By Matthew Becerra

On humid North Carolina nights, the rain would fall for hours, slicking the cracked concrete where a young Kwesi Holloway learned to push. From his bedroom window in Raleigh, he’d watch older kids ollie and kickflip under the streetlights, their boards clapping against the pavement. “I just thought it was cool,” Holloway said. “I wanted to be outside, kickflipping like them.”

He was seven when he first got a board, a Superman deck from Walmart that his grandma surprised him with after school.

“I came upstairs and saw it sitting there,” he said. “Ever since that day, I’ve been serious about skating.”

Raleigh wasn’t exactly a skate hub. The weather alone made progress tough, too hot in the summers, too cold in the winters, and raining almost five days a week.

“It’s really hard to skate over here,” he said. “That’s why I had to reroute. Make a new way for myself.”

That new way led him to Los Angeles. By the time he was 14, Holloway was traveling back and forth between coasts, fueled by the dream a lot of skaters share.The desire to make it out west.

“My homie Thomas moved to California,” he said. “He told me to come visit, and one thing led to another.” By then, Holloway was already on the radar — getting boxes from Birdhouse, Asphalt Yacht Club, and Emerica. He even hit Hollywood High 16 on that first trip. From there, he said, “it just went up.”

Today, Holloway rides for Nyjah Huston’s brand Disorder Skateboards, calling it “like being on the Lakers with LeBron.”

He caught Huston’s attention after a filmer who worked with both of them noticed Holloway’s knack for big rails. “I never fanned out or acted weird,” he said. “It was just genuine. I think that helped.”

Holloway in Disorder’s “Distress” video

That authenticity is a theme in everything Holloway does. At the Disorder facility, he trains late into the night, sometimes from 10 p.m. to 4 a.m., alone or with friends.

“It’s like Kobe in the dungeon,” he said. “Just me practicing free throws.” His mindset is simple, treat skating like an athlete treats their craft.

But for all his discipline, Holloway stays grounded in the people around him. Whenever he’s back in Raleigh, he throws local events — “tricks for cash” contests, product giveaways, and skate days for kids. “I just try to give back to my community,” he said. “I’ve met pro skaters who weren’t humble, who acted too good. I never want to be like that.”

He’s serious about taking that mission even further, talking about building resources for kids both in the States and abroad. “I want to go somewhere that don’t got clean water, provide energy, build something that matters,” he said. “That’s what I want to use my platform for.”

Fatherhood has only strengthened that drive. At 25, Holloway’s son has already been to some of the biggest rails his dad has skated.

“He was at the bottom watching me,” Holloway said. “I want to be a role model, show him to always push your limits. Even when you’re scared, you can overcome things.”

That philosophy runs through his entire approach to skating, a balance between fearlessness and purpose. “Some people slow down after having kids,” he said. “For me, it made me go harder.”

Now splitting his time between North Carolina and LA, Holloway keeps his focus clear. He’s filming new parts, and refusing to overthink the process.

“When you put too much pressure on yourself, it kills the fun,” he said. “I just skate. I just let it happen.”

And even as he pushes toward bigger opportunities, Holloway’s outlook stays the same, stay humble, stay real, and remember why you started.

“Skating saved me,” he said. “It kept me out of trouble. So now I just want to give that back, show kids there’s another way out.”

Kwesi Holloway’s journey from raleigh to LA’s rails

Cletus Strap’s Quiet, Independent Climb Through LA’s Underground