Community, Leadership, and Risk: Lessons from Will Peckham on Building Better Businesses and Stronger Cities

On this episode of The Ownership Advantage, Will Peckham explores the ties between local business, leadership, and safeguarding your future.

Returning Home: Why Round Rock Matters

It’s not every day you meet someone whose roots run so deep in their local community, but Will Peckham is just that person for Round Rock. In his conversation with host Tanner on The Ownership Advantage, Will recounts his journey coming back to Round Rock after college. It wasn’t just nostalgia for local donuts or familiar bike paths that brought him home. Instead, it was a strong sense of belonging and the persuasive encouragement of family—a sentiment familiar to many who find purpose in giving back to the places that shaped them.

Will’s return story highlights something powerful: when people reinvest in their hometowns, they carry forward both legacy and leadership. As he says, “Round Rock was phenomenal to us and our family business…we wanted to help others.” This intergenerational cycle of support is a key ingredient in the community’s continued growth.

The Power of Consistent Leadership

One of the first things Will mentions as a standout quality of Round Rock is its “consistent leadership and opportunity.” He credits the community’s success to its ability to have the “correct mayor at the correct time.” But more important, perhaps, is the can-do spirit he sees in his neighbors—a blend of ambition and openness where new arrivals are met with the invitation: “Come on, come with us, let’s go create something great.”

Will’s own leadership journey has seen him serve on city council, numerous boards, and nonprofit organizations. What fuels his ongoing commitment? Family values. Growing up, his parents instilled a sense of service: “We were lucky enough to have a little bit more, and we wanted to help others.” Giving, he insists, isn’t just about charity—it’s about investing in a better future for your own children and, perhaps selfishly, making sure the place you love remains somewhere your family wants to live.

From Mentee to Mentor: Embracing the Lessons of Failure

A striking theme emerges as Will talks about his evolution from being mentored to becoming a mentor. He’s guided by the wisdom passed down from community stalwarts, but he also recognizes the importance of peer support and the collaborative process. For Will, it’s about “passing along lessons”—not just successes but failures too.

He reflects, “I think in our careers...a big part of that is learning from our failures. It’s never a stopping point. It’s just, okay, that’s one way that didn’t work. Let’s try to figure out a different way…” For today’s emerging leaders, he encourages embracing discomfort and seeing setbacks as necessary growth opportunities.

Connection Between Small Business and Community Strength

Will’s work as an insurance advisor and small business advocate puts him on the front lines of local economic health. He’s quick to emphasize that the local business community is “really talking about small business…those are the individuals that are the leaders...taking chances.” Their efforts ripple out, building networks, forging reputations, and attracting talent—all of which make Round Rock a place “people want to be.”

A thriving community, Will suggests, isn’t just about altruism; it’s also smart business. Community involvement helps attract and retain great employees, reduces risk, and ultimately contributes to a business’s success.

Risk Mitigation: It's About Relationships, Not Just Policies

When the conversation shifts to insurance, Will’s expertise shines, but his emphasis remains on relationships. “The most important aspect is that relationship,” he says—whether it’s understanding your policy, adapting to business changes, or navigating claims. He stresses regular, honest communication with your insurance advisor, ideally yearly, but more frequently if your business is growing or changing fast.

Insurance, he notes, is rarely top of mind—until it’s urgently needed. The value of having coverage and trusted advisors in place before disaster strikes can’t be overstated.

Giving Back: Finding Your Fit in Community Service

Will encourages business owners to analyze where their business best fits into the community and to target their efforts where they’ll make the most impact—whether that means giving time, talent, treasure, or a combination. As he puts it, “Find your niche and start giving with what you can, and it’ll keep growing as time goes on.”

Looking Forward: Building a Legacy

For Will, success means making the world better for future generations—a sentiment echoed by the idea of “planting trees you’ll never see the shade from.” As Round Rock grows, he finds excitement in the promise of new leaders and the innovations they’ll bring, all built upon the shoulders of those who came before.

Final Thoughts

Whether you’re a seasoned business owner, aspiring entrepreneur, or passionate community member, Will Peckham’s insights are a reminder: invest in your community, learn from each other, and protect yourself from risk. In doing so, you’re not just building a business—you’re building a legacy.

Check out the full episode on YouTube HERE

Listen to the full episode on Apple Podcasts HERE