Reflecting on what I’ve learned from a friendship with Roger.
Captain Roger Gildersleeve gave me the support and confidence to live the life I lead. He was my first marketing client on Maui, where I help promote his beautiful vessel the Kai Kanani. He gave me a shot, and his confidence in me was priceless. I now have 70 clients, support a family of four, and am positively growing every day thanks to his inspiration.
His loss is being felt throughout the islands, but his absence is not what this article is about. It’s important we share what he left behind.
I’ll never forget my first meeting with Roger. He’d seemed to have figured things out. Having had been through a life threatening illness (physically evident from a scar on his head.) He admitted to looking at the future with a positive nature and love for life. He was taking advantage of the gift of second chance.
For those not on Maui, it would seem that running a successful luxury catamaran in paradise would leave very little room for negativity. Those that live on Maui know that life’s challenges follow anywhere you go. But for Roger, even during a particularly stressful time in his life, he remained positive, celebrating each small success he managed during the turmoil. At least to me, he always seemed to be living with that 2nd lease on life mentality. Each additional breath was a blessing. Can you imagine our world if we all had that gift?
Over the near decade that I’ve had the pleasure of knowing him, he’s increased his dependency on his Kai Kanani ohana. He treated his captains and crew like family–he’s given his trust to great people like Captains Cary and Anthony–in order to spend his valuable time doing what he loved (even more than being on the water): time with his kids and grand kids. He’d also spent countless patient hours taking the most beautiful photos of birds I’ve ever seen. He dove into photography like a boy in love. His passion was infectious.
I loved meeting with him. We would talk work, but we mostly talked family and art. He would always emphasize how important it was that he support what I was doing. What client does that? (Now that I write that, I have a few clients that do. Unique to Maui? Not sure. Whatever it is, it’s a beautiful thing.) His trust was a big boost for me, which gave me more motivation to promote his business.
Roger Gildersleeve left behind qualities that are instilled more than ever in his Maui ohana. Kindness, respect, love, passion, accountability, great humor, creativity, stability, encouragement, and warmth. His loss is crushing, but what we have gained from his time with us eclipses all.
He would listen, but he didn’t waste time. I regret not having shared with him the kind words I spoke about him to others. He will be greatly missed and I’m so grateful for his being here.
On that note, I’d like to share my thoughts on someone else that has helped shape my life on Maui. Greg Hoxsie introduced me to Roger, ultimately encouraging him to take a chance on this web geek. Greg has helped dozens of people (at the very least) towards success on Maui. His selfless guidance has been an inspiration. There are many others on this incredible island that have similar generosity. I’ll make sure to let them know how I feel from now on.
Captain Roger, you will be missed. Mahalo for everything.
Most of the photos were taken by 
