Stepbrothers Dayyan Armstrong and Ross Beane have been adventuring together since they were seven years old. Through "Sailing Collective," they aim to take more people out on the open sea.

Dayyan Armstrong and Ross Beane are stepbrothers. At sixteen, the two pooled together $1,000 to buy a 24-foot sailboat. With only a little sailing knowledge picked up at summer camp, they set out on their own around the waters near their hometown of Portsmouth, New Hampshire. About a year later, they embarked on a week-long voyage along the rugged Maine coast. Armstrong said, "Looking back, it was somewhat bold of our parents to let us go out to sea, but it became a life lesson for us, teaching us to figure things out on our own."

The two are now 41 years old. When they were just seven, Armstrong's mother and Beane's father formed a new family together. Armstrong added, "Our family encouraged us to go out and discover the world, rather than just taking sightseeing-style vacations." His mother is a retired professor of world cultural studies who once took him on research trips to South America. In his early twenties, Armstrong worked as a sailing instructor at a yacht club and traveled to the British Virgin Islands. Gazing out at the deep blue sea, he had an idea: to start a yacht adventure travel company. He immediately called his stepbrother Ross Beane, who had already begun his entrepreneurial journey. Soon after, Armstrong completed a trial run with his sailing students; about a month later, they completed their first small fleet group voyage in the Spanish Virgin Islands. Sailing Collective was officially born.

Today, the company operates across six continents and has approximately 60 captains and chefs. Armstrong, who now lives in Brooklyn, New York, recounted how he and his brother resolve disagreements, the hidden risks of adventure travel, and an unforgettable experience swimming with whales in French Polynesia. From left to right: Ross Beane, Dayyan Armstrong.

What is it like doing business with your own brother?

There is a deep mutual understanding and ability to see things from each other's perspective. We have clear boundaries regarding the division of responsibilities, and when disagreements arise, we come up with pragmatic solutions. To a large extent, this stems from our experiences adventuring together since we were seven. We witnessed firsthand how our parents maintained a healthy relationship, which set an example for how we treat each other as business partners.

How did you reconcile your very different leadership styles?

As stepbrothers, we know exactly what the other is good at and where their weaknesses lie, and the business was built around those differences. Our division of labor is very clear: I am responsible for envisioning the big picture, and he is responsible for execution.

How did you decide on your business model?

We did not want to sacrifice our operating principles for the sake of fundraising, so we did not accept any outside investment. The company started entirely on our own sweat and capital, operating like a small family workshop, with profits continuously reinvested. This allows us to control the scale of the business on our own terms and ensure that our service capacity matches the number of bookings we take on.

How many times per year do you personally lead voyages?

About five to six times a year. Running a business involves countless difficult and tedious matters—conflicts, problems, and business iterations keep coming. When I am mired in the daily grind of operations and cannot step away, I lead a voyage as captain. After an incredibly wonderful week, I am reminded: we do all of this to enjoy life more.

The Collective's chef prepares dinner.

Both of you are qualified captains. Why is that so important for the business?

Experiencing firsthand everything our customers go through gives us an empathy that many business operators lack. If you have only ever stayed in resort hotels and never joined an adventure trip, it is hard to anticipate what might go wrong along the way. We can really relate to our customers' situations, and we also guide them toward what we call "Type 2 fun": the experience is not comfortable in the moment, but looking back afterward, it becomes a valuable life gain.

What values did your family instill in you two brothers?

From an early age, we were cultivated to stay curious about the world and to respect diverse and foreign cultures. The most important principle: rather than desperately chasing conventional success and fame, learn to enjoy the process first.

What was your most memorable wildlife encounter?

On the company's maiden voyage to French Polynesia, we sailed to the lagoon of Huahine. It was sperm whale mating season. Extremely rare in the lagoon, two adult sperm whales and one calf appeared. A local resident was preparing to get in the water and swim with the whales, so we approached and asked if we could also get in, and they gladly agreed.

All night long, the whales swam around our boat. I lay in the cabin, and just ten feet away from me, the sound of them surfacing to breathe kept coming—it was an incredibly magnificent scene.