131: Dawn Riley, part 1: After winning the Americas Cup, revitalizing sailing (transcript)

February 6, 2019 by Dani Mihaleva
in Podcast

Dawn Riley

I wish you could see the context of this conversation at Dawn Riley’s sailing center. Dawn Riley has sailed in three Americas cups. She’s won around the world races, she’s won the America’s Cup, she’s led other teams. We’re at the sailing center that she runs to restart the elite level of American sailing. A couple of hours before this conversation she sent me out to see Olympic medalists competing on the Long Island Sound. Shortly after that conversation, they all came in for a barbecue. So there’s medalists, there’s gold medals there’s, cross fit games winners and more. Actually, you’re going to hear these world class athletes, their trainers, the organizers and so on talking the background over the course of this conversation because we’re sitting there at the center. To me a top measure of leadership is who follows the leader. Dawn has surrounded by themselves top leaders, themselves world class people and she is taking them to the next level. She leads athletes, business people, educators, parents and more. I wish that I could describe the force of nature that she has in action. Her results speak for themselves. I hope that this conversation shows the potential of leadership and cultural change because she is living it. You can see it in everything that she does and you can hear it in everything that she says.


Joshua: Welcome to the Leadership in the Environment podcast. This is Joshua Spodek. I’m here with Dawn Riley. Dawn, how are you?

Dawn: I’m doing great today.

Joshua: And if you hear the noise of a sailing crew behind us it’s because we are at Oakcliff Sailing Club. Sailing club? Sailing school?

Dawn: Sailing center.

Joshua: Sailing center. And now Dawn, you know those but before all of this I am going to say you are a woman of many victories and many firsts in the sailing world. You’re a really big character.

Dawn: Yes. In the sport of sailing I’m quite well known. I’ve been doing it for 40 some years professionally, no 40 years exactly professionally. So that kind of brings you a little bit of notoriety.

Joshua: And there’s so many directions I could go on with this because I want to talk to you probably most, eventually about the environment but I think I want to talk to you most about leadership and sailing and teamwork and learning how to lead through athletics and sports, sailing in particular which is unique. I can’t help but ask, I know you get asked this a lot. What’s it like to win at America’s Cup?

Dawn: It’s complicated actually. Of course, yeah, we won but it’s not just the moment you know and the moment that you win isn’t the moment that you remember, to be totally honest. You remember a little bits and pieces leading up to it and then you re-remember with your friends when you see them 10-15-20 years later.

Joshua: The team element of sailing seems unique and different and incredibly… I mean I guess there’s solo… Even if there’s solo sailing it’s still going to be a major team effort.

Dawn: Yeah. So solo sailing which is not my thing, they talk about the other competitors are their team but in like around the world race you better have a good team, you better like the people because you’re going to be in wet, cold, miserable conditions with no sleep, bad food for 30 days at a time. So if you don’t like the person next to you you’re in big, big trouble.

Joshua: So I feel like on a boat there’s this mix of a lot of people out there. They see leadership is a command and control thing. It’s what’s in the movies. It’s certainly sells a lot more movie tickets. I think on a boat there’s got to be a very strong chain of command. But I feel like it can’t be just that. There must be a lot of…

Dawn: What you first need this organization which is the first step of leadership, which you second need is in an emergency situation and that might be an emergency because you’re going to lose some minutes on the race course or an emergency because of life and death, no different. In an emergency situation you need a strong chain of command. But those are very few and far between. The rest of the time it’s an organized leader and circular loops of communication and conversation and you actually have like a speed team and a technical team within a boat and a tactical team and some of those teams overlap. The tactician needs to understand what the speed is and needs to be able to be aware of how to adjust the sails if you’re having a problem but he’s not regularly in the speed loop. The speed loop is the tremors in [unintelligible] people. So I’m talking on a boat with seven to 10 people. You have this complex organization all getting to the point of where you’re making a boat go seven knots.

Joshua: When the other guy is going 6.9.

Dawn: Exactly, a tenth of a knot, a hundredth of a knot. That’s what you’re looking for.

Joshua: And to get there, as you’re saying and I am thinking to myself, that means you’ve got to practice and practice. You’ve got to train and train. You’ve got to know each other and you’ve got to know the ship. You got to know the team. Let me transition here. So what you’re doing now is you have a center that teaches people at the individual level but you’re also promoting the entire sport in this country. You transitioned from learning leadership and learning teamwork to now you teach it.

Dawn: I teach it experientially so I question people. So yes. But we have Oakcliff sailing. We are training the next generation. And specifically, our tagline is “We are building American leaders through sailing” which is really important because yes, we’re sailing and we want to win sailboat races and we want to make a difference in the sport. But what we’re really doing is building the leaders using sailing as a tool. And some of those leaders will stay in the sport. Some of those people will go and be leaders in other businesses and realms and you know areas of society.

