When he won the gold medal in snowboarding at the 2006 Olympics in Torino, everyone knew how Shaun White's story would end. The corporate advertising complex would line up to capitalize, just as it has with every gold medalist since decathlete Bruce Jenner. And White, with his strange equine beauty and crazy pile of long red hair, would assume the position, allowing his action-sports cred and new America's-darling status to be sucked out of him and slapped on every can, box, and cookie bag in the nation. All the elements for cashing in and selling out were in place: Take a kid with working-class roots (his mom was a waitress, his dad worked for the water utility in San Clemente, California); add Olympic gold and huge endorsement checks; run the cliché. Heinz would offer six figures to put White on everything from ketchup bottles to stewed tomatoes (White's then-nickname: the Flying Tomato). Maybe a toothpaste company would come pushing tubes of new Shaun Extreme Whitening. Throw in some potential heavy-rotation spots for Schick Xtreme Shaving and Doritos Extreme Nacho Cheesiness and the caricature is close to complete. As a final inspired bit of packaging, someone would lay down the big bucks to insert Mr. White in a straight-to-DVD production of Faster Times After Ridgemont High, where he would be cast as a snowboarding Spicoli attending a junior college somewhere near Banff. White would then spontaneously combust into the most awesome! bitchin'! rad! gnarly! D-list spokes-celeb ever.
But Shaun White took a pass on becoming the Crown Fool of Gnarnia. "I was so fortunate to have had some success before the Olympics," he says. "So when the time came for everyone to come at me, I was able to step back and say, 'Do I really want to do that? Do I want to be known for airing over some dude who is going aaaahhh! with his teeth gleaming?' "
Considering the risks involved in his day jobs — in 2003 he added pro skateboarder to his résumé and took gold at the 2007 Summer X Games — control is a survival instinct. (At 11, a midair collision with another skateboarder left him with a cracked skull, a broken arm, and a fractured foot.) Even as a teenager, White understood the power of his image — his pre-Olympic sponsor list included Mountain Dew and T-Mobile — and felt compelled to protect it. "A photo would go out that I didn't approve, and a kid would come up and have me sign it," says White, now 22. "And it's an awful photo, and I know because I'm signing it he's going to put it up on his wall. Now he's got this awful photo on his wall. That stuff would get to me." So much so that at 15, he made sure his agent wrote a right of approval into all his contracts to control the use of his name or likeness. "A lot of people will just put their name on anything, and you can tell," he says. "I just can't do that."
Unlike gymnast Shawn Johnson with McDonald's, or human fish Michael Phelps with Subway, White has sought out companies he truly connects with. Working with a tight team of advisers that include his 29-year-old brother, Jesse, and his agent, Mark Ervin of IMG, White sees these deals as a long-term investment portfolio, something that will outlast his knees. Each corporation meshes with a discrete slice of his actual life, and with each one, White dives in and takes a central role, from the design of specific products to pulling deals together among his various partners. Last fall, his street-wear line appeared in Target stores across the country. This year, he expanded his best-selling Burton collection of snowboarding gear to include a stand-alone extension for women. There are marketing deals with HP, Oakley, and Red Bull. He collaborated on a snowboarding video game with Ubisoft that went on sale just before the holidays. And whether it's the quirky commercials for Target, the reality-style video shorts in the back-to-school Web campaign for HP, or the high-energy ads for Ubisoft, the ecstatic look and feel of the White DNA comes through. "Every week, we get presented with a big opportunity from someone," says Ervin. "Shaun turns down a lot of money. And I couldn't be more proud of him."
The companies that do make the cut look to White as a tractor beam to the $150 billion youth market. "Shaun White has this ability to juggle his authentic world and the corporate world and be that third platform between the two," says DeeDee Gordon, a trend expert whose L.A.-based company, Look-Look, focuses on youth culture. "He is living by his own code, and young people admire that. He has definitely stayed true."
