Sailing Is A StartUp Sport

Sailing Is A StartUp Sport

By: Michael Youngblood, Co-founder & CEO, Unsettled.


When we sail in Croatia – the local winds are known as the  Maestral (Mistral), Bura (Bora) or Jugo. The Maestral (Mistral) blows from the northwest. The Bura is a cold, dry wind that blows from the northeast.

The ancient Greeks created a god – an entire deity – for a specific wind. Boreas is the ancient Greek god of the winds that blow from the Balkans. 

I can see why.

In sailing, you focus an incredible amount of attention on the wind. 

The crew constantly adjusts, adapts, and corrects from subtle changes in the pluffs, guests, and shifts.

At Unsettled, the crew is you. It’s a group of solo travelers – creatives, solopreneurs, and entrepreneurs – who often have modest if any sailing experience.

I can see why so many entrepreneurs, solopreneurs, and business owners are attracted to Unsettled’s sailing trips (more than 50% of our audience owns a business).

On Unsettled trips, you are fully part of the crew. There are no passenger princes or princesses on these trips. You’re hands-on, learning as we sail.

Sailing feels like a startup.

Much like navigating a startup through shifting markets, sailing demands constant adaptability and courage to chart new paths when the road ahead isn’t always predictable. You are constantly thinking about where you want to place your team just ahead, in the future. 

On any sailing trip, I remind myself of the adage, Plan the Sail; Sail the Plan, which works until it doesn’t. Planning is necessary, and I love having multiple scenarios in place, ready to execute, because rarely does the plan go well on the first go.

In startups, setbacks and adversities are inevitable but can ultimately lead to valuable lessons, growth, and success in the long run. “Everyone makes a mistake once, but you’ve got to learn from it,” an entrepreneur once said to me when we were sailing together.

We’ve learned to set very direct expectations at the start of Unsettled sailing trips. They’re crazy amounts of fun. Everything won’t go according to plan, there will be adversaries and setbacks. You will feel uncomfortable at times and have the time of your life moments later.   

This isn’t a cruise ship just as a startup isn’t a stable corporation. 

Expect the unexpected. Embrace the unknown. This is unstructured, unbounded travel at its best. It’s more than a mantra. 

Sail Croatia with us in June to find out first hand. 


Unsettled is a global community for those who live and work differently. 

Growth | Meaning | Adventure

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