We had the good fortune of connecting with Captain Woody Henderson and we’ve shared our conversation below.

Hi Captain Woody, how do you think about risk?
My career as a yachting and conservation captain has been focused in four areas. Charter flotillas, where we organize multi-boat sailing trips around beautiful islands all over the world. Writing about sailing for sailing magazines. Yacht deliveries both sail and power, specializing in long range ocean and international voyages. And running ex-Coast Guard fast cutters for the conservation group Sea Shepherd. I would say the first two have limited risk. Deliveries and on-site Conservation are a little different. Everyone has a different way that they look at risk and often, their view depends on the activity. Most people have no fear of driving everyday yet many of those people consider the risk of crossing an ocean on a relatively small boat, out of the question. Stats indicate you are safer on the boat. The risk increases of course, as the boat condition declines. Most people that hire out the moving of their yacht have decided that it was not safe for them to do it themselves. And there are many reasons including: time of year, condition of boat, a tricky or upwind route. My process? My crew and I show up and check out the boat. I don’t think I have ever written about it but for a long time, I considered my risk on a 5% rule. If surmised that there was a ≥ 5% chance that I thought the boat would sink during our delivery, we would get back on a plane. More accurately, with information on hand before flying to the vessel, I would create a list of tasks for the owner to complete before we would take on the project. And rarely, a boat not designed for, or too structurally weakened to handle a rough ocean voyage, I would stipulate a delay until the bad season ended. Another way to mitigate risk is with amazing crew. I have a short list of individuals that I have sailed with whom I tap for deliveries. All are solid in situations that can appear sketchy. Another strength is their ability to carry out tasks asked of them, without extensive questioning or panic. And we like funny. You are going to spend some time with these people. Most of it is going to be beautiful, some of it is going to be rough, all of it is better if you are with people that can spread some light during both the rough and calm patches. And I know that kind of calm under pressure is an attribute that increases safety. All that being said, we like to have our third or fourth crew member be a relative newcomer to ocean sailing. All of us, regardless of industry, have benefited from more experienced people taking the time to share their tips and tricks… and confidence. It is an ‘intern’ style position that saves the owner a couple bucks. I don’t believe this raises risk overall. We prefer younger people as they are less likely to require a long conversation before carrying out a task. I am always excited to delve into how we chose a certain action and how we manage situations at length during the less exciting parts of the passage. Younger people learn faster and within a short time, absorb the basics that keep us all safe on their watch. And we have learned that women seem to be more solid than men on boats. I find they are less likely to be gripped by the slippery overlap of fear and ego. Being the captain of a conservation ship ticks all of the boxes for me but there are risks here too. The Sea Shepherd cutters are full of volunteers, 15 crewmembers that are mostly young (20 & 30 somethings, I’m 51) with biology backgrounds. These motivated ‘kids’ are very excited to be part of a frontline solution to illegal animal exploitation. Mostly, I have delivered untested 110 foot fast cutters (29 knots) and then run them on the Milagro campaigns in the Sea of Cortez. Endemic to just this area, there are two at risk species. A nearly extinct, super cute, porpoise (picture a dolphin) called the Vaquita and an endangered large fish called a Tatoaba. We (Sea Shepherd) have gained approval from the Mexican government for unrestricted removal of illegal fishing nets that are killing off both species. It’s brutal work for our young volunteers, pulling mostly dead animals over the rail all day. And then we save one and a warm gratitude flows through the ship. Though most legal fishermen are supportive, the poachers setting illegal nets for huge profits can be combative. The crews and ships receive threats at sea and molotov cocktails on occasion. There a lot of measures the ships have learned to take but risk remains. In a world where it can be hard to make a difference, these conservation experiences remain blissfully satisfying.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
Before he passed, my dad gave me some great advice, “Do what you love and eventually someone will pay you for it”. Our passions will be the fields in which we will excel. I admit that I didn’t initially follow his advice. I was in college when I realized that if I completed four years, I would be qualified to sit in a cubicle all day. I left college and soon found sailing. Sailing inspired me in every way. It was adventurous with the challenge of having to earn each change of scenery, culture and landscape. A more natural way to travel and explore places that almost no one else could get to. And a massive un-ending learning curve of: electronics, engines, solar and wind power, weather prediction, wind and wave tells, sea life and conservation techniques. Oh, the business? I manage sailing vacations around exotic island groups all over the world. I have gained a lot of experience sailing and love to impart what I’ve learned to our sailing clients. I want them to feel the excitement I have coaxing our sailboat to the next destination. To learn some navigation, to feel and interpret the wind, waves and current. To bask in the achievement of another blissful landfall after a few hard fought sailing hours. To experience peak living. My partner in the sailing vacations is a fellow circumnavigator, sailing legend Tania Aebi. Our other captains are famously low key, immensely qualified friends who are also excited to teach and guide. I can’t say getting to where we are today was difficult as it grew organically. I wrote a sailing column for a long time and have earned a large client list. Our people know what they are getting and come back year after year. We have sailed many of the destinations before and know the ins and outs and get group deals from local operators. We have done multiple Cuba sails and are experts at navigating the tricky paperwork. And we throw in a new exotic destination now and then for our more adventurous clientele. And of course, my crew and I will deliver your yacht from anywhere to anywhere. We utilize our currents, wind and weather prediction to sail faster while using less fuel and minimizing wear and tear. Our global connections get us in and out of fueling ports quickly.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
I was raised on the beaches south of LA’s only marina – Marina del Rey. There are a lot of sailing options out of MdR. It used to be the world’s largest man made marina so it is large enough to sail friends around in the calm interior all afternoon. Or we can go out and sail one of the nation’s finest coasts, enjoying it’s consistently great weather. Paradise cove, Malibu is not far for lunch ‘on the hook’. If we have the weekend, I cannot emphasize enough how lucky we are to be half a day’s sail from the supremely cool and quaint island of Catalina. From Avalon to Cat Harbor, there is a place and pace for everyone. For my landlubber friends … I have traveled the world and have realized that we have the most expansive if not among the best beaches anywhere. A futbol field of sand from the strand to the surf. I highly recommend borrowing/renting a strand cruiser bicycle and enjoy some part of the changing scenery from Palos Verdes to Gladstones. Hermosa Beach promenade has a little of everything. I love my towns of Hermosa and Manhattan but Santa Monica and Venice have their eclectic appeal. And restaurants to suit all tastes and budgets along the way.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
There are a few sailing legends that have inspired myself and many others with their passionate pursuit of adventure and new experiences. Some I have only read, others inspire me still.

-Captains Magellan, El Cano, Cook, Drake et al, for the immense scope of their sailing explorations.
-Tristan Jones for documenting his widely varying sailing adventures.
-Bernard Moitessier for passion for the sea and for detailing his out-of-the-box thinking.
-Bob & Jody Bitchin for choosing me to crew and showing me that anyone can jump on a boat and sail the world.
-Tania Aebi, the youngest female to solo circumnavigate in her day. I am grateful for her inspiration and friendship and getting to run amazing sailing vacations with her.

Website: AdventureVoyaging.com
Instagram: @captainwoody
Linkedin: captainwoody
Twitter: @capwoody
Facebook: facebook.com/captainwoody

Image Credits
Octavio Carranza, Heidy Gross

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