Cooper Dressler – Elite Performer Q&A [25]

There are many in the sailing community  we consider the legends of the sport; the ones who have taken our sport to the next level as an athlete and/or coach.  As part of Sailing Performance Training’s continuous mission to inspire, empower, and enable sailing athletes to reach their highest potential, I have started to interview the best, the high performers, the ones who have truly made athleticism a lifestyle, which enhances their performance in the sport.

Inspiration for this type of interview actually came from another podcast I listen to, The Tim Ferriss Show, where he interviews top performers in all domains of life, ranging from business, sport, nutrition, doctors, etc.  If you haven’t listened to his work, check out the link above, well worth the time.

I found Tim Ferriss’s interview questions a perfect solution to dig deeper into the essence of the elite performers in our sailing community.  Hey, why change something that works.

On to the interview with Cooper Dressler….

Cooper Profile Shot
Cooper Dressler – Oracle Team USA

It is awesome to have Cooper be my first elite performer on the Sailing Performance Training Blog. I first met him during a Melges 32 regatta in Miami in 2014 when he was living out of his car and sailing everything he could get his hands on. Right away I got the sense he was going to become something big in our sport. During that time, we were both searching for the best path in our career (sailing vs office job, professional vs Olympic, etc…). Nonetheless, his path took him far, quickly, as he is now a sailor on the Oracle Team USA America’s Cup team, working to defend their America’s Cup Title.

He has a great story, and completely awesome routines, that any young sailors with aspirations in becoming professional, can learn from.

Here is Cooper, enjoy!

I grew up sailing in California. Racing dinghies was my primary sporting activity throughout my youth, however by the end of college I almost abandoned sailing altogether.  Out of the blue, I was called up to join a team for the Redbull Youth America’s Cup in 2013. Training and competing at such a level gave me a renewed outlook; I made it my goal to sail professionally.

I spent the whole year of 2014 living in a car, working odd-jobs, and flying around to race everything from 49ers to 70-ft trimarans. I took a job at Oracle Team USA’s compound in San Francisco as a laborer.  I would help demolish structures, paint floors, pack 40-ft containers, retrieve miles of heavy, 3-phase electrical cabling from underground and in the rafters… I’d drive forklifts, bottom-paint chase boats, weld steel frames – though it was difficult, I was willing to do anything to remain involved.

The big break came when I was offered a full-time position on the shore crew, with relocation to Bermuda for the next America’s Cup. Gradually, my responsibilities became more sailing-related (rigging, chase-boat driving, etc.) and after six months in Bermuda, I was offered to trial with the sailing squad – which came as a huge surprise to me. I was told my work ethic and attitude were the main drivers for receiving such an opportunity. I have since embraced my new role.  It has been very satisfying to work alongside some of the biggest talent in the sport, and as a diverse team unit with one common goal in mind: defend the America’s Cup.

*Video Via Team Oracle USA

Sailing Performance Training Rapid-Fire Q&A:

1. When you think of the word “successful” who’s the first person who comes to mind and why?

Jeremy Jones – adventurer/explorer, big-mountain rider, conservationist, humanitarian, inspirational film-maker, family man… To me, Jeremy is an athlete who embodies what it means to forge one’s passion into an entire lifestyle, make a decent living, and positively influence others along the way.

2. What have you changed your mind about in the last few years? And Why?

I’ve recalculated what I think is necessary versus excessive – choosing to give up certain hobbies and striving to live with fewer material possessions.  I’m also getting a lot better at saying “no,” as you can become weighed-down with too many commitments just as easily as frivolous stuff. In order to maintain focus it’s important to make room for yourself.  Traveling light keeps your options open.

3. What is something you believe that other people think is insane?

I believe in keeping an immaculate kitchen. My roommates have always considered this to be insane.

4. What are your morning rituals? What do the first 60 minutes of you day look like?

I always make a cup of coffee first thing in the morning.  I then try to meditate for 10-20 minutes (with help from an app called Headspace). If it’s a big day of training ahead, I’ll have a small snack before the gym. I always hit the foam roller before warming up.

5. What obsessions do you explore on the evenings or weekends?

If I’m feeling switched-on then you’ll find me surfing, free-diving/spearfishing, cliff-jumping, kite-boarding, sailing my moth, exploring, etc. If the mood is mellow then I’ll be lounging, reading, playing guitar, or staring at a screen.

Cooper Spear Fishing
Cooper and Tom Johnson spear fishing in Bermuda

6. What is the best or most worthwhile investment you’ve made? Could be an investment of money, time, energy, or other resource. How did you decide to make the investment?

When I was 22 I joined a CrossFit gym. I had no formal fitness training before this, and I found regularly working out – especially in a group/competitive environment – really helped to build my self-confidence. I became fit enough to sail very physical boats. It changed my life in a very positive way.

7. How has a failure, or apparent failure, set you up for later success? Or, do you have a favorite failure of yours?

I once bought a boat in hopes of restoring it and sailing down to Central America.  After miscalculating the time and money needed to achieve this, I considered it a massive failure. Although frustrating at the time, that little sailboat connected me to the industry and community in a way I would argue is greatly responsible for where I am now.

8. What advice would you give to your 20-year old self?

I would tell my 20-year old self: “Drop out, go explore, try a few odd jobs, get away from California, climb mountains, sleep outside, take your time.”  I was in college, I thought I had everything figured out, and I couldn’t have been more wrong at the time.  I’ve seen too many people commit to a career before they’re certain, and there is the risk of ending up miserable.

Cooper Down Time

9. Do you have a quote you live your life by or think of often?

“If it is right, it happens. The main thing is not to hurry. Nothing good gets away.” – John Steinbeck

10. What purchase of $100 or less has most positively impacted your life in the last 6 months?

If you’re a sailor, you can never go wrong with a waterproof iPhone case.


Big thanks to Cooper for allowing us to see his life from a deeper perspective.  Be sure to follow him as he works to defend the America’s Cup title via Instagram and Facebook.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s