the mechanic. I’m flying a photographer or a videographer out. Just the whole machine is so big sometimes.” – Kai Lenny

Photography

WSL/Pompermayer

Have you brought up prize money with WSL management? Because, if we’re being totally honest here, twenty five thousand dollars isn’t very much money. It’s a nice check, but it’s not going to buy you a house. It’s not enough to build a future.

Their reason is, typically, that it’s hard to run events. The same story you’ve always heard. But there’s never been a concrete reason why.

I know that all the athletes have requested more money. Or throw some more events. Instead of three have six events so you can, hopefully, run four. So at least you have more opportunities at events.

But that’s definitely something that’s been coming up quite a bit internally, among the surfers. After Jaws, and Nazare, I heard that viewership was five times as big as any of the [WCT] events. But you’re getting paid a lot less. And getting physically hurt doing it.

When you look at it logically – we have the most viewers, we only have three events, and I think the extra prize money would inspire more people to want to get into it. Because I know there are a lot of guys who don’t even want to get into it.

In a perfect world it’d be great to have equality for big wave surfers. It’s great that the women have equal pay, but the next step is equal pay for big wave surfers. We’ll even take a little bit less.

You’re definitely in the hole after each event, if you’re not winning.

I have to give it to everyone, the surfers, they’re all being very solution oriented. No one is angry, they’re just trying to figure out how to make our tour better for us, and for the next generation that are going to be competing on it. And prize money is a part of that conversation.

Have you heard some of this talk of forming a Union?

Yes. The big wave surfers are creating one right now. Jamie Mitchell, who is the surfers’ rep for the BWT, is spearheading unionization. And everyone is on board. After a couple years of certain ups and downs everyone has realized that we need to get together.

Kai Lenny at this year’s Eddie Invitational paddle out.

Photography

Sam Moody

What other changes would you like to see on the Big Wave Tour?

I’d love to see an updated judging style, focusing more on progression than just pure charging. We’re at a point now, in big wave surfing, that everyone is so comfortable and is starting to push so hard and I think certain people have gone underscored for some truly incredible surfing. Maybe not on the biggest wave of the day, but making already big waves and doing incredible things on them. In the past it’s always just been about getting the biggest wave of the day and making it to the bottom.

I think including priority into big wave surfing would help us move down in board length. During my freesurfing sessions I use much smaller boards than I would in a heat. Because you only have forty five minutes to catch two waves and it’s hard to battle on a 9’4 with guys on 10’6s.

To me it’s kind of ridiculous that there already isn’t priority, since it’s in every other form of surfing. And in big waves, that’s when it’s most critical. I would sit in a much different position, on much different equipment, and I think it would allow all the athletes to surf at a higher level. Because then they could focus on their surfing, and not on the hassle. The hassling is pretty gnarly.

It would also be nice to see a little more emphasis put on showcasing the athletes. Doing pieces on them. Because, for a lot of people, it’s hard to break in because they don’t get any play on it.

It’d be nice if the XXL awards were able to retain money, instead of lose money. Because that’s another sort-of event that we have. But in this newer XXL the prize money has been slashed dramatically. To the point where it’s almost not worth flying to Portugal to go do it. Especially if you’ve gone back and forth all year.

To be honest, I really do feel like the WSL is trying hard. And I do think they want to do all these things. I don’t know why it isn’t happening more quickly, but I have faith they’ll pull through and be able to step everything up.

I know it’s tough times for the surf industry, but I think big waves have a place in households all around the world that don’t surf.

It’s pure gladiator entertainment and people love that.

“I know it’s tough times for the surf industry, but I think big waves have a place in households all around the world that don’t surf. Because it’s pure gladiator entertainment and people love that.” – Kai Lenny

Photography

WSL/Bidu Digital