Joshua: It’s not amazing to me that it’s so obvious to you. Maybe it’s what’s amazing to me is that it wouldn’t be obvious to everybody that this is a great way to learn. I mean sports and athletics has always been…. Here’s how I put it. There’s a lot of athletes who become great leaders, say like political leaders. Not a lot of political leaders become great athletes.

Dawn: Good point. Yeah. And you know any sport is going to help you and that’s why I am the past president of Women’s Sports Foundation and it’s super important for young girls to play sports so they have the same equal footing of men. Everybody can benefit from learning how to compete and how to lose and how to get back up and how not to take it personal, how to leave it on the field or leave it on the race course. So those are skills that every sport is going to help people to some extent. I think what’s sailing has on top of it is again it’s complex. You’ve got the technology, the boat, the different teams, the short team, the design team, the marketing team. It’s a business, it’s a whole world. And then even when you’ve done everything perfect, you have the environment and that can change. Poof! A hurricane can come in, a wind shift, a current, a whale can surface. So no matter how perfect you are you can still lose that race.

Joshua: And then you’ve got to get back on and get that… I think that’s another big thing. Maybe this is what you meant by leaving it on the field that pick great you know Serena, Lebron, Michael, whatever, they lost on a bigger scale than anyone else. And they didn’t give up and they got back in it.

Dawn: Exactly. And the key to that is you have to love what you do. If Serena Williams didn’t love tennis, she not only would choose to do something else but she’d probably suck at it no matter how physically amazing she is. If she didn’t love it, she wouldn’t still be doing it.

Joshua: Do people come to you already full of passion or just some people come in and…

Dawn: For the most part they’re pretty passionate about some part of sailing. We deal with 15-year olds. So we like to say that their brains are not fully developed. So they might be like absolutely passionate about something that’s completely unrealistic to them. But the amazing part about Oakcliff is we have inshore, offshore, high performance, map tracing, foiling, you know the shore side, the [unintelligible] side. So in their passion for one particular thing they get to discover the whole world of sailing and they almost always leave passionate about either the same thing or something else. They don’t lose their passion here. It might just be better defined and formed.

Joshua: I hope everyone else is listening to this in a way that I am which is one, I am fascinated about the sailing. Now people who know me know that I’ve got into sailing this summer but also, I’m also taking what you saying and translating it… It’s hard for me not to think of it from a corporate perspective. And I hope that a bunch of my listeners are corporate people and… OK, they don’t have to deal with the wind in the same way but there are so many teams and so many interacting with each other and every now and then a lot of it’s preparation for the future. Everyone now and then it’s like it’s now, like we’re in a competition or whatever you know like we’re about to IPO or something like that. And so one, what you’re saying is I’m reading it as incredibly valuable and I’m wishing I’d learned sailing when I was younger and I played my own sports. And every sports can bring something different. Can you tell a story of someone who came through… You’re building leaders through sailing and some will continue to sail. Some will not. That’s a very gracious thing to say, I think. I feel it’s very generous.

Dawn: Well, one person who came here is now working in commercial real estate and doing really, really well and the skills that he learned here are the project management because he was the captain of you know a 300-thousand-dollar boat. They had to put the team together. He got all of the project management skills that supplemented his education. A sponsor saw that and pulled him out. He still sails for the passion of it. Nobody ever gives up sailing once you’re a sailor but he gets to have a as we call it a real job and make money and sail you know in his pastime. On the other end of the spectrum, Mark Towill and Charlie Enright were in the early program here with the all-American offshore team. They’ve gone on to do two Volvo round-the-world races.

Joshua: Like that video I told you about before…

Dawn: Yeah. So those two… You know Mark was a kid. He is a good kid and he still seems like a kid a little bit but super smart, super hardworking and just decided and he’s from Hawaii and decided, “I’m going to do this.”

Joshua: Yeah. When we were talking the other day in Manhattan you were talking about how you speak to corporate organizations as well and that it’s like a natural fit. Do you take extra classes in leadership at some business school in order to be able to speak to them?

Dawn: No. I finished school and I enjoyed school. I sailed in school. I put myself through school by sailing. So that was my experience but in the America’s Cup in particular is like a startup. We say IPO. It is very much like a startup and that’s not a stretch to say these are the things I learned real time, fast-paced, time limit because you say “I want to do an America’s Cup.” generally you have two years maybe to put together your company and to go to market and there’s a hard deadline because you have the first race and so you have real life experiences and tough decision making and things that you learn along the way and things that don’t go so well along the way.

