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

Page: https://stenobird.com/podcast/preferred-shares-podcast-6594967/david-gearhart-s-journey-in-building-a-private-insurance-holding-company
Text version: https://stenobird.com/podcast/preferred-shares-podcast-6594967/david-gearhart-s-journey-in-building-a-private-insurance-holding-company.md
Podcast: [Preferred Shares Podcast](https://stenobird.com/podcast/preferred-shares-podcast-6594967)
Published: 2025-12-05T20:12:15+00:00
Episode link: https://www.preferredsharespodcast.com/p/david-gearharts-journey-in-building
Audio file: https://api.substack.com/feed/podcast/179412672/7d50c4a7a05c2da24d9584e71640d582.mp3
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JSON: https://stenobird.com/v1/public/podcasts/preferred-shares-podcast-6594967/episodes/david-gearhart-s-journey-in-building-a-private-insurance-holding-company
Duration seconds: 2799

## Resource

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…

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