White's most valuable asset of all, the key to that $150 billion, may be an eccentric charisma that is an irresistible draw for kids — and, more important, their parents. In a post-Olympics interview on CNN, White marveled at the attention flight attendants lavished on him after seeing his gold medal: "I had unlimited service after that. I was gettin' drinks. I was gettin' snacks. I was taking photos in the back... ." The anchor interrupts, "Wait a minute, drinks? You're 19 years old!" Without missing a beat, White drawls: "I'm talking about Mountain Dews, baby." And with that, a little backstage bragging was transformed into boy-next-door wholesomeness. A little sass to impress the kids, an apple-cheeked smile to win over parents everywhere, and for his sponsor at the time, Mountain Dew, a plug money can't buy.
White has just returned from a surf trip in Bali and the Maldives, and he looks tan and fit, though his rolling SoCal twang is hoarse from a previous night's karaoke party in Los Angeles. He and Jesse are tucked into a booth at Freemans, a restaurant on Manhattan's Lower East Side with a vintage zinc bar and a taxidermy collection that ranges from a white goose in a landing approach to a wall of jackelope skulls.
White is describing the properties of the fabrics in the clothes he designs with brother Jesse, noodling an inside joke about the amount of blood snowboarders and skateboarders tend to spill. "With snowboarding, there are only a certain number of fabrics that are waterproof. It's a lot of function with the fashion," he says. "For Target, it'd be nice, but my cotton doesn't need to be blood wicking."
The Whites have been building their professional partnership since 2002, around the time when Burton Snowboards offered Shaun a chance to design his own pro boot. He had been riding for Burton since he was 7, when the company expanded into kids' gear, but after several years on the pro circuit, he was looking to throw his leash. "I was getting older and didn't think I could roll with Mom and Dad anymore," he says. "So what's the next best thing? Older brother."
In his new role as quasi-adult supervision for a 15-year-old, Jesse handled the travel schedule, shot promo photos, and explained to the occasional New Zealand rental company how the car got wrecked. "I was 22 and just learning how to be an adult myself," he says. "It was way too much responsibility." Adding to it, Shaun asked him to take on the design work: "I've always loved Jesse's art, so he designed the boot. It sold out in the first hour of a trade show, and we had to do a re-release. That's where it all began."
For four seasons now, the Whites have created boards, boots, bindings, jackets, pants, and underwear for Burton. Together, they brought a radical reinterpretation to the boxy, baggy snowboard style by incorporating splashy colors and menswear elements: lapels, asymmetrical zippers, motorcycle-jacket cuts. "When I first started, I didn't have a clue about the difference between houndstooth and herringbone," Shaun says. But he had ideas that Jesse was able to translate into patterns.
"I'd say, 'Why don't we do a jacket like this?' " says Shaun.
"And then I'd draw it and say, 'Like this?' " says Jesse.
"And I'd say, 'Yeah, but with a pinstripe lining,' " says Shaun. "We wanted it to fit well and be different. It worked."
Already in touch with their inner marketers, they even titled the pieces: Puff the Magic Jacket, Jacket of the Gods, the Most Unholy Jacket Ever. "I wanted parents to have to call and ask, 'Do you have the Most Unholy Jacket Ever?' " laughs Shaun. It's a classic White touch, a way for rebellious kids to feel like they're buying from a peer. But since the rebellion stopped well short of Satanic cults or Columbine jokes, parents could laugh along. And drop the $200.
Despite the immediate success of the Whites' early gear, it took some convincing to get Burton to produce the women's line. "At first we were like, yeah ... no," says Greg Dacyshyn, Burton's creative director. "But then they came at me with full creative boards, showed me the presentation, and it wasn't about Shaun. It was about this design aesthetic Shaun saw. He was like, 'You're not making clothes for the girls I want to hook up with.' " The line tapped a market no one had targeted. "We always kept a smaller size of my pro model board because a lot of girls rode it," says Shaun. "There was this void. The clothes were all built for men, and in my experience, I think chicks ... ladies ... er ... they know what we call them ... special lady friends ... they want to look hot."
