How to Sell an Insurtech Startup in a Down Market with Daniel Metcalf

In this episode, we sit down with Daniel Metcalf, co-founder of Smart Harbor, to explore the complete lifecycle of building and exiting an insurtech business. Daniel shares the origin story of Smart Harbor, a company born out of the belief that independent insurance agents needed modern digital tools to compete with direct writers. He talks about the company's evolution from its startup days to a strategic acquisition by Vertafore, revealing hard-earned insights into timing the market, building valuable tech for a niche audience, and navigating a sale in a down market. Daniel also reflects on what founders often get wrong about exits, how M&A differs when strategic buyers are involved, and what he would do differently if he started again today. This episode is a must-listen for insurtech founders, operators, and investors who want a clear-eyed view of what it really takes to succeed and exit in today's market.

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