"I've just had this fight since I can't even remember," he told Simon.
It soon became clear he would be unstoppable. By the age of seven, White was winning competitions and landed his first sponsor, Burton snowboards.
"And it wasn't 'cause I was awesome or anything. It was just because…I was kind of awesome. I don't want to lie," he told Simon.
But snowboarding took a lot of time and money. Back then, Cathy and Roger White didn't have much of either. Still, they managed to take their three kids from their home near San Diego to the mountains, where White could compete. They traveled, and slept in an old camper van.
Asked what it was like when they pulled into a resort in their van, Shaun White told Simon, "I don't think we were always welcome. We were pretty dirty to be in Aspen and stuff. They're like, 'You can't park that here.' Like the propane heater would break down in the middle of the night. And we're all sittin' in there. It was just wild times. And I think those are the times that make me appreciate what I have."
Like when he was a teenager and won more money in one contest in Japan, than his parents earned in an entire year. "And I was sitting there just eyeballs like this, looking at this pile of money," he remembered.
Asked how that made him feel, White told Simon, "I remember thinking that I'd way rather give my parents my money, and not have to like have them go to work anymore, you know what I me. Because I'd way rather spend more time with them."
He could do that when he was home in the off-season, as his star was rising in another sport - skateboarding, which he learned here at his local YMCA, and where he still practices today.
"Even though I'm not on my snowboard, I'm still doing the same motions and pumping and pushing and looking around where I want to do my airs and my tricks and it's definitely like a kind of cross training I guess," he explained.
It may have improved his snowboarding, but back in 1997, as his parents recalled, skateboarding nearly ended it all. White was 11 and performing at an exhibition with a skateboarder twice his age, and almost twice his size.