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Five Startup Lessons I Learned While Sailing


I recently had the opportunity to join a small group sailing from Warwick, RI to St. Augustine, FL. As we made plans for what would be a fabulous trip, it occurred to me that there are so many parallels between this kind of adventure and the experiences of a startup founder. Since supporting smart startup founders is an integral part of what I do for a living, I started listing out some of the lessons I learned from my sailing trip...


We started the trip full of optimism and excitement for this rare opportunity to get away from it all out on the open ocean. This reminded me very much of the energy and enthusiasm that exists in the very early days of launching a startup. Everyone is dreaming of the possibilities and is full of energy for the task. You develop a plan and begin to execute until reality hits.


Lesson 1 - Start with a plan and adjust to real world conditions.


On the trip we planned for great weather and strong winds to make our journey an easy one. Very much like all the pitch decks that show immediate growth up and to the right, all our forecasts from our wind prediction program signaled a smooth journey. We were an experienced crew who had done it before, and our confidence was high.


The reality was quite different. Once we were out on the ocean the winds shifted and we were headed dead into the freezing wind for most of the eight days of our trip. All our careful planning went out the window and we had to adapt by changing course and adjusting our sails for the prevailing conditions. All startups face headwinds and challenges and the ability to shift to changing market conditions is essential for survival.


Lesson 2 – Running out of cash is a surefire way to fail.


There are many variables for a CEO to watch but none is more important than cash and burn rate. Cash is the fuel for the business journey and if you run out of cash, you fail. We planned our fuel usage for the journey based on the forecast of the predicted wind. Once the wind shifted, we switched from sailing to motor sailing which requires fuel. Much like a startup we were low on fuel and fortunately had extra on board just in case of an emergency like this. We also changed our course from a straight line to our destination to a pattern of jumping from port to port for fuel. It is essential to have enough runway to reach your next milestone so that you can raise additional capital to achieve your goals.


Lesson 3 - Everyone must work together to do their job in the face of adversity.


A few days into the journey my attitude was poor. I was asking myself, "Why did I agreed to this? I could be home and dry and here I am: cold and miserable." Every startup faces adversity and moments of doubt when the going gets tough. The ones that succeed adjust to the conditions and persevere through adversity and work together as a team to succeed.


Then slowly but surely something amazing started to happen. I noticed my crew members working constantly and enjoying the challenge of the journey even though it was cold. We started to have success in mastering the navigation system on the boat and we had small glimpses of nice weather and wind so we could hoist the sails. I never heard my crew members say that it’s not their job or responsibility. Everyone was aligned in our mission to arrive safely in St. Augustine.


The same is true for a startup. Everyone has a role to play but we are all responsible to deliver a product on time, without running out of cash. Each member of the team must do their part. However, in small teams you wear many hats, and the mission takes precedence over personal comfort or convenience. There are many long nights without sleep as you sprint towards a deadline. On the boat you stand your watch even if you are sick. You arrive early for your watch to get an update before taking over the operation of the boat. It is important to watch the instruments to stay awake and alert for danger in the night from other vessels and land formations.


Lesson 4 – There can only be one person in charge – The CEO.


On a sailboat the skipper is in charge. While it is wise to have a strong number two and an experienced crew, ultimately the skipper must make the tough calls. That same dynamic is true in a startup. Successful startups consist of teams with strong co-founders and in technology startups the most successful teams tend to consist of a businessperson as the sales leader and CEO and a strong CTO to build the product. However, there should be no doubt that there is only one CEO who must set the direction and make the tough calls.


Lesson 5 - The teams that succeed are the ones that never quit.


The parallels from sailing to a startup are endless. The personal growth came for me when we began to have success and fun despite the conditions. My attitude turned around and even though we faced more challenges we all banded together and never quit.


The most important lesson of all is that successful founders never quit even in the face of adversity and extinction. The power of the team to overcome all obstacles is the secret to success.




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