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When former accountant and roofing contractor Demetrius Gray talks about his personal journey to become founder of a fintech with ties to the insurance industry, he doesn’t dwell on the challenges for even a second.

Executive Summary

Demetrius Gray, the CEO and founder of Captain, spoke to Carrier Management soon after Captain announced that it emerged from stealth mode with $104 million in financing. Gray, a second-time founder who previously led a property damage prediction company known as WeatherCheck, explained what he learned from his prior experience: that alerting homeowners and carriers to hail or wind damage isn't enough to get victims of natural disasters back in their homes quickly. Contractors need funding and the incentives to make it happen.

Still, it can’t be easy to move from the back office up to the top of a residential property—literally standing on the shingles—and then to dive into entrepreneurship with a mission to help homeowners recover quickly after natural disasters by advancing capital to building contractors, not to mention also founding the first Black-owned InsurTech meteorology company in the U.S. along the way.

“It’s not that it’s easy. But frankly, we don’t have the hard part. The hard part is what the policyholder is having to do. They’re having to put their life back together. That’s much harder,” he told Carrier Management when asked about that during a recent interview. “We keep that top of mind.”

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