Gary Hartfield is no stranger to leadership. As a father, entrepreneur, landlord and longtime community advocate, he has built a reputation for pairing business acumen with a heart for service.
As Tampa Bay Business & Wealth’s September cover star, he sat down with Bridgette Bello, CEO and publisher of TBBW, at CEO Connect to reflect on leadership, community impact and the challenges facing Tampa Bay. What follows is a slightly edited version of the conversation.
READ GARY’S STORY: Tampa business leader Gary Hartfield considering run for mayor
Bello: Mr. September, what’s it been like being our cover star this month?
Hartfield: It’s been phenomenal — truly a once-in-a-lifetime experience. Bridgette and the team, along with Jason and Jolynn, captured an intimate, personal story and shared it with a trusted partner. The sponsors and the crowd here tonight reflect your ability to tell a powerful story. My kids even read it and asked, “Who were you talking about?”
Thank you for the opportunity. And yes — you’ve now ensured I’m the only guy who’s ever handed you roses on the CEO Connect stage.
Bello: This room is full of leaders. You wanted to talk about leadership. How do you define it, and what shaped the way you lead?
Hartfield: I think about leadership across my roles as a father, community advocate and entrepreneur. I align with three characteristics often attributed to Bishop Desmond Tutu:
● Service: A leader serves selflessly on behalf of the people.
● Sacrifice: If a leader isn’t giving more of themselves to the cause and those they lead, they may be in the wrong role.
● Inspiration with direction: Not generic inspiration — capturing people’s aspirations and inspiring them to reach them.
Those three threads run through our businesses, families and communities. I ask myself every morning: How am I living those three?
Bello: What’s the most urgent issue facing Tampa, and what leadership is needed to tackle it?
Hartfield: Housing affordability. Before COVID, our wages were relatively low, but housing was relatively affordable. Now you must factor four variables — principal, interest, insurance and taxes — and insurance and tax costs have jumped.
Stable, attainable housing underpins student performance, workforce stability, tax base growth and social capital. Get housing right and you strengthen everything else.
On transportation, we’re not yet ready for full light rail. First, maximize PSTA and HART bus ridership and performance. Then, as Brightline expands, go to Tallahassee and D.C. with the results and make the rail case.
Bello: I’ve lived the affordability squeeze personally — my college-educated daughter left because she couldn’t afford to live here. If talent leaves, it weakens our business base and recruiting power. Now is the time to act.
Bello: What solutions do you bring from your own experience?
Hartfield: I’m a father, an entrepreneur who built from the ground up, a commercial property owner and an insurance agency owner. That gives me:
● Empathy and a practical P&L lens.
● A view of how Triple Net Lease passthroughs hit small tenants. If a Thai restaurant pays $12,000 a month and my building’s insurance rises 50 to 75 percent, their share can jump from about $2,500 to about $7,500 a year. Add rising property taxes and their margin disappears.
● A balanced approach to wages and viability. Raising the minimum is good, but businesses also shoulder payroll taxes, benefits and soaring health care costs. Policy can’t be unilateral; it must be integrated so employers remain viable.
And yes — I’m the guy who signs the front of the paycheck.
Bello: Name one bold priority you’d pursue as mayor.
Hartfield: Public safety, defined broadly. It’s not just policing; it’s economic inclusion. Bring CareerSource Tampa Bay, HART, banks and civic partners into underserved neighborhoods so people have real pathways — training, transit, capital — so that “operating illegally” isn’t the only perceived option. Safer, opportunity-rich neighborhoods attract and retain employers.
Bello: When people think of your impact, what do you hope they associate with your name?
Hartfield: A heart for service. I’ve tried to pour into others — through formal and informal learning, building businesses and then returning that value via board service with groups like CareerSource Tampa Bay, HART, United Way Suncoast and BayCare.
An old Rotary line sums it up: “He who profits most must serve best.” As I’ve earned and profited, I’ve tried to serve best.”
A look inside TBBW’s CEO Connect:
