In February, Harper announced a $47M combined Seed and Series A led by Emergence Capital, the largest publicly disclosed Series A ever raised by a Black founder.
The receipts back it up. More than 5,000 businesses served in 13 months, with hundreds of thousands targeted by year-end.
Harper is one of the earliest movers in AI-native services: companies that don’t sell AI into an industry, they become the industry. In their case: an AI-native insurance brokerage.
For this week’s 18 Minutes or Less, I sat down with Harper CEO Dakotah Rice, a founder I’m proud to back through Outset Capital.
Pizza diplomacy
For most of tech history, startups have sold software into an existing industry. Dakotah and his cofounder Tushar started Harper that way, too. They drove around Alabama with boxes of pizza, trying to show insurance brokers how to use AI tools like Claude and Clay. They wouldn’t. “These folks were not the workforce of people who found value in it or were going to adopt it.”
So they did the bigger, harder thing: they became the brokerage themselves.
The thesis isn’t “AI for insurance.” It’s that AI lowers the coordination cost of running a service business so much that, for the first time, a software-native operator can compete on operational scale with the incumbents.
The harder question is who can pull this off. Owning a service business at scale isn’t building SaaS. Most founders don’t have the operational stomach.
The moat is not the model. The moat is the workflow.
“You actually have to know how to work with people in process. It is as much a technological endeavor as it is moat building around your operations.” Or, more bluntly: “It’s messy. It’s very messy.”
Battle scars
Harper isn’t Dakotah’s first company. Before Harper, there was Poolit. Poolit failed.
The founders who get a second swing usually had the most going for them the first time around: pedigree, network, the reflexive second chance. Dakotah didn’t inherit any of it. Low-income rural Alabama, single mother, dad lost young. Brown, Goldman, Carlyle, Coatue, HBS, all earned. When Poolit failed, no safety net. The CV looks orderly. The lived version wasn’t:
“Beneath all of those transitions are a lot of battle scars, a lot of imposter syndrome, a lot of being very nervous I was making the wrong turn, not feeling like I was going as fast as the people who were around me.”
When I asked what raising the largest Series A by a Black founder actually felt like, he didn’t lead with the win. He led with the weight:
“Not a lot of people who have those situations where something bad happens really get a second chance. Having an opportunity to take such a large next shot at what’s happening is not something that I think a lot of people that look like me always get to have. I’m just hoping and always working every day to make sure I meet the moment so that there could be lots of other Black founders who do way more than I do.”
His bet: radical honesty as operating system.
“I think I owe it to the world to be honest. I wish more people were honest with me about the challenges they face. I wouldn’t have felt so alone on the journey of doing these things. One of the biggest things I emphasize at Harper is authenticity.”
Two cofounders driving around Alabama. Cold pizza in the back seat. The brokers said no. Eighteen months later: $47M, 5,000 customers, and a thesis every VC and founder is now chasing.
Dakotah says Harper hits a million customers by 2027. I’m not betting against him.
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