Sailing teaches us to lead, follow, or get out of the way. Dawn Riley, Executive Director of Oakcliff Sailing is the first woman to win an America’s Cup. She led two Whitbread Round the World races, was the US Rolex Yachtswoman of the Year and the former President of the Women’s Sports Foundation.
To sit down with Dawn, Fran Racioppi docked in Oyster Bay alongside Maiden, the boat Dawn sailed around the world to talk leadership, Title IX, the evolution of the sport, winning the Cup, leading an all women’s team around the world and what it will take to put US Sailing back on top.
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About Dawn Riley
As CEO and captain of America True, Dawn Riley was the first woman to manage an America’s Cup sailing team. She has raced on four America’s Cup and two Whitbread (now The Ocean Race) teams. She is the former president of the Woman’s Sports Foundation, served on the board of US Sailing, and is an advisor to several public service organizations.
- 2004-2007, General Manager K-Challenge America’s Cup 2007
- 2002, IC45 world champion
- 2000, America True CEO and captain, America’s Cup
- 1999, Winner again, Santa Maria Cup
- 1995, Team captain of America3, the women’s team in the America’s Cup
- 1993/1994, Skipper of Heineken, the only all-women’s entry in the 1993-94 Whitbread round-the-world race
- 1992, Pitperson for America3, winner of 1992 America’s Cup and first woman to have an active role on an America’s Cup team
- 1992, 1st place in Women’s Cup in Portofino, Italy
- 1992, Winner, Santa Maria Cup
- 1989/1990, Watch captain/engineer on Maiden, the first all-women’s team in the 1989-90 Whitbread race
Taking The Helm – Oakcliff Sailing Executive Director Dawn Riley
Sailing teaches us how to lead, follow, or get out of the way. There are times for discussion and to do exactly what you’re told, the way you’re told to do it, and when you’re told to do it. Sailing teaches us how to compete and win as individuals and how to be effective members of any team. My guest in this episode is Dawn Riley, one of the greatest competitors in professional sailing and a pioneer in the integration of women into the sport.
Dawn Is the first woman to win an America’s Cup, the pinnacle achievement for professional sailing. She was later the team captain of America3, the first all-women’s America’s Cup team. Dawn was the first American man or woman to sail in three America’s Cups in two Whitbread Round the World Races. She was the US Rolex Yachtswoman of the Year and the former President of the Women’s Sports Foundation.
To sit down with Dawn, I crossed Long Island Sound on a dead flat day. I docked my boat in Oyster Bay, New York, right alongside Maiden, the boat Dawn sailed around the world. Dawn and I talked about leadership and what sailing teaches us about building great individuals and teams. We spoke about Title IX, women in sailing, the evolution of the sport, and what it was like to win the America’s Cup as the only female. Finally, we talked about what it was like to answer the call, take the helm, and lead an all-women’s team around the world and the ocean race.
Dawn’s a no-nonsense inspirational leader who will stop at nothing across the finish line first. She’s the Executive Director of Oakcliff Sailing. Her mission is to build American leaders through sailing, put US Sailing back on the medal stand, and return the cup home to America. Dawn and I tour Oakcliff Sailing and I see firsthand what it’s like to live aboard an ocean racer.
Learn more at JedburghPodcast.com. Follow us on all social media @JedburghPodcast, and don’t miss our full video versions of all our conversations on YouTube. Find out more about Dawn at DawnRiley.com, OakcliffSailing.org, and @OakCliffSailing on social media. Check out her book, Taking the Helm, to hear more about her story.
Dawn, welcome to the show.
Thanks for having me.
I am so honored that you would take the time to sit down with me. You and a lot of the readers who tune in to our show know boats are a big part of my life. I grew up sailing. The first pictures that I have with my dad and my family are of me on our 37-foot endeavor. I don’t even think they make those anymore, but that was a bathtub with a sail.
It’s been a huge part of my life to have my own children and bring them up on boats. My son turned two. Every weekend, he’s like, “I’m driving.” I’m like, “You’re not driving yet.” My daughter and I went to Newport. It was awesome because she was driving. She’s twelve. It was the first time that I was confident. I was like, “This kid knows what’s going on.”
Your impact on sailing and on boating is profound, and not only in terms of what you’ve done for our generation but the younger generation that’s up and coming. A few things that stand out, and I know I won’t hit them all, but you’re the first woman ever to manage an entire America’s Cup syndicate, team captain of America3, the all-women’s team entry into America’s Cup, pit person on the ‘92 America’s Cup winning team, and the first American man or woman to sail three America’s Cup and two Whitbread Round the World Races. You’ve won it at every level. You’re a multiple-time world champion, US Rolex Yachtswoman of the Year, and Board Member and President of the Women’s Sports Foundation, which I want to ask you about too.
You serve as the Executive Director of Oakcliff Sailing where you are building America’s leaders through sailing. This is a dream to sit here with you. I know we’ve met and have been talking on and off for several years. You invited me here to speak to one of the development camps in 2017. It was truly an honor for me, but now, it’s my turn.
I’m glad you’re here. Oakcliff has grown in the past couple of years to something that’s unlike anywhere else in the world with athletes coming through the doors and experiencing all different levels of the sport of sailing. That history that you read off was the background and the building blocks so that I could create Oakcliff. I did it accidentally, which is the best way.
That’s an interesting point. I was going to go to Oakcliff later, but let’s go there now because it’s important to set the scene. In 2010, Hunt Lawrence came up with this vision for Oakcliff that there was something wrong. There was a challenge. I say this all the time. The greatest inventions or the greatest things that are made by mankind solve a problem. The problem that they saw was a problem in the US Sailing, and you were one of their first calls. They wanted to bring you in and figure out what problem you see and how you will solve it. Can you talk about that call you got from them, what their idea was, and what you thought you could bring to the world at sailing?
Their idea was we have too many boats and we’re not sure what to do with them. At that point, they had 36. Now we have 100, so I’m not positive that I’ve solved that problem. What was happening was they were being very supportive of a lot of people with quite a few boats, but they didn’t have a mission, direction, or organization. I came in as a business consultant with a background in sailing. I did a SWOT analysis of what was happening in the United States from the amateur level to the pro level and came up with a few business plan options, and they chose this one.
