Overview
“And what we call freestyle today is what Lou Wainman and all these Shannon Best and all these boys were throwing down in Maui before any of us…”
Lou Wainman is one of the most influential pioneers in kiteboarding and a legendary rider known as the “Godfather” of the sport. Originally a wakeboarder and windsurfer from Florida, he moved to Maui and realized the infinite possibilities of combining early kites with wakeboarding. By mounting wakeboard boots onto boards, he brought the concept of “wake style” into kiteboarding and played a crucial role in shaping its history. Recognized as a top innovator, he stayed ten years ahead of his time, turning wild and revolutionary ideas into reality.
Career
At a time when riding directional surfboards was the norm, he established a new style by bolting wakeboard boots and snowboard bindings directly onto short twin-tip boards. Around 2000–2001, alongside legendary Hawaiian shaper Jimmy Lewis, he helped develop extremely short custom boards (around 125 cm, and sometimes even as small as 90×33 cm) ridden with an ultra-wide stance matching his foot spacing. This significantly contributed to establishing the outline and rocker of modern twin-tip boards.
In Maui’s howling winds, he dared to use super short 10-meter lines. Riding “unhooked”—detaching from the harness to hold the kite entirely with his arm strength—he created insane tricks like “Kung Fu,” where he steered the kite straight down to hang completely sideways in mid-air while extending his body one-handed. Seeing him carve violently on flat water with a tiny twin-tip in Hood River inspired many to take up kiteboarding.
He has no official contest winning records from the modern era. This is because he was already pulling off technical tricks like handle passes, KGBs, and mobes in 1997—long before world tours or freestyle competitions even existed. Disliking the idea of being constrained by contest rules, he chose to broadcast his wild riding to the world through classic kite movies like “Awake” rather than wearing a jersey for judges. This makes him the ultimate original freerider who proved a pro could make a living on style and video edits alone.
The Legend of the ‘Carrot Board’
During the wild early era of DIY gear, he literally strapped a custom handmade board shaped and colored like a giant carrot (“The Lou Wainman Carrot”) to his back, heading out into the water to get airborne. Years later, video surfaced of Kai Lenny mounting a hydrofoil onto this legendary carrot board to surf waves, proving that the madness and legacy of the carrot board lives on.
“I don’t think we’ve seen a development in the sport that’s been that impressive and that fast-paced, probably since the early days of the sport when guys were going up with carrots on their back and riding anything.”
Sponsors and Brands
He later launched his own brand, Wainman Hawaii. Featuring a distinctive rabbit logo, the “Rabbit Gang” kite series gained a cult-like following due to its unique delta shape and punk-inspired branding. Today, living in Maui while raising his daughter, he works behind the scenes with friends’ brands (such as ON kiteboarding) designing kites, boards, and wings as a veteran developer who tests gear to its limits.
Personality and Relationships
He grew up as a multi-sport athlete, pursuing inline skating and springboard diving in his youth. Beyond his identity as a pro rider, he showed great professionalism by coaching kids and publishing newsletters to spread the sport. In the early days on Maui, he collaborated with other pioneers like Shannon Best, pushing each other to build the foundation of modern kiteboarding.
Quotes and Episodes
“I came out here to be a pro windsurfer. And then I saw Manu on a kite. I was a wakeboarder from Florida and also a windsurfer, so I put two and two together, bought a kite, and started kiteboarding.”
— Lou Wainman
“I guess my favorite kite video would be ‘Awake’ by Chris and Buster here in Maui.”
— Lou Wainman
“I’ve just been kiting and working on designing all sorts of stuff—boards, kites, wings, everything—living in Maui, raising my daughter, and just having a good time.”
— Lou Wainman
“I kind of started as an athlete. My dad was a good football player. I played racquet sports, got heavily into inline skating, and then from ages 10 to 15, I was super into springboard diving.”
— Lou Wainman
Competition Results
He has no official contest winning records from the modern era, as he was executing highly technical tricks long before organized world tours existed in 1997. He pioneered the path of a pure freerider and explicitly avoided the constraints of competition rules.
Search Aliases: Lou Wainman, LouWainman