In Plant City, Florida, a town famous for strawberries and rooted in tradition, a 26-year-old young mother of two named Gail Calhoun made a bold move. Recently divorced, raising two young boys, and tired of being told to leave her kids behind for business trips, she founded Hillsborough Title in 1984. It was more than a career pivot—it was an act of defiance and hope. Her son Aaron, watching from the sidelines, couldn’t have known that one day, her story would become the foundation of his own.
Aaron’s first job title? Stapler re-filler, at age nine. By 16, the company courier. By 18 he was post-closing files and learning to process. But even then, he wasn’t sold. He bought and flipped a house at 19, cashed in the $12,000 profit, and went off to the University of Florida, determined to write his own story, away from small-town title work.
He graduated in 1999 with a finance degree, joined Norwest Financial, broke sales records... and hated it. He didn’t want to trap people in debt. He pivoted again, this time into financial planning, but the dot-com bubble burst and financial recession, and his plan started to crumble.
But during a quiet moment on a family vacation, something shifted. Gail pulled him aside. “I know you wanted to carve your own path, but you should take another look at title. I’ve never shown you the operations or the finances,” she said. “But this can be a good life.”
That conversation changed everything.
Aaron dove in, learning the business from the ground up. But just as he found his footing, the Great Recession hit. Hillsborough was on the brink. Gail had invested in commercial real estate and other real estate ventures that were floundering under the weight of the economy. The agency was losing $20,000 a month, and as Aaron was still in his early 30s, he could have walked. Instead, he risked everything to save the family business.
In September 2008, he bought the company from his mom outright and poured over $100,000 of his own money into it. He drained his 401(k), maxed out his equity lines, and held on by a thread. For six months, he bled cash. Then one day in April 2009, his bookkeeper showed him the P&L: a $1,000 profit.
“Is that real money?” Aaron asked.
They’d made it.
From there, it was full throttle. While some of the larger players in the market were retreating, Aaron went on offense. He acquired small agencies, recruited top closers, and landed national accounts through college connections. The company exploded, from one office to five, then ten, then dozens. But rapid growth needed structure, so he centralized operations, creating Network Transaction Solutions to handle the behind-the-scenes work. What began as an internal fix became a national platform. Today, it supports nearly 1,000 agencies.
In 2015, Aaron unified 13 title brands under the Florida Agency Network (FAN), launched Premier Data Services for IT infrastructure, and built Closing Suite to help others scale. In 2018, he led Florida’s first remote online notarization, and by 2020, his team of 60 RON-trained notaries gave him a head start when the pandemic hit. He wasn’t just keeping up. He was rewriting the playbook.
But Aaron’s legacy won’t just be measured in offices or revenue.
After “Snowmageddon” as they call the Texas Snowstorms of 2021, Aaron found himself in the small Texas town of Harper helping a local volunteer fire department which landed him in People Magazine with the moniker of “The Tampa Chainsaw Man”. Years later, Hurricane Ian devastated SW Florida, Aaron and his brother Nate showed up. Not in a suit, but in boots, donating and handling chainsaws. Now known as “the Chainsaw Brothers” they were featured in People magazine and on The Kelly Clarkson Show, not for business acumen, but for heart. Then last year, Hurricanes Helene and Milton both pounded Florida, and he organized a relief effort in his hometown of Plant City, organizing food delivery, cleanup efforts, and gave away 100 chainsaws to families in need.
His future nonprofit, Hometown Emergency Response Organization (HERO), channels that same spirit: act fast, help first, make a difference.
“When I talk about this, I choke up,” he says. “I know it’s what I’m meant to do.”
That calling runs deeper now. When his oldest son graduated college, Aaron expected him to head off into the corporate world. Instead, he asked to work in Austin close to his dad. Same Finance background, same desire to cut his own path, but perhaps that leads back to the family business. It was unexpected. It was full circle. Just like Gail investing in Aaron decades ago, Aaron now invests in his son—and the broader legacy of a family that builds.
Today, Hillsborough Title is the founding agency of the 52-office Florida Agency Network, with 14 brands and a reputation as one of the most forward-thinking operations in the nation. But Aaron’s proudest titles aren’t CEO or founder. They’re son, father, and neighbor.
He saved the business that saved his family. And now he’s helping others rise - from clients to colleagues to hurricane survivors - with a chainsaw in one hand and a mission in the other.
Aaron Davis’s story isn’t about escaping the past. It’s about honoring it, elevating it, and paying it forward. In a business built on paper trails and signatures, he’s building something bigger: a legacy of resilience, love, and service that echoes far beyond the closing table.