I was going to go continue my merry way sailing super yachts in fun places like Saint-Tropez. They said, “You have to come and run this.” I’ve been here since 2010. We’re building American leaders through sailing,
and until we came up with that alliteration of what it is that we’re doing, we were a little bit jumbled up. We have high-performance, offshore, match racing, the business side, the motivational side, special events, and a bunk house. We’ve added a high school, but the thing that ties it together is we’re trying to build good humans going forward. If they become professional sailors and do America’s Cup, that’s great. If they never sail another day because they’ve explored it and decided, “That’s not for me,” that’s great too.
The number one Special Operations Force truth principle or core value is people are more important than hardware. I talk about these five components of a performance mindset, and at the center is character because people matter more than anything else. We’ve built this entire show on talking about the importance of people and what leadership does to organizations. We can build the greatest boat.
If you sail it like crap because you’re not a team and everybody’s working in their own little area, you’re going to lose.
Talk to me about the development camp side of Oakcliff. We went through your background. We’re going to circle back and talk a little bit about some of the leadership lessons you learned in various roles that you held. As you look to develop what you’ve called Acorns, Saplings, and Mighty Oaks, and you can define those for me too, tell me what sailing teaches you about leadership.
The progression is because we’re Oakcliff Sailing, which meant nothing. It was just a word like Nike doesn’t mean shoes. It does now. Oakcliff is on land and on the sea. It’s a cliff near the sea. Somebody said, “What are you going to call the trainees?” Somebody said, “Acorns.” It was a joke. I’m like, “We can do that. Acorns progress. They stay longer. In more than a few weeks, they become saplings. When they graduate, they go on and be mighty oaks.” What we’re seeing is a lot of the young people that come in, especially in the Acorn program, are still very fresh. They’re 15, 16, or 17. They’re very individual. They’ve been hatched. They think they’ve invented and discovered the world. They’re these little ripe pods. They are awesome, wonderful, and curious, but we have to help lead them to make some smarter decisions than they may make if left to their own devices.
In terms of putting them on a boat where they are in charge, we have a team doing the Mackinac race where the skipper and the coach were high school students here in 2021. He was part of Oakcliff High School. He has a Farr 400 and they’re going to do the Mackinac races. I might pop in and check on them, but he’s learning the lessons the hard way. I’m like, “If I told you to do this, you do it. If you come back and I have to save your butt, I will do that, but you’re going to hear about it.” There’s a little bit of fear as well.
There’s a part of boating that is a little bit like flying. It’s one of those great sports that teaches you how to be in charge, how to lead, how to follow, and when sometimes you need to shut up and get out of the way. Talk about that in terms of why that’s so important and how sailing reinforces that. I’ll put it in context, too, for readers. I was with my daughter. We were coming in to anchor the boat to go swimming. I said, “Take the helm. I’m going to drop the anchor.” We go put it in neutral. I got up and I said, “Do a one-click reverse.” She’s like, “Why? I don’t get it.”
Meanwhile, we’re drifting and I’m looking at the boats behind. I’m like, “Do it.” My wife’s yelling at her. Why are these things so important and reinforcing to teach young people or all of us about when you need to be in charge or follow everybody, do what you’re told, and when you need to understand that you don’t know what you’re doing and you have to get out of the way.
Using the mechanics of sailing in making a boat go fast, you’re in the zone and working. Everything is fine. There are all these micro communication loops and the helmsmen who are talking to the trimmers. The trimmers are telling them what they feel. The main sail trimmers are telling you what you’re boat speed is. The helmsperson is saying, “I’m going to go down a little bit. That site feels good.” You have that communication loop.Sailboat racing is one of those great sports that teaches you how to be in charge, lead, follow, and sometimes you need to shut up and get out of the way. Click To Tweet
The front of the boat is going, “We’re getting closer to the mark. We’re going to have to get a spinnaker. We better make sure the back of the boat is off there and fantasy land is understanding what’s going on.” We’re going to be ahead of it so when they say to get the 8-2, we’re like, “We’ve already got the 8-2. We know exactly where it is so we can get on there.” The way back of the boat is looking long-term, trying to figure out what the next wind shift is. They’re like, “Is that a storm on the horizon?” That’s the smooth communication loop and everything is going along.
When the shit hits the fan, you need to have one-way communication. We’ll say, “Pretend that there’s a ship and we have to tack.” The helmsperson went to tacking and everybody needed to react. The only way that you can get back is if it’s an emergency, which would be saying, “Override. Cannot tack. Need a knife.” That’s the time you cut the sheets, but that has to happen. The word why is not during a race. It doesn’t happen. I wanted to go to the Naval Academy and then my band instructor in high school was an ex-Marine Drill Sergeant. I came home one day and told my mom, “I don’t think I want to go to the Military Academy because I like the word why way too much.”
That is another great place where that teaches you you don’t need to ask a whole lot of questions sometimes.
You do need to have the opportunity to come back with critical, quick information or you’re going to run into a tanker. Most of the time, it’s not that dramatic because we’re going to lose half a boat length on a tack. We use that pressure in that critical life and death adrenaline to do a simple thing like win a sailboat race. To us, it feels like that. That’s where you have lessons because you race over and over, so you’re learning that. There’s no, “I didn’t like your tone of voice.”
That’s what my daughter got into when she started crying after my wife yelled at her. You just need to sometimes do what you’re told to.
I was the only woman on the men’s team, and I had sailed most of my life until Maiden the first Round the World with all-women. I sailed almost always with men, maybe a couple of women, occasionally. All of a sudden, in 1995, I’m the team captain of the women’s team. The debriefs were completely different. Not to mention that we had people that were rowers and bodybuilders, and then people that only sailed dinghies by themselves. They have never been part of a team. Maybe they didn’t do a lot of other team sports. Title IX was way back in the ‘70s, but it’s still progressing.
We were having debriefs and people were crying. I’m like, “Are you kidding me?” I went to our video editor. We had a professional video guy that would cut the training videos, which was amazing. I had him edit that part of Tom Hanks in A League Of Their Own. He put it in six times, and then everybody started laughing and we got over the crying.
That’s what I’m telling my daughter. I told her last time like, “I’m going to video you and I’m going to show you exactly what you look like so that you understand what I’m looking at.”
Show her the movie A League Of Their Own first.
That’s a good idea. Let’s talk about America3. Let’s talk about ‘92 and ‘95. You were on the men’s team in the ‘92 Cup. The boat won the Cup. Talk to me about what it was like to be the only woman in a male-dominated sport.
