Dakotah Rice’s Bold Comeback: From Startup Failure to AI-Powered Insurance Revolution

In a stunning comeback story that blends resilience, innovation, and cutting-edge technology, Dakotah Rice—once the founder of the now-defunct investment platform Poolit—has reemerged with a bold new vision: Harper, an AI-native insurance brokerage that’s poised to disrupt the $800 billion U.S. commercial insurance industry.

On Wednesday, Rice announced that Harper has raised $46.8 million in a combined Series A and seed funding round, backed by powerhouse investors including YC (Y Combinator), Peak XV Partners, and Emergence Capital. But behind the numbers lies a deeply personal journey of failure, reflection, and reinvention.

The Fall and the Rise: Lessons from Poolit

Rice’s first venture, Poolit, was an investment company aimed at democratizing access to alternative assets. Despite early promise, the company shut down in 2023 after struggling to find a sustainable business model. “My ego made it hard to accept the failure,” Rice admitted to TechCrunch. “In hindsight, I should have shut it down a year earlier.”

The collapse of Poolit was a humbling experience, but it also became the catalyst for his next move. “I went back to my roots,” Rice said. His family had owned an insurance brokerage, and he remembered the frustration of entrepreneurs walking through the door, trying to navigate the complex, slow-moving world of commercial insurance. “I hated insurance,” he confessed. “I swore I’d never end up in it.”

But ideas have a way of pulling you back in.

Harper: The AI-Native Insurance Brokerage

In 2024, Rice and his longtime friend and former Poolit CTO, Tushar Nair, launched Harper—an AI-native insurance brokerage designed to make commercial insurance faster, simpler, and more accessible. Initially, they considered building AI tools for existing brokerages, but they quickly realized the real opportunity was to build an entirely new kind of brokerage from the ground up.

Harper is part of a broader trend identified by Y Combinator: the future of agencies will look more like software companies, with software-like margins. Harper embodies this vision—it’s an almost fully autonomous, licensed commercial insurance agency that matches small- to mid-sized businesses with over 160 insurance carriers for services like workers’ compensation, general liability, and professional liability.

Speed, Scale, and AI: The Harper Advantage

What sets Harper apart is its speed and scale. “What often takes a traditional broker five to seven days, we can often do in one to two,” Rice said. While a typical human-led brokerage sales team handles 20 to 30 deals a month, Harper’s AI-powered system can handle over 1,000 customers a month. To date, Harper has served more than 5,000 customers.

“AI handles the operational weight,” Rice explained. “Submission routing, underwriter follow-ups, document collection, pipeline management—it’s all automated.” This level of efficiency allows Harper to offer a seamless, almost instant experience for its clients, many of whom are small businesses that have traditionally been underserved by the insurance industry.

Targeting Middle America: The Real-World Businesses

Rice is clear about Harper’s mission: to serve the “real-world businesses” that form the backbone of the American economy. “We’re talking about daycares, manufacturers, car dealerships, local bars and restaurants,” he said. These are the businesses that often get lost in the shuffle of the fragmented insurance market, where big players dominate and everyone else relies on “email and spreadsheets.”

While there are other AI-native brokerages like Gyde, and companies using AI tools like FurtherAI and Vantel (all YC alumni), Rice believes Harper’s focus on middle America sets it apart. “We’re not just building software,” he said. “We’re building a voice for entrepreneurs.”

The Road Ahead: Big Dreams for Harper

With the new funding, Harper plans to expand its engineering team and grow its brand. But Rice’s ambitions go far beyond insurance. “We want to become the voice for entrepreneurs, starting with their insurance,” he said. “But over time, we want to become a focal point for all things related to risk, compliance, and their entire back office.”

In other words, Harper isn’t just an insurance company—it’s a platform for simplifying the complex, time-consuming tasks that entrepreneurs face, so they can focus on what they do best.

A Second Chance, a New Vision

For Rice, Harper represents more than just a business—it’s a second chance. “The first time, I was chasing a dream,” he said. “This time, I’m building something that solves a real problem for real people.”

And with $46.8 million in fresh funding, a cutting-edge AI platform, and a clear vision for the future, Harper is poised to redefine what’s possible in the world of commercial insurance.

Tags:

AI-native insurance, commercial insurance, Dakotah Rice, Harper, Y Combinator, startup comeback, AI automation, small business insurance, insurance brokerage, tech innovation, entrepreneurship, risk management, compliance, back office solutions, middle America, venture capital, Emergence Capital, Peak XV Partners, FurtherAI, Gyde, Vantel, insurance disruption, AI-powered brokerage, YC W25, insurance technology, business efficiency, entrepreneur support, insurance for small businesses, AI-driven insurance, insurance industry transformation.

Viral Sentences:

“AI handles the operational weight—submission routing, underwriter follow-ups, document collection, pipeline management.”
“What often takes a traditional broker five to seven days, we can often do in one to two.”
“We want to become the voice for entrepreneurs, starting with their insurance.”
“The real-world businesses—like daycares, manufacturers, car dealerships, local bars and restaurants.”
“My ego made it hard to accept the failure. In hindsight, I should have shut it down a year earlier.”
“We’re not just building software. We’re building a voice for entrepreneurs.”
“The future of agencies will look more like software companies, with software margins.”
“Harper is part of a trend YC recently wrote about—the future of agencies.”
“We want to make it simple for them to do their core work, and we basically do everything else over time.”
“This time, I’m building something that solves a real problem for real people.”

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