Cowritten by AgencyFocus & Landon Bentham, President of Callahan & Rice Insurance Group

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Meet the Agent: Landon Bentham

In 2014, Landon married the love of his life. Shortly after, his new father-in-law approached him about joining the family agency to learn the industry and potentially have a future pathway to ownership as there was no current formal perpetuation plan in place. In 2015 Landon took him up on it and decided to take the plunge and join Callahan & Rice Insurance.

Both of Landon’s grandparents were entrepreneurs, so he knew what came with business ownership, but didn’t know what industry to turn to. He had the schooling for business, but no practical application of it.

Upon his entrance into the agency and having been given a long runway of opportunity, as a team, Mark and Landon were able to grow the business multiple times over. Landon attributes the reason for the successful growth to the fact that Mark had given him runway and trusted him with the right amount of decision-making, while still holding the reins and keeping the agency on track.

Eventually, the role turned into a new chapter in the family legacy, but it wasn’t because he was family. Landon tried new things and was creative in how he modernized the agency. His father-in-law, Mark W. Rice, had led their North Carolina-based agency for over three decades, building it into a respected, community-focused firm, which made for a solid foundation to build on.

“There wasn’t a master plan when I got here. Mark didn’t know exactly what retirement would look like. And I didn’t come in expecting anything. I just saw a great opportunity to contribute.” – Landon Bentham

Over time in his roles as “Insurance Agent” and then “Director of Marketing and Sales”, Landon proved his value. His focus throughout this time was on building trust with the team, modernizing processes, bringing in new business through creative opportunities, and consistent marketing.

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The Situation: A Legacy Without a Roadmap

Callahan & Rice was founded in 1966, with Mark Rice taking the reins as owner and principal over 30 years ago. By the time Landon joined in 2015, the agency had a strong client base and a loyal internal team but no formal perpetuation plan.

Landon’s approach wasn’t to demand change. It was to listen, learn, and implement small but impactful improvements. He started by throwing himself into the deep end, rerouting generic new business calls to understand client needs and increase conversion. Modernized the agency with a new website, SEO optimization, and Google reviews to increase the number of new calls the agency was receiving.

These changes alone created noticeable momentum.

“I didn’t come in to flip tables. I just asked, ‘What’s one thing we can make better today?’ And then I asked permission to try.” – Landon Bentham

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The Conflict: The Emotional Reality of Perpetuation

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Family perpetuation sounds clean on paper, but it rarely is. Despite a strong relationship and mutual respect, Landon and Mark still had to navigate the unspoken complexities that come with passing the torch: timing, valuation, communication, and readiness on both sides.

“It’s easy to assume things. I started asking myself, ‘Why isn’t this happening faster?’ But I realized I hadn’t voiced all of my questions directly.” – Landon Bentham

Mark and Landon both had to figure out how to be more intentional about the discussion surrounding the ownership transition. They had to answer questions like …

• What consultants need to help us?
• What tax implications are there for us individually and the family?
• When would we both be ready financially, mentally, and physically to make the transition happen?

Mark worked to find ways to transfer leadership opportunities over to Landon, first in sales, then in human resources, then in agency management.

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The Coaching: How AgencyFocus Helped Bring Clarity to the Process

That’s when Landon turned to AgencyFocus.

“I believe in coaching. I’ve had coaches in fitness, finance, and leadership, and this was no different. I needed someone to help me see around corners I didn’t even know existed.” – Landon Bentham

With AgencyFocus as a coach, Landon and Mark structured the transition, aligning everyone around valuation, legal logistics, and the emotional pacing of the deal. Bringing in an outside party allowed Landon to lead his portion of the process with confidence, bringing structure to conversations that often stall in assumptions or emotion.

One of the strategies that was discussed involved a “price lock” based on a valuation a couple of years in advance of the official transition. This encouraged Landon to continue putting forth as much effort into growth as possible, and allowed Mark to have the benefit of a fully engaged partner in the growth of the business, without giving up equity in the short term.

Throughout the coaching process, AgencyFocus helped:

• 2019:
  
  • Execute the fair market valuation of the agency
• 2022:
  
  • Refresh of the valuation
  • Met with all parties, including spouses, to facilitate a conversation that everyone was on the same page and informed of the deal.
• 2024:
  
  • Define a fair and clear timeline for transition
  • Create a step-by-step perpetuation plan that respects the legacy of an agency while preparing for the future
• 2025:
  
  • Provide 1:1 coaching and leadership support during the transition year

“They didn’t just walk me through the deal. They coached me through the leadership journey. That’s what made the difference.” – Landon Bentham

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The Growth: A New Kind of Leadership

On January 1, 2025, the transition became official. Landon became the President and owner of Callahan & Rice.

Mark still remains active in a focused capacity, bringing decades of experience to a specific division of the business. Landon has taken full ownership of agency direction and quickly realized the weight of leadership.

“I thought I was prepared. And I was, in many ways. But sitting in the seat is different. It can be exhausting. Not because I don’t love it, but because I care so much about doing it well.” – Landon Bentham

Since stepping in, Landon has:

• Restructured internal leadership to reduce direct report load
• Launched a leadership development program within the agency
• Updated core values and vision statements to reflect the agency’s next chapter
• Partnered closely with a Fractional CFO in AgencyFocus to evaluate and anticipate staffing needs and deploy resources efficiently
• Developed a 7-Year strategic vision and execution plan that aims to
• Vision of having an agency location in all North Carolina’s major metro markets and being a destination employer
• To acquire or absorb other agencies

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The Outcome: A Legacy Sustained and Evolved

Today, the agency is operating at its best and is rooted in legacy.

“This isn’t about changing everything. It’s about stewarding something meaningful and making it stronger for the next generation.” – Landon Bentham

The success of this transition wasn’t just in the documents or the deal. It was in the conversations, the coaching, the patience, and the mutual respect that made space for a new kind of leadership to emerge.

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Callahan & Rice Perpetuation Timeline: 

• 1966 – Callahan & Rice founded
• 1966 – Callahan & Rice founded
• 1997 – Mark W. Rice assumes management responsibilities
• 2014 – Landon Marries into the family
• 2015 – Landon Bentham joins Callahan & Rice
• 2019 – Fair Market Valuation Completed
• 2022 –
  
  • Landon Bentham begins acting agency manager role
  • Refresh of the valuation
  • AgencyFocus held a meeting with all parties, including spouses, to facilitate a conversation to inform of the deal terms and schedule
• 2024 – AgencyFocus engaged to support the perpetuation plan
• January 1, 2025 – Ownership officially transferred to Landon Bentham
• 2025 – Ongoing leadership support and coaching
• 2032 – Strategic Vision Landing