I always had been, so for me, it was normal to start with. The only thing that was super upsetting in a weird way was that I was tired of wearing men’s clothing. It all came to a head because it doesn’t fit as well. It’s not a vanity thing, but the vanity got in when we had America’s Cup Ball, and we were sponsored by Ralph Lauren. They gave me the khaki pants, blue blazer, and white button-down to wear to America’s Cup Ball where all of my friends that were female would be in ballgowns. I went to the marketing people and I’m like, “I’m so disappointed.” To them, they’re like, “Let’s call Ralph up. We’ll get you something.”
I didn’t get a gown, but I got these cool palazzo pants and a women’s blue blazer. They also fit me at the La Jolla store. I was like, “I got a little bit of girl going on.” It’s those weird things you don’t expect, but being on the boat and part of the team, you’re a team member. I’m sure it’s much like the military. When you’re in the field and in the fight or the battle, taking the spinnaker down or something more life and death, you’re happy to have another competent person next to you. You don’t notice that it’s male or female. You’re just like, “Let’s get this shit done.”
What did they see in you?
I don’t know. In hindsight, you have a little more time to think about it. I’m being inducted to the Hall of Fame and all sorts of crazy stuff, which I’m way too young for. They told me I was too young and then somebody said I wasn’t. I would hit the sweet spot between being competent, determined, not phased by a bunch of BS, able to give as good as I took, and I love the sport of sailing. Some of that had to come through.
America’s Cup is the purest, especially back then. It’s changed now with technology. Technology was important then, but you still had a lot of sailors and human interaction. Now, it’s much more human to the computer, hydraulics, and electronics. It’s more like flight than pushing buttons. There’s probably more mental forethought for split-second decisions, more like a fighter pilot than a ship’s captain. The purity of being able to say, “We want to change a bulb. What happens if we do this? How does the wind or the sea flow over this foil?” It is so cool.
You have referred to yourself as a female obsessed with sailing in the ‘70s. You grew up on the one hand with people telling you that you couldn’t do it. On the other hand, you had people saying that you could do it. You did mention Title IX.
What did they do the day after Title IX? I was furious. I couldn’t even post on Facebook celebrating Title IX because I was so horrified.
A lot of people were very upset about the correlation there.When you don't know what you're doing, you have to get out of the way. Click To Tweet
We need to fix that.
These are two contrary perspectives. You’d been sailing since you were thirteen. Why did you get involved with the sport in the first place?
It was pretty simple. I have sailed since I was born. My dad yelled at me. I don’t remember crying, but I’m sure I did. When we were bored, he would make us do a spinnaker change or jive a wooden spinnaker pole. When I was thirteen, we sailed from The Great Lakes out to the Barge Canal, Hudson River, to New York up to Maine, down to Florida, the Bahamas, the Virgins, Grenada, and back. We had a lot of experience, and I was the oldest. When he would go racing, before that, mom would say, “Can you please take one of the children?” I was the one that got to go. I’d done some racing. We had that experience of being in charge of the boat on our own when we were on watch. We were able to explore, have freedom, and do amazing things.
When we came back, there was a party at the yacht club, which we didn’t belong to because we weren’t clubby. We just had a boat. There was somebody that said, “Do you want to go racing?” I’ve told this story a million times, but I was thirteen. I was a girl. I went out on the Etchells with some old people that, in hindsight, were 25 or 30. I was like, “They suck. I’m good at this.” I had the skills and the confidence, and that propelled me to explode.
I also saw America’s Cup in Newport, Rhode Island. I saw Ted Turner, ESPN, and Gary Jobson. I didn’t know their names at that time. I just knew that there was some excitement and glamour. The twelve meters looked amazing. This whole town went sailing. I became obsessed that year. You mentioned your daughter’s twelve. That is such a critical time. The middle school age is so important for young people.
It’s the time that they discover they have a future, but hopefully, they haven’t discovered all of the limitations that may be set on them for their race, gender, or socioeconomic situation. It’s a time of enlightenment. It makes a difference more so than super young and high school. It’s the time when their lives are changed forever, hopefully, in a good way.
She’s involved in lacrosse. We’re trying to get her to go to a tennis camp. They’re like that, but then they also get fixated on one thing and like, “I want to do one thing.” I’m like, “You can do a few things.”
Somebody told me, “You’re good, but you’re always focused on the next thing.” I’m like, “I have to be. I’m a female in this sport. I need to have my next plan. I can’t just sit back and wait for the phone to ring.” I also talked to high school kids and middle school kids. I say, “Keep trying stuff.” In my third America’s Cup, the True Youth program was to dream it and do it. We took kids from varied backgrounds, specifically at-risk, first-time offenders, boys and girls clubs, and inner city groups, and said, “Come sailing.”
We never said, “We want you to do an America’s Cup.” We said, “You could sail around the world. You could travel to Russia and play chess. You could invent a new sneaker. Keep trying things.” When I get to the older kids, I’m like, “This is the deal. Tell your parents you can do ten different things. If you hit one, you win. Keep trying it.” Unless you’re positive that you have that one goal, there’s nothing wrong with that. You know that inside and out. You still have a couple of plan Bs and plan Xs in case.
That never goes away. I tell my wife that all the time. She’s like, “Why are you involved in all these things?” If you have one that works, it can be life-changing. If they all work, you got some real decisions to make. You mentioned the third America’s Cup. Go back to the second America’s Cup first in 1995. The decision was made to create an all-female crew. Why was that decision made?
We won. When you win America’s Cup, it’s like you won the 100-yard dash and you get the Olympics. They’re like, “You got to organize it.” We won the America’s Cup in ‘92, and then Bill Koch had the power to make it all happen. He didn’t necessarily want to do it himself. His business didn’t want him to do it. I don’t know about his family. It’s a pretty intense thing. He had a corporation to run.
All you’re doing for three years is planning this.
You’re living it and breathing it from 5:45 workouts until you fall in bed at 10:00 or 11:00 at night. We averaged less than two and a half days off a month for that time, so it was pretty intense. He decided to come up with an all-women’s team. He contacted me and I wrote what we called the manifesto, but it was a business plan. We took it from there.
How did you go about selecting the team?
I wrote the manifesto and then there were some other people that came in. As soon as there’s a thing, people are coming in. They were all guys. One had a wife. He was a sailor, and he’s like, “I’m going to come in and my wife is going to be the skipper.”
