From a Founder: How Two Brothers Turned an Oyster Bar Into an Empire

Editor’s Note: Welcome to From a Founder, a monthly entrepreneur profile about the highs, lows, and plateaus of building a successful brand or business.

While living in New York City in their twenties, brothers Alex and Miles Pincus did not have a master plan to build a small business empire that reached all the way to New Orleans. But, in 2014 after the launch of their first restaurant, Grand Banks, a docked oyster bar aboard a wooden schooner, the pieces began to fall into place. 

Now, six years later, the brothers own and operate destinations like Pilot in Brooklyn and Seaworthy in New Orleans, and even a Manhattan port, Pier 25 Marina, all under their parent company, Crew. Along the way, they’ve honed their ability to launch new ventures, without losing the spontaneity and drive that have guided their entrepreneurial achievements.

Alex and Miles recently sat down with Squarespace to recount the chaotic, uncertain, and deeply fulfilling process of launching Grand Banks, the professional failures and successes that preceded it, and the problem-solving approach they continue to apply in every business endeavor.

SQUARESPACE: What inspired you to launch Crew?

Alex and Miles Pincus: Our company is based on a very simple premise, combining the things we love — boats, drinking, eating, revelry, and design —  into a single experience. Surprisingly, this works. 

At the beginning of the process of formulating our company, it was not entirely clear what we were aiming for, nor did we have a clear concept. It really started as an inkling of an idea and something that we kicked around for a few years before it became anything at all. 

We had each previously launched a few companies that would find a way to become the DNA of Crew. When we both had just finished grad school, we launched a mid-sized sailing school and sailboat charter company in New York City on a shoe-string budget. A year into this, Alex started an architecture firm and Miles started a tour company aboard the largest passenger sailboat in the US. For a while we were running all of these businesses out of the same office. 

We had a lot of fun with these ventures, pretending to be adults, making a little bit of money, and running wild in New York. We learned a lot about how to (and how not to) run a company and what it means to be your own boss. Each of these entities was successful to a degree, but we came to the conclusions that the things required to grow any of these businesses were things that we did not want to spend our time doing. Each venture lacked something we were seeking in our day to day lives. The sailboat charters were great fun, but too niche. Architecture was deeply rewarding, but required singular and dedicated clients that are hard to come by. The tour boat was amazing on its own, but the tour business itself is dreadful, don’t ever do that. :)

We lucked into the first hint of the idea for Crew one birthday while we were still in the thick of these initial businesses. Alex decided to have a party aboard the tourist sailboat that Miles owned, and invited about 30 friends. It turns out that, when you’re having a party on a big sailboat, everyone also invites their friends, and the friends of friends invite their friends as well. 

A few hundred people showed up — way too many to all get on board and set sail. So we ended up having a party on the boat while at the dock. It turns out that this is great fun, with all the feelings of being on a boat and without a lot of the logistical challenges. Plus, the captain can drink. 

It got us thinking about how we could put a boat somewhere and just hangout. This was the seed of a thought that sat with us for a few years and that we kicked around without a clear concept. After some time, when things had run their course, we sold each of the companies we had started to our partners and employees, and then spent a couple of years tinkering on various projects. 

Then, by chance, someone sent Alex a copy of a book on the history of oysters in New York. We both read it and discovered that in the 18th and 19th centuries, the shores of Manhattan were lined with hundreds of floating “oyster barges.” These were little wooden barges that were built up like two story saloons where you could buy oysters and sometimes a drink as well. For a while these were the primary food source of all New Yorkers, rich and poor. This really blew our minds! 

It struck us that the idea that had been in the back of our minds for so long was really a sort of modern day oyster barge. From there we took off running, trying to figure out how to create what seemed at the time like a very far fetched, but very cool idea. 

SQSP: What was the first step you took to make it a reality?

A + M: The first step was by far the hardest part. We had an idea but nowhere to make it a reality. We began searching for a location in New York where we could dock a large ship and have guests come aboard. It turns out that most of the waterfront in the city is owned or managed by various public agencies, so getting a waterfront lease began to seem impossible. With a very lucky introduction, we got in touch with a trust that manages several miles of the Manhattan shoreline and pitched them our idea. They seemed slightly interested, but then went on to explain all of the reasons why it would not work. One by one we got to work on each of these issues and came up with solutions that we continued to present to them. We were lucky to have backgrounds in the maritime and architectural worlds as we at least knew where to begin to sort through each issue. After months of meetings and getting the sign off from multiple city agencies, we convinced the park to give us a one year trial period to bring our first floating restaurant, Grand Banks, to life.

SQSP: In every entrepreneurial endeavor, there are unexpected risks and challenges. What was the biggest risk you took?

A + M: We faced a major chicken and egg crisis when pitching the trust on the idea of opening our first venue. Even though the trust was tentatively on board with the idea, we had to have a historic ship that met certain requirements and could operate as a restaurant before we could get approval to operate. 

Having a ship, however, did not guarantee that we would be approved. Without a ship though it would never happen.

In our typical decision making fashion, we decided to go ahead with procuring a ship and restoring it before we had a final approval to proceed. We built out the ship with friends and family and in the process used all of our capital and maxed out all of our credit cards. We finished construction just days before we got approval to open and operate. 

SQSP: What surprised you the most?

A+ M: That it worked! We truly did not know that it would work technically. We are talking about a wooden ship built in the 1940s that is floating in the Hudson River, going up and down 10’ with the tide everyday and rocking with the waves, and then it has a modern kitchen on board, real bathrooms, a bar. The infrastructure alone was a huge guess. We also did not know that people would come. We assumed that we would at least have a handful of old salts who loved boats hanging out at the bar and we also naively assumed that those folks would be enough to support a business. Luckily (and also terrifyingly), when we first opened the doors to Grand Banks in 2014, we had a line down the pier to board that did not go away for the entirety of the summer.

SQSP: After a challenging day, week, or month, what keeps you both motivated?

A + M: Everyone has heard that owning a restaurant is challenging and that boats are a nightmare to maintain. We took the two of these things and combined them! So the very nature of our business is to face challenges. Funnily, there is a magical feature to our business that if there is something absolutely crazy that you never could imagine happening, it somehow finds a way to happen. 

By nature we are tinkerers / builders / designers. So when we have a problem or a challenge (which happens almost every single day) we obsess over how to fix it. We don’t stress much, we just get to work. Typically this is by diving into the process of problem solving, whether it be conceptual from a hospitality standpoint or technical from a boat maintenance perspective, or even dealing with the industry-wide fallout from COVID-19. 

At least until now, we’ve always made it through in one piece. At some point, we may not. In any case, it usually makes a good story to sit at the bar at the end of the week and share a drink over. 

SQSP: How has your online presence contributed to your business success? 

A + M: We have been Squarespace users since the earliest version, and our understanding of how we represent ourselves online has evolved in tandem with Squarespace developing its products and offerings. While we operate in the physical world, guests often learn about us through social media and then end up on our website. This is where we get to really tell the story of who we are and move guests towards making a commitment to join us at our venues. As we’ve gone more digital in all of our processes, we also use Squarespace to host our onsite menus, to book our reservations, and send quick email blasts to our customer base. 

SQSP: How do you see your online presence evolving in the future?

A + M: We're looking for efficiencies as we scale our business. We love good web design and content creation, but managing everything ourselves becomes more challenging as we add more restaurants and ancillary businesses. We're imagining a world where we can manage our content from one location; where our online presence is more cohesively intertwined on the backend of things. Exactly how this plays out is a bit of an unknown, but it seems like a problem Squarespace can solve.

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