Demetrius Gray

Post-pitch story

Demetrius Gray and Jermaine Watkins founded WeatherCheck in Louisville, Kentucky, in 2016, using weather data and AI to detect hail and storm damage on properties — a Y Combinator-backed insurtech serving insurers and mortgage companies. Gray appeared on the show's "Friends & Family Gap" episode in late 2020, and the company kept growing through 2021, pivoting during COVID to work directly with homeowners by pre-building insurance claims. But Gray has been candid about how it ended: WeatherCheck, he's said, "didn't work out the way he envisioned it," undone by misaligned incentives in the insurance world. What makes this story remarkable is what came next. In May 2021, Gray founded Captain, a fintech that advances money to contractors for post-disaster home repairs — same storms, smarter model. Captain emerged from stealth in March 2022 with more than $100 million in funding, and Gray's journey from WeatherCheck to a nine-figure raise has been featured in TechCrunch. WeatherCheck itself is gone, but its founder turned the lesson into one of the biggest raises by a Black founder in recent memory.