From Early Day Hustles To Reaching $40M/Year As A Yacht Sales Company

Published: October 11th, 2023
Estelle & Stephen Cockcroft
Founder, Catamaran Guru
Catamaran Guru
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I am Estelle Cockcroft. My husband, Stephen, and I co-founded Catamaran Guru to help sailing enthusiasts live the life they dream of, whether that is living aboard a boat or owning a catamaran to cruise on holidays. Catamaran Guru offers advice, yacht sales services, and a way to connect with others in the sailing community.

But, when we started out in 1992 after having built a boat in a friend’s backyard with plans to set sail from South Africa to the US, our dreams were wild and big as we set off on our sabbatical, but Catamaran Guru was not formed in our minds yet. I should mention that it was my naivete that put me in the middle of the ocean because I knew nothing about sailing but trusted Stephen, an accomplished sailor. If only I had known, our fate may never have led to where we are today.

Our business was borne out of us following our dreams and connecting with like-minded people around the world as we sailed 30,000+ NM to the US, passing through pirate-infested locales like the Red Sea, partying with a real-life sultan, experiencing the aftermath of civil war firsthand, and getting an insider’s view of Cuban life. We even had a monkey who lived aboard with us for a while. You can read more about the interesting people we encountered and the historic events we experienced up close.

As realities of the sailing life set in and the cruising kitty (funds to support yourself) emptied, we put our entrepreneurial ingenuity to the test. When our kitty needed an infusion, we would set up residence in a port and learn the language well enough to sell our homemade crafts such as baskets and trinkets, tend bar, or hire out as captain and crew on a charter boat.

As we neared more civilized locales such as the Bahamas and other Caribbean islands, we found work as boat delivery crew, divers, sailing instructors, and offered our yacht for charter with us as crew.

When we got ahead a bit and could stock up, the ocean inevitably called and we set sail to explore worlds new to us and meet amazing people. This gypsy life may seem haphazard, and it probably was in the beginning, but as we met lifelong friends and came to stay mostly in the US and Caribbean, we became familiar with how the yacht charter industry worked, which eventually put us on a path where we became the experts in this field, and we were able to advise others.

From our humble beginnings peddling week-long cabin stays on our vessel, we've now ascended to become a leading Yacht Sales Company in the United States. Those early days saw us hawking those onboard charters as a means to finance our globetrotting adventures, where we pinched pennies to explore the far reaches of the world.

Fast forward to today, and our enterprise boasts an impressive annual revenue surpassing the $40 million mark. We have not changed much from when we were "ocean nomads". We still live aboard and work from our yacht; it is just a bigger yacht!


What's your backstory and how did you come up with the idea?

Stephen and I loved living port-to-port, but we realized we had seen the yachting industry as few have. We were intimately involved in the building process of our first boat, we operated a successful charter business and sailing education program on our boat. By doing this, we realized how intense people’s thirst for knowledge was about catamarans and the charter business. There was not much information out there at the time and we thought we could parlay that insight into a successful yacht charter business.

So, we bought into a charter company. For about 4 years, we had 70 boats under yacht charter management. It was hard work, but we were helping make others' dreams of yacht ownership and sailing come true. This is where we learned so much about yacht buyers and owners, their concerns, and what the financial benefits are of placing their yacht into a charter fleet.

A few years later, we jumped at the chance to purchase a stake in a South African catamaran builder, Island Spirit. We were part of the team that designed the exterior and interior features as well as the sail plan of the popular Island Spirit 401. Some of these features, unique at the time, are now standard features by most of the popular catamaran brands like the galley design, anchoring system, and Jack-and-Jill bathrooms. Over the years, we have been invited to participate in designs of sailboats of popular manufacturers.

Our first boat had been a monohull (single-hull boat), but we were one of the early adopters of the catamaran concept and learned everything we could about it. But it was always outside our price range and like most sailors, stayed with our monohull. It was affordable and a known entity for most. But compared to monohulls, the catamarans (2-hulled boats) were very stable and offered expansive living space. The cats were more like homes ashore. We had a hunch that this burgeoning trend of catamarans was going to take hold and we decided to buy an Island Spirit 401 and use it as a display model. It was a roaring success and we established that brand in the US. The Island Spirits became very popular in the charter market because of their unique and spacious design and we sold 30+ of them before the manufacturer changed hands and we sold out.

The popularity of the catamaran (2 hulled boat) was rising in the US and around the world. Until then, the monohull had dominated the sailing world, including the yacht charter market. As we lived aboard, we became more convinced that catamarans were going to be the yacht buyer’s choice, and we knew that we had a lot of valuable advice to offer. As with most new concepts, there was a lot of misinformation thrown about, mostly by monohull manufacturers and salespeople who did not want to lose market share. As liveaboards who had built catamarans and operated a charter fleet, we saw the vision of helping others live the sailing life.