I’m thinking about the movie Wind, with Matthew Modine in the hangar.
There’s a whole bunch of politics going on. I was told by the person that was hired to select the team that I would never be in the back of the boat because there were all these dinghy sailors. What the idiot didn’t understand was I was the only individual who was going to be on the boat who had ever sailed an America’s Cup boat.
At that time, I was pissed off, so when I got a call to go around the world again, I was like, “I’ll go around the world.” They announced the team while I was around Cape Horn. They had a telephone sitting on the desk at the New York Peninsula Hotel, expecting me to call in. We got miscommunication time zones, so it doesn’t matter. I was grandfathered into the team. I didn’t sign a contract yet, so I had an option for another team, and I chose the women’s team.
The other team was a better deal financially. It was a guaranteed A-team spot. There were all sorts of perks. They were trying hard. I was like, “Somebody wants me that much they can throw money at me?” I used it to negotiate my contract a little bit. The biggest thing is I realized that the women’s team was going to be so impactful to society that I should be a part of it.Having a diverse team, diverse thought, and diverse background will strengthen your company. Click To Tweet
People still talk about it.
I signed my contract on my 30th birthday, and then I may not have been so fresh the next morning.
You go through that America’s Cup and the results weren’t as where you wanted them to be. They weren’t ‘92. You didn’t win.
We would never have won because the Kiwis were so fast, but if there hadn’t been a backroom deal made by all the guys in charge of our team, we would have gone to the finals. Instead, there was a three-boat final. Dennis Conner eliminated us with a stroke of luck. He tacked or jived around the top mark and went to shore.
We were six and a half minutes ahead of him at the last mark. He got a puff-off on the shore by La Jolla and came in. We finished overlapped and he nosed us out to eliminate us. Otherwise, we had already eliminated him, but there was a backroom deal that allowed him back in. We almost eliminated him a second time, and he came back and got us.
I think about that in the movie Wind when they lose. The owner of the team, who was the skipper, mentally goes crazy. What is it like at that level? You referenced it and said, “This is three years of preparation.” This is one of the premiers. A lot of people don’t know a lot about sailboat racing. I would encourage anyone who doesn’t know to go watch these things. I want to ask you about sailboat design in a minute and where we’ve come from. It is one of the premier athletic events in history. It’s been going on for so long. What’s it like to win and lose?
The losing part, let’s go on that. It’s going to sound corny, but with everything I’ve done in my life, I truly enjoyed the process.
I love the quest, being curious, the physical, the endurance, and the blood, sweat, and tears. When we lost, there were a lot of tears. They were not mine. When you see a professional player when they lose, they’re like, “Damn it.” They’re angry, but they’re not a puddle of jello. A lot of the women were, and one of the youngest women on the team referenced this. She said, “You told us it’s a sailboat race. There will be another one.” She brought that up.
What I didn’t realize is that for me, that was my fourth campaign. I’d already done America’s Cup and two Round the Worlds. This is the fourth one and I fully expected to do more. I had the perspective that the babies on the team or the puppies on the team, their world had ended. You have to have that perspective and know that, “Let’s do another one.” Right around that time, I was already planning my America True campaign.
Let’s talk about America True. That was your third America’s Cup entry. With companies and organizations I work with, we talk about selecting the right person. It has come up a lot when we talk about DEI, Diversity, Equity, and Inclusion. We have these DEI campaigns. Many times, we’ve put this face on there that you’ve got to be of a different color or religion, but at the end of the day, what are we trying to do? We’re trying to get the diversity of thought.
Diversity of thought is what matters. I can take an Asian person, a Black person, and a White person. If they all went to Harvard, do we have the diversity of thought in this room? Maybe a little bit, but not as much as we were probably truly looking for. You built this America True campaign solely focused on, “Give me the best people.”
With a continuing proactive conversation, are we making this decision equally with equity in mind? We didn’t even use the word equity then. We were like, “Are we saying no because she’s a female? Are we saying yes because he’s a guy?” We would have that conversation and go, “This is real.” From a strict business sense, part of the reason that Bill Koch didn’t do another campaign and did the women’s team is that it’s very simple. Winning America’s Cup is an incredibly difficult thing to do.
We’ve only done it once since 1982.
You’re looking at it and focusing so hard on doing everything perfectly and using every ounce of energy, brainpower, and expertise of every individual on the team. Therefore, if you try to do it a second time, you will not be as good because somebody else will be able to see what you’ve done. They will put a different spin or a diverse spin and they’re going to come back and be faster and better than you. The same goes forward that having a diverse team, thoughts, or background will make your company stronger. The bottom line will be better.
From a male-female perspective, which has been most integrated already and has been studied, if you have a corporation with more than three women on the board, you are statistically more profitable. Anybody who says, “That’s just window dressing,” if they’re a smart, savvy investor, they’re putting their money there. Whatever they want to say, politically, this is a fact.
It’s having a diversity of thought or diversity of background. It’s having different ways, a little bit of character in there, and somebody that does ask why. When you have the time, you need that person that says, “Why don’t we do this?” You’re like, “No. This time, they’re not that so. Let’s talk that through.” With America True, we want it to be diverse.
I’m going to circle all the way forward to Oakcliff. We wanted it to be diverse, and there wasn’t a diverse pool in terms of race and background. We did have gender. We had at least 25% to 26% of women in every department. We had men in every department too, so it was both ways. Instead of saying, “We can’t do it. There’s nobody there that’s qualified. Sorry,” we said, “Let’s change the world.”
We started True Youth. We go into communities and we would expose kids to sailing. We talk about, “What do you want to do with your life? Where do you want to go? What do you want to try?” Through that message with True Youth, we started helping community sailing centers set up all around the country. Yacht clubs started inviting people into their junior sailing programs. We blew the doors off of the yacht clubs, which was in our business plan. We see the fruits of that, and that was in 2000.
In 2021, we rolled the America True Foundation, $170,000, into Oakcliff for scholarships specifically for those kids that have gone through community sailing programs. It’s need-based, but that doesn’t mean that they’re poor kids. It just means that they don’t have the network that the same exact child, if they had been exposed and entered into a yacht club, would have a different network. We’re looking to help expand that network and bring them in.We need to have women in decision-making across the board; we must be fully integrated and diverse. Click To Tweet
This is a job skill training site. It might be sailing, engines, sail-making, business, accounting, PR, or marketing. We are an educational institution here that is giving real-life apprenticeship programs. 1995 was when we started saying, “We don’t have enough diversity. What are we going to do about it? Let’s do this.” Now, we’re seeing the other end of it, which is so rewarding. We have significant diversity in all of our programs, which is amazing.
