As much as Diana Riley loves golf – for all the ways it has shaped her personally and professionally, brought new relationships and different experiences – she still found, upon retirement 13 years ago, that playing golf could not be her full-time thing.
“I said, there’s something left in my tank,” said Riley, now 64. “I just cannot play golf every day, there has to be something more of substance and purpose.”
The project that resulted fills a space previously unheard of in golf. Riley, with a background in reinsurance and a bloodline in caring for others, felt that the philanthropic dollars raised in the golf community could go farther. Focusing on non-profit organizations that serve women, girls and children, Riley made it her mission to get into the community and find the people doing work that could benefit from those dollars. Through Swinging With Purpose, a 501(c)(3) non-profit, Riley gives small non-profits a golf platform and exposes them to her audience.
“For us, for the Swinging With Purpose family of beneficiaries, our goal is to advocate, assist them with their fund-raising or financial needs and create awareness that they exist within their respective communities,” she said. “If we do that for them, we’ve accomplished what we set out to do.”
As Riley, who came to the game through business 30 years ago, dreamed up Swinging With Purpose, she worked with a friend who is a trademark patent attorney to file a trademark. It was also during that time that Riley met Nancy Lopez at the CME Group Tour Championship in Naples, Florida. Riley laughs that during their first interaction in the clubhouse, “I probably acted a little bit like a groupie, I was so excited to meet her,” but Lopez invited her to sit down and visit nonetheless.
Riley felt the two women’s hearts connected, and they developed a friendship. Lopez followed through on her offer to help Riley in any way she could, and she became a spokesperson for Swinging With Purpose. Lopez supports Riley’s mission in person, but she has also become someone with whom Riley can talk through things and collaborate.
“I have Nancy’s heart, not just her name,” Riley said. “That’s what makes our relationship special.”
Riley built the foundation of Swinging With Purpose in Naples and the trademark is still active there with Wellfit Girls, an organization that empowers teen girls through leadership programs, even though Riley relocated to Orlando three years ago and brought her work with her. In 12 years, the organization has made a combined impact of $1.3 million in the two communities and Riley is continuing to build.
“I did not know what to expect about the Orlando community at large, I was new here,” she said of the transition. “I spent a year kind of learning the community, identifying the pockets of need and it moved me to come out of retirement.”
Riley’s marquee event is the annual charity golf tournament, the Applied Underwriters Invitational benefiting Swinging With Purpose. She relaunched that tournament in Orlando at Lake Nona Golf Club in February 2024. Outside of that event, Swinging With Purpose conducts ancillary fund-raising throughout the year, often serving as a support vehicle for a women’s golf association to “swing and make a difference” for a charity of their choice.
Riley already has begun to build a family of beneficiaries in Orlando. She has melded into the community so quickly, in fact, that she and her team have now implemented a grant application process and will award close to $100,000 in grants to five small, grassroots non-profits that serve women, girls and children for 2025.
The 2025 Applied Underwriters Invitational is scheduled for Feb. 24.
Riley is passionate about networking and recognizes that many of the beneficiaries of Swinging With Purpose dollars overlap in the communities they serve. She has been a conduit in that way, which shows that help doesn’t always come in the form of a check.
“We’re hopefully providing a platform and awareness and organic collaboration within the family of beneficiaries,” she said, “and having them reach out to each other and into their communities at large.”
The power of connection is evident as Riley’s reach grows throughout Orlando. Swinging With Purpose recently entered into a strategic partnership with the Boys and Girls Clubs of Central Florida that stemmed from an on-course conversation between Riley and Jacqueline Bradley, who, together with her husband, Clarence Otis, donated funds to open a state-of-the-art club in Orlando’s West Lakes community.
“I’m telling her about the tournament and she said, ‘How come we’re not doing something together?’ ” Riley remembered. So Bradley helped organize a meeting with Riley and Jamie Merrill, the president and CEO of the Boys and Girls Clubs of Central Florida.
Riley is filling a void for the club by opening a door to a golf fund-raising platform and in return asked the club to find ways to share the wealth and reach deep into their community to support the smaller organizations with much smaller budgets.
“Partnering and supporting other non-profit organizations is something we are passionate about and look forward to continuing to do,” Merrill told GGPWomen by email. “Lifting up other leaders and agencies through the power of connection and collaboration supports the community at large and, as a result, benefits even more children, which is always our focus!”
“The future and my vision would be that we’re swinging with purpose for women, girls and children across the country.” — Diana Riley
Funds raised through the Applied Underwriters Invitational will support the more than 200 children, aged 6 to 18, served at the Bradley-Otis Center.
Conversely, Shante Barton-Stubbs, the founder and executive director of New Youth Imaging Center, can’t quite remember how she came to know Riley. The relationship has been transformative for the work her organization does providing a safe space, mentoring and support for youth in the Central Florida area outside of school hours.
In 2024, New Youth Imaging Center was the primary beneficiary of the Applied Underwriters Invitational. The Center received a $50,000 check to put toward summer camp, which helped bring “on the go” services to communities outside their brick-and-mortar location and fund field trips to provide exposure and experiences.
“It was a summer of our dreams and that wouldn’t have been possible without the help of Swinging With Purpose,” Barton-Stubbs said.
A Swinging With Purpose partner also donated new laptops for the center that middle and high school students could use to prepare for college, and younger students could use for things like online tutoring.
Barton-Stubbs said Riley has called her on several occasions since their relationship began. She’s a motivator and a mentor who is always paying attention, always asking questions and always trying to connect the dots to whom she knows may be able to help the bigger picture.
“It’s more than just saying hey, we want to give you some money,” Barton-Stubbs said. “She wants to see you be able to serve more.”
Riley operates with a five-woman board of directors, all of whom are volunteers. It’s a small but effective operation, and Riley is proud that the majority of dollars raised go back to the community. That efficiency is reflected in Swinging With Purpose’s 97-point rating by Charity Navigator, which gathers data on the cost-effectiveness and overall health of thousands of charities.
Riley recognizes that hers is a business model that “takes some time to understand and put your arms around.” The future of Swinging With Purpose lies in expansion, though she’s been cautious about planning growth in a way that doesn’t overstretch her capabilities or compromise success.
“My long-term vision with Swinging With Purpose and the reason it was trademarked is to offer our secret sauce for success in golf fund-raising to organizations nationally,” she said. “The future and my vision would be that we’re swinging with purpose for women, girls and children across the country.”