Dakota Rice is returning to the founder's chair. On Wednesday, he announced that his new company, Harper, an AI-native insurance brokerage, has raised $46.8 million in a combined Series A and seed round.
Previously, he founded the investment company Poolit, which was shut down in 2023. He spoke candidly to TechCrunch about the company's bankruptcy, saying he had no idea how to turn a profit.
“My ego was making it difficult to accept failure,” he told TechCrunch. “In retrospect, we should have closed it a year earlier.”
In his next company, he returned to his roots. His family owned an insurance brokerage, and he recalled all the hassles that happened when founders like himself walked in the door trying to insure their business. “I hated insurance,” he continued, “and swore I would never buy insurance.”
But then he had an idea. Initially, he and Tushar Nair, a longtime friend and former CTO of Poolit, wanted to build an AI tool for existing brokerage firms. So they decided to use that technology to build an AI-native insurance brokerage company and call it Harper, after Rice's mother's maiden name.
Launched in 2024, Harper is part of YC's recent writing trend (Harper was part of the YC W'25 batch). YC's blog writes that the agency's future “will look more like a software company with a software profit.” That's exactly what Harper is: a nearly completely independent licensed commercial insurance agency. We match small businesses with over 160 insurance carriers to help with workers' compensation as well as general liability and professional liability.
“Traditional brokers often take five to seven days, whereas with us we can often complete transactions in one to two days,'' said Rice, the company's CEO. While a typical human-driven sales team at a brokerage handles 20 to 30 trades a month, Harper is able to handle more than 1,000 clients a month thanks to AI, he said. Harper has more than 5,000 customers to date, he continued.
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“AI handles the operational weight: application routing, underwriter follow-up, document collection, pipeline management,” Rice continued.
Investors in the company include YC and Peak XV Partners, and the seed and Series A rounds were led by Emergence Capital. Mr. Harper has raised $54 million so far, and received that amount in just under two months, Mr. Rice said.
Mr. Rice considers nearly all brokerage firms to be Mr. Harper's competitors. He said work remains highly fragmented, with major corporations and everyone else working through “email and spreadsheets.” Of course, there are other AI-native brokerages in this space like Gyde, as well as companies using AI tools like FurtherAI and Vantel (both also YC alumni).
Rice said what sets Harper apart is that it wants to target Central America. “Real-world businesses include daycares, manufacturers, car dealerships, and local bars and restaurants,” he says.
The new funding will be used to strengthen Harper's engineering team and support the growth of the brand. In his second game, he has big dreams for this company.
“We want to be the voice for entrepreneurs. We're starting with insurance, but over time we want to become the focal point for all kinds of things related to risk, compliance and the whole back office,” he said. “We want to make it easy for them to do their core job, and basically take their time doing everything else.”