Dakotah Rice, CEO of Harper, was always racing to make it to the business big leagues. Raised in rural Alabama, he grew up surrounded by entrepreneurs – just in a small-town kinda way. His dad owned a nightclub, his uncle ran a trucking company and his mum provided home health services. Rather than follow suit and start a local firm of his own, he studied at Brown University, then jumped into a career on Wall Street. “I thought to myself if I was going to grow a business in the future, or wanted to be a part of the big boy version of the thing I've seen in my small town, I needed to learn to live and breathe finance,” he says. 

Dakotah spent a year at Goldman Sachs, then at Carlyle followed by Coatue, moving into private equity, then hedge funds. All the while he was seeking more autonomy. After four years doing internet media investing he started to think to himself: “Wow, I might wanna branch out and do this on my own….” He left for Harvard Business School and in 2021 started his first company, Poolit, a fintech platform that makes it easy for users to invest in private equity and VC funds. It was a pivotal moment. “I got bit by the bug,” says Dakotah. “I just knew this is what I was meant to do.”

A perfect ying-yang

It was also the moment that Dakotah found his perfect match for a co-founder, Tushar Nair, a friend from Goldman Sachs who joined and became CTO. “We have a perfect ying-yang,” says Dakotahh. “I'm the one with the more chaotic vision, like let's bring this to life. And he really grounds me and helps to bring systematic thinking to the things I'm doing…” Dakotah knew he was the person he wanted to build with, so when they wound down Poolit they decided to pursue a new project together. After joining an Antler residency in Spring 2024, where the pair explored a number of ideas, Harper was born. 

Harper – named after Dakotah’s mother’s maiden name – is an AI-native insurance brokerage that integrates cutting edge tools into a traditionally slow-moving, technologically conservative industry. It can sometimes take weeks, along with countless calls and paperwork, for a business to secure insurance – particularly if it has complex needs. Dakotah himself remembered the extent to which insurance – and the convoluted process of securing it – had been an obstacle for his family members running small businesses around him, and Harper aims to do it better. By using AI to handle the “judgement-heavy, unstructured work” inherent to the industry – from reading applications to chasing underwriters – Harper can transform the experience of buying insurance for both the broker and the customer. Now, the process can take as little as 24 hours. 

“Why not us?”

At first, Dakotah and Tushar planned to offer their product as an outsourced sales service for existing insurance agencies, but they came up against resistance from brokerages who felt threatened by a service that could undermine their existing brokers. As they came to understand the complications of integrating within existing workflows, the pair realised the market was ready for a new type of brokerage all together; one that has been built from the ground up with AI integrated in every level and a workforce trained to use it. “Somebody was gonna build a brokerage this way,” says Dakotah. “And so we thought to ourselves: why not us?”

Today, Harper is rapidly gaining momentum. In February 2026 it announced it had received $46.8 million in a combined Series A and seed round. It currently has around 6-7,000 customers and is aiming to hit 100,000 by the end of the year. A traditional broker can only handle 20-30 customers a month, Dakotah explains, but Harper’s system can handle 1,000, meaning it has a strong propensity for growth. “The name of the game for this year is all about scale,” he says. 

The latest funding round will go towards building out the tech and the team, which currently stands at around 25 and they will invest in brand building too. For Dakotah, who wants to target the same kinds of middle-America businesses he grew up around, success will be getting to a place where Harper is the natural choice for anyone trying to get that new contract, or open their doors for the first time. “That's when my world will be made,” he says.