#068: Taking The Helm - Oakcliff Sailing Executive Director Dawn Riley

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.

Find out more about Dawn at dawnriley.com, oakcliffsailing.org and @oakcliffsailing on social media. Her book is “Taking The Helm.” 

Read the full episode transcription here and learn more on The Jedburgh Podcast Website. Check out our video versions on YouTube.


 -Dawn discusses the vision of Oakcliff Sailing, the support given by the Lawrence Family and how they have grown into a premier sailing development school by growing Saplings, Acorns and Mighty Oaks. (6:35)

-Dawn was the only woman on A3, the 1992 America’s Cup winning team; she describes what it was like being a woman in a male-dominated sport, what they saw in her and how we reach gender equality in sports. (15:34)

-Fran and Dawn engage in critical conversation on raising middle school kids, why Dawn entered sailing in the first place, and how her initiative America True is helping kids. (19:00)

-The importance of diversity in building great organizations. (29:19) 

-”Taking The Helm” is Dawn’s autobiography highlighting the 1993 Round The World Race and how Dawn was thrust into the skipper role to lead the team. (35:22)

-Dawn shares her unique leadership style, how to balance empathy with authority and what America needs from the next generation of politicians. (41:08)

-Fran challenges Dawn to explain how the evolution of sailboat design has changed the sport, but the basics of sailing are still critical to winning at every level. (51:51)


-”We’re building American leaders through sailing.”

-”The only things that were super upsetting, like in a weird way, I was tired of wearing men’s clothing.”

-”I just hit the sweet spot between competent, determined, not phased by a bunch of bs, able to handle it, give as good as I took  and I love the sport of sailing.”

-“I was told by the person who was hired to select the team that I would never be in the back of the boat.”

-”Everything I’ve done in my life, I truly enjoy the process.”

-”Having a diverse team…diverse thought, diverse background…will make your company stronger.”

-”I want to be proud to be an American. I want to be emotional when the Star Spangled Banner goes.”

-“You need to have women in decision-making across the board.”

-”You need to have a space to clear your brain…sailing and on the water engages all your senses.”

Dawn’s 3 Foundations to Success

-Wake up and create task list

-Work out

-Look at (or be in) the water

This episode is brought to you by Jersey Mike’s, 18A Fitness, and Analytix Solutions