One of the little things that I learned early on and one of the tenants that helped us with America true my third campaign which I was a CEO was we knew we were going to have as much money but we wanted to have, one, a passion that everybody knew that we were doing something that was important, bigger than ourselves, bigger than a sailboat race. So we reached out into the community and we did the beginning of community sailing and reaching into inner city kids and working with at risk kids in our spare time during America’s Cup.

The other thing is that we knew that we had to be so far ahead of the game in planning and using every single resource we had including our brains. One of the saying we said is that if we have to use Federal Express, we have failed because we have not planned in advance.

Joshua: So many things I want to ask about. Now what I’m picking up an incredible passion and… OK, you say once someone starts sailing, they never lose it. But sailing is like such a… It seems to be a core thing. But like you’re starting the center, you started nonprofits, you work with many other organizations in bringing women to sport and bringing sport to women. I guess sailing isn’t as big in the United States as it once was.

Dawn: That’s probably true although it depends how you define it, is it how many people sail, how many hours you sail, if you watch it on TV. You know 20 years ago it wasn’t on TV so maybe it’s less popular in some of the resort areas where it’s a leisure sport. But I would say that it’s definitely more accessible to the general public than it ever has been. And so it’s evolved.

Joshua: OK. And you’re working at the top levels.

Dawn: Yes.

Joshua: Where’s your passion coming from?

Dawn: I think it’s simply a combination of I like what I do. I love being outside. I love competition and I’m good at it.

Joshua: OK, good at it. It could be sailing, could be teaching, could be…

Dawn: Specifically organized and thinking ahead. Being a visionary might sound conceited but seeing the future and seeing how we can progress forward and what we can do and how we can work everybody together to be absolute the best we possibly can.

Joshua: “We” Oakcliff? “We” all sailors?

Dawn: “We” the people that are close. We’re open to everybody to join but we don’t tolerate subpar. And that’s not me saying you suck it out. It’s everybody else having a moment talking to somebody. You got to up your game. This is a team. We’re all in this together. I mean bizarre. This is somebody who’s visiting but one of my guys just came down and said, “There is gum in the urinal and there’s crumbs on top. Was somebody really that hungry?” It is disgusting but I’m not going to have to say anything. He’s going to go and make an announcement, peer to peer, step up your game or you’re not invited back.

Joshua: This reminds me of the quote I told you before from Martha Graham, “Either the foot pointed or is not. No amount of dreaming will point it for you.” And I think that that level of… When I hear that level of attention to detail like that’s not too little detail. That’s not something you just hire someone to take care of like the toilets. Gandhi clean toilets. That’s one of my big thing, like a blog post of mine. Gandhi cleaned toilets. Are you so big that you don’t do that? On the contrary, it’s not where the art is.

Dawn: The art is in cleaning toilets. I am going to tell them that.

Joshua: The details.

Dawn: Yeah. The details. Yes. Everybody here… Could we afford somebody to clean? Actually, we do have somebody who comes in once a week to clean the whole facility so the best they can do is you know vacuum and sweep and the big stuff and yet we’re always re-cleaning because it’s not to the standard that we want. And it’s not a matter of asking somebody else or yelling at somebody else to do it. It ss a matter of stepping up and cleaning as you go.

Joshua: You do what it takes.

Dawn: You do what it takes but also…

Joshua: You take responsibility.

Dawn: You should have pride of your space and pride of your ownership and pride of your work and your work ethic. And you know it reflects poorly on me if you do shoddy work and we’re part of the team as vice versa if I do something stupid it reflects poorly on you. When everybody says, “What do you get when you leave Oakcliff.” And I say you get to be an Oakcliff graduate and of course the parents are like, “Where’s the certificate?” Well, first of all, they’re going to get a job if they want a job. They will get a job being an Oakland graduate. But one of the worst things that can happen is that it’s verbal right. Then if you fail, if you disappoint us for stupid reasons not because you just had a bad day, we will remove your status as graduate and it’s not on paper and it’s not in some kind of a database. It is just they can no longer call themselves a graduate.

Joshua: So I’m hearing honor…

Dawn: Definitely.

Joshua: …discipline, respect, teamwork. They must be clawing to get you to speak in places because… How long has this organization been around? Because I’m seeing a really tight ship here. I’m seeing like really tight community and people have each other’s backs. People who are listening can hear you but I’m here and they don’t know that I just walked through and there’s like the big shot back here with like sales being worked on and this. I think I saw sewing machines and like sanding down and like…

Dawn: Sanding and mastering, coding the mask for the class [unintelligible] shorthanded boat and they’re doing this. That’s Sean and Greg we’re talking about how they can come in earlier after work to get the right timing between the coats because they’re making this like the perfect job. I’m so proud of them for that.

Joshua: So if you told me this has been around for a century, I’d be like that’s the way you get to be like this but I know it hasn’t been a century. It’s been… How long have you been around?

