What Ray Dalio taught me about Authentic Leadership and Taxidermy

I would not be an entrepreneur specializing in Authentic Leadership if it were not for my experience working for Ray Dalio at Bridgewater Associates. For approximately six months, I supported Ray Dalio (Founder), Bob Prince (Co-CIO), and Ray’s brilliant, philanthropic son Matt Dalio (Founder of The China Care Foundation) as their Executuve & Personal Assistant. Despite its brevity, this previous position has proven time and time again to be a major contributing factor to the person I am and the work I do in the world.

I learned more about self leadership in that six months than most people learn in a lifetime. Seeing the recent article on Ray in The New Yorker, titled Mastering the Machine, I was compelled to write this blog.

Lesson #1: Don’t waste time on formalities.
It all started with the interview. After I had been vetted by the recruiter, Ray’s assistant #1 and the woman whose place I was taking, I was brought back into meet with Ray. I don’t recall much of what was said, but more so that he excused me after what seemed like the longest 10 minutes of my life. I left the conference room and made it back to my car in a complete blur. When I regained my sense of time I realized how short the interview was and chalked it up to ‘good practice for the next one’. The next day the recruiter called to tell me I got the job. I can only hope that what Ray saw in me that led him to choose me, was my authenticity.

Our greatest power is that we know that we don’t know and we are open to being wrong and learning. -Ray Dalio

Lesson #2: Be confident, make friends, and ask questions. Gambling on assumptions leads to chaos.

As Assistant #2 to Ray, I often received my directives via his Assistant #1. She was your typical high-functioning, high-strung, high-energy powerhouse assistant. Once I was adequately trained she started to take days off. With limited access to Ray’s Outlook calendar I did my best to stay on top of his needs while also attending to Bob and Matt as needed. Often times the information I was left with was sparse and/or misleading. This helped me to develop and polish my skill of ‘logistical anticipation’. I created a list of contacts and established strong relationships with them. This included my fellow assistants, Ray’s driver, private chefs, owners of businesses that Ray frequented, and most importantly, Jim Bookman–at the time, the most reliable and trusted IT person at the company.

Lesson #3: Play is inherently linked to productivity. Whenever possible inject humor and fun into your work.

Bridgewater prides itself on being a ‘work hard…play hard’ company. This is more than likely a major contributor to their success. One day in the summer of 2004 employees from the marketing and client service department deciced they were going to coordinate a race, or “scrum” as they called it, through the moat-like stream that surrounded the buildings. When Ray got wind if this he was ‘all-in’. Emails of the scrum went intra-company-viral in minutes, projections and statistics of who would be the winner came next, and then an official email from Ray himself, instructing all willing participants to “suit up” in the gym. There were a few candidates in that day and Ray walked into the offices where they were interviewing dressed in shorts, a T-shirt and his then famous Crocs…he wore them before they were widely popular…I know this because at the time I thought “who besides Ray would be caught dead in those things?” – Clearly, Ray is the Master Trend Spotter! Ray then invited the candidates to participate in the scrum. If I recall, two out of three of them agreed. Footage of the scrum was captured by interns and later turned into a slow-motion video set to Eye of the Tiger. I’ve searched YouTube on numerous occasions to see if anyone has uploaded it…but to no avail.

On another occasion, I was asked to organize a team-building retreat in Vermont, complete with paintball, skeet shooting, hiking and golf. I was asked to come along for the weekend and just assumed it was so that I could manage the catering logistics. To my surprise (and fright) Ray expected me to participate in the team-building activities. Mind you, I was one of two or three women on the trip…who were MUCH more outdoorsy than me. I immediately started looking for a good place to hide out. But then my Irish courage started to surface and I was like, “I can do this!”. In short, I almost busted my clavicle firing the shotgun and was covered in welts from the paintball. I came home from the trip in pain, but with a renewed sense of limitlessness.

Pain + Reflection = Progress – Ray Dalio

Lesson #4: Anything is possible, as long as you believe it has to be.

In the chapter I wrote for the book A Coach’s Story, called ‘The Administrative Duckling’, I shared the following experience. As I remember it, one of Ray’s clients from Japan had visited his home in Vermont and the two of them went hunting. The client shot a very large and unique looking bird. In what I imagine was a gesture of respect for the man and the bird, Ray had the thing stuffed by taxidermy and mounted on an engraved plaque. It was my job to get it shipped to Japan. I’ll never forget. It was a particularly windy day in Westport, CT and I delicately placed the mounted bird in my passenger seat, gingerly wrapping the seat-belt around its midsection without mussing the feathers. Carrying the bird in and out of the post office and several shipping stores became more hilarious each time. People stared. I smiled back. Finally though, when I’d reached the last place in the area that I could try before getting back to the office on time, I wasn’t going to take ‘no’ for an answer. The clerk gave me a look of disbelief when I placed the bird on the counter and I said, “I need to ship this to Japan.” He just laughed at me. I then looked at him sternly and said, “This is no laughing matter. This bird needs to make it to Japan in flawless condition or I will lose my job.” The guy looked back at the bird and then back at me. By then I had used my acting skills and summoned some tears. Finally he agreed to try and crate the bird for shipment. I still don’t know to this day if it made it past customs, but I was satisfied that I had not given up on my task.

I believe that the biggest problem that humanity faces is an ego sensitivity to finding out whether one is right or wrong and identifying what one’s strengths and weaknesses are. – Ray Dalio

Lesson #5: Know yourself, and don’t let anyone else determine your worth, but you.

I often wonder where my career would be if I had stayed at Bridgewater. My reason for leaving was due to an ongoing conflict between myself and Ray’s assistant #1. I have chosen not to share the details of that because it’s in the past, and the lesson I learned as a result was invaluable. The lesson I learned was how to be strong and stand up for myself, regardless. I also learned that walking away from something after trying your best is not the same as giving up. Had I not left CT and moved to NC, I would not be where I am today.

Like Ray, I did poorly in high school and didn’t begin to thrive academically until I discovered my authentic passion. Like Matt, I knew from a very young age that I wanted to have a significant positive impact in the world. It just took me several more years to realize my purpose. Their stories of brilliance, bravery & boldness, for example how Ray built Bridgewater from his living room, continue to keep me inspired and motivated…(as I type this blog from my own living room couch…that I’ve had since college….from IKEA!)

Ray and Matt,….if you happen to see this…from the bottom of my heart, THANK YOU!

Authentically Yours,