Demetrius Gray

Founder & CEO, Captain · 1 appearance on the record.

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Demetrius Gray founded WeatherCheck, a Y Combinator-backed insurtech platform that tracked storm damage for homeowners and insurers. He subsequently launched Captain, a fintech platform that raised over $100 million in debt and equity to front repair capital to contractors following natural disasters.

5statements → 2claims → 0claims resolved → 4/5average certainty → 2.2/5average debate potential →

2 not yet assessed how the 2 claims stand · each chip opens the sources

1 prediction · 1 assertion · 1 opinion · 2 disclosures · every statement was checked. The prediction and assertion are the 2 claims: statements the public record can support or contradict. 0 are resolved, 2 are not yet assessed. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

What they said5 Episodes1

Everything Demetrius Gray said on the Pitch that made the record, most notable first. Filter by type, assessment or year in the ledger →

Opinion

Demetrius Gray: The onus is on VCs to fund Black founders

“I just don't have tons of confidence in VC. Like, they have a track record, and their track record speaks for itself. Nobody, it's not a secret, and so the onus is really on them to improve. You know, it's not on me to try to convince a VC that a Black founder…”

Demetrius Gray Mar 3, 2025 ▶ 22:32 #99 The Friends & Family Gap

Disclosure

Demetrius Gray: Use accelerators for enterprise customer acquisition, not fundraising

“Part of our internal strategy is using accelerators to get to customers.”

Demetrius Gray Mar 3, 2025 ▶ 20:21 #99 The Friends & Family Gap

Disclosure

Demetrius Gray recruited weekend hackathon teams for free engineering labor

“So Jermaine and I would go, and then you'd recruit to the team, and so you got Free labor for the weekend. Then if everybody on the team had done what they were supposed to do, you won. You know. And so, we started winning.”

Demetrius Gray Mar 3, 2025 ▶ 18:44 #99 The Friends & Family Gap

Prediction Open · timeframe Mar 2028

Demetrius Gray predicts WeatherCheck will become a billion-dollar company

“That also means that I own more of the company than most founders ever do, and I think that's beneficial in the context of, like, look, we will become a billion-dollar company, and the byproduct is that I'm gonna be super rich, and Jermaine's gonna be super ri…”

Demetrius Gray Mar 3, 2025 ▶ 23:35 #99 The Friends & Family Gap

Assertion Not publicly verifiable

Demetrius Gray: $75,000 startup grant required spending $75,000 upfront for reimbursement

“But it was paid when paid. Meaning that you won the grant, but you had to spend 75,000 dollars to get the benefit of the 75,000. Yep. So it didn't really solve anything for us. We just had it.”

Demetrius Gray Mar 3, 2025 ▶ 17:37 #99 The Friends & Family Gap

Appearances (1)

Episode	Date	Speaking time
#99 The Friends & Family Gap	Mar 3, 2025	5m

Demetrius Gray

Appearances (1)

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