The Story of Authentic: The Company Building the Future of Insurance Distribution

The Story of Authentic: The Company Building the Future of Insurance Distribution

Late 2022. Cole Riccardi’s inbox was empty. No meetings scheduled. No warm introductions pending. Just a conviction that insurance distribution was broken and a family story about horse farms that somehow held the answer.

Most people would have taken this as a sign to keep their day job. Cole started walking.

In a recent episode of Category Visionaries, Cole Riccardi, CEO and Founder of Authentic, shared the origin story of a company that’s raised 16 million dollars to fundamentally reshape how small businesses buy insurance. It’s a story about pattern recognition, calculated wandering, and betting everything on an idea that made sense to almost no one.

The View from Aquiline

The story begins not with entrepreneurship but with observation. Cole spent six years at Aquiline, an investment firm focused on financial services. It wasn’t glamorous work—analyzing portfolio companies, sitting in strategy meetings, watching vertical software companies struggle with the same problem over and over.

“I was fortunate enough to spend six years at an investment firm called Aquiline, which focuses on financial services investing,” Cole explains. “And we had a number of vertical software companies that sold software and payment services to small businesses. And were trying to figure out how to offer an insurance product to these small businesses.”

The problem was clear. Every vertical software company wanted to offer insurance to their customers. The economics never worked. They could partner with carriers and sell leads. They could hire consultants and build brokerage programs. Both options meant giving up control, giving up margins, and offering a mediocre product through someone else’s infrastructure.

Cole watched this pattern repeat across portfolio companies. He saw the problem. But he didn’t see the solution—not yet.

The Horse Farm Connection

Sometimes the most important business insights come from the most unexpected places. For Cole, it was a family member in the insurance space who had done something unusual: formed a captive insurance program for horse farms in the northeast.

“Instead of horse farm buying insurance through Liberty Mutual or State Farm, they could join the captive program of their fellow horse farms and essentially join an insurance pool of their peers,” Cole shares. “And they could get much better rates. They get the money back at the end of the year if there’s leftover profits.”

Most people would have filed this away as an interesting anecdote. Cole saw the pattern. Captives worked for large enterprises like Walmart, who could afford to start their own insurance company to self-insure and save millions. They worked for niche groups like horse farms, who could pool together for better rates. But they didn’t exist for the vast middle market of small businesses—not because they wouldn’t work, but because the infrastructure didn’t exist.

“That’s sort of when captive came as the AHA moment for embedded insurance,” Cole recalls. The vertical software companies at Aquiline didn’t need to partner with carriers. They needed to become the carrier, using a captive structure. And if the infrastructure existed, they would.

Wandering in the Desert

Having an insight and building a company are different problems entirely. Cole left Aquiline in late 2022 with conviction but nothing else. No co-founder. No first customer. No warm pipeline. What he calls “wandering in the desert” had begun.

“I think one of the most challenging parts of being an entrepreneur is when your inbox is zero and you don’t have meetings and nobody probably wants to talk to you, but you just need to kind of keep wandering in the direction that you believe is the right path,” Cole reflects.

The path was straightforward but exhausting: talk to everyone who might need this. Franchisors who could offer insurance to their franchise network. Vertical software companies trying to crack embedded insurance. Associations looking for member value-adds. Cole pitched the same idea hundreds of times: if you had the infrastructure, would you start your own captive insurance program?

The feedback was overwhelmingly positive. But positive feedback doesn’t pay rent. “You never know if someone’s actually going to be a customer until you put a piece of paper in front of them and ask them to sign it,” Cole learned.

What made those conversations worth it wasn’t validation—it was compound learning. “With each of those conversations, you learn one new thing every time, which compounds after your hundredth conversation and all of a sudden you’re pitching something that’s a little bit more of a real product.”

By conversation one hundred, Cole wasn’t pitching his idea anymore. He was pitching their idea, refined by the market, expressed in the market’s language, solving the market’s actual problem.

The Slow Ventures Bet

A few months into the desert wandering, Cole got a meeting with Slow Ventures. No product. No customers. Just conviction and six years of domain expertise. They wrote the check.

“I was really passionate about this idea. I still obviously am,” Cole explains. “It’s obvious to me, maybe more people in my demographic that I would rather buy insurance through a trusted channel that I already interact with, as opposed to some insurance brand that I haven’t worked with.”

The investment thesis was simple: distribution in insurance is shifting. “If I’m a gym and I use Mindbody for scheduling and payments and lending, I’d rather get my insurance there as opposed to googling around for gym insurance and then calling into some call center at a large insurance carrier.”

Slow Ventures saw where the puck was going. More importantly, they saw Cole’s conviction level and his years in the space. “I think that’s what really prompted them to write the check,” Cole notes.

From Theory to Practice

With funding secured, Authentic needed to prove the concept worked in practice. The regulatory complexity was real—captive insurance involves state domicile approval, reinsurance arrangements, underwriting infrastructure, and front-end platforms. “We’ve spent a lot of time with the regulators and our state of domicile. We’ve spent a lot of time with some incredible lawyers to really work within the existing captive structure, but make it scalable,” Cole shares.

This complexity became a moat. Competitors would need to navigate the same regulatory maze, find their own reinsurance, build their own infrastructure. Or they could just give Authentic “a small sliver of the economics” and get everything turnkey.

When Authentic had a working prototype, Cole went straight back to the hundred conversations from the desert wandering period. “Immediately went back to the folks I had one or several meetings with and said, hey, you know that captive platform you were so excited about in theory? Well now it’s here and I’d love for you to sign a contract.”

Not everyone said yes. But enough did. Authentic had its first customers.

The Future of Insurance Distribution

Today, Authentic is a team of twelve across New York and Dayton, Ohio. They’ve raised 16 million dollars. They’re five months into launching their product, and word-of-mouth is already working in the small, interconnected world of insurtech.

But Cole’s vision extends far beyond the current state. “Insurance used to transact with a broker, a carrier, and a reinsurer. And in the future it will transact through some type of affinity group that has a captive, that has capital and reinsurance behind that captive,” he predicts.

The shift isn’t limited to small business insurance. “Over time, it won’t just be for small business, it’ll be for your home and auto insurance or your renters insurance,” Cole adds. “It makes sense to purchase these products through other platforms as opposed to traditional brands.”

Authentic is also exploring something Cole doesn’t talk about much publicly: “There’s a huge opportunity for us to open up the capital markets to more insurance yield as an asset class. That’s something we don’t talk a lot about, but we’re very excited to do medium and longer term.”

The big picture is about fundamentally changing the value chain of insurance. “I think if you ask a lot of folks where the puck is going that are deep in the space, they do see distribution shifting,” Cole observes. “And I think we want to be on the leading edge creating that shift in distribution.”

From wandering in the desert with an empty inbox to building the infrastructure for the next generation of insurance distribution, Authentic’s story is about seeing what others miss, walking toward it even when no one’s following, and building the future while everyone else debates whether it’s possible.

The inbox isn’t empty anymore.