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Estelle Cockcroft on The Art of Monetizing What You Love


Estelle Cockcroft is President of Catamaran Guru


Can you begin by telling our audience a little about yourself, your business, and what led you to pursue your particular passion as a profession?

My husband, Stephen, and I are originally from South Africa and we co-founded Catamaran Guru to help sailing enthusiasts live the life they dream of. We are now US citizens and is one of the foremost experts on large catamaran sailing, living, buying, and selling. We have traveled more than 70,000 nautical miles of remote waterways, explored 45 incredible countries, and we broker dozens of catamaran transactions each year with a 40M+ annual revenue.


We share our passion for sailing through our blog on the Catamaran Guru website.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 around the world, our dreams were wild and big as we set off on our sabbatical, but Catamaran Guru was not formed in our minds yet.


As we sailed the world's oceans, we learned and absorbed every wonder and every obstacle that this lifestyle had to offer like passing through pirate-infested locales like the Red Sea, partying with a real-life sultan in the Mediteranean, experiencing the aftermath of wars and conflicts firsthand in places like Eriterea, Somalia, Yemen and getting an insider’s view of Lebanese, African and Cuban life. We even had a monkey who lived aboard with us for a while in Turkey. You can read more about the interesting people we encountered and the historic events we experienced up close on our website.


It was only after we hit the Caribbean that we realized that we had very valuable knowledge, skills, and experiences that others would pay us to learn. A local sailing school on Sint Maarten employed us to teach tourists on the island how to sail and the rest is history. This gave us the jump start for our business and we grew this passion in the a global business.


I'm curious to know, what was the defining moment that made you realize that this passion could actually become a business? How did you identify the unique value it could bring to others?

We started teaching people how to sail a catamaran on our own boat and it dawned on us just how popular these boats will become. It was at a time when very few people knew much, if anything about catamarans. Most monohull sailors viewed them with scepticism and potentially dangerous. While everyone was initially sceptical, everyone loved the space and the stability of the vessel.


For us it was about recognizing the market potential, understanding the unique value of the product and creating market acceptance. We found a way to dispel the negative through education to potential buyers. You will need an iron will and determination to turn your passion into a sustainable and successful business but the potential could be enormous. From humble beginnings peddling week-long cabin stays on our personal 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! LOL


Every entrepreneur faces obstacles, especially when turning a passion into a business. Can you share some of the initial challenges you encountered and how you overcame them?

Building a team was a challene initially. As your business grows, you have to hire employees or collaborate with partners. Finding the right people who share your vision and complement your skills can be challenging especially in a niche market like ours and business owners like us, tend to not want to "tarnish" the brand or reputation by employees who do not know the business as well as we do or does not have the same passion. But is essential for long-term success and you have to learn to let go. It is probably the hardest part to deal with in a passion business. Scaling a business while maintaining quality can be a tricky balance. Developing scalable processes and systems, reinvesting profits wisely, and continuously improving your operations are key to sustainable growth. My best advise - surrond yourself with smart people who can guide you in this phase of your business.


Monetizing a passion requires a solid business model. Can you walk us through how you developed yours, and the key factors that make it successful?

We realized early on in our sailing career that there was a "knowledge" gap in this niche market. We were one of the very first sailing nomads in the early nineties, who explored the world on a sailing catamaran and very few people knew much about catamarans and even fewer people knew how to make a boat pay for itself while living onboard and sailing the world. So, the first thing to do is to identify your niche market, become and expert in that field and create valuable content or products that cater to your target audience. Invest time and effort in marketing and promoting your passion-based business. We taught sailing schools onboard our boat, did online seminars and exhibited at boat shows and got paid for it. Soon enough we acted as advisors for people who wanted to buy boats and a hugely successful business was borne from that. These are all the things that we know how to do well and we wanted to share it with others anyway, so it did not feel like a business. Once we created our website and got the word out, people naturally gravitated towards us because we were considered an authority on the subject. We developed a strong sense of community with our customers who were eager to put the word out for us because they received value and benefitted from our teaching and guidance.


Many people worry that monetizing their passion may take the joy out of it. How have you managed to balance the business aspects with staying true to what you love?

We are lucky enough to be able to actually "live our dream" lifestyle and call it a job! Being in the thick of things in real time gives us a unique insight and it is very easy to relate to our customer's challenges and how to offer solutions. There definitely is business "creep" into your passion and you will have to sacrifice some things to gain others. You will have to decide what is worth the sacrifice. Understand that turning your passion into a business may come with challenges and setbacks. Be prepared for these and maintain realistic expectations. It may take time to navigate this balance, but with careful planning and dedication, it's possible to enjoy both the creative and financial rewards of pursuing your passion.


As your business grew, what strategies did you employ to scale it while maintaining the core values and essence of what made it special in the first place?

We created efficient and scalable processes that can handle increased demand easily. While this is still a "peoples's business" and we have to be close to our customer, automation and technology is crucial to streamline operations and maintain consistency with our partners and employees. We encourage a culture of adaptability and innovation. As we scale and market conditions change, we may need to pivot quickly and either change our strategy or expand when the opportunity comes along. The Covid Pandemic certainly taught us that.


Your journey is truly inspiring. What key insights or pieces of advice would you offer to someone looking to turn their passion into profit?

Establish yourself as an expert in your chosen field.


Reflecting on your journey so far, what are you most proud of? What future developments or projects are you excited about in your business?

We take immense pride in the thriving community we've cultivated and the accomplished graduates emerging from our sailing academy. These individuals represent the very essence of the sailing future we envision. In an era where technology advances at an astonishing pace, we're committed to substantial investments to ensure we remain at the cutting edge of innovation. Our goal is to continuously extend our reach within the community and beyond, utilizing the latest advancements to further our mission.


For those interested in learning more about your journey or connecting with your business, how can they get in touch or follow your work?

twitter: @catamarangurus / Instagram: @catamaranguru



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