How This CEO Is Combining AI and Human Creativity to Revolutionize His Industry


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Raised by a businessman father and an opera-singing mother, David McFarland learned the art of blending creativity and pragmatism early on. He initially pursued a history degree, but a single philosophy course sparked a love for mathematics.

With a newly discovered passion for math, McFarland switched his major to actuarial science, a field where complex numbers and risk meet real-world application. Little did he know, this would set the foundation for his future as a CEO who would bring a fresh approach to the traditional world of insurance.

On this episode of The Founder CEO, we sit down with the founder and CEO of Coterie Insurance to learn how a combination of audacious vision and a deep understanding of data led him to create one of the most innovative companies in the insurance space.

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An Unlikely Entrepreneur

By the time McFarland entered the insurance industry, he had gained experience at both legacy companies and startups. It was during his time at the National Council on Compensation Insurance (NCCI) that he saw a glaring gap: small businesses were often underinsured or uninsured because it was too costly for agents and companies to serve them.

This realization sparked an idea. Could data and technology make the insurance process more efficient and accessible for these businesses? In 2018, with a family and children at home, McFarland took the leap and founded Coterie Insurance to solve this exact problem. Today, Coterie uses cutting-edge technology to reduce the time it takes to secure insurance from hours to just minutes.

A Vision Fueled by AI

As Coterie grew, McFarland’s vision expanded to include artificial intelligence. He sees AI as a game-changer, not just for his company but for the entire insurance industry. While some fear the displacement of jobs due to AI, McFarland believes it will lead to a new era of innovation. He likens it to the advent of the combine that transformed farming by making processes more efficient, thereby opening up new industries and opportunities.

“AI will replace many of the mundane, repetitive tasks, allowing us to focus on higher-value work,” McFarland says. For underwriters and actuaries, he sees the future as a collaboration between humans and AI, much like the best chess players today who partner with computers to outperform even the most advanced software.

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Navigating the Founder-to-CEO Transition

The transition from founder to CEO isn’t easy. Many entrepreneurs struggle when their companies outgrow their initial scrappy stages. For McFarland, it was about finding the right balance between innovation and commercialization. He stresses that once product-market fit is achieved, it’s time to switch gears and focus on scaling in a financially sustainable way.

“I realized that some of my team members were better suited for the early-stage guerrilla warfare, while others were better at scaling operations,” McFarland explains. Making tough decisions about team composition is part of evolving as a leader, something McFarland has learned through experience.

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Coterie’s Bright Future

Today, Coterie is one of the fastest-growing companies in its niche, providing small business owners with the insurance they need quickly and easily. With 50% of small businesses underinsured, McFarland sees a massive opportunity for growth. He envisions a future where small business owners no longer have to worry about being financially devastated by unexpected events.

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