Charting My Financial Course: Adventures Between the Buoys
Part 2 of 3 – Stone Capital Growth™ Series
(Sailing Memoirs Continued)
Growing up sailing meant that no two trips were ever the same, and Part 2 of this series dives into the behind-the-scenes adventures that shaped so many of those summers. These weren’t the dramatic rescues or the stormy nights—those will come later—but the smaller, human moments that happened between the buoys. These sailing life lessons shaped the way I see risk, calm, and long-term planning.
After one long day sailing across Long Island Sound, the very first thing I did when we reached shore was hunt for a shower. The water was lukewarm—barely warmer than the Sound itself—but after hours of sun, wind, and the slow rhythm of the boat, it felt like a small luxury. Salt and sweat rinsed away, and for a moment, everything felt still again.
Every race had its traditions, and ours always ended the same way: the nearest bar, and a Dark ’n’ Stormy in hand.
Rum, ginger beer, and the comfort of being back on solid land after a day of trimming sails and reading currents.
And on certain nights, especially when the bar had a good crowd, we’d swap the Dark ’n’ Stormy for margaritas and listen to Jimmy Buffett drifting through the speakers — the unofficial soundtrack of tired sailors easing back into land-mode.
That drink, that music, and that moment marked the shift from race-mode to shore-mode.
Post-race events were entire worlds unto themselves. Big white tents glowed with warm light, long tables were piled with food, and groups of sailors retold the day’s stories with bigger gestures and louder laughs each time. Awards came first, then music and dancing, and of course, another walk to the bar for one more Dark ’n’ Stormy. It was a floating community briefly brought ashore.
Another part of our preparations often gets overlooked, but it was essential to every trip: my mom made our sails by hand. She wasn’t just the cook—she was also our medical expert, a deckhand when we needed an extra set of hands, and the person who spent hours sanding and varnishing the brightwork on deck until it gleamed. Her work was in everything the boat did. Every tack, every gust of wind, every mile under those sails carried her craftsmanship and the quiet strength she brought to every part of sailing life.
We raced around Fishers Island near Block Island more than once, building layers of memories each time. On one voyage I invited a friend from college—just friends—but it added a whole new energy to the crew. Sailing always seemed to attract characters, and each trip came with its own cast.
St. Augustine & The Sailor Folklore Moment
There’s an old bit of sailor folklore—the idea that a sailor fresh off the sea always seems to “find luck” as soon as he hits shore. The ocean makes him mysterious; the voyage makes him interesting.
On our trip up from West Palm Beach, the folklore ended up playing a funny trick on us.
My eldest brother Charles was the skipper on that trip, and his friend Joe N. was essentially the co-skipper. Both were single, in their 20s, and plotting all day about the bar they planned to hit in St. Augustine that night.
We tied up at a public dock, hopped into a cab, and headed straight for the bar.
At the door, the bouncer checked our IDs.
Charles and Joe N. walked right in.
I didn’t.
I was underage.
Back to the boat I went.
But the night wasn’t over.
While I was sitting on the dock, two 20-something women wandered over and started chatting. We ended up talking for hours—easy, natural conversation, carried along by the warm night air. They loved hearing about the trip, the boat, and the adventure we were having.
I never asked for their numbers. I was just enjoying the moment.
When Charles and Joe N. returned later—having struck out at the bar—they found me talking to exactly the kind of people they’d gone looking for. They laughed the rest of the trip about how the folklore had chosen me instead of the two skippers.
Sometimes the sea has a sense of humor.
A few days later, we reached Beaufort — and that’s when the ocean surprised us again.
Beaufort, NC — The Vivaldi Porpoise Encounter
A few days later, we had one of the most magical moments of any sailing trip.
We were moving slowly toward Beaufort, North Carolina, barely making three knots on a hot, still summer day. Someone put on a Vivaldi flute concerto, and the boat seemed to turn into a giant wooden speaker cabinet.
Then, suddenly, the water erupted with life.
Around forty porpoises appeared around us—gliding in arcs, doing figure-8s under the hull, and leaping ahead of us as if they were performing choreographed jumps. It was surreal, like the ocean had decided to host a ballet.
Charles leaned over the side and said it looked like the porpoises were turning their heads up to look at him. And honestly, it really did feel like they were studying us while we were watching them.
Then, just as quietly as they arrived, they slipped beneath the surface and were gone.
We joked that we had discovered a pod of Vivaldi fans with flippers instead of hands.
Looking back, these sailing life lessons helped me appreciate calm in the middle of chaos.
For reference, here’s the official NOAA Eastern North Carolina Marine Forecasts we often used at sea.
The African Queen Moment — Taking on Water
But the sea never gives magic without tests.
Not long after the porpoises left, we realized we were taking on water.
The boat’s old Mercedes engine started without trouble, but the moment it ran, seawater began leaking in from a loose or compromised fitting on the engine’s seawater intake. That engine was cooled by raw seawater drawn straight from outside, and with every chug of the motor, more water seeped into the bilge than the electric pump could keep up with.
And the heat below deck was brutal — around 85°F, bright sun beating down, the loud engine shaking the hull, and almost no ventilation.
What followed looked like something straight out of The African Queen.
We took turns below deck manually pumping the bilge, sweat pouring off us as we tried to keep pace with the incoming water. Pump… breathe… pump… breathe… climb up the companionway for air… back into the heat.
Above deck, the sails kept us moving just fast enough.
Below deck, grit kept us alive just long enough.
Little by little, we made progress — sweat, determination, and a breeze carrying us toward Beaufort.
It struck me later how, just an hour earlier, we were watching porpoises dance to a flute concerto.
Now we were fighting seawater in stifling heat.
That’s the sea—beautiful one moment, humbling the next.
- the folklore that comes alive
- the unexpected encounters
- the heat, sweat, and teamwork
- classical music drawing wildlife
- humor, chaos, and camaraderie
- the unpredictable balance between reward and risk
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The real lessons aren’t learned at the finish line, but in the quiet moments between the buoys.
What These Sailing Life Lessons Mean to Me
Part 2 of this story isn’t about winning races or navigation techniques.
It’s about the moments in between:
These trips taught me that the ocean is a world of contrasts.
In one hour, you can move from magic to challenge, from calm to crisis.
And the lessons stay with you.
Those trips — the humor, the heat, the music, the chaos, the unexpected calm — shaped the way I see everything today, including how I invest. Sailing taught me to expect volatility, to adjust without panic, and to appreciate moments of calm while staying ready for change. And just as important, it taught me that the most valuable lessons often come between the buoys, not at the finish line. Part Three will bring the strongest example of that — the night the ocean truly tested us on the return from Halifax.
These sailing life lessons stayed with me long after the summer ended.
These are the stories that shaped the investor I eventually became — patient in calm seas, decisive in storms, and always aware of the horizon.
Join me as I continue charting my financial course toward calm, growth, and compounding results.
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