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Meet Sean Bolebruch of Sail Rockaway

Today we’d like to introduce you to Sean Bolebruch.

Sean, we appreciate you taking the time to share your story with us today. Where does your story begin?
I grew up in Port Washington New York, sailing and boating my locals water of long island sound. My mother Mary Rice taught me to surf on long islands southern shores at the age of 8 years old. Going into high school, I developed a passion for riding waves. After college in New Hampshire, far away from the coast, I was wave starved and moved straight to Rockaway Beach. At that time, around 2008 Rockaway was a fairly neglected neighborhood with cheap rent, but also right on the ocean. My father kept his little Norfolk Oyster 17, a British made boat, only about 20 minutes away in Nassau county. On day when the ocean was flat, I wpuld ho out to sail to simply stay connected to the wind and the water; 2 key elements that guided my surfing. Rockaway is somewhat of a barrier island with a large back bay, called Jamaica Bay. The bay is NYC’s largest open space; speckled with grassy marshland, creeks, and uninhabited islands. I had so much fun exploring the bay, that I thought I might share it with other folks. At the time, not much sailing was taking place in my sleepy little section of Jamaica bay, so opening a business and getting the urbanites of the new york sailing in their aquatic backyard seemed like a good idea.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
In order to sail on a commercial level, I had to get a commercial captains license from the coast guard which involved a series of rigorous tests involving charting, navigation, rules of the road, and deck safety. Aside from that, running a small business, solo for the mist oart the first few years was a challenge. It seemed like I never had a day off if work until winter rolled around and sailing season came to a close for around 5 months until Springtime. So winter, was a bit of a scramble to fill the time and continue to make ends meet. Over time the business grew and more captains showed up who knew how to sail and wanted to be part on the operation. As a result, the business grew and really started to take off. Around the same time, my only business competitor, who had been my friend previously, now seemed like he had a bone to pick with me. I gather it was due to Sail ROckaways rising success which cut into his sailing business. In actuality, it was healthy competition at its finest and it motivated me to strengthen and grow the business even more. Nonetheless, this was a challenging time, however it paid off simce my competitor closed his business the following season. The only challenge Sail Rockaway faces now is keeping the offerings fresh and creative, to iffer something new and different, rather than standard tours and lessons on the same stretch if water day in and day out. We are getting there and it will be better than ever.

As you know, we’re big fans of Sail Rockaway. For our readers who might not be as familiar what can you tell them about the brand?
Sail Rockaway offers sailing tours and lessons at an affordable price to the good people of New York. We try our best to get as many people out on the water. Our boats are unique; traditional British boats that are perfectly suited to the shallows waters of Jamaica Bay. We offer free children’s sailing lessons to those in need and host occasional free sailing events open to everyone. Getting here is easy simce we are inly one block from the subway and the ocean beach is close by, so its a magical place to exist as far as NYC is concerned.

What makes you happy?
Im happy when I get to express my creativity with whatever I am doing, whether surfing or crafting the ins and outs of running a business. I also love cooking, archery, exploring new places, nature, and knowing that I am blessed to be where im at in life.

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