We talk about hiring for character and training for skill. If you bring somebody in who demonstrates the character traits that you want and need, you can figure out what they want to do skill-wise. Put the program together and train them up. They’re far superior to someone who might be technically proficient but lacks values, morals, and the intentional courage to want to work hard.
That last part, the morals, courage, drive, and ethics, you need that to have skills or success. If you’re skilled, you don’t care, and you treat people like crap, I don’t even want to know you, and you certainly shouldn’t be walking through Oakcliff doors. We will bounce a few people every once in a while, and it’s always for that. It’s never because they keep falling off the boat. We’re like, “Put a life jacket on him. We’ll get him better.”
I want to ask about the Whitbread Ocean Race. It’s now the Volvo Ocean Race.
It’s The Ocean Race. It was the Whitbread, and it was the Whitbread Round the World Race for the Heineken trophy, and it was the Volvo Ocean Race. Now, it’s just The Ocean Race.
You wrote a book about it called Taking the Helm. You and I were talking about it earlier, and it recaps the 1993 Round the World race in which you had gotten the call when they were in Uruguay to, “Will you take charge of what’s going on here? The previous skipper had stepped down.”
She hadn’t stepped down. There’d been mutiny there.
There was a problem. This is fitting because in the episode we’ll release right after yours, we’re interviewing a Harvard Professor named Eric McNulty. He wrote a book called You’re It. He is one of the world’s foremost experts in leadership. He advises FEMA and the White House. Their book is called You’re It solely because when you are a leader of an organization, you cannot predict when the chaos and when the crisis is going to happen. At some point, someone is going to look at you and go, “You’re it. What are you going to do?” My question to you is now preempting this conversation I’m going to have with the professor. What would you do when you were it?
I got the call when I was in Michigan. That was when America’s Cup was on pause. I was being told that I was never going to be in the back of the boat. I got the call on a Sunday. I was at my mom’s house in Michigan. I had to quickly go buy some long underwear and some gear and fly to Uruguay on Wednesday. I showed up and made some phone calls back then. That was way before cell phones. It was the time when people called people’s mothers to find out where they are.
There were two people that can go with me there. One was my best friend, Renee. I was like, “Remember how you said you wanted to race around the world? Pack your bags. We’re going Wednesday.” She was like, “What?” She went down with us. I pulled in some other people when I got down there. I did make a mistake textbook-wise, but they didn’t have a lot of choices.
Peter Blake, who is an amazing mentor, friend, and leader said, “You need to fire everybody and then interview them and rehire.” I was trying to figure out what their names were because, by the time I got there on Wednesday, we started on Saturday. I didn’t have that option. I made a critical mistake. I should have made a different person, the navigator. I should have gotten rid of one person and gone shorthanded with that type of decision. I made the decision.
We went into the Southern Ocean and realized the level of skill that I was dealing with but got through it. They tried to have a bit of a mutiny again. At 2:00 AM, we were having an all-team meeting in the cockpit in the Southern ocean. I’m like, “This is bullshit. This is the way it’s going to be. If you guys haven’t made it, I’m in charge. We’re moving forward. I don’t want to hear any more of this crap. You’re going to stand watch when you stand watch. You’re going to be off-watch when you’re off-watch. We’re going to get this boat to Australia and hopefully get some new sails.”
You said, “The race taught me how to lead, how to trust my own decisions, and how to overcome challenges. Many of which threatened our lives.” You went on to talk about this great adventure. It was this crash course in what leadership is. What were those things that were life-threatening? I can imagine the seas.
If you don’t know what you’re doing on the boat, you shouldn’t be steering because you’re going to do a crash jive, and that was one of the things. It was pretty dangerous. I came on deck because I didn’t trust the team for very justified reasons. I was in the nav station. I put on my boots to come on deck and my harness that was built into my faux leather jacket, but I didn’t have pants on because we were going downwind.
They had jived and I ended up being washed off the back of the boat. I was still clipped in, so they pulled and got me back on. With the cold shock and the hypothermia, I ended up in my bunk for probably sixteen hours, warming up, which was not good for the overall team. If you could do it again, I would have taken two more minutes and said, “I’m just one person. I need to preserve myself before I go in and try to preserve the boat and the rest of the team.” That would have saved sixteen hours, but still, it was not a comfortable thing.
We ended up making one crew change. It wasn’t the correct crew change, but one crew change in there and kept moving forward. I didn’t realize until I double-checked it to put it in paperback. We got to Australia and got new sails. I did a media tour. I came back and we were third on the next leg. I had completely forgotten that because of all the drama of the race. I’d written about it in the book and I didn’t remember we’d done so well.
You achieved the mission.
There were few rudder breakages after that. Heineken was the first time that I was solely in charge and didn’t have the team that I had built around me. I had a few people I trusted, which is not the way that you want to go into battle ever.
Let’s talk about your leadership style because you opened it up. I love talking to coaches. In this show, we’ve had a number of them on, including Andy Towers, one of the most famous lacrosse players. He is the Head Coach of Chaos. He has come on a couple of times. People have said that your coaching style is rough. We talked about it here you can’t be meek or soft in sailing.
It’s also been said that you teach from what I call effective intelligence. Effective intelligence is 1 of the 9 Special Operations Forces characteristic traits that SOF uses to assess talent in their recruitment and selection process. Effective intelligence is the ability to take your experience of the past that you’ve learned and apply them to the future. That has been defined as your style. It’s also been said that you will never ask anyone to work harder than you do. I know from knowing you that you know every job in this sport. You’re always willing to get your hands dirty.
We were up on a boat and working dirty. I was like, “I want to be a boat captain. It’s so less stress to fix stuff.” I don’t mind getting dirty at all, but I also would be completely frustrated if I was doing one part of a program. I don’t mind standing on the bottoms or fairing a bulb. I enjoy it. I can feel it and see what it’s going to do. If I was doing that while other people were making poor decisions, I would lose my mind. Somebody asked me. They said, “What is something that people don’t know about you?” I’m like, “It’s that inside, I care, but I don’t necessarily have the time or the patience to say, ‘I care about you, but get that done.’” I just jump to the, “Let’s go.”
