Living Legends: Ten Questions with John Kretschmer

We actually have a little bit of history with famed sailor and author, John Kretschmer... When we were first getting ready to sail from Chicago back in 2010, a friend of ours told us that a client's brother was a famous sailor, that he'd be speaking at Strictly Sail, and that we should meet him. Scott and I, total greenhorns and eager to soak up any knowledge from anyone who'd 'walked the walk', went to his seminar and met him afterwards. He was easygoing, unassuming, and kind. Totally relaxed despite the fact that he'd just come off an ocean passage and was now on his feet all day doing seminars and entertaining questions from (possibly annoying) newbs like Scott and I. Yep, it was instantly apparent that John Kretschmer was not only a class-act and a super nice guy, but the real deal. Afterwards, we devoured a few of his books, and loosely kept in touch via email over the years.

Fast forward to 2015 at Nanny Cay, Tortola. Scott, never forgetting a face, had seen John at the bar and struck up a conversation. He learned his was there on one of his sail training passages and invited Scott and I aboard his boat, Quetzal, the following day. Despite being a tad on the shy and easily intimidated side, the next morning I approached him and said, "Hey John, not sure if you remember me but..." and with a friendly smile he replied, "Windtraveler! Sure, Brittany! We have a lot of passengers who love your blog, you're inspiring a lot of people... Come on aboard." He's the kind of guy who is devoid of ego and will make your day with a passing compliment like that. We chatted with him and his crew in the cockpit and got the grand tour of his beautiful boat. "What seminar is this you're doing?" I asked him. "Heavy weather training," he replied, as casually as if he were selecting a dish soap. This man is one with the ocean and if he smiles at you just so, he even looks a little like the real-life Popeye.

Here's our interview:

#1. How did you know that sailing was going to be more than just a hobby, but a way of life for you? 

My father died when I was 16 and that had a profound impact on me, and my decision to make sailing my life.  I already leaned toward the existential idea that life was what you made of it, your choice to live an interesting life was yours alone to make, and take responsibility for, but it always backed up to idea of time, time was the x factor, there wasn’t time to mess around because life might be snatched away at any time.  I wrote in Flirting (With Mermaids) that my dad’s death drove me to sea, and in a circuitous way that was true. Also, I loved the freedom ocean sailing seemed to present on one hand, and the raw challenge on the other. I never wanted it to be easy.

#2. You sail predominately long distances - ocean deliveries and training passages - this is obviously very different from the traditional “cruising” (i.e island hopping) that many people dream of - why do you love it?

I guess I touched on this a bit in the first answer but crossing oceans presented the sense of adventure I was looking for.  I had been an athlete, a pretty good pole-vaulter alas, and while I never viewed ocean sailing in a competitive way I really responded to the idea of personal challenge.  I grew to love passage making when I learned that there is no “personal challenge,” at sea, that notion is actually absurd. The sea is dispassionate, storms are not personal, small boat seamanship is a matter of figuring out how to fit into the ocean environment. There’s no room for chest pumping at sea.  

Image courtesy of the John Kretschmer sailing Facebook Page

#3. You’ve sailed with a lot of different people and personalities - is there one glaring character trait that you think does not jive well with the sea?

Hubris, and a lack of respect for the sea, not good traits at all for it is (pathetically to paraphrase my own book,) a serious ocean out there.  But it is also a beautiful environment out there too, and you don’t need to be afraid and drape yourself in the latest safety gear.  The safety scolds are rather sad folks and I am sure you have run up against them for taking, Neptune forbid, your young children to sea. Screw them. Also, a lack of irony is not a good trait, you need to be able to laugh at the vagaries of the sea.  

#4. Sailing on other people's boats can be risky business, you are - in many ways - putting your life in someone else’s hands (by trusting their boat) what’s your “ritual” before you take off on another boat? Have you ever turned a delivery down due to the boat’s condition?

It usually depended on how much I needed the money, referring to deliveries.  I have delivered some sad vessels in my day. I am pretty good about sussing out a boat quickly, I have come to know what is important and what isn’t.  Things I check are the through hulls, not just where they are and if they work but more importantly if they will be prone to back siphoning underway. I check the rig, a quick check is to see if the turnbuckles have ever been adjusted, tells you a lot.  The sails are often in amazingly poor conditions, especially on boats that have not been used in a long time, sitting in the tropical heat deteriorating.  The engine is also essential, and I probably spend more time making sure it’s ready to run and collecting spares than I do on anything else.  

Image courtesy of the John Kretschmer sailing Facebook Page

#5. What are three things you would not go offshore without?

