Hagerty CEO McKeel Hagerty Talks Car Culture and Insurance

McKeel Hagerty, the CEO and Chairman of Hagerty Insurance, sat down with Barry Ritholtz on the latest episode of Masters in Business to unpack what it takes to run one of the most recognizable names in collector car insurance. If you're into alternative assets or niche markets, this one's worth your time.

Hagerty isn't just an insurance company — it's built around a community of enthusiasts who treat their vehicles as passion investments. The brand has become synonymous with classic and collector car culture in the U.S., and McKeel has been central to that identity. Understanding how a niche insurer scales while keeping its core audience loyal is a masterclass in brand-driven business strategy.

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For traders and investors eyeing the collector car market as an alternative asset class, conversations like this offer rare insight into the demand side of that equation. Classic cars have long attracted capital from buyers looking beyond stocks and bonds, and Hagerty sits at the intersection of insurance, valuation, and community — a uniquely defensible position.

The full interview digs deeper into Hagerty's leadership philosophy, the evolving collector car market, and how passion-driven businesses compete in a world dominated by data and algorithms. This is the kind of candid C-suite conversation that cuts through the noise.

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