Dawn: This is our eighth year and the first year was like finding out what was here and you know just getting our feet on the ground. And we planned to have the program, the training part of it, the first year is just organization. We planned on not having the training program till the second summer and people just started showing up. We’re like, “Oh, OK, let’s train you then.” But I would say that it took the third year, towards the end of the third year is when you just step back. It had a life of its own.

Joshua: I’m just amazed at how much is going on and there are all these things I wanted to ask you about and there’s so many… Like this is what sailing has been for me. Every time, and I know you’ve heard this before, every time I learn something, I learn more of what I have yet to learn than what I do learn. So I thought at the beginning I learned like five percent of sailing and now I’m down to… I feel like I know less than 1 percent.

Dawn: Like I said, there’s always something to learn and then technology changes and sometimes it helps to be a little bit older because you can go, “Yeah, that was a good idea in 1989 and that’s why this didn’t work.” Or you can say, “That was a really good idea in 1989. It didn’t work for this reason but technology has changed. Let’s try it again.”

Joshua: Yeah. I feel like if someone came to me and said, “Should I get an MBA?”, I’d be like, “Maybe Oakcliff’s what you want.”

Dawn: I totally believe in that and I’m sure that there’s a lot of academics listening. But for me like I said I used college and high school as a way to get experience. You know editor of the newspapers, in the band, I tried out to be a play girl. Instead I’ve played tuba. You know it was just like let’s try, let’s try, let’s try, hunger for learning. For me here it is not as structured in terms of there’s not book in curriculum. Well, there is a curriculum more or less but it’s an Excel spreadsheet. There’s more of like a really, really, really long-to-do list than checklist of what you have to learn. But it is learning and that that is the key we were talking earlier with Serena. And one of the super important keys that sailing lends itself to is you never stop learning. And I believe that most people enjoy learning.

Joshua: Yeah. I mean when I got here you set me up with Greg and Allen I was just watching some Olympic athletes. It was amazing. Thank you for making that available to me and that I can see… I mean it certainly looked grueling. Today is not like the most beautiful weather but it’s graceful. That I can see as learning is fun. Now people also have to sit in rows, listen to teachers lecture – that learning is not fun and I don’t think that particular affective except that… It’s effective at something. I wouldn’t call it learning though. It’s effective at like beating the spirit out of people. And this is a totally different environment.

Dawn: What’s so fun like I said is that if somebody says, “Can I do this?” I hardly ever say “yes” or “no”. I’m like, “I don’t know. Can you? How are you going to do it? Tell me. Explain to me.” Even if I already know, even if I already know what it’s going to be, sometimes I’m sitting there trying not to laugh because what they’re going to lay out to me can be so ridiculously bad. But by them actually saying it out loud they’ll usually realize how ridiculously bad it’s going to be.

Joshua: Are you really pulled away to the corporate world to help them with their stuff because…

Dawn: No. This keeps me so busy right now. I squeeze in when I can.

Joshua: Yeah. I mean I’ve been to a lot of… There’s a lot of places. I just don’t get it. And they’re still like bring someone in and teach theory or…

Dawn: I enjoy it. Just two weeks ago, it might have been one week ago, I was in Chicago in UL, an amazing organization.

Joshua: Underwriters Labs.

Dawn: Underwriters Labs.

Joshua: They check if equipment works, if it’s going to break or how it can be insured.

Dawn: And very much the same type of thing we do here. People that are driven to be exact. I met this guy that was their safecracker and he basically said…

Joshua: That’s cool.

Dawn: He was cool and he was you know army ranger and he was showing me how you know how he could do this and how he could do that. And at one point in just talking about all the geeks and the gadgets and the technology and what his job was and like the person giving the tour was starting to get a little bit like, “Oh, it’s time to keep moving on.”, at one point in there he was talking about bullet proof safe pods for schools and he was talking about the exact rules that he used to test that because he said, “This is not going to fail. Not on my watch.” And I went, “Yes!”

Joshua: Because you felt like that’s how…

Dawn: That’s how it is. Yeah.

Joshua: OK, you said you started off eight years ago and the first few years it was getting started and a big piece of leadership is getting great people. Look, I’ve only been here this morning or this afternoon but this dedication, this drive, this loyalty, this responsibility, was it just because you’re the only one who’s doing what you’re doing? Or was it because…

Dawn: Well, we are the only ones doing what we’re doing. There’s no place else like this in the world for the sport of sailing. Part of the success and this has been in past campaigns as well and every company should do more with apprenticeships and interns because it’s basically a tryout and they get to buy into you and you get to be part of their growth. And almost everybody here was a Sapling or an Acorn so they trained here before they were hired here.