Charts, my sextant, and a basic toolkit.  Sounds crazy, but everything else can fail but I can always find my way. I am big on notion of finding my way. I’ve logged a ridiculous amount of miles, and I love GPS and all the accouterments there of, really I do, but many of those miles were done pre GPS and they were, in a weird way, more satisfying.  I don’t like the idea of being lost, just being hard to find.

#6. You are the author of several fantastic books and you are clearly a gifted writer. When did you discover this talent and would you say your passion for writing is greater than your passion for sailing, or visa versa - and/or do they share a symbiotic relationship in you?

You know that these days I conduct offshore training passages, and funnily enough my old high school English teacher signed aboard a few years ago. He amused the crew, telling them that he thought there was a remote chance I might make the Olympics as pole-vaulter but would never have believed that I’d write a book!  Actually books have been my friends forever, longer than boats.  Peter Freuchen, the great Arctic explorer and voyage wrote the he “discovered the ocean in his imagination.” I did too, in books.  I wanted to be an explorer and when I realized that explorers had a hard time finding work in the late 20^th century, I decided I wanted to be a sailor and write about my adventures, and I made this decision when was 13 or 14.  Thanks for the kind words about my books,  I still feel exposed when I write, if it’s not emotionally honest it’s no good, that’s my motto I guess. 

#7. As someone who’s husband worked term charters for a while (being away at sea for weeks at a time), I imagine that your roving lifestyle can be difficult on your wife. How do you two make it work?

This has been a very difficult thing for me to balance.  My wife Tadji is incredibly understanding, independent and super capable on her own, but still it is hard for us to be away from each other for long stretches. In some ways I have two worlds, home and at sea, and keeping them both going is not easy.   The ability to leave my boat all over the world has been quite liberating.  Indeed, Quetzal is in St. John’s Newfoundland and I am in Ft. Lauderdale now, and I’ll head back in a couple of weeks, pressing on for Nova Scotia, and then later in October for the Caribbean  Also, now that 3 of 4 kids are either on their own or in college, and the last is a senior in high school, we are able to spend more time together.  (Sorry to make you envious!  Not really, these years with your kids aboard are to be  treasured. My girls still tell sea stories.) Tadji and I have a plan to be on the boat together most of the time in the future, with Tadji accompanying me on some training passages, and leaving me to do my thing on others.  But we will definitely be in more of a cruising mode between passages than I’ve ever been before and I am really looking forward to it.

Image courtesy of the John Kretschmer sailing Facebook Page

#8.What is something that people might find surprising about you?

That I am really easy going on the boat, that I am not all a stickler for rules and rote learning, that I am flat out ok when folks make mistakes.  That’s probably not right, people already know that. Hmm what else, that I love the Miami Heat and that I know more about books than boats. 

#9. You’ve had countless adventures at sea - what is your mantra when the shit hits the fan?

To be active, not to assume that the weather will suddenly improve or the problem will somehow fix itself.  I have well-honed instincts, mostly because I have made a hash of things so many times that I’ve finally learned to listen to my hunches. If I feel a hint of being over canvassed, I reef.  If I suspect conditions are going to deteriorate I prepare.  I almost never go into bunker mode, I believe that storms require action, clear thinking, collaboration when possible, and engagement as conditions change.  

#10. What is one thing you haven’t done yet, but wish you could?

Hmm, can I have two? Although I have sailed a lot of miles, I’d like to do a trade wind circumnavigation with my wife and occasional friends/crew.  And, I’d like to write a good novel.

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Thank you, John, for that insightful and thoughtful interview! Can't wait to catch up in person again soon!

Want more John? Check out his website and Facebook Page, and be sure to check out some of his incredible books:

Flirting with Mermaids: The Unpredictable Life of a Sailboat Delivery Skipper - this was the first one Scott and I read, it's a great collection of tales from John's life at sea full of adventure, romance and wry humor. A good laugh and an enjoyable read for anyone cruising, or dreaming of sailing off into the sunset.

At the Mercy of the Sea: The True Story of Three Sailors in a Caribbean Hurricane - this book is insane. It's the true story of three Caribbean-based sailors (one who was a personal friend of John's) who got caught in they eye of Hurricane Lenny in 1999.  John tells this story with incredible accuracy, precision and care, and brings you right there into the storm with them. It's harrowing and tragic, but a fantastic - and important - read for any boater. I loved this book.

Sailing a Serious Ocean: Sailboats, Storms, Stories and Lessons Learned from 30 Years at Sea - this is one we have not read, but it's on my Kindle! "Tales of storm encounters and other examples of extreme seamanship will help you prepare for your journey and give you confidence to handle any situation―even heavy weather. Through his personal stories, John will guide you through the whole process of choosing the right boat, outfitting with the right gear, planning your route, navigating the ocean, and understanding the nuances of life at sea."

