Episode Details

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.

Enjoy this episode? Share it with someone who loves business history as much as you do!

You can also follow Preferred Shares, Devin, Doug, and Lawrence on Twitter.

Other Sources

David Gearhart also did an interview with At Home With Roby which was released on October 6, 2024.

Additional Reading & Listening

Curious to see what else we’ve been working on? Check out some of the interesting things we’ve done recently:

* Douglas Ott (Andvari Associates and @yesandnotyes)

* 📖 Cranberries & Ocean Spray: Part I

* 📖 Constellation Software: A People Business

* Devin LaSarre (Invariant and @DevinLaSarre)

* 📖 Nicotine Certainty

* 📖 Philip Morris International: ZYNsn’t It?

* Lawrence Hamtil (Fortune Financial and @lhamtil)

* 📖 Aerospace: After A Century of Growth; A Bright Future Ahead

Enjoy this episode? Share it with someone who loves business history as much as you do!

You can also follow Preferred Shares, Devin,

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