Joshua: And so Sapling and Acorn these are the programs for youths that build into…

Dawn: Right. Well, for any age but the Acorns are more novice and specialized in short tournaments that you know tow in and then Saplings both feet then they come here the whole summer and they’re essentially an unpaid intern. And then we hire the cream of the crop or the ones that want to stay.

Joshua: Yeah. I want to point out how proud I am when Greg was telling me about this. I was like, “Oh, I get it. Sapling Oakcliff acorn.”

Dawn: Yes.


Joshua: To the listeners I try to get a story going through but here I’m trying to get a lot of little bits from lots of different areas of what you do because there’s so much of it but it all comes together as one unified thing. Actually, a lot of… I mean I feel like at the root of it is the joy of sailing and the joy of teaching and growing and learning. So now it’s the Leadership and the Environment podcast so I want to talk about the environment. Sailing is fundamentally environmental.

Dawn: Absolutely.

Joshua: Yeah. I mean it’s incredibly so. And so the listeners know that when you and I spoke the other day in Manhattan we were going on about getting garbage out of the water and things like that. And you didn’t sound like you’re faking that at all. You were I mean, on the opposite, it was clearly like you’re like, “Yeah, then people do this.” What do you think about when you think about the environment?

Dawn: It’s a really broad question. But just to give you an idea, sailors who are out there in the pristine ocean where you don’t have people around you and you see a fricking garbage bag, that’s disheartening. On the second round the world race we broke our radar and it was after we had a big piece of plastic wrapped around it in the middle of the North Atlantic.

Joshua: So thousands of miles…

Dawn: And the difference between the first time around in 89-90 and 93-94 was market so since the Earth… Since the Berlin Wall came down, I’ve been worried about plastic in the oceans. I didn’t know about micro plastics until the late ‘90s and then it’s like you’re sitting here telling people about micro plastics and they think you’re talking about outer space. I’m like no, they’re in the fish, at a microscopic level they’re in the plankton. The fish are eating the plankton, you’re eating the fish, you’re eating plastic, you’re eating your own garbage. What don’t you understand about this?

Joshua: Yeah. I mean it’s so disheartening. It’s disheartening. And well, you like me, I feel disheartened but then I also feel like, “Am I going to let this happen?” And you don’t seem resigned about it.

Dawn: No, no, no. And the other thing that’s important to know is that at least on an interpersonal level with the sport of sailing and people who see it and younger people which are unlikely to be around it’s not a hard conversation. Here we have complete mixed string everything recycling and people will come up to me and go, “Why don’t you recycle here?” I’m like, “Oh, no, no. We do. We do. We do.” I went down to Brooklyn and toured the recycling plant. It was amazing. It was like Willy Wonka and the Chocolate Factory but with garbage. You think how is it possible? And then you see how they have like readers that pop, with puffs of air pop the color glass they want to separate from all the other pieces of glass and you have the shakers and you have the magnetic wheels. It was amazing. It’s possible.

Joshua: This is really can-do because so many people… When someone says to me…

Dawn: Simi. Simi is the recycling.

Joshua: They give tours. Yeah.

Dawn: Yeah. I got a behind-the-scenes tour. I was special.

Joshua: I got invited to one of those. I couldn’t make it. But someone in my building is on that.  And I hope to go soon. And when I hear someone say, “Well, you can separate it but it all gets in the same place later on.” First of all, I don’t believe them. Second of all, even if that is the case, tip of the hat that you want to check it out. You may have enjoyed it but you didn’t know you would enjoy it. It could have been like a smelly place that you didn’t like.

Dawn: Sure. I actually was a little bit nervous. I was like, “Oh, well what have I done on my one day off in August?”

Joshua: Or August, it is going to be humid and sticky. And to me it’s if we want them to separate downstream and they’re not, the fastest way to do it is to separate upstream so that they know that because people get into the cycle that they really like where one person says like the consumer, a whole class of consumers says, “Well, downstream they mix it. So we won’t put it together.”

Dawn: Part of the reason I went to that was because I had so many people saying no, no, no. And I think we as a society or environmentalists or anybody could do a much better job of explaining that because in Michigan where I lived you separate everything and it would go into the same truck. [unintelligible] so don’t even bother. Nobody educated. All they need to do is tell the public that this is where you’re separating it and it’s going into the same truck on this truck because this takes you to the full mix. You know they had the old rules for the new technology.

Joshua: And I would say even if they didn’t separate it, if you don’t separate it, then they’re going to say, “Well, the people upstream don’t separate it.” Oh my God, so many people who care about the environment, who… I have to distinguish care about the environment / act on the environment because a lot of people say they care. Now to me caring and acting, if you don’t act… Here’s a phrase I hear a lot, “Be the change you want to see in the world.” Gandhi said that I think, and they don’t do it! Be the change. “Well, someone else is not doing it.” Well, you do it!

