John Crupi of Rubicon Maritime Group: “Believe in yourself and your mission”

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a […]

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Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing John Crupi.

John Crupi is the founder of Rubicon Maritime Group, a maritime consulting firm advising current and future boat owners on all aspects of acquisition and operation. With over 30 years as a professional captain John’s knowledge and experience have guided expedition programs throughout the world, covering hundreds of thousands of miles, 70 countries and six continents.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in Stuart, FL, on the water and built my first boat at the age of 9. As I approached the age of 16 I needed to find a job so I could buy a car, at the time my only means of transport was my 12 foot dinghy. I rowed up and down the river which lead me to the local Hatteras Yachts dealership. I was hired to wash boats and at the time these were monsters (mostly 40–50 feet) — I could not believe someone owned these and I was equally astounded that you could actually make a living working on them. Soon after starting at Hatteras I was invited to go on a “delivery” to Ft Lauderdale (I felt like Joshua Slocum crossing the Atlantic). I was now getting paid to go for a boat ride some 100 miles south then have a transport vehicle pick us up — this was way better than a trip to Disneyland. As soon as I realized I could get paid to do something I loved I was hooked. Fast forward through the years, I left Hatteras at 21, opened a yacht management company in Palm Beach, eventually sold it, and then was fortunate to find a private yacht Captain job with a family from Miami. For 21 years I travelled the world exploring and catching giant fish in the most amazing destinations.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Perfect is good enough” — nothing is ever perfect, but the relentless pursuit of this unattainable goal is what keeps me motivated and always looking for ways to improve.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

  1. Strong work ethic. You don’t always have to be the best at something, but you do have to be willing to give it your all. When I started sportfishing I knew very little, but I was persistent and showed up every day until someone gave me the opportunity to prove myself. I worked harder and longer which gave me the advantage.
  2. Initiative. Instead of relying on someone else to teach me all the skills I needed to be successful I researched, practiced and then asked questions to my employers/mentors that showed I was serious about improving and advancing within the industry.
  3. Perseverance. Never give up. Believe in yourself and your mission. There will be situations out of your control that may not go your way. Keep your head down and keep moving forward. An inch forward is better than a foot backwards.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I have been a professional boat/yacht captain for over 30 years. I sport fished competitively, owned a yacht management company, and then transitioned into being the captain of a worldwide expedition yacht program for the last 21 years.

And how did you “reinvent yourself” in your Second Chapter?

Yacht crew, and captains in particular, have a hard time transitioning from life at sea to “land life”. When I made the decision to open Rubicon Maritime, I chose to take my unique skill set and utilize it to assist current, new and future boat owners in all aspects of vessel acquisition and ownership. The knowledge and experience I have gained during my career at sea is vital to assisting others who want to experience something similar whether on a smaller or larger scale.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

Over the years colleagues and friends would reach out for information and assistance in various aspects, and I saw firsthand the different frustrations within the industry that could be done differently and better. At some point I realized that I had knowledge to share and that I could be the start of that change.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing?

I realized that my current skill set could be utilized in a different way that would allow me to build a business and offer my expertise to those that needed it.

How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

Starting a new business is frightening and the fear of failure is always there, but I found the confidence to believe in my knowledge and my ideas and with assistance and feedback from others within the industry, I decided it was the right move for me.

How are things going with this new initiative? We would love to hear some specific examples or stories.

With any new business there are challenges and setbacks, but I am building an international client base and have several exciting ongoing projects as well as some interesting options for the near future. Currently I am managing two simultaneous shipyard refit projects which are extremely demanding yet rewarding. In this industry it is all too common for shipyard refits to exceed the estimates for both time and money. My company goal is to prove this does not have to be the norm and that with proper planning and management time spent in the shipyard can be successfully controlled to optimize the outcome.

Can you share the most interesting story that happened to you since you started in this new direction?

I have done a series of videos about various aspects of my travels, refit management and the concept of my new business. I recently received a phone call from a director in Hollywood asking if I’d be interested in participating in a documentary series related to exploration cruising. Not sure where that will lead, but it is definitely a new direction!

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I have always known I have a unique skill set, however I questioned if I would be well received in my distinctive approach to things. People don’t like change.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

Initially I bounced ideas and concepts off friends and colleagues in the industry to determine the viability of my business. For every positive reaction there are usually two negative ones. I had to determine who had my best interest in mind and follow my gut.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I would not consider myself a “people person”. I realize that the success of my business requires me to promote and advocate my experiences and ideas throughout the industry and in order to do that I must make myself available and accessible whether in person, in print, online, etc. I have begun participating in a variety of platforms including in person and online presentations, writing for publications, and this year I will be a guest speaker at the 2021 Explorer Yachts Summit in Monaco.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Throughout my career I have initiated and supported various charitable causes while traveling the world and using the vessel I operated as a platform. The yachting industry, specifically captains and crew have a unique opportunity as they travel to impact the lives of many, especially in remote or impoverished areas. I would implore them to make that effort however small and team up with organizations that align with their goals. My crew and I raised money, donated school computers and supplies, provided support and delivered necessities to areas hit by cyclones and hurricanes just to name a few. Any person, company or organization has the ability to make a positive influence in some way.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂

Michael Jordan because he never gave up, he never looked for excuses, and I think he’s the greatest athlete of all time. Plus he’s a fisherman so we could share fishing stories…

How can our readers further follow your work online?

On my website and blog, Facebook, Instagram, YouTube, and industry publications which I contribute to as often as possible.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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