When Diana Riley heads to the golf course, she is doing more than hitting a little white indented ball. She is swinging with purpose.
When Diana moved to Naples in 2012, she wanted to do much more than play golf, socialize and relax. She wanted to transform her love of golf into helping others. She founded Swinging with Purpose, a nonprofit dedicated to raising money to help organizations in this area that assist women, girls and children.
“I have always been involved in the community and always around golf,” Diana says. “I have always had a passion about giving back to the community. When we made the transition to here, I couldn’t play golf every day. This way I get the best of both worlds.”

Alex Driehaus
Diana Riley poses at Quail West Golf and Country Club in Naples.
Diana teamed up with golfer Nancy Lopez who acted as the spokeswoman for SWP.
“I met Nancy Lopez and shared my vision of Swinging with Purpose and she said, ‘If there is anything I can do, let me know,’ and the rest is history.”
Swinging with Purpose raises money through an annual golf tournament and a yearly Battle of the Sexes golf tournament. Some local country clubs help raise money, too. Since the group was founded in 2014, it has raised $575,000. Every year organizations apply for a grant. Every group selected is local and helps women, girls or children.
Laces of Love, which gives shoes to local children in need, is one of the recipients.
“Diana Riley has been like a big sister to me,” says Laces of Love co-founder and president Jeanne Nealon. “She has not only supported our charity, but she has helped me partner with other charities in the area, so Laces of Love can extend its arms out and help so many other groups. She has helped so much over the years, supporting us, coming to our events, motivating me, giving me guidance and her wisdom and experience. She is the real deal. She is really one special lady.”
Our Mother’s Home of Southwest Florida has received funds from SWP for years. It has paid for vehicles, employee retention and more.
Karen Watson, executive director of Our Mother’s Home, says the vehicle purchase allows the girls living there to have transportation without having to be in a huge van.
“It helps them feel less institutionalized than in a big group home van,” Karen says. “They want to feel like other kids. It helps the girls feel normal. She has helped us in many ways.”
Donors to Swinging with Purpose receive a bracelet of black onyx beads with a tiny golf ball. Diana hopes that will become a known symbol of the organization.
“My goal is creating this brand, which is Swinging with Purpose,” she explains.
It’s a name that she knows fits her cause.
“I always believed that purpose is important in who we are and what we are,” she says. “Purpose to me is very important. When I wanted to do this philanthropic approach, it just made sense to swing with purpose.”
Diana comes from a history of giving.
“My father was always involved in the community,” she says. “It was what I learned growing up. I do think that parents pave the way for a generous heart for their kids. I believe it is learned behavior. I attribute a lot to him. He was always giving.”
She’s passed on that trait to her husband, Hollins Riley, and her children.
“I am blessed that I have a husband who is OK that he has a wife that is giving up her time and our dollars for Swinging with Purpose,” she says. “We just believe that as a family if you are blessed you should want to share those blessings.”
Sharing those blessing didn’t begin when she moved to Southwest Florida. It was something she has done all her life.
Diana grew up in Annapolis, Maryland, and she received a business degree from the University of Maryland. She owned a travel agency and later a reinsurance consulting business. Diana was also dedicated to giving back to that community. She volunteered with The First Tee, a group that helps introduce poor inner-city children to golf. The children learned the game and got to travel to competitions as long as they met certain academic criteria in school.
“This particular facility provided stability for them,” Diana explains. “For so many of these kids, it was their safe haven. They were fed, safe, exposed to the game. Its message is ‘Golf is the carrot, education is the key.’”
Diana says the experience was incredibly rewarding.
“I love young people, so working with young people is always inspiring for me,” she says. “A lot of them never left the city, and we had golf tournaments and golf venues where they would compete with kids in the Bahamas. Many of these kids had never been on an airplane, never seen the ocean. So for many it was life changing.”
She was also part of a program to mentor young entrepreneurs.
“We were geared to teaching them to make a difference in their community and make some money,” she says.
Diana stresses that SWP isn’t just a one-person group.
“The Swinging with Purpose is the result of my board of directors, and I have an amazing village of people on my board that are so committed to the purpose of Swinging with Purpose,” she says. “It happens because of this village of support I have behind me, both my family and the board, and we all make this happen.”
As an avid golfer for more than 25 years, Diana says she loves a life where she can play the game and help others at the same time.
“To be able to do what I love to do in a fundraising perspective is a win-win,” Diana says. “It doesn’t get any better than that.”