His instinct for pushing sponsors into new ideas and new territory is becoming part of White's value. He worked with Oakley to create its first signature goggle, which quickly became a best seller, and today, the company's top athletes all have goggle and sunglass models. Similarly, when HP decided it wanted to connect to the youth market, it saw White as a logical choice to star in the first of what it hoped would be a series of commercials. "This first ad was very difficult because we had to explain what this thing was going to be," says HP marketing VP David Roman, describing what became the "Hands" campaign. "We were saying, 'We're going to show who you are by what's on your computer and have all these graphics and animations, and you're just going to stand there and move your hands and it will all come together.' It was an act of faith. Shaun got it immediately."
The campaign eventually featured Jerry Seinfeld, Serena Williams, Jay-Z, and Pharrell Williams. "We've done 10 of those commercials and Shaun White got the biggest pickup of all," says Roman. When asked about the experience, White just laughs. "They had this hand stunt double for me in case I couldn't do it," says the first person to pull a 1260 (three-and-a-half rotations) at the Winter X Games. "It was hilarious."
As a mogul in training, the White mantra is to keep it light. But as his medals pile up — and as his various ventures post big numbers — getting him to sign on has become an increasingly high-stakes moment for his pursuers. In the run-up to NBC's new Winter Dew Tour last December, for example, the mood at 30 Rock was tense. "It was really important to get a commitment from Shaun," says Kevin Monaghan, a senior vice president at NBC Sports. "I remember telling Dick Ebersol [NBC Sports' legendary chairman] when White had signed on and was going to appear. Dick said, 'He has to appear. It can't be called the best winter tour if you don't have the best athlete.' "
But the easiest way to calculate White's commercial draw may be to listen to video-game maker Ubisoft. "We wanted to move our portfolio to include sports and create a snowboarding product," says Tony Key, SVP of sales and marketing. "Our only condition was to get Shaun White attached to the project. If he signed on, our plan was to build a billion-dollar franchise. If not, we wouldn't pursue it."
During our long lunch, Jesse and Shaun finish each other's sentences and follow random thoughts to illogical conclusions. Blood wicking evolves into an imaginary album title and often ends their sentences as a kind of exclamation point. "I would not have gotten where I am if it wasn't for Jesse," says Shaun in a serious moment. "There are so many people who want to pull you in the wrong direction. Jesse keeps me straight."
The red neon sign of Hollywood's Roosevelt Hotel casts a monochrome glow over a rooftop party after the X Games last August. Mark Ervin, White's agent, is wearing jeans and a dress shirt, tails out, and sipping a Budweiser. Even though his client didn't win the vert skateboarding competition earlier that day, he's in a fine mood. He should be.
Seven years ago, while primarily representing skiers at IMG, Ervin was advising Target on how to gain access to the action-sports world. His recommendation was simple: sponsor Shaun White. On this night, that part of White's life is coming full circle and expanding in a widening gyre. Throughout the packed crowd of attractive Southern California skate groupies, pieces from the Shaun White 4 Target collection can be seen on various members of the White inner circle. "When Shaun and his mom approached me to represent him, my only hesitation was whether I could devote the time it would take to do it properly," Ervin recalls. "Even back then, I believed what was possible for him."
The two met for lunch at an Italian restaurant on Pacific Coast Highway to discuss working together. Was it weird to be a 31-year-old man talking to a kid about managing his career? "Shaun makes that part of the equation easier," he responds. "He's spent so much time with adults that he was more articulate than half the people my age." Ervin was surprised to find a 15-year-old who could make him laugh. He also saw how driven White is. "I knew Shaun well enough and what his expectations were going to be. He was the perfect storm: a prodigy in two sports, plus a magnetic personality in front of the camera. I also knew that he would hold up his word." Bemused at how easily it all went down, Ervin laughs, "He and I shook hands, and I never looked back."
There's a calm about Ervin that must appeal to White. He's no Ari Gold. And he refuses to slag any of the proposals he has received for Shaun, including the Flying Tomato routine from Heinz: "Look, it's fun to see corporate America embrace a kid like Shaun, and I appreciate that these people are willing to step up, even if the idea is totally wrong for him.
