He told everyone he would never sell insurance. Then he built an AI agency that quotes a small business faster than most brokers can return a phone call.
CO-FOUNDER & CEO, HARPER // SAN FRANCISCO
Harper closes a workers' comp policy for a daycare in roughly a day and a half. A traditional broker takes five to seven. That single gap - days versus an afternoon - is the whole argument Dakotah Rice has been making to investors, carriers, and the manufacturers of middle America. And in February 2026 the argument landed: a combined seed and Series A of about $47 million, led by Emergence Capital, with Y Combinator, Lobster Capital, and Peak XV Partners alongside.
Rice runs Harper, the AI-native commercial insurance brokerage he co-founded in 2024 with Tushar Nair, his former chief technology officer. The pitch is deliberately unglamorous. Harper is a licensed agency that matches small and mid-sized businesses to more than 160 carriers for the coverage nobody thinks about until they need it: general liability, professional liability, commercial auto, property, cyber, bonds. The customers are car dealerships, fleet operators, restaurants, healthcare facilities, the kind of businesses a polished insurtech demo usually skips.
What makes it move is the choice not to be a software vendor. "Harper isn't selling software to legacy brokerages and hoping they figure it out," Rice has said. "We do the work." The company's models take on the judgment-heavy, unstructured tasks - reading a messy application, profiling risk, finding the carrier that will actually write the policy - that keep human brokers tied to twenty or thirty deals a month. Harper says it handles more than a thousand.
The reported headline traveled fast: the round was described as the largest publicly disclosed Series A ever raised by a Black founder. Rice tends to redirect that conversation back to the work. The interesting number to him is the 98.78% of clients who stay.
The customers Harper chases are the ones the industry treats as too small to bother with and too varied to standardize. A car dealership has nothing in common with a daycare, which has nothing in common with a long-haul fleet, except that each one needs coverage written quickly, priced fairly, and renewed without a fight. Harper's bet is that this messiness - the exact thing that makes the work expensive for humans - is what machine judgment is good at. Read the application, profile the risk, find the carrier in the network of 160-plus that will say yes, and bind it before the business owner has had time to call a competitor.
"It was watching my family navigate a system that never seemed to work for them. That memory never left me."
"I got bit by the bug. I just knew this is what I was meant to do."
"After Goldman, Carlyle, and four years at Coatue, I could have kept picking stocks."
Rice grew up in rural Alabama in a family that ran things. His father owned a nightclub. His uncle ran a trucking company. His mother provided home health services. He watched all three wrestle with the same paperwork, the same renewals, the same coverage that never seemed built for them. Insurance, in that house, was the thing that worked against you.
So he left to learn what he later called the "big boy version" of business. Brown University, a political science degree in 2016, then straight onto a Goldman Sachs technology, media and telecom team. From there: The Carlyle Group, then four years at Coatue Management investing in internet and media, with a stint connected to ByteDance. The plan was simple and stubborn. "I thought to myself if I was going to grow a business in the future," he has said, "I needed to learn to live and breathe finance."
The bug bit at Harvard Business School. In 2021 he started Poolit, a fintech platform that let everyday investors buy into private equity and venture funds. It scaled to roughly $100 million in assets under management. It also did not survive.
What is worth noticing is the shape of the resume before the founding. Goldman, Carlyle, Coatue - the institutions that teach you to underwrite a business from the outside, to look at a balance sheet and decide whether to bet. Rice spent years learning to price risk for a living. It is not a coincidence that the company he eventually built is, at its core, a machine for pricing risk faster than the people who taught him.
"My ego made it hard to accept the failure. In hindsight, I should have shut it down a year earlier."
When Poolit closed in 2023, Rice did the unthinkable for someone who once swore off the industry: he went back to insurance. The first instinct was the comfortable one - build AI software and sell it to the brokerages already in business. He and Nair talked themselves out of it. Legacy brokers move slowly, and a tool only works as well as the people who adopt it. The harder, more honest move was to become the brokerage and let the AI execute the judgment directly.
They named the company Harper, after Rice's mother's maiden name, and joined Y Combinator's Winter 2025 batch. Rice describes the founder chemistry plainly: he is the one with "the more chaotic vision," and he goes looking for systematic thinkers to ground it. Nair, the engineer who built Poolit's technology, is the ground.
The wager is that AI can do at scale what used to be a luxury. "Because AI can execute judgment at scale," Rice has said, "we can deliver the quality of service that used to be reserved for Fortune 500 companies to every manufacturer, every healthcare facility, every fleet operator in middle America." Emergence Capital, which has made a thesis out of what it calls "AI-native services," bought the argument and led the round.
Graduates Brown University, BA in Political Science. Joins Goldman Sachs (TMT investment banking).
Investing roles at The Carlyle Group and Coatue Management; work connected to ByteDance.
Starts at Harvard Business School and founds Poolit, a fintech platform for PE and VC fund investing.
Winds down Poolit after it scales to roughly $100M AUM.
Co-founds Harper with Tushar Nair. Names it after his mother's maiden name.
Harper joins Y Combinator's Winter 2025 batch.
Announces ~$47M combined seed and Series A led by Emergence Capital.
"We do the work."
"Our proprietary models handle the judgment-heavy, unstructured work that slows traditional insurance down."
"Harper isn't selling software to legacy brokerages and hoping they figure it out."
Harper is named after Rice's mother's maiden name - the company is, quite literally, family.
He once said he hated insurance and swore he would never enter the field. He now runs an insurance company.
His father owned a nightclub, his uncle a trucking company, his mother a home health service. Three different insurance headaches, one founder.
He and Nair nearly built AI tools for other brokers before deciding to become the broker themselves.
Harper says it processes 1,000+ customers a month - roughly forty times a traditional broker's deal flow.
"The voice for entrepreneurs."
Rice talks about Harper the way founders talk about platforms they have not finished building. Coverage is the entry point. The longer ambition is to handle the unglamorous machinery that every small business runs on - risk management, compliance, the back office - and to become, in his phrase, "the voice for entrepreneurs." He wants Harper to be the natural choice for anyone chasing a new contract or opening their doors for the first time.
It is a big claim from a one-year-old company. But the through-line is consistent with everything before it: a kid from rural Alabama who watched a system fail the people he loved, learned its rules on Wall Street, lost once, and came back to rebuild the part that broke. The retention number suggests the customers, at least, are convinced.
The candor about Poolit is part of the appeal. Plenty of founders bury a closed company in a single line on a slide. Rice puts it in the open - the ego, the year he waited too long, the failure he had to accept before he could build again. That kind of honesty is rare enough in venture pitches that investors tend to remember it. It also reads as the difference between a first-time founder and a second-time one: the second time, you know exactly what losing feels like, and you build to avoid it.
For now the scoreboard is early but legible. Thousands of businesses insured across dozens of states in roughly a year. A carrier network deep enough to actually place complex risk. A retention rate most consumer companies would envy. And a founder who keeps pointing past the funding headline toward the boring, durable thing underneath it - whether a daycare in a small town can get covered in an afternoon instead of a week. Rice has spent his whole life on both sides of that question. Harper is his answer.