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Speaker Series: Dawn Riley

By Sandra Santana
Emma Willard School welcomed 2021 Commencement speaker, Dawn Riley, back to Mount Ida this week as part of our 2021-2022 Speaker Series and launch to Women's History Month. Dawn is a world-renowned sailor, speaker, author, commentator, consultant, coach, and mentor. As CEO and captain of America True, she was and still is the youngest person and only female ever to lead an America’s Cup Challenge. She went on to be the first American, man or woman, to sail in four America’s Cups and two Whitbred Round the World races, now known as The Ocean Race.
How do our journey’s shape us? Well, part of that answer depends on where your launching point is. In Dawn Riley’s world, the starting line was the open seas, where she made a name for herself in competitive sailing. While her journey was never as simple as A to B, over the years she learned how to guide herself, and others, through uncharted waters– literally and figuratively. 

Sailing was about as natural for Dawn as riding a bike is for most kids. Just about everyone in her family had spent their lives out on the boat, dating back to her great-grandfather, a sail and canvas maker in his day. When Dawn turned 13, her parents decided to take their family from dry land in Michigan to the sea on a year-long sailing trip. Together, the Riley family ventured from Detroit through the Erie Barge Canal, up to Maine, down to Florida, over to the Bahamas, Virgin Islands, Grenada, and eventually headed back to Michigan. During this time, Dawn never actually stepped foot in a classroom for her entire 8th grade experience. When she returned for her freshman year of high school, her new life experiences helped her notch straight A’s for the first time in her academic career. “You can do things unconventionally and still be successful.”

Back home in Michigan, Dawn realized she needed sailing, she craved sailing. The only problem was there were not exactly resources set aside for junior sailors at that time. If she wanted to get out on the water, she needed to make it happen on her own. “I would go accost people at the yacht clubs that had boats and say, I want to go sailing! Pick me up!” And that they did. Once Summer rolled around, Dawn found herself working on the boats, picking up odd jobs to be closer to the water. “Anything I could to feed my passion and my obsession with sailing.”

Dawn’s journey across the seas steered her to Michigan State University, earning herself not only a roster spot on the sailing team, but team captain distinctions. Her best advice for any student-athlete pursuing sailing? “The education is first, and the sailing is second. You know why? Sailing is one of those sports that is a lifetime sport… you don’t have to force it all in right when you’re trying to get your education.” 

Shortly after college, a 24-year-old Dawn met Tracy Edwards, another experienced sailor looking to build the first all-female team for the 1989 Whitbread Round the World Race. It was the first time The Whitbread was making a stop in America, calling into Fort Lauderdale, Florida. Dawn knew she had it in her to be a part of the Maiden crew, and Tracy believed in her too. 

After nailing the audition, Dawn officially joined the Maiden crew for the ’89 Whitbread, cementing her place in history as part of the first all-female crew in this race. Although this was a great win for all, Dawn and her teammates abilities were scoffed at by their male counterparts. “We were at a point in society where they figured that we were going to cry, we were going to get into fights, we were going to quit. They even made the jokes that if we didn’t put our hair in ponytails, we wouldn’t be able to see because the wind would blow it in our face.”

Dawn and the Maiden crew would have the last laugh, finishing in second place, once again marking their place in history with their all-female team. Dawn would go on to race in another Whitbread, but found her love of racing with America's Cup, which she opted for over a stint in the Olympics. America's Cup was a chance for Dawn to continue to blaze a path forward for other female sailors. The only woman on the ’92 America’s Cup team, she was a vital piece of capturing her teams’ victory. 

Once Dawn took the reins of the America’s Cup team, she leaned into breaking down all the barriers that once held her back. As the first female and youngest person to ever hold the title of CEO of an America’s Cup team, her crew made a point of putting the right people into the right places. “This led to about 25% of women in every department, from the sailing team, to the shore team, to the design team, and support team.” It wouldn’t stop there. Dawn would also go on to coach the French International team, joking, “It was really helpful that I had just taken two semesters of French in college.” 

Dawn’s experiences have now led her to the helm of the nonprofit organization Oakcliff
Sailing, which is building leaders through sailing. Oakcliff is the training partner for the New York Yacht Club’s America’s Cup team, American Magic, The Ocean Race’s 11th Hour Racing, and is working with US Sailing training the next Olympic champions. Dawn 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. 

Dawn’s hard fought journey has helped create the space and awareness to welcome other women into positions they had never previously held before in the sailing world. Although she has encountered storms along the way, Dawn has always found a way to run her checklist to success. “Sometimes your day starts out really crappy, but if you keep your strategy, reboot, deep breath, focus– the sunrise is going to be very special.”
    • Dawn Riley returns to Emma Willard School!

    • Maiden, the documentary, by Sony Pictures

    • Dawn at sea

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Honoring its founder’s vision, Emma Willard School proudly fosters in each young woman a love of learning, the habits of an intellectual life, and the character, moral strength, and qualities of leadership to serve and shape her world.
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