There is a joke on Supertaff that the ARC starts long before you leave Las Palmas. For some boats it probably begins with a yard contract and a big cheque. For us it started with a seven day, double handed push from Portugal in a 50-year-old ketch with tired sails, an elderly engine, and a very specific budget.

Getting to the start line is the first ocean crossing. The rest is details.

A heavy boat in light and heavy weather.

Supertaff is not a modern, lightweight flyer. She is a 1970s long-keel fibreglass ketch, about 13 tonnes, built for reaching across oceans rather than wiggling upwind. In flat numbers she is “only” 42 feet, but on the water she feels like a small ship. That is a blessing and a curse.

On the delivery from Portugal to Las Palmas we saw just about everything. Strong wind, very light wind, confused sea states, and wind shifts from every direction. It was probably one of the most technically demanding passages I have done in years. There were times when the wind would swing 30 or 40 degrees over just a couple of hours, which meant constant trimming, tacking, reefing, and un-reefing.

People often assume the hard part is big wind. In a heavy old boat, light wind can be just as brutal. Below about ten knots of breeze Supertaff becomes a stubborn piece of sculpture. You are working every tenth of a knot of boatspeed, trying to keep momentum in a hull that really wants to sit down and have a rest.

Add to that a steady procession of commercial traffic. The AIS did its job, but there were plenty of occasions with five or six ships within a couple of miles, day and night. Double handed, three hours on and three hours off, with one eye on the plotter and one eye on the horizon, it adds up.

We do at least eat properly on Supertaff. That is a rule. Even so, with most of the systems and maintenance falling to me, sleep was thin. The boat never lets you forget who is in charge.

Old gear, tight budget, and learning to fix the unfixable.

Supertaff is not an Instagram “refit project”. She is a working boat that has to be kept going on a medium sized but quite tight budget. On average we spend around £12,000 a year on her, which sounds a lot until you start pricing new masts, new engines, and the sort of electronics packages that seem to be standard issue on many ARC boats these days. We have to make the old stuff work.

On this trip the weaknesses showed up in predictable places. We had a leaking water pump on the engine. Belts that needed attention every 4 hours of run time. Sails that are 20–25 years old and getting towards retirement. Nothing dramatic, but with age comes anxiety. You are always conscious that every small failure can cascade if you ignore it.

Traditionally I would have taken a tired water pump to an engineering shop and asked them to rebuild it. This time, somewhere off the Portuguese coast, I stripped the Johnson pump on board, replaced the water seal, and put it back together with nothing more than the tools on the boat and a bit of patience. It worked. It was a small job in the scheme of things, but an important one for me. If you want to move an old boat around the world on a budget, you cannot outsource your courage.

The same applies to electronics. Our main Garmin GPS is over 30 years old and still going strong. Old does not automatically mean “replace”. It means “maintain, understand, and respect the limitations”.

There is always a list. Reinforcing on a couple of sails. Engine jobs. Locker doors that work loose. On a boat like this the list never ends, it just changes shape. The real skill is knowing what is urgent, what is important, and what can wait until tomorrow for the sake of crew sanity.

Which is where the CEO bit creeps in.

Leadership: cleaning stanchions versus staying afloat.

There was a night on the delivery when the wind sat stubbornly on the nose and kept shifting just far enough to make it awkward. I tacked, re-rigged, and reefed four times in about two hours. Tired, slightly cold, and increasingly irritated, I reached that familiar point where you either carry on grinding yourself down or you stop, heave-to, make tea and reset your brain.

We chose tea.

That decision is leadership. Not in a grand, LinkedIn-meme sort of way, but in the basic sense of “what actually matters right now”. Getting all the crew up at six o’clock to polish stanchions feels decisive; it is also pointless. Letting people rest when rest is the thing that will keep them effective is often the harder call.

It is the same in business. If people do not understand why a task is important, they will do it badly or resent it. At sea the feedback loop is shorter and sharper, but the principle is identical.

Living with the past: rollover, family business, and “just do my best”

Some of this is coloured by history. In 1998 Supertaff and I were rolled 360 degrees off the Irish coast in storm force conditions. We lost both masts, most of the gear on deck, and a lot of pride. We were eventually taken off by lifeboat. It took two years of money and effort to rebuild the boat in the first place, and in one rotation the whole project was under water, literally and figuratively.

After that sort of experience you either sell the boat and take up golf, or you get back on the horse. I chose the second option. Every time I step back on board, some part of that decision is with me.

The same stubbornness is tied up with Boatshed. I left a busy family hotel business with siblings, parents, aunts and uncles all involved, to start an online boat brokerage in the late 1990s. Failure was not really an option. Not because of money, but because of the idea of having to go back and explain that the whole thing had fallen over. “Shame” is a stronger motivator than most business books admit.

I carry that with me. It is not heroic. It is just how I am wired: do your best, accept that things break, fix them, and keep going.

Las Palmas: big boats, small conversations.

