Legacy Building Secrets
Legacy Building Secrets
What motivates leaders to embrace new challenges?
I’ve been CEO at Choice for about 13 months. Initially, I was an investor and board member with the original founder, who eventually sold the business to a private equity firm—a common occurrence in our industry. They asked me to join the company full-time, but I initially said no because I was at a comfortable place in my life. I was consulting with four clients and had complete control of my schedule.
As the private equity firm became more insistent, I discussed it with my wife and prayed about it. At 58, with most of our kids grown, my wife pointed out that this was an ideal time to finish my career the way I wanted to. My career had a major interruption in 2017, which changed my perspective, leading me to embrace the role of a mentor and “sage” in my industry.
My purpose also includes mentoring. About 40% of our partners who’ve sold their insurance agencies to us are under the age of 45. They receive cash and stock, which has significant growth potential, and I love mentoring these young entrepreneurs. That’s a big part of my “why.”
Why is a shared vision important for integrating acquired businesses?
I think the best decision I made was investing time to understand the mindset of the person selling. Numbers and financials tell part of the story, but this was pre-COVID, so all our meetings were face-to-face. In the insurance brokerage industry, there’s a network of investment bankers who connect buyers and sellers. I was fortunate because they knew my family’s name, which brought opportunities my way.
One thing I focused on—and which sometimes frustrated private equity—was whether the person selling would be a good cultural fit. I wanted to ensure they would genuinely buy into our vision. For instance, everyone who sold their business to us became a shareholder in the holding company, sharing in the wealth. It was crucial that wealth wasn’t concentrated only within the leadership team.
One memorable example was with a partner who was growing rapidly but had overhired. His expenses were impacting his EBITDA, which in turn affected our stock price. I flew to meet him, broke down his stock ownership, and explained how the overhiring affected our stock value. He understood, and while he didn’t like it, he made the necessary cuts. This personal touch and making everyone shareholders are strategies I would repeat without hesitation.
What core values should guide business relationships?
After I was fired in 2017, I realized I’d made my leadership team my friends, which was painful when I was suddenly cut off from them. Back then, I cared a lot about people liking me, so this was a difficult lesson. But the blessing was that it forced me to focus on cultivating personal friendships outside of work. I was fortunate to have a few longtime friends who stepped up, mentored me, and helped me through.
Today, my top priorities are my kids, my wife, and my friends. I tell everyone considering partnering with Choice that my values are simple: faith, family, and business—where friendships are part of family. If a situation goes against my values, I won’t do it, even if it causes friction with the leadership team or private equity partners. I was upfront with them before taking this role. I’m a capitalist and want to make a profit, but there’s a right way to treat people, and that matters most.
Why should business owners set boundaries to prioritize family time?
When my kids were young, I traveled constantly. I’ll never forget when my daughter, now about to turn 26, walked in while I was packing and said, “Oh, daddy never home.” That hit hard and was part of why I initially left the insurance business. When I re-entered the industry in 2009, with my kids at ages 14, 12, and 7, I promised my wife I’d never be on the road for more than two nights, and I’ve largely stuck to that.
The other commitment I made was attending my kids’ sports games—lacrosse, field hockey, and so on. I’d block those games off on my calendar as a non-negotiable time to support them. I didn’t make every game, but I was there enough to build a strong bond with my kids and create that sense of community.
These commitments, made 15 years ago, are why I have a good relationship with my kids and a solid marriage today. My wife was understandably frustrated with my earlier constant travel and work, so learning to step back from that was crucial.
*This interview has been edited and condensed for clarity.*
