Room to Grow: Woolley Brothers

Images by John Hook

North Shore twins find time to surf in between shaping boards and making tees.

On a late September morning, in the sleepy town of Waialua on O‘ahu’s North Shore, Shaun and Nat Woolley are hard at work filling a last-minute order. In their office, the pair stands vigil over a massive screen-printing machine carefully churning out batch after batch of custom-designed tees. Their building, which was once a turn-of-the-century bank and then an iconic roadhouse bar, drips with history.

As lifelong surfers, they ask if I know whether or not a projected swell has begun to fill in, and I’m left with the feeling that they’re secretly yearning to postpone the interview and finish the rest of the order later. But I’m wrong.

Instead, they invite me inside and we get to talking about how a pair of twin brothers have come to become so respected by their peers, helping reinvigorate a small town with a deep history, while still finding time to squeeze in a daily surf session.

As twins, both Shaun and Nat have always been close. Growing up on the North Shore, they cut their teeth surfing some of the world’s most famed lineups and were surrounded by a wealth of the world’s best surfers. Their youth was marked by days on end of time spent in the water, but when it came time to step into adulthood, the way they approached their respective career paths set them apart.

Both held a keen interest in shaping surfboards and art and yearned to turn their passions into careers. Nat found work cutting boards for famed shaper Eric Arakawa. Shaun hunted for a space to house his budding screen-printing business. But no matter what endeavor the other undertook, they were there to help each other.

In 2007, their separation ended when the brothers set up shop in the aforementioned building in Wailua. When the duo learned the dilapidated old structure was available, they quickly jumped at the opportunity – and it just as quickly consumed them, giving the brothers careers and sparking new life in the neighborhood.

In this space, not far from where he shaped boards for Arakawa, Nat was able to focus on his art, which had gained a solid following over the past few years, and Shaun grew his screen-printing business.


“Growing up, we were around this place all the time. When we were groms, it was called the Sugar Bar. I’d guarantee you that some super heavy stuff went down right here. Right where we’re sitting right now. It changed hands a bunch of times and whenever someone left, they gutted it pretty hard. It was basically a place for homeless people to post up for a while,” says Nat. “When we took it over, man, it needed some work.”

From the outset, the brothers had a goal to transform this Waialua landmark. “We wanted this place to be something positive for the neighborhood. When the mill closed down, this place had become a little seedy with some drugs and homelessness. We wanted to turn that tide. We wanted to be one little blade of green grass in a mud patch, and then hopefully another one would pop up. All we had going for us was psych. We didn’t have a lot of money, just a lot of passion. So we started to build it up from there and everything sort of worked out and has started to grow,” says Shaun. “I think that’s true of life. When you’re following something you’re really passionate about, good things seem to happen.”

Good things have been happening both for the Woolley Brothers and Waialua. Now flooded with both orders for boards and screen-printed tees, you’ll find that if the two brothers had a gripe (and trust me, they don’t) it would be that they’re not able to surf as much as they would like.

“We still get in the water every day, but we’re not able to just drop it all and go surf when it’s good,” they say with a laugh. “Well, most of the time we won’t drop it all to go surf. But since we’ve opened up our shop, everything has gone really well. Not only for our business, but for the community as well. There’s a farmers market now, new restaurants … all sorts of rad stuff. We’ve come a long way, but there’s still plenty of room to grow.”


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