Cape Horn to Starboard - "Legendary account of the author's voyage around Cape Horn in a 32-foot sailboat, sailing east-to-west (thus the Horn is to starboard, or on the right). This is a notoriously difficult and dangerous passage, especially in a boat this size." - Amazon

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Enjoy this series? Check out my other interviews with awesome sailing people:

Living Legends: Ten Questions with Cap'n Fatty Goodlander
Living Legends: Ten Questions with John and Amanda Neal
Living Legends: Ten Questions with Former US Sailing President Gary Jobson
Awesome Sailing People: The Delos Crew
Awesome Sailing People: Katie and Jessie on a Boat
Awesome Sailing People: Ten Questions for Distant Shores
Awesome Sailing People: Q & A with Solor Sailor Emily Richmond

Living Legends: 10 Questions for Former US Sailing President Gary Jobson

There are few things more impressive to me than humility. In the rockstar world of top-level sailboat racing, it's easy to get caught up in the dangerous habit of self importance. So when Scott and I were strolling around Strictly Sail and one of our friends (who also happens to be a professional racer and sailmaker) called us over to his booth and introduced us to the man pictured above, it was easy to mistake him for your run of the mill sailing enthusiast. A nice guy who was just enjoying talking to friends at a sailboat show.

But he is so much more.

Most cruising sailors probably don't know who this is - but anyone who loves the sport of sailboat racing does. This is Gary Jobson, the former president of US Sailing, the voice of sailboat racing for ESPN, editor at large for both Cruising World and Sailing World Magazines, accomplished author, public speaker and, quite possibly, the biggest advocate for sailing out there today. He was Ted Turners tactician for the victorious 1977 America's cup, has raced the Fastnet, and taken all sorts of titles in various sailboat races around the world. He has been inducted into the America's Cup hall of fame and even has a couple Emmy's on his mantel for his work in television production. As if that is not enough, he also happens to be a cancer survivor and the creator of the Leukemia Cup.  The man is unstoppable.

So, yeah, he's kind of a big deal. But meeting him you would NEVER know it which makes him even more awesome in my book.  He's your every day, super exceptional, guy next door.

We got to chat with him casually for a while at the show and, despite being tremendously busy with speaking engagements and writing his umpteenth book, he graciously agreed to a short online interview for our site. Here it is:

1) Your illustrious sailing career spans generations and you are, quite possibly, the most decorated and celebrated American sailor of this day and age. How did you get bitten by the sailing bug? Did you always have big sailing dreams and aspirations from a young age?

I first started sailing at the age of 6 in Toms River, NJ. For me it was just a summer activity until I turned 12. That was the defining time. I started sailing 12 months a year. I kept track of all my races. When I was 17, I became a sailing instructor. I’ve been promoting sailing ever since.

2) What is your greatest "take away" from sailing as a lifestyle and sport?

The great thing about sailing is you get to do it your entire life. The great rewards are all the places you visit and the people you get to know. Thanks to racing with highly accomplished people like Ted Turner, Walter Cronkite, Herbert Von Karajan and Sam Merrick, I’ve learned many life lessons that have been beneficial in my sailing career, business career and my family life.

3) You have had a tremendous amount of success in this sport and many opportunities have come your way; from racing with Ted Turner on Courageous for the 1977 America's Cup to winning an Emmy for your coverage of the 1988 Olympics... from becoming the "voice" of sailing with ESPN to getting inducted into the sailing hall of fame...the list goes on. Were you always ambitious about pursing these things (i.e. it has been said you have an entrepreneurial spirit), or did you sort of fall into one thing after another?

Today, looking back on my long career, I have to smile because one opportunity seemed to lead to the next opportunity but I did set goals and worked to achieve them.

4) Speaking of accomplishments - you are also a cancer survivor. What was the overwhelming driving force that lead you to fight and, once again, emerge victorious in the most significant "battle" in your life? Has surviving cancer changed your outlook on sailing and racing at all?

10 years have gone by since my cancer disappeared. It’s hard to believe I actually went through two years of treatment. At the time, I felt I had far more things to accomplish in life and did not want to give up. There are many ups and downs when you go through aggressive treatments but the most important message I can give to people is to keep fighting.

5) Of all the things you have done and accomplished - and the list is LONG - what are you most proud of?

My wife of 40 years, Janice, and I have three grown daughters all with Master degrees, each with a husband and two with their own children. Very cool!