How do you balance this authoritative nature that’s required to run this program and compete at the highest levels of this sport, but also be friendly, empathetic, and be somebody that everybody’s going to latch onto and look to and say, “I’m comfortable talking to her.”
They’re not always comfortable every day, but that’s part of what has to happen. Humor is the biggest thing. It’s not necessarily self-deprecating humor because then, it’s insincere. This happened. Our 9:00 meeting every day is digressing into story hour because somebody will say something and I’ll go, “I probably shouldn’t tell you this, but one time,” and I’ll go off on a story. That wouldn’t be written in a script, but it’s real and fun, and people learn from them. They always have a mission or a message. It makes them understand that while I’m telling them to do this, I’ve had a fair amount of screw-ups as well.
We had this conversation with somebody. I’ve considered running for politics and I’m trying to figure out how I can split myself in two. When I went to Emily’s list and they started doing oppo research, they said, “You’re a sailor.” I said, “Yeah, but everything I’ve done, I’m proud of. If I can get the people here to understand everything that you do is going to be known, you should be proud of it and you can keep that in mind, you’re going to make better decisions. They’re not always going to be perfect.” Also, as long as you’ve taken the time to think through the process, you’ve made a decision, and that’s where you ended up, that’s okay. Even if there could have been a better decision, you have to be active in it. If you just sit back and go along with the group and run a Jeep off the road, that’s on you, dumb ass.
That’s one of the core principles of leadership. I was speaking with one of the coaches that I work with. We’re embarking on some different tactics going into a new season. We’re starting to up the standard and reinforce accountability. Often, when you do those things, there’s resistance. The question I asked was, “Do you believe that every decision you’re making with respect to this is the right decision? Based on the totality of your multiple Olympic medals and your decades of coaching, is this the right decision for the team? Yes or no?” If the answer is yes, drive on. What do you want to run for in politics?
I wanted to run for Senate in Michigan. That ship has probably sailed. I need to be vocal and active. I don’t have enough money to influence any election. I donate as much as I can to people that are in power that I worked on Hillary’s campaign. I want to be proud to be an American. I want to be emotional when Star Spangled Banner goes. I’m horrified, especially when I see it through the eyes of all my friends from other countries. That’s a difference. A lot of people don’t have that luxury of being a citizen of the world and knowing what we represent and seeing what we’re reflecting.
We are at a critical time in this country. I’ve talked about it in other episodes that we need the next generation of leaders to come in. We’re spoiled. Anyone between the ages of 40 and 60 is super spoiled. Our grandparents were the greatest generation. They saved the world.
They saved the world, worked their butts off, and were satisfied. I’m from Detroit and some of the most satisfied, happiest people when I was growing up were not like the rich people on the hill. They were solid Americans that worked hard and had Budweisers and a barbecue with their friends in the backyard every Friday night. It was regular, but it was this huge family.
That’s trickled down. Their kids were the Baby Boomers and we fell on the back of them. We still sit here and say, “Our problem is by and large. Life’s been good. These generations solved all of our problems.” Those generations are gone. The generation of the Baby Boomers has been in control of senior political positions for 30 or 40 years. What we’re having is we’re experiencing a void in leadership because the generation that we sit in has not stood up and said, “Somebody has to do this.” We’re the ones who have enough life experiences to be able to make the right decisions. We’ll follow you on this and see what happens. Who’s the mentor?
My mentors are eclectic. There was a guy Tim Woodhouse, who’s no longer with us, that was completely inappropriate to be the mentor of a sixteen-year-old girl. Anybody that knew him would say the same thing, but he gave me some chances. He’s the first one that gave me a job to fly out here to Manhasset to trim a sail. There were other people that I worked for that taught me lessons that had nothing to do with sailing. Billie Jean King is a mentor to so many people. I don’t want to throw her name around, but she’s a friend to so many.
I saw Julie Foudy who’s also a friend. She was the president before me of the Women’s Sports Foundation. It was in an airport, so it was the subtitles. There was soccer and they wanted to have equal pay. They came to Billie, and Billie said, “What are you doing about it?” I didn’t remember that story, but that’s exactly what I said to the women from SCA.
The all-women’s team called me. They wanted to start the Magenta Project. They wanted me to be the CEO. I’m like, “I’ve done this. I’ve shown you how. It’s time for you to step up.” That’s what we need to get with the politicians as opposed to, “Come help me be greater.” We should be like, “It’s your turn. I will support you. I’ll be on your advisory board. I will give you my advice.” Even with Oakcliff, everybody says, “Come set up a program in my hometown.” I’m like, “Copy me. I’m good with that. Have at it, but don’t expect me to try to dilute what we have here because it’s such an amazing central base. Send your people here. I’ll train them and you can take the expertise back.”
I want to ask you about boats. I joked earlier that sailboats used to be this bathtub with a piece of cloth on a piece of wood. Now, they’re more like an airplane. They’re calling it a wing. They’re multi-hull hydrofoils. America’s Cup went back to monohull hydrofoil. They’re not even in the water. They’re flying. Explain a little bit about the evolution of sailboat design. I’ll tell you why I’m asking this question and then I’ll probably help you to go where I’m looking.
People ask me, “What was it like being in the Special Forces?” I talked about it here with your group. I said, “There’s nothing special about being in the Special Forces because you have to do the basics and the fundamentals better than everybody else. That’s the only difference.” What teaches you that in sailing is not these multi-hull hydrofoils. It’s the optimist, the sunfish, and the laser where you have this core set of skills that teach you about how you react to the wind and what a boat does.
As we’ve evolved tremendously over the last couple of years, how has that changed the sport? What’s happening is people are coming into the sport and they’re seeing this on TV. It’s glorified. These athletes have WHOOPs and heart rate monitors. We’re all looking at their bio-data on the screen, but there are still seven-year-old kids out here dragging an optimist out into the bay and sailing around.
I mentioned earlier that it’s like fighter pilots. It has become more electronic and mental. I’m not going to say that an optimist teaches you a lot about high speed.
If you’re six years old, that’s fast.
