Dakotah Rice is returning to the role of a founder. He recently announced that his new venture, the AI-native insurance brokerage Harper, secured $46.8 million in a combined Series A and seed funding round. Rice, who previously founded the investment company Poolit, which closed in 2023, candidly spoke about Poolit’s downfall, admitting he never achieved profitability. Reflecting on his experience, Rice mentioned, “My ego made it hard to accept the failure. In hindsight, I should have shut it down a year earlier.”
For his new endeavor, Rice drew inspiration from his background. His family owned an insurance brokerage, and he remembered the challenges faced by founders seeking insurance for their businesses. Initially resistant to the idea of working in insurance, Rice eventually embraced the concept. Along with Tushar Nair, a longtime friend and former Poolit CTO, he considered developing AI tools for existing brokerages, but eventually opted to create an AI-native insurance brokerage named Harper, honoring his mother’s maiden name.
Harper, launched in 2024 and part of the YC W’25 batch, is part of a trend where agencies resemble software companies. YC’s blog mentioned that the future of agencies “will look more like software companies, with software margins.” Harper is an almost fully autonomous licensed commercial insurance agency connecting small- to mid-sized businesses with over 160 insurance carriers for workers’ compensation, general, and professional liability. Rice, the company’s CEO, stated, “What often takes a traditional broker five to seven days, we can often do in one to two.” While a typical sales team at a traditional brokerage handles 20 to 30 deals monthly, Harper, fueled by AI, manages over 1,000 customers monthly, boasting over 5,000 customers to date.
“AI handles the operational weight. Submission routing, underwriter follow-ups, document collection, pipeline management,” Rice explained. Harper’s investors include YC and Peak XV Partners, with seed and Series A rounds led by Emergence Capital. To date, Harper has raised $54 million, achieving this in under two months, Rice noted.
Rice considers nearly all brokerages as Harper’s competition, highlighting the fragmented nature of the work where many depend on “email and spreadsheets.” Other AI-native brokerages like Gyde and companies using AI tools such as FurtherAI and Vantel are also in the space. Harper distinguishes itself by focusing on middle America’s “real-world businesses” like daycares, manufacturers, car dealerships, local bars, and restaurants.
The recent funding will bolster Harper’s engineering team and enhance brand growth. With experience from his first venture, Rice has ambitious goals for Harper. “We want to become the voice for entrepreneurs, starting with their insurance, but over time becoming a focal point for all types of things related to risk, compliance, and their entire back office,” he said. “We want to make it simple for them to do their core work, and we basically do everything else over time.”