When asked about a word that he thinks his friends and colleagues might use to describe him, Chip Gaylor says,“I believe it would be humorous. I try to find humor and the positive side to issues.” This light-hearted attitude has served the senior law partner well in his personal, professional and philanthropic endeavors, as evidenced by his 2023 SRQ Good Hero nomination. 

W. E. “Chip” Gaylor was born at Sarasota Memorial Hospital and lived in Sarasota until age 10 when his family moved to Nokomis. There, he attended Nokomis Elementary, Venice Junior High and Venice High where he graduated in 1982. He later graduated from Asbury College in 1986 with a BA, The Washington College of Law at the American University in 1989 with his JD and the University of Miami Law School in 1990 with his LL.M. (Master’s in Law in Estate Planning). He feels fortunate to have his parents who still live in Nokomis and is proud to be married to Bryle Gaylor, a CAD interior designer with Westwater Construction. 

Gaylor first practiced law with the Sarasota/Venice law firm of Isphording, Korp, Payne, Muirhead, White and Horlick, PA. In 1992, attorney Bill Muirhead asked him to join him in a new practice which is known today as Muirhead Gaylor Steves & Waskom, P.A. where Gaylor serves as managing partner.  In his first year of practice in the Isphording firm, attorney Cliff White introduced him to Stewart Stearns, the CEO and President of the Community Foundation of Sarasota County. Shortly thereafter Gaylor was asked to serve on the board of directors, which he did for nine years, serving as Chair of the board from 1995-1997. After he termed off the board in 1998, along with his partner David Steves, he was asked to serve as general counsel to the Foundation. He still serves in this capacity today.  

Gaylor’s philanthropic spirit is something that comes naturally to him, although he attributes much of it to being a local resident. “Living in Sarasota County, one is surrounded by a history of extremely generous people who gave so selflessly,” shares Gaylor. “That giving spirit continues with new arrivals daily. It is life affirming to be around these individuals, and it just inspires me to do what I can to add to the philanthropic fabric of our community.”

With many success stories to share, Gaylor especially enjoys hearing feedback about how a scholarship to a non-traditional student has changed his or her life. “Having a direct positive impact on an individual who is trying to better his or life is extremely satisfying,” he says.

In addition to his involvement with the Community Foundation of Sarasota County, Gaylor has served on several boards, including the Sarasota County Bar Association (President 2017-2018.), the Southeastern Council of Foundations in Atlanta, GA (Chaired 2000-2002), the New College Library Association, the New College Foundation, the Sarasota Yacht Club, the Sarasota Arts Council, SCOPE, the American Cancer Society—South county and the Laurel Civic Association. Currently, he does not serve on a board, nor does he intend to. Instead, he enjoys serving on task forces with a defined goal to be achieved. Most recently, he served as co-chair of the Disaster Recovery Task Force at the Community Foundation addressing needs after Hurricane Ian. Good friend and nonprofit consultant Julie McMullen says “Chip’s concern and desire to make a difference is deep within his character. Most people who know him have witnessed his charitable spirit.”

In his free time, Gaylor enjoys all water-related activities including boating, scuba diving and fishing. He also likes to work in his yard and read, and is currently exploring setting up a podcast to discuss solutions to our nation’s problems instead of just complaining about them. “I plan to call it Down the Middle,” he says “as the vast majority of Americans are sick and tired of the two extremes.   

“All of us are smarter than one of us,” a saying that he freely admits stealing from Roxie Jerde, the CEO of the Community Foundation of Sarasota County is a favorite of Gaylor’s, and a testament to what can happen when a community works together to solve issues. “I also love the saying, ‘if money can fix a problem, it is not a problem’,” he adds.  

Living by his own personal rules: ‘if it is not chocolate, it is not desert’ and ‘visiting family is not a vacation,’ Chip Gaylor’s sense of humor, outstanding civic and charitable leadership qualities and commitment to the community make him a true local hero. Chip Gaylor was honored as one of SRQ Magazine’s good heroes in March 2023.