3 Generations Strong

Winston Churchill once said, “We make a living by what we get, but we make a life by what we give.”

Rachel Chiles, Betsy VanderLey and Kay VanderLey – a daughter, a mother and a grandmother – have passed the giving gene from generation to generation.

Inspired by childhood flights with her maternal grandfather, Rachel Chiles took to the air for her career. Before she took flight, Chiles earned her bachelor’s degree in international business with a minor in French from Stetson University, traveled to Kenya to work with HIV/AIDS orphans in Nairobi, and worked as Commissioner Scott Boyd’s aide for his first four years in office. Then she joined the U.S. Army to earn her wings.

Chiles served one tour in Germany where she flew United Nations missions, transporting ground forces to and from the battlefield. She is now a Blackhawk helicopter pilot stationed in Fort Benning, Georgia, where she flies medevac assignments and Ranger missions.

The importance of philanthropy was instilled in Chiles at an early age. Her grandmother, Kay, is a trained minister for Stephen Ministries, which provides life-transforming care to millions of people across the country. For six years, Kay spent two days a week volunteering at the Lake County Jail. She is also the former president of the Bloom and Grow society. Her philanthropic efforts earned her the award of West Orange Community Champion from the West Orange Chamber of Commerce in 2003.

Chiles’ mother, Betsy, is the president of the Continuum Collaborative LLC, a business development and strategic planning firm. She is a member of Commercial Real Estate Women and the Society of American Military Engineers. As a member of the West Orange Chamber of Commerce, Betsy participated in the Leadership West Orange program and earned the WOCC Member of the Month Award in 2013 and the WOCC Chairman’s Award in 2014. Her dedication to local nonprofits includes involvement with Home at Last, Matthew’s Hope, the Winter Garden Relay for Life, the Oakland Heritage Days Festival and more.

This remarkable family of women has given their time and support to others through three generations, an inspiring example of leadership and selflessness for others in their community.


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Written by Kristi Gomen

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