Dawn: I think my dad said it one too many times just the old thing about if a job’s worth doing is worth doing right. And that I tell myself that like I will be walking down the street and I’ll see a piece of plastic and I’ll be like super busy. And I’m like, “Man. Back up. Pick it up.” But it does take, and I think people here are like, “Well, you’re always picking on us.” I’m like, “I pick on myself too.” So I had to hold myself to that standard. But it’s not that hard. Just do it.

Joshua: Actually, I’m reading from you… When you said it’s not that hard, it may take calories and time or effort but I’m not reading that you’re suffering.

Dawn: No.

Joshua: What is it? When you act on something environmentally that other people might pass that trash by and not stop and pick it up?

Dawn: I don’t know. I think we talked the other day, I use it as my workout so I hate wasting time more than anything. So if I can figure out a way to pick up plastic, clean up the environment, enjoy the beach and get a good workout, win-win-win. So I pick up the garbage, I do squats, I do lunges, I sometimes stop and do push-ups, I use the heavy bags to do arm curls and tricep exercises. It’s fun.

Joshua: I love that. So many people are like “Deprivation, sacrifice, distraction from what I really want to do in life.” And you’re like, “What are you talking about?” Everything in life…

Dawn: I would rather do that than go to the gym. Sometimes I have to go to the gym because it’s a harder workout for what I do. But if I could just walk the beach every morning as my workout picking up garbage and then tragically at this point, I can’t enjoy the beach with the plastic and there’s always garbage so thus I must pick up the garbage to enjoy the beach. It’s a circle.

Joshua: Yeah. We’re not thanking people for putting the garbage there even though it gives us a workout. So let the record also show that there’s a barbecue going on and we’re not there yet. And so more gracious with your time. And I hope the people are getting the value that you can get from sport in general but also you’re at the peak of this. You could have retired and you’re… I didn’t meet you earlier, I mean earlier in your life, but I feel like if anything you’re accelerating.

Dawn: Yeah. Evolving but yeah.

Joshua: And on the environmental side as well. I presume when you were younger it was not an issue as much because you didn’t see as much plastic in the ocean.

Dawn: No, we didn’t see plastic at all. I grew up in the Great Lakes and we would drink the water out of the lakes. The biggest environmental thing we did was put a sweater on and I’m not turning the thermostat up. Take shorter showers. We’re like, “Well, the hot water is going to run out anyways so we better take a short shower because you have the hot water heater turned down so low, mom.”

Joshua: So when you spoke in New York I told you about how I ask people on the podcast based on what the environment means to them if they’re up for it and it’s at your option to…I mean you’re already doing a lot and maybe you probably… I want the listeners to hear this. You’re probably doing more than most people and some people think, “Well, I’m doing enough. Why should I do more?” But I have a feeling that’s not how you look at it.

Dawn: No, no, no.

Joshua: And did you come up with anything that you want…

Dawn: There’s one thing that I want to do. So here at Oakcliff obviously we have mixed recycling everything. We don’t allow single use water bottles although I see one hiding behind a computer. And if they saw me seeing them walk in with it, they’d be in trouble. We have everybody bring their own lunches other than the volunteers and umpires because we found that when you try to package up a lunch for a sporting event to give to your competitors, it’s a huge amount of waste. Not only of the packaging to get it to them but also the food that they don’t like, “Oh, they don’t like tomatoes.” That goes in the water. We cut our garbage in half per week by doing that, one simple thing which is amazing. We have solar tubes upstairs so we don’t have to have the lights on as much as possible. We do compost. The one thing that I want to do, there’s a whole list when you’re nonprofit, but I want to build the deck out of the dorms upstairs so that we can then use the rain garden to grow some of our own vegetables for here. So then we’re feeding ourselves using the compost because right now I bring some of my compostable stuff from home in my car, up the stairs, under the roof into the compost bin and then take the compost home with me which seems a little bit crazy.

Joshua: So I want to point out that when we were speaking last time I was talking about how I found it more convenient now that I cook from scratch and you were like, “Yeah, of course.” And you talked about the salad that you made and you’re just grabbing all these vegetables and herbs and things from your garden. And you know when you get home after a late night you still do…

Dawn: That’s a classic. Everybody’s like, “Oh, I don’t have time to garden. I travel too much.” I’m like, “Are you kidding me?” I travelled a lot before I was here and I would have my garden just outside. I lived on the Lake St. Clair and Michigan. And so it was naturally being watered because there’s [unintelligible] next to the lake and the canal. And I would come home and I would have like a piece of chicken in the freezer and go outside and get some peppers and some tomatoes and I would have a wonderful fresh salad that was so much more convenient and it was because I was so busy that I needed that.

