Founder Profile • Insurtech
Cole Riccardi
The investor who got so obsessed with an idea he had to stop investing and go build it.
Cole Riccardi / Authentic
The investor who got so obsessed with an idea he had to stop investing and go build it.
Cole Riccardi / Authentic
Cole Riccardi spent six years looking at insurance from the outside. As an investor at Aquiline Capital Partners, his job was to study insurance companies, price the risk in a deal, and decide whether they were worth backing. He was good at it. He was also, by his own account, becoming distracted by a single idea he could not shake - an idea he was not allowed to build from an investor's chair.
The spark came from a family connection. A relative had set up a captive insurance program for a network of horse stables. Captives are not exotic in the corporate world; large companies have used them for decades to pool their own risk and keep the margin that would otherwise go to a national carrier. What struck Riccardi was how far that tool sat from the businesses that might benefit most - the gyms, salons, restaurants and small operators who buy off-the-shelf policies and never see a dollar come back.
"I became obsessed with the idea that I actually couldn't do my day job," he has said of that stretch. In 2022 he left Aquiline and started Authentic.
The technical term is a captive. Riccardi's term is simpler: "captive-in-a-box." Historically, launching one required lawyers, actuaries, regulatory filings and enough scale to justify the effort. Authentic collapses that into software. A platform - say, the app a gym uses to manage memberships - can plug in and offer its own branded insurance program to the businesses on it. Authentic handles the parts that used to require a specialist: underwriting, claims management and regulatory compliance.
The pitch to those platforms is not charity. It is economics. Authentic splits upfront fees roughly 50/50 with the software provider, and after claims are paid, returns about 80% of what is left to the partner while keeping 20%. If the businesses in a program stay safe and claims stay low, the partner and its members share the upside - the money that a traditional carrier would have pocketed.
The result is a different answer to a question most small business owners never think to ask: who should sell me insurance? Riccardi's bet is that the platform running your business day to day understands your risk better than a national brand ever will - and that trust, not brand recognition, is the thing worth building on.
Riccardi grew up in Madison, New Jersey, and played lacrosse at the University of Notre Dame, where he earned a finance degree from the Mendoza College of Business. The path from there ran through Aquiline, a firm that specializes in financial services and insurance. Those six years gave him two things that turned out to matter more than a founder's usual resume: a working knowledge of how insurance actually makes money, and a rolodex of the people building in it.
One of those people became his co-founder. Kyle Babirad, an insurance pricing and actuarial specialist with more than a decade of experience, ran a consulting firm that many of the insurtech companies Riccardi had been evaluating hired for help. When Riccardi decided to build rather than back, Babirad was the natural partner - someone who could handle the pricing and risk math while Riccardi drove the company. The early team filled in the rest: a former Amazon engineering leader on the technical side, and product leaders with years in commercial insurance.
Authentic started with a $5.5 million seed round in 2022. In May 2024 it announced an $11 million Series A led by FirstMark Capital, with Slow Ventures, Altai Ventures, MGV, Upper90 and Commerce Ventures joining. Some of the checks came from former Aquiline colleagues - people who had watched Riccardi analyze the industry and decided to back him building inside it.
By the time of the raise, Authentic had doubled its headcount, sold more than 100 policies through partners, and projected more than a thousand by the end of that summer. Its named partners read like a list of the software small businesses already live in: Mindbody for wellness studios, Restaurant365 for food service, theCut for barbers, PushPress for gyms.
The funding is aimed at engineering hires and new products. Today Authentic's core is property and casualty coverage. Riccardi's stated ambition is to push into workers' compensation and, eventually, health insurance - the same model, applied to bigger and more complicated lines, until a small business can get coverage tailored to its exact industry through software it already uses.
He is the founder and CEO of Authentic, a New York based insurtech startup that lets software platforms and affinity groups launch their own branded insurance programs.
Authentic provides "captive-in-a-box" infrastructure so brokers, platforms and small business groups can create and manage captive insurance programs, with Authentic handling underwriting, claims and compliance.
Roughly $16 million, including a $5.5 million seed round in 2022 and an $11 million Series A led by FirstMark Capital in 2024.
He studied finance at the University of Notre Dame, played lacrosse there, and spent about six years as an investor at Aquiline Capital Partners before founding Authentic in 2022.
Kyle Babirad, an insurance pricing and actuarial specialist he met through the insurance industry, is his co-founder at Authentic.