For Kai Lenny, happiness comes from being in the water.
Whether paddling, surfing or sailing, as long as he has the salt spray on his skin and the wind at his back, the Hawaiian is game for just about anything. Growing up in Paia, Maui, Lenny learned to stand on a surfboard about the same time he learned to walk, and he has been on an upward trajectory ever since.
Today, at 21, Lenny stands on the precipice of becoming one of the world's greatest watermen. With windsurfing legend Robby Naish passing along his knowledge of wind and water and big-wave veterans Laird Hamilton and Dave Kalama showing him the ins-and-outs of the 30-foot waves at Jaws, Lenny is the beneficiary of some of the most dynamic teachers in their respective athletic pursuits. He recently paddled the grueling 32-mile race from Molokai to the Oahu channel, finishing as a runner-up. But true to form, Lenny smiles about it all, saying, "I love what I'm doing. It's the best life. It's a dream."
Lenny also made quite a name for himself this year with what he was able to accomplish at Jaws.
"We have been blessed with incredibly consistent Jaws [waves], and I have had the opportunity to really find my bearings out there," Lenny said. "Besides my mentors and my parents, the ocean [and Peahi in particular] has been the greatest teacher of my life."
To date, Lenny has six Stand Up Paddle World Champion titles, but the big breakthrough came in 2012 when he won the SUP Race World Championship at the iconic Waimea Bay on the North Shore of Oahu. Paddling for the world title, Lenny pushed himself through two days of intense competition, ultimately finishing victorious.
"If I can handle Jaws mentally, and I feel super scared out there, I shouldn't be scared pushing hard out here," said Lenny.
While a world title is an accomplishment not to be scoffed at, Lenny's roots run deep, and he dedicated his win to the memory of the late Harold "Iggy" Ige, a famous surf and paddleboard shaper who was a key figure in crafting boards for the Naish label, one of Lenny's main sponsors.
In May 2012, Lenny became the first person to ever cross Lake Michigan on a windsurf board. Averaging 25 knots, the 56-mile crossing took him just under three hours to finish. But that was just the beginning of a busy summer.
Then came the Naish International Paddle Championships on Maui, which Lenny won handily. He followed that up with the Molokai to Oahu race, where he finished a respectable third in the SUP category. "It was a busy summer," he said with a smile.
Never one to rest on his laurels, at the 2013 America's Cup in San Francisco, his sponsor Red Bull set up a race between him on a windsurf board and the Oracle sailboat. Lenny led out of the gates, forcing the crew of the boat to actually work.
"I had them for a few minutes there," said Lenny with a laugh, "but that boat is built for speed and there was no way my kitesurfing rig was going to beat that multimillion dollar boat once they got up to speed. Either way, it was a great experience and demonstrates just how powerful kitesurfing can be."
Lenny had little chance of being anything other than a brilliant waterman. He was practically born with gills.
"I was in the ocean before I could walk," Lenny said. "My parents would bring us down to the beach every day. It's just what we did as a family."
By 3 he was surfing, by 6 he was windsurfing, and by 8 or 9 Naish had already taken him under his wing. Then Hamilton and Kalama entered into the picture, coaxing the young pup into stand-up paddling surfing and tow-in surfing.
"One of the best things about this kid is not his work ethic, not even his incredible athletic ability, but his humbleness," Kalama said. "He's not doing it for him, not for you or me to praise him but rather because he loves it, and when you have that as your motivation, there are literally no limits."
When you pursue as many sports as Lenny, packing to go on the road is no easy feat. "The airlines love me," he joked.
But seriously, Lenny travels with a quiver of short boards, a windsurfing kit, which includes two boards and complete rigging, one kite surfing setup, two stand-up paddle boards and paddles. He typically squeezes all that into five large board bags.
"My shortboard friends freak out at the cost and hassle of one board bag, but that's a piece of cake," he said with a laugh.
As for his most recent exploits, he is now one of the premier surfers at Jaws, undaunted by hold-downs that can last over a minute.
"I remember watching the videos of Laird, Buzzy, Dave and Robby riding gigantic waves at Jaws," said Lenny, reflecting on how he first became drawn to riding the famed big-wave break. "I would just watch the videos over and over wondering how they could do it so well. I would rewind the tapes to watch the takeoff, the bottom turn and the kickout.
"When I was 8 years old, Laird rented a house down the street from our home. I remember wanting to meet him, so my little brother and I walked down the street and we would knock on his door. Every time we went down, Laird was never at home. Then one day, I knocked and Laird opened the door. Ridge [Lenny's brother] and I were so excited that we just stood there and looked at him. I don't even remember what he said, but I remember that on that day I left his house determined to ride big waves at Jaws when I grew up."
After that encounter, Lenny's path was set. He now surfs and sails at Jaws when the conditions come together and has even fooled around on a foil board out there. His parents might be a little freaked, but they take solace in knowing that he has been smart about everything he has done and, be it sailing with Naish or towing with Hamilton, that Lenny is in good hands.