Cole Riccardi's Journey From Investment Analyst to Insurance Innovator

PayPod: The Payments and Fintech Podcast

Episode Topic:

In this episode of Pay Pod, host Kevin Rosenquist sits down with Cole Riccardi, founder of Authentic, a company revolutionizing the insurance industry through captive insurance programs. Captive insurance allows businesses, especially small ones, to pool resources and create tailored insurance solutions that can return profits to the group if claims are low. Cole shares his journey from being inspired by a horse stable’s insurance program to launching Authentic, which is now helping various businesses, from gyms to salons, build their own insurance programs. This episode offers valuable insights into a lesser-known aspect of the insurance industry and how it can benefit small businesses.

Lessons You’ll Learn

Listeners will gain a comprehensive understanding of captive insurance, a concept that allows businesses to take control of their insurance needs, potentially saving money and creating more aligned incentives. Cole Riccardi explains how Authentic simplifies the complex process of setting up these programs, making it accessible to small businesses and affinity groups. The episode also touches on the challenges of entrepreneurship, including the importance of timing and passion when starting a business. Additionally, listeners will learn about the potential for captive insurance to expand into areas like health insurance, offering even more benefits to small businesses.

About Our Guest

Cole Riccardi is the founder of Authentic, a company that helps businesses build and manage captive insurance programs. Originally from Madison, New Jersey, Cole played lacrosse at Notre Dame before embarking on a career in finance. He worked at Aquiline Capital, where he gained deep insights into the insurance sector. Inspired by a family member's success with a horse stable’s captive insurance program, Cole left his stable job to start Authentic in 2022. His passion for the idea and his expertise in insurance have driven Authentic’s success, with the company now serving over ten platforms and continuing to grow.

Topics Covered

The conversation covers the basics of captive insurance, including how it works and why it’s beneficial for small businesses. Cole Riccardi explains the process of setting up a captive insurance program, the challenges involved, and how Authentic has streamlined this process to make it accessible to a wider audience. The episode also explores the potential for expanding captive insurance into health insurance, offering even more value to small businesses. Cole shares his journey as an entrepreneur, discussing the risks and rewards of leaving a stable job to pursue a passion-driven idea