6) To become as famous and successful as you have in this industry is not easy, was there a single moment in your career when you had to "pinch" yourself and thought "I have arrived!"? 

I think an important moment was being with Ted Turner on Courageous winning the America’s Cup. I realized that I would have many opportunities to pursue.

7) You are both a racing sailor and a cruising sailor - two VERY different things. Which do you prefer? Or does each fill it's own niche in your life?

Fundamentally I’m a racing sailing and I enjoyed racing at all levels. I didn’t start cruising until I was in my 40s. The interesting thing about cruising is that I still enjoy lots of hours sailing on the way to new destinations.

8) If you didn't have a career in sailing, what would you be doing?

Interesting question. I’m sure I would have been involved in some form of sports. I enjoy producing television programs and films because you start from scratch and try to make a topic interesting to viewers. Having said that, I really enjoy speaking to groups to try and get people interested in sailing. It’s very rewarding.

9) You have touched SO many lives and inspired SO many people, sailors and landlubbers alike. What inspires you?

Many people are passionate about sailing. Really it is the icing on the cake of life. I hope I have helped people to understand and appreciate the sport. I find it immensely gratifying when people say thank you. It inspires me to continue.

10) You are the father of three girls, two of whom are a set of twins - what one piece of advice can you give to Scott about becoming completely and hopelessly outnumbered by women?

The funny thing is we now have three son-in-laws and two grandsons so the ratio has gone from 4 to 1 to 6 to 4 in favor of the males.

Thank you Gary for your time, contributions to our sport and for your inspiration and kindness!! The world needs more folks like you!

For more Gary Jobson, check out his website and these books and DVD's:

• Gary Jobson: An American Sailing Story
• Sailing Fundamentals by Gary Jobson
• Gary Jobson's Championship Sailing : The Definitive Guide for Skippers, Tacticians, and Crew
• Racing To Win with Gary Jobson
• Championship Tactics: How Anyone Can Sail Faster, Smarter, and Win Races
• Bennett DVD - Racing To Win with Gary Jobson

Living Legends: Ten Questions for Cap'n Fatty Goodlander

If you are a sailor and are not familiar with the name "Cap'n Fatty Goodlander," then you have clearly not picked up a single cruising/sailing/boating publication in the past twenty years.  Aside from being a stellar shoestring circumnavigator who has lived almost exclusively on boats since childhood, he might just be the most prolific sailing writer the world has ever seen with a slew of excellent books and hundreds upon hundreds (maybe thousands?) of articles in his wake.

While I have never met him personally, we share roots in Chicago and a background in theater, and I have read and enjoyed many of his touching/funny/witty stories.  He is humble, funny, kind and clearly loves the heck out of life (and his beautiful wife, Carolyn).  His smile is genuine.  His stories are colorful and entertaining.  His travels impressive.  It is truly my honor to share with you our online interview so that you can get to know this incredible man, this living cruising legend (and one of my idols), a little bit better.  I hope you find it as inspiring and enjoyable as I did!

1) First things first - how'd you get the name "Fatty"?

I was an actor as a teenager, and the guys on the corner in Chicago used to joke that 'I was FAT,' as in lucky. (If you rob a bank and don't get caught, you are even Fat City! ) This isn't new... Think of the Fat Buddha that the starving Chinese adored. But at 15 I purchased my own sailboat, Corina, and the guys were blown away. "He's Capt Fat now!" said one as I walked by. This rapidly turned into Cap'n Fatty, which everyone calls me - wife, mother, and child included. For years, I wrote for SAIL mag under my real name of Gary. But I wanted to write some funnier, truer, grittier stuff, and used Cap'n Fatty. Honesty always resonates with the reader. At SAIL, I started out pretending to be something I am not. I learned an important lesson. You can be okay pretending, but only great being honest.

2)  You are a living legend and an inspiration to so many boaters all over the world.  How does this pseudo celebrity status make you feel?   

Mostly great! I'm honored to earn my living with my pen. The readers are the people that ultimately sign my paycheck. I am grateful. And I feel each of the fans I meet deserve a moment of civility. I try to make each one feel special for a moment or two. 

3)  Born to "penniless sea gypsies" you say you were "blessed" to have grown up almost exclusively on sailboats.  Did you always feel this way or was there a time you felt like you were missing out on land life and longed for normalcy?  Or were you always aware that your lifestyle was a gift? 

I was born an outsider. We were misfits. We were broke. My father wore a skirt (pareo). We bowed to no god. The dreaded do-gooders even got court orders a few times to take me away from my loving family... It was a GREAT way to grow up. 

