Dakota Rice returns as founder. On Wednesday, he announced that his new company, native AI insurance brokerage Harper, has raised $46.8 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 this company, saying that he never figured out how to make it profitable.
“My ego made it hard for me to accept failure,” he told TechCrunch. “In hindsight, I should have booked it a year earlier.”
For his next company, he returned to his roots. His family owned an insurance brokerage and he remembered all the hassles that came with founders like himself walking through the doors trying to insure their businesses. “I hated insurance,” he continued, “I swore I’d never end up with it.”
But then he had an idea. At first, he and Tushar Nair, a longtime friend and former Poolit CTO, thought of building AI tools for existing brokerage firms. They then decided to use this technology to create a native AI insurance brokerage and call it harper after Rice’s mother’s maiden name.
The Harper released in 2024 is part of a trend that YC recently wrote about (Harper was part of the YC W25 batch). The YC blog wrote that the The future of agencies “will look more like software companies, with software margins.” That’s exactly what Harper is — an almost completely stand-alone licensed commercial insurance company. It suits small to medium-sized businesses with more than 160 insurance carriers to help with workers’ compensation, general and professional liability.
“What often takes a traditional broker five to seven days, we can often do in one to two,” said Rice, the company’s CEO. He said a typical sales team at a human brokerage handles 20 to 30 deals a month, but AI allows Harper to handle more than 1,000 clients a month. Harper has more than 5,000 customers to date, she continued.
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“Artificial intelligence handles the operational burden. Submission routing, contractor tracking, document collection, pipeline management,” Rice continued.
The company’s investors include YC, Lobster Capital and Peak XV Partners, and the Series A round was led by Emergence Capital.
Rice sees almost all brokerage firms as competition for Harper. He said work remains too fragmented, with the big players and everyone else running on “emails and spreadsheets”. There are, of course, other AI-inherent brokerages in this space, like Hydeas well as companies using artificial intelligence tools such as FurtherAI or Vantel (both also YC alums).
Rice said what makes Harper different is that she hopes to target middle America. “Real world businesses,” he said, “like daycare centers, manufacturers, car dealerships, local bars and restaurants.”
The new funding will be used to build Harper’s engineering team and grow the brand. The second time in the game, he has big dreams for this company.
“We want to be the voice for business people, starting with their security, but over time becoming a hub for all kinds 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 business, and we basically do everything else over time.”
This piece has been updated to clarify the total funding amount and investors in the round.
