Dakotah Rice is stepping back into the founder’s seat. On Wednesday, he announced that his new company, the AI-native insurance brokerage Harper, has raised $46.8M million in a combined Series A and seed round.
Previously, he founded the investment company Poolit, which closed in 2023. He spoke openly to TechCrunch about the collapse of that company, saying he never figured out how to make it profitable.
“My ego made it hard to accept the failure,” he told TechCrunch. “In hindsight, I should have shut it down a year earlier.”
For his next company, he went back to his roots. His family owned an insurance brokerage, and he remembered all the hassles that came when founders like himself walked through the doors, trying to insure their businesses. “I hated insurance,” he continued, “swore I’d never end up in it.”
But then he had an idea. At first, he and Tushar Nair, a longtime friend and former CTO of Poolit, thought about building AI tools for existing brokerages. Then, they decided to just use that technology to build an AI-native insurance brokerage and call it Harper, after Rice’s mother’s maiden name.
Launched in 2024, Harper is part of a trend YC recently wrote about (Harper took part in the YC W’25 batch). The YC blog wrote that the future of agencies “will look more like software companies, with software margins.” That’s exactly what Harper is — an almost fully autonomous licensed commercial insurance agency. It matches small- to mid-sized businesses with more than 160 insurance carriers to assist with workers’ compensation, as well as general and professional liability.
“What often takes a traditional broker five to seven days, we can often do in one to two,” Rice, the company’s CEO, said. He said a typical sales team at a human-led brokerage handles 20 to 30 deals a month, but AI enables Harper to handle more than 1,000 customers a month. Harper has more than 5,000 customers to date, he continued.
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“AI handles the operational weight. Submission routing, underwriter follow-ups, document collection, pipeline management,” Rice continued.
Investors in the company include YC and Peak XV Partners, and its seed and Series A rounds were led by Emergence Capital. Harper has raised $54 million in funding to date, nabbing that amount in just under two months, Rice said.
Rice thinks of nearly all brokerages as Harper’s competition. He said that work remains very fragmented, with big players and everyone else running on “email and spreadsheets.” There are, of course, other AI-native brokerages in this space, like Gyde, as well as companies that use AI tools, like FurtherAI or Vantel (both of which are also YC alums).
Rice said what makes Harper different is that it hopes to target middle America. “The real-world businesses,” he said, “like daycares, manufacturers, car dealerships, local bars and restaurants.”
The fresh funding will be used to build out Harper’s engineering team and help grow the brand. The second time in the game, he has big dreams for this company.
“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.”