Take us through the process of building the first version of your product.

Our early sailing days offered many diverse experiences in the maritime industry and introduced us to many fun and sometimes influential people. We continued our sailing dreams by establishing Catamaran Guru, which was both a blog that educated and entertained those interested in sailing life, and a yacht brokerage that offered advice on properly leveraging tax advantages.

We were advised very early on by some very smart people, to build a brand and to

adopt social media as a medium to get our brand to the market. We took it to heart and decided to build a website in 2004.

I had no knowledge or education about how to create a website and frankly, I was almost computer illiterate at the time. I had no money to pay developers so, I enlisted a friend for some tutoring on the basics to build a Joomla site (at that time, there was no such thing as drag-and-drop websites then that I was aware of).

Mostly I learned through trial and error, and watched YouTube tutorials on “how to code”. It was tough, and frustrating and I almost gave up a few times, but I am stubborn by nature, so I would invariably go back at it and solve the problem.

It took me almost six months before I had a working product, but it was one of the most rewarding things I had ever done and it taught me several things: perseverance, patience, the power of education, and “where there’s a will, there’s a way”.

I went on to build and rebuild the site a few times as I became more adept at it but ultimately, we moved the site to Wordpress. While I now have help, I still like to be involved in every part of the website and I write most content (over 1000 pages) myself.


Describe the process of launching the business.

I began writing about our adventures and captured information Stephen had to share about the yacht-buying process and how to reduce the costs of ownership with various yacht charter programs and business tactics. We joined up with the largest yacht charter company to offer programs on their platform worldwide. We also helped them formulate new programs to address the concerns and desires we had learned about when we were charter managers and shipbuilders.

We built our reputation through attending boat shows and spreading the word about our services and our blog, which offered a one-stop shop for people wanting to learn more about sailing or boat ownership. People gravitated towards us because we did not only sell boats, but we lived the lifestyle that everyone dreamed about.

We have actual real-life experience, and we can address the concerns and questions people have from firsthand experience. We are believable because we don’t just teach people about the lifestyle, we live it.

The sailing community is so supportive of one another that we found it quite easy to enlist sailing magazines and other bloggers to partner up to cross-promote one another. Our fantastical stories of pirates, sultans, and an ape living aboard opened doors, and our solid business acumen that revealed ways to make sailing dreams come true gave us staying power.

We steadily built our reputation using traditional boat marketing tactics as well as digital tactics, including social media. We continually focused (and still do today) on how we can build the sailing community.

We don’t just sell this lifestyle; we live it, and that goes a long way toward guiding and educating our customers to believe that they too can do this.

Since launch, what has worked to attract and retain customers?

Direct email campaigns are our most powerful and successful way to communicate and reach our target audience. We have a 30,000-strong mailing list which we have collected mostly from boat shows over the last 20 years, as well as seminars and liveaboard sailing schools, which all drive traffic to our website.

This is a very powerful list of names because everyone on the list is interested in boats, whether it is for education to buy a boat to charter a boat or to get some boating tips or just to be part of the community. So, everyone is interested in what we have to say as long as we keep it new and fresh, and we give them value.

Our YouTube channel has brought us a ton of business tthroughour educational seminars on boat purchasing and charter programs. We now understand the value of YouTube and are in the process of upping the ante by posting regularly and consistently, something we never had the time for. But I highly recommend that everyone establish themselves as an “expert / specialist” in their area of interest and use their channel to get the word out. It is highly effective.

Our channel does not have a ton of subscribers (although we hope to change that in the next 6 months) though the subscribers we do have, buy boats and they will buy them from us since we are the experts in our field, which is evident on our channel. We practice what we preach (also shown on the channel) and our testimonials are great. People always buy from someone they trust and if they feel connected to you through your channel and you are authentic and believable, they will become your customer.

Another way that we have fostered a stronger sailing community is our annual Catamaran Rendezvous in the Bahamas. This open meet-up invites any catamaran sailor, no matter the boat they sail or their stage of life, to come to have fun, meet other sailing enthusiasts, share their knowledge and experience, and get to peek at other catamaran brands. This gives many yacht owners the urge to trade up and we are there to help them sell their boat and find ways to afford the next boat of their dreams.


But our biggest draw is our testimonials. We are so fortunate to have so many boat owners kind enough to take the time to write about their experience with us. And so many of our prospects tell us that the testimonials are what convinced them to talk to our team.

We think because we love what we do, great customer service follows. We pride ourselves on being the “can-do” company. No matter what, we stand by our customers, sometimes even years after the sale when they come back for advice or to solve a problem.

How are you doing today and what does the future look like?

