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

About this episode

David Gearhart shares his journey in acquiring and growing Wilmington Holdings Corporation, 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; *…

People in this episode

Hosts: Devin, Doug, Lawrence

Guest: David Gearhart

Topics covered

• private insurance
• business acquisition
• insurance underwriting
• company growth
• investment strategies
• business history

Keywords

• insurance business
• acquisition process
• underwriting
• business growth
• investment
• Wilmington Holdings
• David Gearhart

Mentioned in this episode

Organizations: Wilmington Holdings Corporation, Wilmington Insurance Company, National Indemnity Company

More episodes of Preferred Shares Podcast

• Duke Dynasty: The Legacy of the American Tobacco Monopoly, Part Two · June 12, 2026 · 54 min
• Duke Dynasty: The Legacy of the American Tobacco Monopoly · May 25, 2026 · 56 min
• Class 1 Railroads with Matt Reustle of Business Breakdowns · April 28, 2026 · 54 min
• The Ferguson Water Thesis with Todd Wenning · April 16, 2026 · 45 min
• Veteran Analyst Mark Purdy on Nestlé · March 20, 2026 · 1h 5m
• Nestlé: The Building of a Global Behemoth · February 17, 2026 · 54 min