Joshua: I love it. Yes. Thank you for living this way. Oh, and also when I got here and you said there’s sandwiches and you’re like, “They’re wrapped in plastic wrap.” So you’re sensitive to that as well. I appreciate that.

Dawn: I just don’t have a better solution right now to give to umpires to put in their duffel bag to take out in a small boat in the water. We do have reusable coolers so we don’t give them plastic bags or anything but that’s a tough one.

Joshua: I see the wheels turning. Well, is there something you’d want to do? It seems like you want to do the composting here. Is that something that you want to do for this podcast as something that… Because the next step is after it’s done I want to…

Dawn: If your listeners want to help me raise funds to build the deck in the rain garden because all we need to do is put a rain barrel on the roof.

Joshua: I’m definitely going to put links on here so people can learn about Oakcliff and contact you if that’s OK with you.

Dawn: And also, I need to get this building purchased or another 10-year lease and then I can invest in that. So it’s all circular.

Joshua: So helping Oakcliff is helping sailing, helping people learn leadership. I’d look at American leadership and we could use more people teaching like you because we have people from like Ivy League, business schools and law schools and stuff like that. I think they could learn a bit from you. I mean they got these fancy degrees…

Dawn: They could come here, we could do team building. It could be a win-win.

Joshua: Yeah. But I want to see if I can get something like a project that I can talk to you afterward. It doesn’t have to [unintelligible] but something that’s acting on your values and that you want to be redoing. And you don’t have to fix all the world’s problems, it can be small, but something you know a SMART goal so with time…

Dawn: You know what? Obviously, I want to get the rain garden, everything going on the roof but I’m going to try to figure out if there’s a way for me to do some other kind of wrapping for the sandwiches like I use the silicon tops for my dishes. You know I just have a normal dish rather than using Saran Wrap but that’s plastic again but it’s reusable forever and ever and ever for bringing my lunches in and that kind of stuff. All right. But you know what? What is cool about Oakcliff is we’re innovative in the sailing and how we run races and how we organize and every single day somebody here comes up with some way of doing something better and we know about the environment. I told them about meeting you. So our morning meeting the next day was all about sailing and how you know flying… You said that being on a train is what one third or two thirds?

Joshua: It depends on the distances and so forth. A third of the greenhouse.

Dawn: Yeah. So a third. So then all of a sudden they were like “wow” and then they started you know…. So we were having the conversations.

Joshua: Oh, awesome. I’m flattered. I am honored. I am humbled. And we have on our calendar for what is it, two weeks from now, something like that when you’re going to be in Manhattan.

Dawn: Yep. Celebrating New Heights. It’s a fundraiser that we’re having at the top of the Nasdaq building. I could say I’d make everybody walk up but I don’t think they can charge them one hundred and twenty-five dollars for a ticket for a fundraiser and make them walk.

Joshua: Oh, I know what you do. If you charge them one hundred and twenty-five dollars, they could take the elevator. If they wanted to walk, they’d pay two hundred and fifty dollars. So when we meet then maybe could we talk about how the sandwich issue gets resolved? If that’s enough time.

Dawn: We can try. The simple one is aluminum foil better than plastic probably. I will research. I will have an answer.

Joshua: What would you say if someone came to you with that to you and say, “I don’t know. You tell me.”?

Dawn: Exactly. I’d say wax paper maybe. I don’t know. I’m going to research it. I’ll let you know.

Joshua: Okay. Yeah. I’m thinking it could be reusable containers that you just… But I don’t know if they need to…. I don’t know the conditions. Do they have to hold on the sandwich for a while before they eat it?

Dawn: Yeah. It goes in their duffel bag.

Joshua: And now you got me thinking.

Dawn: I tried to make a lettuce wrap today and that was a failure. Just to give you an idea. I get the three-foot beggar, I cut it, I put like cream cheese or something to protect the moisture and I put the fixings in and then I squish it and kind of stretchy it with the Saran Wrap. I use as little as I possibly can but I still use a piece of Saran Wrap or…

Joshua: I wonder if maybe something like more kale then or a colored green than lettuce might be a little…

Dawn: No, no. They have the bread.

Joshua: Okay. Now you got me thinking.

Dawn: Yeah. Well, I could have done a better job of the lettuce wrapper. That guy was also lactose intolerant so I couldn’t use cream cheese to glue it together. So many, many, many challenges.

Joshua: Man, I love your take on sailing but I want to focus on the leadership part of the attention to detail, the empathy, the enthusiasm, the social and emotional skills, the method by which you approach it is not like, “Here’s what to do.” but “Here’s how to get there.” That’s what I’m reading.

