One evening, you might find Jason Stephens dressed in a tuxedo at one of Naples’ premier resorts, attending a multi-million-dollar fundraising event. The next day, he may be on a baseball field in shorts and a T-shirt, coaching a Little League game.
For Stephens, giving back has always been part of being a member of the Naples community he calls home. Throughout the years, he has dedicated his time, resources, and leadership to supporting a wide range of local causes.
Stephens and his wife, Kelly, attend roughly a dozen charitable events each year benefiting Southwest Florida nonprofits, including the David Lawrence Center and the Boys & Girls Club. He recently served as chairman of the American Heart Association Heart Ball at Hyatt Regency Coconut Point and continues to serve as vice president of the board for SWFL Children’s Charities, the organization behind the annual Southwest Florida Wine & Food Festival.
Alongside his philanthropic commitments, Stephens is raising four children, coaching youth sports, and growing his financial advising business. Managing it all requires dedication and balance.
“Well, I get maybe four hours of sleep a night,” he says with a laugh. For the record, he admits the number is closer to seven.
Born in Birmingham, Alabama, Stephens moved to Naples with his family when he was about 8 years old. After attending the University of Florida and spending time in New York, he returned to Naples nearly two decades ago, reconnecting with the community where his parents and grandparents still lived.
Much of Stephens’ philanthropic focus has centered on children’s charities, driven by his belief in the lasting impact of early support and opportunity.
“The rewarding part of it is being able to see the results—funding a scholarship for a child and then later on seeing them working in the community,” he says. “I’m a big believer that if you get to people early, you can really make a difference in people’s lives.”
For Stephens, investing in children means investing in the future. “With children, they’re very resilient. If you can give them the tools, they can change.”