The only thing better than being a boat kid was raising [daughter] Roma Orion aboard! (Yes, we've already sailed many a mile with Sokù Orion, our wonderful granddaughter.)

4)  If you had to pick one place you've been to stop cruising and settle down, where would that be and why?  

If I had to settle in an English-speaking place, that would be New Zealand. Luckily, I don't! When our health fails, we will retire to SE Asia. Or St. John, USVI, the nicest place under the American flag.

5)  You are a prolific writer (at one point sold over 200 articles a year for 10 years!) and seem to have articles in a sailing publication (sometimes more than one) every single month.  How much time do you spend writing and how do you maintain a work/life balance?  Does Carolyn ever begrudge all the time you spend in front of a computer?  

No, Carolyn never does, as she likes to eat as much as I do. Basically, I write four hours a day, from 8 to 12, minimum... and have done so for over 30 years. Each day, I am VERY excited to get to work. I do not really care about educating my readers; I want to emotionally touch them, make 'em laugh or cry. I believe I have written between 18 to 50 good pages in my life. I hope to write a few more before I die. 

6)  Speaking of Carolyn, behind every great man is a great woman and it is no secret how much you love and adore each other.  You met and fell in love so young and seem to have a charmed relationship, what is the secret to your obvious happiness?  

I do not know. She is very passionate, very smart, and very hardworking. We occasionally argue, etc, but we have always been there for each other since the age of 16. I can be a selfish little prick at times and we've been dead-broke for years at a stretch... chalking it all up to penis size seems simplistic. (Poor Carolyn has a permanent dent on her forehead from slapping herself and moaning, "I can't believe you said that!")

7)  Full-time live aboard cruising can be very challenging, and you are no stranger to the sometimes frustrating combination of project boat and low funds.  How, after over 50 years of living aboard, do you keep it fresh and not get "burned out?"  

I really like to sail, and Carolyn really likes to travel. We sail really hard for a couple of years (last year we sailed 10,000 miles and repowered) and then 'chill' with some coastal gunkholing for awhile. My boat is my everything: job, sport, love, passion, home, office, profession... I am still very turned on to living aboard, and feel that after 54 years... I am starting to get the hang of it! 

8) You've owned a bunch of boats and sailed a lot of miles on all of them.  When outfitting a boat for a voyage what are your top five pieces of equipment that you wouldn't head offshore without (aside from obvious things like sails, water and, of course, Carolyn)?  

I have a well deserved reputation for being cheap—but it is really VALUE which I seek, not price. The piece of gear I love most is my Monitor windvane. It is just about the only 'must have' piece of metal aboard. The AIS is a wonderful advance. I believe in Max props. Harken makes a wonderful roller furler. I prefer a tiller. Solar cells sure are swell. I grew up on a wooden boat with cotton sails and hemp anchor rodes and a sextant and a coal shuttle and kerosene running lights... so, yeah, I have seen a lot of changes. 

9)  I have a feeling you are not a 'regret' guy, but what is the biggest mistake you have ever made at sea or while cruising?  

I dunno. I've swam away from two vessels, so you'd think I'd have some! But most of my major mistakes are shoreside. (Pauses. Thinks) Mostly, I regret not doing stuff.  Sitting on your butt is boring. Fortune favors the brave.

10)  Are you shocked by how your life has turned out, or has the Universe conspired exactly how you thought it would?  Are you ever surprised or impressed by all your accomplishments?  

I'm happy. My boat is my magic carpet, my freedom machine. So I knew I'd sail. But I only went to school for five years.... 3 grammar, 2 high... and thus was worried I could not be writer. Luckily, I rapidly learned that good writing has little to do with intelligence and almost nothing to do [with] modern education. It's just transparency of personality on the printed page, that's all. It just takes a little grit. And I've got plenty of that. 

Want more FAT?  

First, Check out Cap'n Fatty's Facebook Page and Website and then buy his books, they are sure to give you a good laugh, a healthy dose of gypsy-tinged inspiration and maybe even tug at your heartstrings a little.  He is an expert story teller and his passion for life and living it to the fullest is infectious...

Books by Fatty:

• Chasing The Horizon: The Life And Times Of A Modern Sea Gypsy
• Buy, Outfit, Sail: How To Inexpensively and Safely Buy, Outfit, and Sail a Small Vessel Around the World
• Collected Fat
• Red Sea Run: Two Sailors in a Sea of Trouble
• Cruising World Yarns
• All At Sea Yarns: The All At Sea Stories
• Somali Pirates and Cruising Sailors
• Seadogs, Clowns, and Gypsies