"We look at everything through a long-term lens," he continues, "and ask, How does this affect us in three years? Five years? Ten years? I look at my job as allowing Shaun to make informed decisions. I give my opinion, but never tell him what to do."
As evidence of White's expanding ambition, Ervin points to White's decision to leave his sponsor Volcom, a $216 million action-sports cult brand, to design the Target line. "The Volcom-to-Target transition is an example of how Shaun had to choose between two long-term relationships," he says. "It was tough, but he saw that Target was a better platform to pursue an entrepreneurial drive and also fulfill a dream of creating cool, affordable clothes." That move also highlights White's understanding of brand balance: Target's line focuses on street wear and skateboarding for a mass market, and is therefore completely differentiated from the more sophisticated and expensive technical winter outerwear he produces with Burton. Instead of creating a situation where one deal could cannibalize another, White cranks up his exposure in a new market without diluting his presence in the first. Even his former boss reluctantly understands. "I looked at it and said, 'I can see it from his perspective,' " says Volcom CEO Richard Woolcott. "We had a great run with Shaun. He has an extraordinary opportunity to pioneer a name and a brand and to connect with a lot of customers. It's like when Nike and Michael Jordan took it to another level. I would rather have him, but he'll always be family."
As the party ramps up, Joe Prebich, a team manager at Red Bull, is goofing with White and some special lady friends. Prebich, 25, looks like Jesus if the Son of Man had a stylist; for White, he's a kind of work-life-balance guru — packing a lifetime supply of caffeine. "Joe is like a guy from the hippie days," says White. "I just look at him and think, What would it be like to live back then? Then I realize he is from back then, just somehow transported here."
Prebich, who wears gold-rimmed aviators and blond hair down to the middle of his back, often helps White choreograph his runs in both snowboarding and skateboarding. "Unlike other riders who just wing it or have a vague idea of what tricks they're going to pull," Prebich says, "whether it's in snow or skating, Shaun has three runs worked out in his head that build from serious to crushing."
In contrast to other beverage brands, Red Bull likes to think of itself as a cultural company that encourages creativity in its athletes. "We try to identify where Shaun hasn't been and make it happen for him," Prebich says. As on a recent trip to Japan: "He's been, like, 27 times, but he'd never gone just to shred powder. So we took him to this remote island, stayed in a traditional ryokan and just lived it." Of course, Red Bull also brought along a small film crew and shot the whole experience, releasing it on MTV as Shaun White Big in Japan — and later reselling it as a DVD, The Ultimate Ride: Shaun White.
A look at the structure of White's network reveals a pattern: He sits at the epicenter of a multipronged onslaught. After the party, Target's head of lifestyle marketing, Troy Michels, recounts a trip he took to Costa Rica with White in 2006. They were on a boat in the Pacific, he says, sore from the previous day's surf session, hot and salty from a morning of chasing dorado and bigeye tuna. Taking a break from their labors, he and White hung their legs over the side of the boat and had an informal meeting. White had just signed his deal with Ubisoft and mentioned the Target chalet in Aspen, where the company puts up White and other riders and clients during the annual Winter X Games. "Shaun was just riffing on how he thought the chalet would be a good virtual meeting place in the game," says Michels, remembering how White looked out on the sun on the water and said, "You guys sell a lot of video games, right? I think it would be a good fit." Michels shakes his head and laughs. "It was so casual, but at that moment, I knew it was going to happen."
Weeks later, during the Dew Tour skateboarding final in Portland, Oregon, the announcers heckle Jesse White for getting married that weekend and preventing Shaun from competing (White played Led Zeppelin's "Over the Hills and Far Away" on guitar as Jesse's bride walked down the aisle). "There is a Shaun factor," says NBC's Monaghan. "When he competes, not only do the events seem much more important, but the crowd gets into them much more, and there are more people."