Dawn: Right. Right. It’s always the process and how can you do it better and you know every once in a while, because I’ve been doing it for so long I’m like, “Guys, just trust me on this. This is the way you do it.” With that being said most of the time we have some kind of circular conversation/argument about how to do something is when we agree that there are many ways to do it but we choose the Oakcliff way. There’s all sorts of different ways to do it but this is the way that we’re going to agree to do it. Done.

Joshua: I’ve learned a lot from this conversation. And sorry to the listeners but I’ve learned more from being in this environment and if anyone was listening to this, I mean I’m 47. I think you’re at your peak is like 18 to 30, high school kids, college kids…

Dawn: In the sport of sailing it keeps going. But yeah.

Joshua: I guess because cruising is like accessible at all ages and…

Dawn: Even racing. It just depends which part of it. They always say you start off young and dumb and strong in the front of the boat and as you get smarter and older you move to the back of the boat and tell those people what to do.

Joshua: So man, people look up… I’ll have the links, so follow the links to Oakcliff, follow links to look up more about Dawn herself and I hope this sends people your way whether it’s… One, for the people I hope they get it, people who are more interested in sailing and on the business side, I hope I get people tugging away from this as much as…Does that make your life difficult?

Dawn: No, it’s okay. And they also within you know schedule and I truly enjoy going and speaking to companies and people you know that are themselves hungry to learn.

Joshua: Well, I like to close with a couple questions. One is, is there anything I didn’t think to ask that’s worth bringing up? And the other is is there anything you want to say directly to the listeners, to the Leadership and the Environment listeners?

Dawn: We could talk for 10 hours so we’ve covered probably enough. And then the other thing is is that obviously I’m a you know passionate about the sport of sailing. Oakcliff is open to the public. We’re a public nonprofit. We’re in Oyster Bay, New York. We’re relatively close to Manhattan about an hour depending on which train you take. But there’s places all over the country that are reaching out and advocates for the sport as well. They’re just not quite Oakcliff but anywhere in the country if you want to get involved in the sport of sailing, it’s not that hard. It is not elitist. There’s a lot of really good passionate people in the sport.

Joshua: Oh, then I have to add to that. From my experience the reason I didn’t sail before was I viewed it as elitist. And the reason I’m sailing is that it’s not flying and because I want to get some more of that flying and flying costs a lot more than sailing. I mean I joined this thing so I could go all summer long and I’m like the amount of time I’m getting out of it compared to the cost is so much better than the flying. And it’s really accessible. I mean I go out on the water and it’s maybe a mile or two from home and it’s a world away. And I mean physically, emotionally, mentally, the people it’s just… And yet how long have humans sailed? 10000 years?

Dawn: Egyptians. I mean the first navigators, the people that left we don’t know where exactly Hawaii and New Zealand, Tahiti, those are all the same people and they got there on rafts with sails, they followed the stars and the currents and the stories, the oral history came back. There’s the book I mean it’s called The Last Navigator or something. it’s been forever and ever and ever.

Joshua: Yeah. I mean it’s such an amazing experience and so accessible. I had no idea how accessible it is and how much when you show interest to people who have sailboats they’re like, “Come on.”

Dawn: Exactly. Yeah.

Joshua: So yeah. Thank you for mentioning that. And I hope you don’t mind that I augmented that. Well, let’s leave it there. I look forward to talking to you in a couple of weeks. And Dawn Riley, thank you very much.

Dawn: Thank you. Thanks for coming out. See you soon.


Did it come across the force of nature that she is? Very few people succeed at her level in sports or business or education or in life. If you’re thinking of ways to follow up on this, first I recommend getting yourself on a sailboat. If you haven’t done it before, I think Dawn would be very pleased to learn that one of the outcomes of this is that a lot of people got on sailboats. If you didn’t know, I met her because I’m learning to sail. I’m learning to sail because I’m learning how to travel without flying and just because it’s not flying, it doesn’t mean it won’t be really enjoyable. Sailing is really great. It’s a whole other world. Second, what everyone says that they don’t have time for that is bothering with the environment she does without a second thought. I put to you that maybe not paying attention to the details keeps us from succeeding at her level and maybe paying attention to details creates leadership, not distracts from it because she’s worrying about the bathroom, she’s worrying about how you wrap up sandwiches, she’s making meetings happen in preparation for meeting me that she didn’t have to do. She pays attention to these details and you might not have heard it in the conversation with me but you can see it in the conversations she has with everybody that she knows details about everyone, she cares and it comes off and people want to follow her. You just can’t argue with that level of success despite or because of that level of detail because she’s not faking anything. Anyway, I look forward to hearing how she resolves this issue of how to wrap sandwiches because I can tell that once she gets the sandwiches down, she’s going to use what she learned there for other things and then I can learn from her.

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