How I Built A Business Helping People Learn And Operate Yachts In Exotic Destinations

Published: May 27th, 2023
Estelle & Stephen Cockcroft
Founder, Nautilus Sailing
Nautilus Sailing
from Headquartered in Crested Butte, CO while offering courses in 6 stunning destinations; Tahiti, Mexico, Bahamas, Grenadines, Mallorca and Croatia.
alexa rank
market size
starting costs
gross margin
time to build
270 days
growth channels
Publicity stunts
best tools
YouTube, Instagram, Facebook
time investment
Full time
pros & cons
24 Pros & Cons
2 Tips
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My name is Tim Geisler, and I am the founder of Nautilus Sailing. Nautilus Sailing is an international sailing school that helps people pursue and embark on their sailing journeys and dreams.

We specialize in what is known as week-long live-aboard courses, intensive, immersive experiences where students learn to sail and operate a yacht in an exotic destination. At the moment we run courses in 6 stunning destinations; Tahiti, Mexico, Bahamas, Grenadines, Mallorca, and Croatia.

We have been in business since 2010 and have experienced tremendous growth and have been fortunate to become one of the premium international sailing schools in the world. In 2019 we were approached by Dream Yacht Charter, one of the largest sailing companies in the world, to partner with them and act as their official sailing school.


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

I grew up in an adventurous, travel-loving family. My parents are American, but I was born in Morocco and moved to southern Spain when I was 10 years old. I worked jobs in the travel industry and then became an elementary school teacher in inner-city Los Angeles in my 20s.

I got disillusioned with the bureaucracy and waste in the public school system and ended up accepting a job running an international non-profit working with high-net-worth entrepreneurs.

In 2008 the economy crashed, and I lost my job and had a chance to reinvent myself and pursue my passions. I was able to combine sailing, travel, and education, and Nautilus Sailing was born.

The crazy thing is that we started this sailing school while living in a ski town in the mountains of Colorado, more than 1000 miles from the ocean. People thought we were nuts!

Don’t start a business just to make money, as the motivation will peter out when the crap hits the fan (which it will!)

We had many friends early on that didn’t understand what we were doing, but we believed in our fledgling business. We were excited about the prospect of how owning our own business might better help shape our family’s future.

Initially, we were operating on a bare-bones budget and so we didn't have much money to put into branding. We hired freelancers via 99 Designs and other similar websites to design a logo and we brainstormed lots of names.

It was basic, but we just wanted to get something to get up and running! Over time our brand identity has been involved.

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

We first started offering weekend sailing courses here in Colorado, on Blue Mesa, the largest lake in Colorado. We used a small 25-foot sailboat and had folks from all over Colorado and occasionally neighboring states that would drive out to learn to sail with us.

We designed a curriculum to take people from knowing very little about sailing to feeling comfortable sailing and operating a boat by the end of their course. We coach people to sail by first modeling what they need to do, then turning the ship over to them and giving them chances to learn and practice the skill on their own.

In the early stages, we offer lots of encouragement and constructive feedback, and then gradually we let students be more and more autonomous.

After our first summer, we realized that the sailing season in Colorado was VERY short (3 months) and we had to do something else for the other 9 months of the year to pay the bills.

Early on our first customers were people from here in Colorado, mainly Denver and Colorado Springs, that wanted to do weekend sailing courses. One of our first successful ways of reaching people was to advertise on Craigslist, which was truly unusual!

We came up with the idea of offering week-long live abroad courses in the Caribbean and marketing to adventurous Coloradoans to escape the winter months. We launched a new website and got an amazing response and discovered that people from all over the US and from Canada started signing up for our courses!


Describe the process of launching the business.

I was incredibly fortunate to work with very successful entrepreneurs, many of whom had built brands that one would immediately recognize, in my previous job. As we thought about the launch of our new business I was able to pick their brains and gain so much valuable insight into how to launch a successful business.

Seek the counsel and advice of successful entrepreneurs who have started and run their businesses.

