This Dock Master is Building a Serious Sailing Club for All New Yorkers

For Stephen Glenn Card, the New York Sailing Center isn’t just a boat business for tourists who come and go. Instead, the boutique boating school in southern Brooklyn is a family legacy dedicated to educating the next wave of ocean-lovers about the true art of sailing.

“The idea is to properly teach people how to sail so that they’re truly able to take out the boat they learned on without us,” says Steve Card, owner and operator of NewYorkSailing.Club. 

It all started in the 1960s when his father, Glenn F. Card, an ad executive and licensed captain, bought a small sailboat. He didn’t have time to use it so he put an ad in the newspaper to rent it out. “Demand was robust,” says Steve. “So much so that he got another boat, then three. It boomed. So, he started Sail-A-Season.” 

The business was modeled as a fractional sailing plan; and it soon began to take off and compete with Glenn’s day job. “He was an original Mad Man!,” Steve recalls of his father. “So, he added a sailing school, gave up the day job, and put his copywriting skills to work on his own business, New York Sailing School was born.” Over the next decade Glenn would retire and sell the school. After he passed away, Steve felt compelled to act on his own passion for turning rookies into skippers. “I started my own school and followed in his footsteps,” says Steve. 

The New York Sailing Center—which also coaches people on how to charter, buy, and even race in Brooklyn, is based in the Miramar Yacht Club, far from the crowds of Manhattan. In 2003, Steve launched a new set of experiences: sailing trips in the British Virgin Islands, where sailing enthusiasts can escape the wintry Atlantic. By 2006, he expanded the sailing trips to Mediterranean destinations like Italy, Greece, and Croatia. “Students get a great balance of training and vacay on these trips,” Steve adds. 

The business continues to grow and evolve, but Steve admits the market has gotten choppy with more competitors. “We’re fighting against businesses that give shorter courses for less money,” says Steve. He advises true, aspiring sailors to invest in accredited and quality schools. “Pay a little more, travel a little farther, and actually learn how to sail,” he says. After all, when it comes to sailing the seas, safety is critical. 

Steve has advice for entrepreneurs who want to take their businesses to the next level. “Make sure you can wear the hats properly, and be ready to adapt and reinvent yourself,” he says. “Technology will change; the client base will change. Be ready to change with it.”

For Steve, the changes in the competitive landscape also called for fresher marketing strategies. Up until the 1990s, the family would largely rely on classic ads in the New York Times’ Weekend Section. But with the dotcom boom, he knew it was time to launch startsailing.com in 1998. Just a few years ago, he decided to rebrand with a shorter name, new logo and website. The creativity behind the next iteration of his business website was largely driven by his own clients, who happened to be experts in branding, web design and SEO. The tech-savvy customers also advised them to choose name.com as their registrar. 

Their original web address now redirects to their new .club URL, NewYorkSailing.Club. “Our .club domain was part rebranding and part SEO,” he says. He says any club-oriented business should opt for the TLD. “My clients thought the domain extension would be picked up favorably by Google as it did for others, and we went for it. At the time I wanted to better emphasize our club sailing plan.”

Choosing Name.com as the web registrar made it simple for Steve to further establish his business’ online presence. “Challenges are mostly how many hats one has to wear,” he says. “Our domain registration process was easy and we’ve had no difficulties since.”

What is it like to carry on your family’s local legacy in sailing, and train the next generation of sailing instructors? What’s the most important lesson you hope they take with them?

After my father sold his school, I took over the marina business. But the school was the true family tradition. I’m very proud and satisfied to have carried on the business, but almost better still, recreated it … My father had mostly very good success with finding and mentoring excellent instructors. I was even pickier, and slower to bring people on board. That kept the standards higher. Eventually, I chose and trained new instructors who had the potential to be great at it. So far, I’ve had a 100% hit rate on that. 

I am most proud of pursuing a second branch for the school that no one else was able to make work before: Sheepshead Bay, Brooklyn. So, to copy detractors of Joe Biden, “I did that!” My dad couldn’t do it, a chief competitor failed more recently, I pulled it off, and it’s the future of our school now. Very proud of this.

What’s it like to run a business in southern Brooklyn? How do you attract tourists away from the crowds of Manhattan? 

While tourists might well enjoy taking a tour of the NYC waterfront via the Circle Line or the Staten Island Ferry, it’s these very things—plus the Fast Ferries, cruise ships, barges, etc., —that make sailing so difficult and disappointing in the Hudson and East Rivers as well as New York Harbor. We cater to NYC locals as well as from many other parts of the New York Tri-State area. Brooklyn continues to evolve as the hot area in NYC. As for running a business here, it’s amazing. It’s a very inclusive and hospitable community.  

I know you offer everything from sailing lessons to evening sails. What’s the most unique or popular service, or what do customers seem to enjoy the most?

We have two specialties that other schools do little of. First, we do a lot of private lessons, both on our boats and on those owned by our clients. We can sail and teach on anything, whether it’s high-performance racing dinghies or large cruising yachts. Secondly, we offer navigation courses on Zoom. When the pandemic hit, I jumped on that as a solution for our coastal navigation course. It was popular, and it works: it’s almost as good as being in the room with the students, and it’s vastly more convenient. We keep the same small group size for individual attention.

What’s the most beautiful place you’ve sailed and why?

Hard to pin that one down. I’d say Anegada in the Virgin Islands, and Ventotene in Italy.  Both are a little remote in their respective territories, and both are worth the extra time to get to. Anegada is a completely stunning and unspoiled Island that’s like the Bahamas in the BVI. Ventotene is a ruggedly beautiful outpost off the Golfo di Napoli. Old Roman Harbor is just that: ancient, with few modernizations. Walking up and around this island is a must, along with the amazing beaches. 

What’s the biggest obstacle you’ve overcome as a business owner?

The weather. We’re a strictly weather-dependent, largely seasonal business. Weather can make or break us, and climate change has been catching up with the sailing industry. We moved to Brooklyn partially due to this, as the weather and wind are better.

On your homepage you have a section titled “Blog: Recent Rants” which I love. Why is blogging important to you as a business owner?

Blogging helps me keep the site fresh, but also lets me speak my mind. I like to include educational and public awareness content, and I like to write my way. I don’t give myself full creative license on the (mostly) static pages of the site. In the rants, I can ramble and roam!

What’s your top advice for others who lead a long-running, family business? 

Be ready to reinvent yourself.

What’s the most important thing people, especially those new to sailing, should know about sailing?

The web has made more and more activities available to everyone. Explore options on the web and then get out and try them! People are constantly amazed when they find our site, and get a flavor of what it’s like to learn and continue with sailing, including how accessible it can be. Sailing has a reputation of being expensive and exclusive, and many organizations have been helping to change that. The internet is integral to this mission.

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