If I don’t trim, I don’t go anywhere. If I don’t sit on the right side, I fall over. You need to learn the basics, the heel, the trim, and the ease, and then you move into the next boat. At some level, you lose the size and the mechanics of the boat that allows you to feel. If you start at the high-end boat where there’s no field because you’re pushing buttons, you won’t be able to sail. You need to have the feel so that you can get into a small boat that’s your body weight, you’re heeling, and moving.
You can then move into like a lot of boats we sail, the Farr 40s, where you have instruments or tools to help you decipher what it is you see and then be able to solve problems on your sail shape, which are wings. We’ve always said that sails are like airplane wings. They just now are literally airplane wings because of the foil shape, the heel of the boat, the angle of a tack, the wind, and the ways the movements. You then start to see how the instruments work and how your boat speed works.
Most top non-America’s Cup level people can sail by just feeling the heel of the boat and looking at the boat speed. That’s all you really need. It drives me crazy when everybody like, “I’ve got these H5000. I’ve got these graphs. I can see the fish.” I’m like, “Stop. Close your eyes. Feel and sail the boat. Hear the wind. Feel the pressure on the side of your face. If you can do that, then that translates into the big and the fast boats, but you need to have all of that built so that you know intellectually what you’re trying to do.” You’re then taking the other clues, which are on your readouts. It’s still physical because you’re grinding to give yourself the power, but it is completely different.
I don’t think that I would be able to get into an America’s Cup boat and contribute at this moment. It doesn’t mean I couldn’t train for it because it’s such a huge leap forward. What we’re doing here is we have the foiling camp going on. We have WASZPs and Nacra 17s. I sail Nacra 17s, Nacra 20s, and WASZP. I do like it, but I like it more for the physical overcoming, the flying, the crashing, and the burning. I’m still at NASCAR. I’m not a Formula 1 yet.
I sail boats with Keels and they don’t fall over. We sailed OC 86 to Bermuda, which was donated by the DeVos family. I’ve been friends with them forever. People are like, “Did you buy that boat?” I’m like, “No. Doug DeVos donated it.” Part of the beauty there is we’re sailing with 22 people. It’s keeping the whole team focused and executing a maneuver. You need everybody on the grinders, so the grinders are going in the right way and at the right speed. You have six different gears on each wind. It’s very technical, but it’s not flying.
You served as the President and a Board Member of the Women’s Sports Foundation. You mentioned Billie Jean King. She founded the organization in 1974 to advance the lives of women in sports. Some of the most accomplished women in sports have been in this organization. We talked about the years since Title IX. We’ve come a long way, but how much further do we have to go when we talk about equality?
It’s pretty simple. You need to have women in decision-making across the board. One of the Round the World teams failed on some significant levels because it was an artificial barrier. The women were on the boat and the men were in the management. Never the twain shall meet. That doesn’t work. That’s 101. Would you ever advise any of your clients that the board member should never talk to the staff? No. You need to have that.
In the sport of sailing, it’s having women as decision-making boat owners, tacticians, skippers, and project leaders that when they put together a team, it is completely natural to have women on their team. Never would I ever say we should have all women’s teams everywhere every which way because we need to be integrated. What happens if we’re fully integrated or fully diverse? What is the solution to win? That’s going to be harder. There’s an easy answer. It’s more diversity, diversity of thought, and women in leadership to promote that diversity.
The water has a healing effect and power. You and Oakcliff have been truly inspirational and also foundational to the SailAhead Organization. We were talking about the Duclay family. Jenny is our production coordinator, and that’s how we met. I’m super close with her entire family as well as involved in SailAhead.
It’s important when we talk about getting people out on the water because there’s this disassociation that can occur between what happens on the water and what happens on land. The reason why I was initially drawn to SailAhead, why I’ve stayed involved, and why I continue to want to bring veterans out and give them this experience when we talk about mental health is because we can have all these problems on land.
It happened to me. I was in meetings. I was up at 4:00 AM preparing for this conversation. I had all these number of things to do. I was on the phone the entire way down to the ramp. I put the boat in the water. I got on the boat and we got out into the sound. I sat back and sighed. I even turned the radio off so that I could listen to the engine and the breeze. Why is that so important? Most importantly, why is that something that whether you’re the 5-year-old or 6-year-old kid in the optimist or you’re the skipper of an America’s Cup foiling monohull, it never goes away?
It’s even more important that you need to have a space to clear your brain. Sailing on the water engages all of your senses. I talk about that all the time. It’s the feel, the sight, the sun, and the smell of the salt water. It’s everything. It’s like you’re being immersed in a different world, and you need it. Going to Bermuda, I turned my phone off and didn’t think about it until we got close. I’m like, “I should do something,” but I didn’t want to. I kept it hidden for a little while longer because it’s amazing how your brain opens up, how much you remember, and how many problems you can solve by being cleansed. It’s that deep breath.
I agree. I find it, in a way, foundational. When you need that time or that moment, you can go out there and you know, “I’m going to get this if I go out there.”
Even to the point of when I am on the computer and scrolling on Facebook, I’ll be like, “This is New Zealand. That’s Antigua.” There’s such a connection with the scenery, the blank palette, and the color of the water. I can scroll through Facebook and know which country and area the photos are taken. They’re all around water. I can’t do that in the city. I’m from Detroit. I can’t tell you if it’s a Ford or a Chrysler. I’m like, “It’s a car,” but out on the water, I can tell you where it is or what cove it is.
I want to ask you about the future and where we’re going. 2020 Olympics yielded no medals for US Sailing and US rowing, which was also a first. Those are two sports that I’m passionate about and have been involved with for a very long time. Sports in the US have dominated. We lost America’s Cup. You were in the boat in ‘92. America has only won one other time in 2013 since 1992 in San Francisco. I was there. That was awesome. You and I talked about that before.
The executive director of US Sailing put out an open letter after the 2020 games. It’s a bit long, but it’s important to read it. It says, “Many of us in America are dissatisfied with our Olympic sailing trend and want to correct our course. While being in the middle of the pack is not a bad thing, it is not how Americans think of themselves. Moving up the Olympic pecking order is not going to be easy. No one is going to get out of our way. We need to build a machine that puts teams and athletes in a position where their usual routine will produce a podium result on a regular basis. This is about cultivation, education, preparation, and execution on game day. This is about proper process and procedure.” These are things that you are passionate about and building here as we talked about with Oakcliff.