Arriving in Las Palmas this year was a reminder that the ARC is evolving. I have done it before, and like many people I had a picture in my head of a slightly scruffy, Corinthian fleet: home-built dreams, old family boats, lots of DIY.
There is still some of that still, but there are also a lot of shiny new 50–60 foot yachts bought specifically for the event, some delivered by captains, some with professional skippers on board for the crossing. That is not a criticism, just an observation. The fleet feels different.
My first reaction walking the docks was a mix of admiration and mild alienation. You say hello, and often people are wrapped so tightly in their own world that they barely register. The ARC organisation does a good job with parties and receptions, but real camaraderie develops slowly, usually once people have left the pontoon.
I found myself clinging harder to a simple rule I was taught in the family hotel: be nice to everyone. Delivery skippers, owners, crew, the kid with the rucksack looking for a ride; it costs nothing to be decent. Call it karma if you like. In my experience it is also just a more efficient way to live.

Boat Tours 2025: an MVP in the marina.

One of the more experimental things we brought into Las Palmas was Boat Tours 2025, a simple community-led idea piloted through BoatshedLabs.
The concept is straightforward: ARC crews can invite other ARC crews to look around their boat during the prep days, using a single format on the fleet WhatsApp group.

Short visits, clear rules about privacy and safety, and a link back to an explanation page. No fuss, no forms, no official status. Just peer-to-peer learning.
It is an MVP in the purest sense. A bit of low-code, a bit of structure, and an experiment in openness.

Check out Boat Tours 2025 HERE

Was it a roaring success? Not yet. Many people are still wary about inviting “strangers” on board and most of us are conditioned now to live in our own bubble. That is exactly why I think it matters. Whether you are talking about sailing or business, silos are the past. Shared experience is where the value sits.
We will pick it up again in the Caribbean and treat this year as iteration one.

Curt, fish, and the serious business of not being too serious.

While Boat Tours was testing cultural boundaries, Curt was teaching people something much more tangible: how to catch dinner.
His “catch supper” talk is basically a handline, some rigging wire as a trace, a double hook, and a cream-coloured plastic squid. Trail it behind almost anything that floats and, in our experience, you catch fish when you want fish. We have taken three so far on this crossing and ate one of them for Thanksgiving. Curt and Shea are both American, so the turkey was replaced by mahi mahi and a lot of laughter.

The mood on Supertaff is deliberately relaxed. We do not take ourselves too seriously because the ocean takes care of the seriousness for you. Safety is non-negotiable; everything else can afford to be a bit loose. Again, the parallels with running a company are obvious. People do their best work in environments that are safe and serious about the right things, and relaxed about the rest.
Passing on Curt’s fishing rig to other crews was another small example of how knowledge should move: hand to hand, without mystery.

Tech, insurance, and a different way of doing risk
Another thread running quietly through this ARC is an experiment with Coast Insurance. I met Marcel, who founded Coast, at a boat show. He is ex-yacht crew and came into a very traditional insurance market asking awkward questions. His answer was to put more technology on the boat: live trackers, data on location and weather exposure, even basic “health” signals from bilge levels and batteries.
For insurers this is gold dust. Better information means better risk management and, in Coast’s case, lower premiums. For me, it also meant an Atlantic extension at a price that was around 60 percent of other quotes, at a time when my previous long-term insurer had simply exited that sort of cover after a corporate takeover.
We are using this crossing to see how that tracker and data actually behave in the real world. It is a small example of what I am interested in: practical, sensible innovation in industries that have been resting on habits for decades.

Music, 160 boats, and writing your own soundtrack in between sail changes, maintenance, and the usual pre-departure noise.

I have been doing something that would have been impossible on my first ARC: creating music for the fleet from the boat.
I grew up DJing in the family hotel, trying to keep turntables, lights and amplifiers alive while 150 people danced. These days the tools have changed. I work with AI to turn my own lyrics into finished tracks. It is a form of therapy for me: you take your frustrations, observations and ideas, shape them into words, and then let a system score them.

For this ARC I wrote “Fleet Rolling”, a track that weaves the names of all 160 boats into something with a loose West Coast feel. We posted the MP3 into the ARC WhatsApp group and the reaction was immediate. People hunted for their boat name in the lyrics, messaged us to say thanks, and for a moment the big, shiny, slightly disconnected fleet felt a bit more like a village.
I might yet do a country and western version. The point is not the genre. The point is that technology now lets you write your own soundtrack to your own adventure and share it instantly with the people living the same weather.

Fleet Rolling MP3 is track 2 is HERE

Why do this now?

I first did the ARC in 2018 and have wanted to do it again every year since. Life got in the way. Boatshed is a well-known brand but still a small team. Taking six or seven weeks “off” never really felt honest.
Starlink changed that equation.
For the first time I can be at sea and still feel like a relevant, contributing part of the business.
We have a small window of connectivity each day and we are using it to write, build tools, test ideas like Boat Tours 2025, share music, and run the company.

I am doing this crossing again for myself, because there are some experiences you cannot fake.

I am doing it for Curt, who is seventy-eight and said he had one more Atlantic left in him.

I am doing it because the technology finally allows me to be CEO and sailor without one side having to pretend the other does not exist.

More importantly, I am doing it to prove a simple point: you do not need a brand-new 60-footer and a professional crew to cross oceans or to run an interesting business. You need a sound boat, a realistic budget, some good people, a willingness to learn, and the right systems behind you.

Over the next couple of weeks I will be sharing more from this CEO@SEA series: what works, what breaks, what we are building, and where I think the Boatshed “business in a box” model can help other people do their own version of this.
Whether that means being your own CEO at sea, or adding boat sales to a marina or marine business, is up to you.

For now, we have done the first crossing: we made it to the start line.
The rest is details.