Leading with Heart: Kathleen Hawkin’s Vision for Tennessee’s Small Businesses

Kathleen heads up our Tennessee team, bringing decades of experience as a business consultant, public speaker, and community leader. She is a nine-time published author and previously founded and sold one of the largest networking organizations in the nation, which grew to over 4,000 members across 73 cities in 15 states. She built the organization on the foundation of helping women promote and grow their businesses while maintaining their priorities of faith, family, and career, a philosophy she carries into her work today.

"Many small businesses are built around the founder’s name or passion,"

Deeply rooted in the Tennessee small business community, Kathleen has spent her career helping entrepreneurs develop business plans and succession strategies, ensuring long-term sustainability and growth. For the last nine years, she has served as President and CEO of the Hendersonville Area Chamber of Commerce, leading initiatives that drive business growth and community development. Her commitment to impact extends beyond her professional life: she has served on the boards of Tennessee Donor Services, Middle Tennessee Boy Scouts of America, and Sumner County Tourism, among others. Kathleen joins Legacy after decades of hands-on experience and continues to bring unmatched insight and passion to our mission.

The Biggest Challenge Facing Small Businesses Today? A Lack of Planning. "The biggest challenge I see facing small businesses in Middle Tennessee—and across the country—is they don’t have a plan," Kathleen says. "They usually have a passion. They stumble into something they love, but they don’t sit down and create a business strategy or analyze their costs. They just hope it all works out by the end of the month."

From Passion to Legacy: Making Businesses Sellable "Many small businesses are built around the founder’s name or passion," she explains. "But that makes it harder to sell. Buyers want a business with transferable value, not something that lives and dies with one person."

Why a Local Focus Matters "The local focus is what kept everyone alive during COVID. I saw it firsthand. Franchises pulled out. Corporates pulled back. But local communities rallied to support small businesses," Kathleen shares. "Being locally rooted builds real community. It’s what makes people care."

Succession Planning is Emotional — But Necessary "It’s their baby," Kathleen says of small business owners. "They pour their lives into it, and the idea of someone else taking over is scary. Most owners don’t have a business degree. They just had a skill and built something around it. We need to coach them through the process—to show them it can live on."

Kathleen on Her Own Experience with Succession "I cried when I sold my business," she admits. "But I knew I didn’t want to go global. That was the next step, and it wasn’t right for me at the time. It took me a year and a half to mentally prepare for that transition."

"I wish I’d had someone like Legacy back then—to help tailor the transition and spend more time supporting the next owner. Instead, I signed the contract and walked away. It wasn’t ideal."

The Importance of Community in Times of Crisis "When tragedy hits—whether it's a tornado or a pandemic—it's your local network that helps you survive," she says. "If you're not connected, you're on an island."

Navigating Economic Uncertainty "When cost of goods goes up, it affects everything for a small business. But I’m starting to see some light. People are opening up their budgets again. There's hope," she says. "We just need to help owners prepare—through budgeting, smart forecasting, and long-term thinking."

"There’s a boom happening here. Nashville and the surrounding cities are growing fast. But land is becoming scarce. Small businesses will continue to pop up, but those that survive will be the ones with a strategy—not just a passion."

Advice to Business Owners Hesitating on Succession "I’d ask a lot of questions before giving advice," she says. "What are your goals? Where are you trying to go? Because if you don’t know where you’re going, there’s no way to get there. It’s not just about letting go of something emotional—it’s about building a future."

What’s Next for Middle Tennessee? "There’s a boom happening here. Nashville and the surrounding cities are growing fast. But land is becoming scarce. Small businesses will continue to pop up, but those that survive will be the ones with a strategy—not just a passion."

Conclusion: Building Tennessee’s Future, One Business at a Time Kathleen’s depth of experience, unwavering commitment to local business, and personal understanding of what it takes to start, grow, and transition a company make her an ideal leader for Legacy Holdings in Tennessee. Her perspective affirms what we believe at Legacy: that small businesses are the heartbeat of our communities, and with the right support, they can thrive for generations.

As Middle Tennessee continues to grow, the need for succession planning, operational support, and long-term thinking has never been more urgent. Kathleen and our Tennessee team are here to ensure that local businesses don’t just survive this period of change—they lead it. Together, we’re building a future where local ownership endures, legacies are protected, and the economy is strengthened from the ground up.