Dakotah Rice is back in the founder’s seat with Harper, an AI-native insurance brokerage he co-founded after the closure of his previous venture, Poolit. On Wednesday, Harper announced it has raised $46.8 million in a combined seed and Series A round, bringing its total funding to $54 million in just under two months. The round was led by Emergence Capital, with participation from Y Combinator and Peak XV Partners. Rice, who previously led Poolit, spoke candidly about its closure in 2023, admitting he struggled to accept its failure. “My ego made it hard to accept the failure,” he said. “In hindsight, I should have shut it down a year earlier.” After that experience, he returned to his roots—his family’s insurance brokerage business. He remembered the frustrations of founders like himself trying to secure coverage, and how difficult and inefficient the process felt. “I hated insurance,” he said. “I swore I’d never end up in it.” But a new idea emerged. Initially, Rice and Tushar Nair, his longtime friend and former CTO of Poolit, considered building AI tools for traditional brokerages. They soon realized they could do better: create a fully AI-powered brokerage from the ground up. They launched Harper in 2024, naming it after Rice’s mother’s maiden name. Harper is part of a growing trend among Y Combinator startups, as highlighted in a recent YC blog post noting that the future of insurance agencies will resemble software companies with scalable, high-margin operations. Harper operates as an almost fully autonomous licensed commercial insurance agency. It connects small- to mid-sized businesses with over 160 insurance carriers, specializing in workers’ compensation, general liability, and professional liability. The company claims it can complete processes that typically take traditional brokers five to seven days in just one to two. Where a human-led team might handle 20 to 30 deals per month, Harper’s AI infrastructure enables it to manage more than 1,000 customers monthly. Rice says AI handles the heavy lifting—submission routing, underwriter follow-ups, document collection, and pipeline management—allowing Harper to scale efficiently. To date, the company serves over 5,000 clients. While other AI-driven insurance startups like Gyde, FurtherAI, and Vantel are also emerging—many of them YC alumni—Rice says Harper’s focus is on middle America: real-world businesses such as daycares, local manufacturers, car dealerships, and neighborhood bars and restaurants. “We want to be the voice for entrepreneurs,” he said. “Starting with insurance, but expanding over time to include risk management, compliance, and their entire back office.” The new funding will support engineering growth and brand expansion. With a second chance at building a company, Rice has big ambitions: to become a central platform for small business owners, simplifying the complex tasks that distract from their core work.