18 Minutes or Less: Harper CEO Dakotah Rice on Failure, AI Insurance, and a Record Series A

Harper Insurance cofounder and CEO Dakotah Rice joined Ali on 18 Minutes or Less to discuss Harper's $47M Series A, led by Emergence Capital — the largest publicly disclosed Series A ever by a Black founder. The conversation covers why selling AI software to brokers didn't work and why that failure became the unlock for building an AI-native commercial brokerage that has served 5,000+ businesses across 35 states in 13 months.

Dakotah also reflects on the cofounder bond forged in his first failed company, the path from rural Alabama to Goldman Sachs to Harper, why he shares the journey out loud, and what Harper looks like in 2027.