The past few years have seen us grow exponentially. Not only in terms of selling more boats and helping more people live their dreams but in terms of exclusive boat brand dealerships and expansion from the South Florida markets to Texas and Annapolis and the Caribbean, which are all sailing meccas.

Plus, we have grown ancillary and complementary businesses such as our sailing school, adding world-standard Royal Yachting Association (RYA) instruction and certification programs that are rare among sea schools in the US.

Our team of brokers and back-office staff have grown to keep up with the demand because we know that customer service is what has fueled this growth, and we want to keep it that way.

Through starting the business, have you learned anything particularly helpful or advantageous?

Learning that making mistakes is part of the journey is important. Each mistake still comes across as difficult to swallow and bursts the ego a bit, but it's truly part of the journey and process of improving what you are doing. While you may not set sail into unknown worlds, you most certainly will experience things you have never experienced before. Make the most of those and learn from them because those obstacles could become your opportunity.

We live and breathe the lifestyle that everyone who buys a boat from us wants, so we are believable, and our product knowledge is exceptional because of that. We don’t just sell this lifestyle; we live it, and that goes a long way toward guiding and educating our customers to believe that they too can do this.

Educate your customers and manage expectations. Our philosophy is to be honest with every customer. Some people are just not meant to own a boat and we must be honest enough to tell them that, even if it means that you will lose a sale.

Make it easy for the customer to buy your product. Streamline the process, respond quickly, know your product, and offer solutions to problems! In today's competitive market, products and services can often be similar. A business therefore must deliver outstanding customer experiences to stand out. Exceptional service can become a unique selling point and help build a positive brand image.

Take action because procrastination can kill your dream. Embrace Change, be positive, and learn from your mistakes.

What platform/tools do you use for your business?

I started out with a Joomla website and had to learn how to write code on YouTube (LOL) to use it. My mentor was adamant that I learned every aspect of the process, and quite honestly, I could not afford to hire it out. It was tough but I learned then to embrace technology. It opens doors to fledgling businesses. In recent years I migrated to WordPress.

While I still prefer Joomla’s flexibility, my marketing support staff tells me that WordPress is much easier to make search engines love the website. And that is important.

We have used several CRMs over the years, such as Constant Contact and Less Annoying CRM, but as we have grown to be a fairly large team of yacht brokers with more advanced methods of bringing in and tracking leads, we have established HubSpot. We are still learning this robust tool, but there are so many ways to make personalized communications with prospects easier and faster.

Nurturing a potential customer is so much easier when things can be automated. We also use Smartsheets as a method of tracking and documenting our warranty work on boats. We have around 100 catamarans in various fleets and this is an easy tool to track those boats and their ongoing warranty issues.

We have used Facebook for years and, recently, Instagram. Our followers’ and yacht-buying demographics suit those platforms. We use a private group for our annual Catamaran Rendezvous so the camaraderie can get started before the event and continue long after.

Our YouTube channel was neglected until recently because we just did not have time to edit our vast amount of footage to make videos. It was a mistake. It is a very powerful platform, as we all know. We are catching up now and it is paying off. We have hired an editor and photographer who will help us make this a go-to channel for catamaran enthusiasts.

What have been the most influential books, podcasts, or other resources?

We have had so many “influencers” and mentors in our lives, but our current favorites are:

Gary Vaynerchuck is a motivational speaker and serial entrepreneur. He is a forward thinker in business, recognizes trends in technology early on, and helps people understand how to apply those trends in business.

Esther Jabobs, the “no-excuses” lady, is a font of information for traveling nomads and building businesses from your simplest ideas. She has delivered two TED talks and has written more than 30 books. She teaches people how to tell their stories and write the book. I am currently on this journey with her to write our book.

"The 4-Hour Workweek" by Timothy Ferriss offers ways to escape the 9-to-5 grind by focusing on automating processes and outsourcing tasks to achieve more freedom. And "The E-Myth Revisited" by Michael E. Gerber addresses the common pitfalls that small business owners face and insights on how to build a scalable business.

Advice for other entrepreneurs who want to get started or are just starting out?

Focusing on what we can control and acting in the present moment is crucial for achieving our goals and experiencing more freedom in life. Define your objectives clearly and break down large goals so they become more manageable. Take action because procrastination can kill your dream. Embrace Change, be positive, and learn from your mistakes.

Surround yourself with positive people. This will better equip you to tackle challenges and achieve the success you desire. Remember, the journey may not always be smooth, but the determination to overcome obstacles will lead you closer to your dreams.

Are you looking to hire for certain positions right now?

We hire independent experts to fill needs where we fall short. But mostly, we are always open to hiring good brokers. Brokers are ten a penny, but closers are far and few between. Of course, we require that the broker reflects our company’s image and dedication to our client.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!