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In the Spotlight: Supporting the Performing Arts

By Alma Tassi

When Ryan Sherwood shifted careers from bank manager to account management at Old Republic Title, he not only found work-life balance, but an opportunity to dive back into an old passion: Theater.

Sherwood performed in over ten productions in high school but had little time for the stage once he began college. Years later, he enrolled his five-year-old son in the youth education program at Maui Onstage. Seeing the joy his son experienced performing reminded him of how much he loved the theater.

In 2022, with a more flexible schedule at his new job, Sherwood decided to audition for the Christmas Carol with his son and aunt. He remembers, “It was a little nerve-wracking. I love the book and knew the story, so it was a good show for me to get back into it.” To his delight, he was cast as Bob Cratchet and his son received two roles as Youth Scrooge and Peter Cratchet.

Since then, he has performed in the musical Something Rotten which involved three months of rehearsal, six nights a week last summer. Sherwood says, “You’re with the cast many hours daily and for weeks. They become family.” In this show, he performed with fellow RAM members Gina Duncan and Bob Wills. Coldwell Banker’s Ray Chin also supports the theater as a sponsor.

The performing arts offer the space for people to express themselves—combining storytelling, performing, costume, and set design. “For kids especially, being in the performing arts has so many benefits,” says Sherwood. “It’s an inclusive group, accepting of everyone with no judgments. It allows you to open yourself up and try new things. You can be vulnerable and experience being a different person and have fun with it.”

Kahiau Article, March 8, 2024

Ryan Sherwood in front of the Historic Iao Theater. Photo Credit: John Duffy

Jessica Nelson, Maui Onstage’s education coordinator, adds, “It teaches students how to work with others and creates lifelong meaningful friendships. Theater education also helps student develop their responsibility skills and helps them learn how to take risks.” Classes and camps include acting, improv, and musical theater for all ages.

Supporting arts education can be as simple as attending live performances at the Historic Iao Theater which features performances from kupuna to keiki.

Currently, Sherwood performs as a larger-than-life nanny named Mrs. Bumbrake in Peter and the Starcatcher. “It’s very funny. I wear a big hoop skirt and bowler hat with feathers eight or nine inches high to make myself bigger than everyone else.” The show chronicles the origin story of Peter Pan, Captain Hook, and Neverland. Sherwood concludes, “This is not something you do in your normal life. And that’s the point!”

Peter and the Starcatcher at the Historic Iao Theater continues performances this weekend on March 8, 9, and 10th. For tickets, visit

REALTOR® means a member of the National Association of REALTORS® Do you know a REALTORS® Association of Maui member who should be recognized for their contributions to the community? If so, send your story idea to Alma Tassi at

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