We’re excited to introduce you to the always interesting and insightful Lisa Keslar. We hope you’ll enjoy our conversation with Lisa below.

Lisa , thanks for taking the time to share your stories with us today Can you talk to us about a risk you’ve taken – walk us through the story?

Life is full of risk, but for me, it’s often shown up in the career choices I’ve made. Early on, I chose to work in entrepreneurial organizations and smaller family businesses instead of the “safer” route of established corporations. That path was a risk in itself—smaller firms are less stable, roles are less defined, and you have to wear many hats. But I took those chances because I believed in the people I was working with, the products or services we were building, and I knew I had the tools in my toolbox to make an impact.

That pattern continued when I moved to startups. Startups are by definition risky—many don’t make it. But I was energized by the challenge. I believed in the solutions we were bringing to market and I wanted to be part of teams that were creating something new. Each time, I weighed the risk of instability against the potential of learning, growing, and contributing to something meaningful—and each time, I chose the risk.

The biggest leap came when I joined my husband, David, to build our own independent insurance agency. That was more than just changing jobs—it was stepping into ownership, responsibility for employees, and competing against much larger, well-resourced competitors. But I believed we could do it differently: build stronger relationships, provide better service, and create an agency that people actually enjoyed working with.

Even today, as every entrepreneur does, I still have moments of doubt. But I’ve learned that risk is part of growth. You can’t eliminate it—you manage it by surrounding yourself with the right people, having a clear vision, and staying focused on the goal. That mindset has carried me through every transition and made each risk worth it.

Lisa , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’ve always been drawn to work that’s entrepreneurial and people-focused. Over the course of my career, I’ve worked with family businesses, startups, and now I balance two roles that might seem very different but are actually deeply connected: I co-own Keslar Insurance, an independent property and casualty insurance agency, and I also serve as a lecturer in management, strategy, and entrepreneurship at the University of New Hampshire.

At Keslar Insurance, we provide personal and commercial insurance solutions across New Hampshire, Maine, and Massachusetts. That means everything from protecting a family’s home, cars, and personal property to helping small and midsized businesses safeguard their operations. Insurance can feel complicated, intimidating, or even transactional. We’ve built our agency on the belief that it doesn’t have to be that way. What sets us apart is the way we focus on relationships—taking the time to understand what matters most to our clients, educating them so they feel confident in their choices, and advocating for them when they need us most. Our goal is simple: to protect what people have worked so hard to build and to be the kind of trusted partner that large, impersonal agencies often can’t be.

At the same time, teaching at UNH allows me to bring my professional experience full circle. In the classroom, I’m working with the next generation of business leaders—helping students understand not only the fundamentals of strategy and entrepreneurship, but also how to think critically, take smart risks, and build something meaningful. My courses are highly interactive and rooted in real-world application, because I want students to walk away with tools they can actually use, not just theories. What sets my teaching apart is the mix of academic grounding and lived entrepreneurial experience, plus my belief that learning is most powerful when it’s engaging, practical, and collaborative.

Across both roles, what I’m most proud of is impact: helping families and business owners sleep better at night knowing they’re protected, and seeing students gain the confidence to step into their careers and ventures with clarity and purpose. If there’s one thing I’d want potential clients or students to know, it’s that I’m driven by integrity, education, and relationships. Whether it’s insurance or entrepreneurship, my work is about empowering people to make smart decisions and equipping them to succeed.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

For me, reputation has always come back to one thing: relationships. I joke with my students that “your network is your net worth,” but I’m not really joking. Time and again, I’ve seen how knowing someone, helping someone, or connecting someone has opened doors and created opportunities that no marketing campaign or sales pitch ever could.

At Keslar Insurance, one of the best compliments we hear is when someone says, “I’ve heard so much about you and your company—I just had to meet you.” That tells me our reputation isn’t built on ads or slogans, but on real people sharing their experiences with us.

The foundation of that reputation is simple: integrity, doing the right thing, and creating value for others. Whether it’s helping a business owner protect their company, guiding a family through the right coverage for their home, or mentoring students to see possibilities in their careers, my focus has always been on making a tangible difference. When people feel that you genuinely care and that you’re there to serve—not just to sell—that’s what drives trust, and trust is what drives reputation.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

For me, it’s never been about one specific book, video, or essay—it’s about mindset. The entrepreneurial mindset has been the single most important influence on how I approach both business and life. It’s a gamechanger.

This way of thinking takes you from being stuck or discouraged to asking, “Why not? What’s next?” It’s about seeing possibilities instead of roadblocks, solutions instead of problems. It’s so central that Babson College—one of the global leaders in entrepreneurship education—has made entrepreneurial mindset a core focus of their teaching.

When I meet entrepreneurs, I can often tell within minutes whether they have “it” simply by listening to how they think. Do they see risk as an opportunity? Do they focus on creating value for others? Do they adapt quickly when plans don’t go as expected? That mindset, more than any one resource, has shaped my philosophy and guided my work as both a business owner and a teacher.

Contact Info:

• Website: https://www.keslarinsurance.com
• Facebook: https://www.facebook.com/keslarinsurance
• Linkedin: https://www.linkedin.com/in/lisakeslar
• Twitter: really?