We borrowed $15,000 from friends and family that wanted to invest in our fledgling business and started off as simply as we could. I cobbled together a website on Squarespace and we were up and running! It was a far cry from what we have today, but I was encouraged to just launch a minimum viable product and test the waters.

The biggest lesson I learned from this phase of our business is that if you wait until everything is perfect, you will never launch, so at some point, you just have to do it! This applies to all aspects of the launch, from setting up the legal side of things, to locations, equipment, and systems! Just get something in place and up and running, and you can then adapt and modify it as needed.

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

Early on, our biggest challenge was getting traffic to our website. When we first launched the website, we ranked between 16-18 for our top keywords, which meant very few people were finding our website.

Early on, we hired a talented firm to help us build a website that would rank higher organically, and they helped us manage a Google AdWords campaign. This was an early turning point for us when we went from 17 trips conducted annually to 54!

A family friend who was an executive for Vodafone in England knew this firm personally and recommended them. So important to utilize your network of friends and contacts!

If you are passionate about what you do, you will attract the right customers! We love teaching sailing in exotic destinations and potential clients can feel this and want to join us for courses. This has been one of the things that has set us apart from our competition and means that from the beginning, we haven’t had to convince folks to become clients.

Recently, another critical step for us has been to hire a fantastic PR firm that has continued to help get the word out about our business in top publications. This has given us increased exposure and added credibility in our space.

We have been featured in Cruising World, Yachting World, Sailing World, and several other smaller sailing publications and platforms. We've also been featured in MSNBC, Euronews, the Guardian, and Newsweek.

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

We are at an exciting stage! Operating in the travel industry has meant being on a roller coaster ever since the pandemic, where we went from almost having to shut our doors to a huge increase in demand.

Nautilus Sailing has grown tremendously in its first 13 years and now has a staff of almost 20 passionate individuals that believe in the mission of the business. Today we are honored to run over 100 international courses a year introducing folks to sailing and helping them pursue their sailing dreams.

Our goal is to continue to increase awareness about the incredible opportunities for adventure, travel, and discovery that sailing can offer.

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

You learn SOOOO much when starting and running your own business! Here are a couple of highlights:

  • You need to have perseverance and resilience when starting a new business, as it will have lots of ups and downs!
  • Only hire the right people, people that are passionate about working with you! You’ll be tempted at times to hire less-than-perfect folks, and these things ultimately never work out and may even damage the reputation of your business.
  • Seek the counsel and advice of successful entrepreneurs who have started and run their businesses.
  • Build systems early on for EVERYTHING!
  • Have a clear growth plan and a detailed concept of what your business will look like 5 years from now.

What platform/tools do you use for your business?

  • Google Workspace for emails, calendars, chats among staff, etc.
  • For tasks and running projects, ASANA is an incredible tool
  • For CRM we are big fans of Insightly!
  • Mailchimp for collecting, managing, and sending out emails

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

There have been many, each one key at a different stage of the journey.

  • Early on I was inspired by Tim Ferriss’ book The 4-Hour Workweek, which talked about creating systems for your business that would allow you to have the freedom in life to pursue the things you are passionate about.
  • The E-Myth by Michael Gerber was an invaluable tool in learning how to structure our business, set up systems, and plan for growth.
  • Blue Ocean Strategy, by Kim and Maurbogne, was another invaluable resource early on, as it talks about creating businesses in uncontested market space rather than copying other businesses and operating in an already crowded market.

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

Leap and do it! Early on, it can be overwhelming and doubts can assail you on every side. Just do it, and launch your business!

Be passionate about the business you are creating and do something you enjoy! Don’t start a business just to make money, as the motivation will peter out when the crap hits the fan (which it will!)

Don’t be afraid to innovate and try new things! Some won’t work, but some will…

Where can we go to learn more?

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

Estelle & Stephen Cockcroft, Founder of Nautilus Sailing
Pat Walls,  Founder of Starter Story
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