Facing Goliath, Deals with Rock Legends: Rick Lindsey Changes the Insurance Game ALP Eps 42

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Facing Goliath, Deals with Rock Legends: Rick Lindsey Changes the Insurance Game ALP Eps 42

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Welcome back to The Adaptive Leaders Podcast! In today’s episode, host Josh Sanchez sits down with Rick Lindsey—the renegade of insurance, founder of Prime and X Insurance, and the man behind a $450 million empire built on no-nonsense principles. Rick’s forty-year career has been shaped by a clear-eyed approach to leadership, unconventional thinking, and an unwavering refusal to accept business-as-usual in a notoriously risk-averse industry. From insuring household names like Drake and the Rolling Stones to taking death cases to the California Supreme Court and winning, Rick’s journey is packed with bold moves, high-stakes decisions, and straight talk that’s uncommon in the world of insurance. He shares how his early dreams of becoming a pro athlete evolved into an entrepreneurial drive, what it means to build partnerships over policies, and why betting on facts over feelings has been his winning formula. Rick’s leadership style is all about common sense, integrity, and staying close to the action—whether he’s managing 4,000 lawsuits, leading a 300-person team, or racing speedboats in Florida. Stick around for a candid conversation full of wild stories, industry insights, and invaluable takeaways from one of the most interesting—and disruptive—leaders in business today.

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