Accountability and ownership are critical in building high-performing teams and owning results. Good, bad, or whatever it is, we as leaders have to stand up and own those results. What’s next for American sailing as we move into the next Olympic Games that are a couple of years away? They’re already planning. It’s all over. America’s Cup is even on LinkedIn. The planning is well underway for the next America’s Cup. How do we get the US Sailing back on the podium?
That letter then went to the committee. A camel is a horse designed by a committee. There are still major problems. They have made some good decisions in terms of leadership, but it is across the board being uncreative and not working hard enough. The only thing in last America’s Cup that I could see that was wrong was that they were too well organized, but they didn’t have that character. They had no discord. I talked to the team about it. I was like, “This is the only thing that I could see that was wrong.” I wanted to butt in, and I did a little bit, but I know when you’re in the zone and working, you don’t want some random lady from New York calling you down to New Zealand and saying, “What’s going on?” I should have a little bit more, but you need to have somebody coming in and out.
On the Olympic side, Cayard is in there, but he needs an operations person. They don’t have an operations person. Alan is the CEO and he’s doing a good job. Andrew, who’s amazing, is the golden child, but he’s a one-person show. There’s still a lot that has to happen. We’re trying to fix it here. We have the boats, facilities, bunkhouse, and the beach. Dingo and Dylan are here as coaches. We have a dinghy in the 470s. We have this amazing training center, but many people in America, especially when they get to that level, have been entitled a little bit. They have been told they’re special and they believe their own Kool-Aid. They’re like, “I’m going to do my own thing.” We have to work together as a country and a team.
I am a member, but I’m not the leadership of the NGB. US Sailing has to say, “This is the way we’re going to train. You have to do it or you’re not part of the team.” It has to be hard work. It can’t be just paying a lot of money for one special coach. There’s no golden egg here. It’s a lot of hard work. It’s a lot of that creativity. It’s sharing resources and your technology. It’s supporting each other and being a part of the winning team.
Two groups have done it, but most specifically, the Nacras. They were here. They trained here. I talked to them about this concept. I said what was going to happen. I was like, “If you guys commit to training together, you’re going to do better than you thought. On the day after the trials, there’s going to be one team that’s super happy. There’s going to be four other teams that are upset, but that pain will go away much quicker because you know you were part of that winning team.”
I was super happy and proud to see the winning team paraphrase that in the press release. It was so good because it works. US Sailing said, “Nacras, you have no chance of going to the Olympics. We’re not going to be able to support you.” They said, “Screw you. Watch me,” and they worked as a team. That is what it takes. It shouldn’t have to be, “Screw you.” US Sailing should be providing that framework. Oakcliff is trying, but it’s frustrating beating on the doors. We’ll see. There’s some hope for France, but the focus is on LA.
There’s a difference between what sometimes you perceive it takes to win and what it takes to win. Closing that gap is often the hardest thing.
What it takes to win is everything. Every single thing has to be done as perfectly as you can. The winning, like that second leg for us in the Whitbread, was like, “We’re on the podium. Look at that. That was easy,” but it wasn’t easy. The end seemed easy because we’d done all the hard work at every single step along the way.
It’s asking the question at the end of the day, “What more can I do?” It’s not saying, “What did I do?” but, “What more has to be done?”
At some point, I was going, “I can’t do this. I will do this in the morning. Go to sleep.”
I wear it on this band on my wrist. It says, “Whatever it takes.” That’s the difference between what it takes to win versus what you hope, think, or want it to take.
We’re lucky to be able to have that single focus. When you’re in the zone and you know that you have to change this bulb on the bottom of an AC boat to get to the race course the next morning and you’re not going to sleep for 24 hours but you know you can do it, it’s awesome. You were lucky.
As we close out, the Jedburghs had three core foundational tasks. You could call them habits if you want it. They had to do them as the foundation of everything that they set out to do in their day. They had to be able to shoot, move, and communicate. If they did these three things with the utmost precision as their foundational tasks, then their energy and focus could be focused on other things that are more complex tasks that came their way. What are the three things that you do every day in your world to be successful?
I always wake up and think about what I can get done. I try to work out every day. I’m lucky because I look at the water every day if I’m not in it.
Wake up, think about what you have to get done, make that list, work out, and look at the water or get in it if you can. I like those.
It’s pretty simple.
The nine characteristics of elite performance as defined by Special Operations Forces, we referenced a number of them here, but they’re our core tenet of this show. It’s the drive, resiliency, adaptability, humility, integrity, curiosity, team ability, effective intelligence, and emotional strength. Elite performers, regardless of what you do, whether they’re business, athletics, or military, it doesn’t matter. They exhibit all nine of these. You exhibit them in different variations and different scales. It’s never all nine at once, but depending on what you’re involved in. You have spoken at length about all of these through our conversation here. You were involved in a near-death car crash in your house in 2019 and have exhibited tremendous resiliency on the back end of that because you couldn’t speak, right?
It was for about three months.
How did you come back from that?
It was so bizarre. In my head, I know exactly what I was going to say. I was frustrated. It took perseverance to go to the doctors and find out that I was having seizures from the TBI. Once the meds and then speech therapy kicked in, I’m almost good. I’m the only one that notices and I’m in my head. A friend of mine who I wanted to punch in the face goes, “Maybe it’s good because I always have trouble keeping up with you.” I’m like, “It’s not good.”
I haven’t noticed it and we’ve been talking here for a long time. It requires true resiliency, adaptability, and the ability to come back. At the end of these conversations, I think about these nine and pick one. I say this is the one that, through getting to know you, I truly believe you exemplify. For you, it is this concept of effective intelligence. You have had this litany of experiences that you are using to develop that next generation.
You are unrelenting. In the military, we call it this relentless pursuit. It’s this relentless pursuit of mission success. That may morph over time, but whatever it is that you’re doing, you’re going to take that experience of the past. Maybe it’s not the same as what you’re facing, but you’re going to figure out how you took something from that and you’re going to make it apply. That is what makes great leaders and organizations. That’s what makes America great.
I’m so motivated and inspired by your dedication to the sport and to women not only in this sport but in every sport and leadership position. I truly wish you the best of success here at Oakcliff, in sailing, whatever comes next for you in sailing, or if you enter into politics. I know that you will take this effective intelligence. You will take the other eight characteristics here. You will apply them. You’ll go all-in and have this relentless pursuit to be successful. We’re all supporting you.
Thank you very much.
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- Taking the Helm
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