As the sports of snowboarding and skateboarding have grown, so too has the power of Shaun White and his impact on the action-sports industry. It's now hard to tell where one begins and the other ends. Shaun has drawn in outside players who have helped expand once-fringe pursuits into multibillion-dollar endeavors. And charting his gravitational field has become akin to the Kevin Bacon game: Shaun White meets Mark Ervin through IMG and connects with Target. Target sponsors White, spends millions on advertising, raising awareness of skateboarding (and, because it's Shaun, snowboarding), and eventually produces his clothing line. White's Target connection eventually leads to a limited-edition Ubisoft game in which players not only meet in the Target Chalet but also outfit themselves in gear from Burton and Oakley. Meanwhile, White sponsor Red Bull produces a documentary that appears on MTV, which has a partnership with NBC to produce the Dew Tour that NBC is broadcasting live in multiple cities for both summer and winter events. And here come the 2010 Olympics in Vancouver, which could just crank the whole cycle up another notch.
On hearing these connections laid out, White responds, "Impactatious!"
He is sharing his admiration for Don King's facility with the language. "That's the way he described a boxer's punch. Impactatious. You can just see him making a fist and holding it there way too long," White says, holding up one of his own.
White is aware of the double-edged nature of exponential growth. He knows he has critics, those who see size as the enemy of cool. But he's okay with it. "I'm still pretty young and just winging it, but on a different level. I'm not really worried about the haters, the Buzz Killingtons," White says. "I had a friend come up to me, an older guy whose wife is in the industry. I'd tell you his name, but he'd love it too much. He'd be like, 'Yeah, that's right!' But he'll know who he is. Anyway, he came up to me after all the Olympic interviews and he said, 'Thanks for making it look legit.' I didn't get it at first, but it was respect. He said I was 'solid' as the voice of this group. It was wild. I have friends who are pro photographers who have shot snowboarders for years and years, and their moms would call them and say, 'I saw that Shaun guy. That's what you do?' It was just a weird take on it. It made me nervous. I thought I could have blown it so hard so many times. I could have said anything. Blood wicking!"
White knows that size can be the enemy of cool. "I'm still pretty young and just winging it, but on a different level," he says. "I'm not really worried about the haters."
Before Shaun White was a year old, he had open-heart surgery three times to correct a congenital defect known as tetralogy of Fallot. Surgeons had to open a ventricular tract, repair valves that were leaking blood, and suture a number of holes to increase blood flow through the cardiac circuit. "Obviously, I don't remember any of it," says White. "And maybe one day, I'll be more interested in the details, but I haven't been that curious." It could be argued that what didn't kill him has made him stronger.
After lunch in New York, White heads next door to Freemans Sporting Club, a menswear shop heavy on tweeds and boiled wool, operated by the restaurant's owners. In the back is a traditional barbershop where customers can get a straight razor shave or a haircut. Before doing anything, White asks about retail protocol, adding with a laugh that he's only just begun buying clothes. "In the past, nearly everything I wore came from sponsors," he says.
White picks out a fitted flannel shirt and a peacoat made from the same fabric used in British Royal military jackets. He emerges from the dressing room wearing the flannel unbuttoned, rocker style. If you look closely, you can faintly see the beginning of a scar that as an infant must have run the length of his torso.
Earlier, a question had come up about that scar, whether it had any special, mystical powers, like Harry Potter's lightning bolt. Did it tingle or burn when he was approached by companies that are the wrong fit for him? At the time, he just laughed and said, "That's funny. I definitely understand tingles ..." and then artfully changed the subject.
As he tries on the peacoat, the salesman explains that the buttons are made from ox horn and are basically unbreakable. (Jesse laughs, "If anyone can break them ...") White flips up the collar and checks himself out in the mirror. The coat fits like it was custom-made; he looks at Jesse, who confirms its coolness. Shaun breaks into a broad, confident smile — the same smile he flashes when he eventually comes back to the question he seemed to be trying to avoid. "Actually," he says, "my scar starts to tingle when I connect with companies I want to work with."
A version of this article appeared in the February 2009 issue of Fast Company magazine.