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Every policy he read had the same clause: more than two marathons back-to-back counts as an "extreme event." He and three friends were about to run 80 in 80 days, and none of them had run one. They went anyway, with nothing covering them.

Sean Stuart is the co-founder of Rosella, an AI-native commercial insurance brokerage.

We cover why he thinks "find your life's work" is bad startup advice, how two Australians landed in Dallas with zero meetings booked and door-knocked insurance offices, what VCs consistently get wrong about AI-native service businesses, why a US trampoline park doing $5M in revenue pays $500,000 a year for insurance, and why his highest-ROI growth channel turned out to be mailing people chocolate chip cookies.

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