David Gearhart's Journey in Building a Private Insurance Holding Company

Welcome to Episode 28 of the Preferred Shares Podcast.

In this episode, we interview David Gearhart, CEO and Chairman of Wilmington Holdings Corporation, a private holding company of several insurance businesses. David tells the story of how he decided to try to find and acquire a small insurance business. In 2017, he successfully acquired Wilmington Insurance Company. After eight years of growth, both organic and by acquisition, Wilmington Holdings now controls about $50 million of annual premiums and has $100 million of assets on its balance sheet.

We discussed a variety of topics:

* David Gearhart’s background and how the business bug bit him;

* What the process was like to search for and acquire a private insurance company;

* David’s search criteria;

* The importance of disciplined underwriting and staying within their circle of competence;

* The importance of people in the insurance business;

* How David thinks about the trade-offs between investing in Wilmington’s insurance businesses versus investing the insurance float;

* Key lessons David learned when he studied the history of National Indemnity Company;

* David shared one of the mistakes he made and his takeaway;

* David’s goals for Wilmington going forward.