Red Bulletin

Ryan Sheckler and the State of Skate

To thrive in the action sports business, a champion must be a CEO, and a ’boarder must be a brand.

Skateboarder Ryan Sheckler in Red Bulletin magazine
© Andrew Peters/The Red Bulletin Magazine

It’s a crisp spring morning near Seattle -- too hot with a jacket on, too cold without one -- and amid the towering pines on the banks of Puget Sound, Matias and Ron Miguel are planning their next trick.

The brothers -- 17 and 18 years old, respectively -- are eyeing the brand new skate park built on the land they call home, the Port Gamble S’Klallam Reservation. Matias and Ron’s plans are interrupted by the appearance of a big black van with tinted windows that bumps down the adjacent street. Riding along outside on a skateboard, hanging on to the open passenger-side window and laughing, is a lanky, tatted-up skater who could care less about rolling alongside a two-ton vehicle that could squash him with one rash move of the steering wheel.

At 18 months, Sheckler took his first ride on a skateboard; by the time he was four years old, he was sleeping every night in his helmet.

The van makes a turn into the skate park’s parking lot and the skater breaks away. He rides up to the side of the park, excited and beaming. He doesn’t hesitate before he drops in, and between the tattoos, the devil-may-care attitude and his brash agility it’s obvious that the skater is Ryan Sheckler.

“Uh oh,” Matias says. “Now I’m going to fangirl.”

It’s no wonder Matias idolizes him: At 24, Sheckler has been a professional skater for almost half his life, a prodigy that has grown with the sport to become the world-famous face of street skateboarding. At 18 months, Sheckler took his first ride on a skateboard; by the time he was four years old, he was sleeping every night in his helmet. He turned pro when he was 13 -- and even before then, sponsors were clamoring to sign him. Besides Red Bull, he includes Plan B Skateboards and Etnies -- which has sponsored him for more than 15 years -- as long-term business partners.

Sheckler epitomizes the current state of affairs in skateboarding: Not only does a professional skateboarder have to be a hell of an athlete, but now thanks to the omnipresence of social media, he has to know how to market himself with the same kind of force and dexterity that he shows on the skate park. This means skateboarders traveling the world to shoot video parts and distributing them online, keeping up with sponsor obligations and charitable events that are catalogued in real time on the Internet, on top of the actual work of skating, competing in events ranging from the X Games to the Dew Tour to Street League.

“As an amateur skater, when you’re just skating for fun, you don’t have to go on trips, you don’t have to go to autograph signings or photo shoots or go promote a company,” Sheckler says. “But the second you sign that contract, you have to agree that the whole time you’re going to give everything you have to these companies. People don’t want to put in the extra work, but you have to.”

All of this equates to tons of opportunities for pro skateboarders, with many companies looking for fresh faces to sport their gear -- and they know that covering the day-to-day of athletes’ lives via social media is an easy way to reach casual fans.

The immediacy of sponsors adds pressures that the previous generation of professional skaters didn’t have. For Sheckler, there were times when one slip-up during competition would send him into a spiral of doubt. It wasn’t just a bad day -- it was his livelihood at stake.

“I used to really freak out if I had a bad contest, like, ‘Ugh, my sponsors are going to drop me, I’m not the same, I’m not relevant to them anymore,’” he recalls. “My dad really calmed me down on that one. He’s like, ‘They still love you, dude. With everything else you do? You can have one bad contest or two bad contests, that’s not life changing. That’s not the decider.’”

Sheckler gives the crowd a show at the S’Klallam skate park as he demonstrates his high-flying routine, soaring over the edge of a bowl and landing flawlessly, physics be damned. There’s no indication of weariness from Sheckler -- amazing, really, given that he’s been in the spotlight the entire time he’s been on the reservation, with constant requests for autographs, hugs and pictures. His charitable foundation helped fund the building of the park.

On top of the dogged attention, this Seattle trip is the latest leg of a relentless two months of travel filming his YouTube show, Sheckler Sessions, as well as other video parts to distribute online: He’s gone from Estonia to Australia to Mexico to Barcelona to Seattle.

“My passion for skating has, if anything, grown just from being able to travel the way I travel and meeting the people I get to meet and helping the people I really want to help,” Sheckler says.

Red Bulletin