In this podcast, Miguel Armaza sits down with Jay Bregman, Founder and CEO of Thimble, an on-demand insurance startup for small businesses and independent workers. Thimble is the first company to offer on-demand insurance by the hour, day, or month to cover the 57 million people who work independently in the US. Jay is an accomplished entrepreneur who previously founded two successful startups, including Hailo, a London-based ridesharing company backed acquired by Daimler Mercedes-Benz in 2016.

Jay Bregman

Jay Bregman is the Cofounder and CEO of Thimble, an on-demand insurance partner for small businesses and independent workers. An innovator in the $100 billion small business insurance market, Thimble is the first and only company to offer on-demand insurance by the hour, day or month to cover the 57 million people who work independently. Thimble has raised over $29 million from top investors including IAC.

Bregman is an accomplished entrepreneur who previously founded Hailo, a London-based ridesharing company backed acquired by Daimler Mercedes-Benz in 2016. Earlier, he founded and sold a technology-enabled services company to Royal Mail, the U.K. equivalent of USPS. Bregman holds a Master’s Degree from the London School of Economics and Political Science and a Bachelor’s Degree from Dartmouth College.

About Thimble

Thimble's mission is to make insurance simple, to help businesses succeed on their own terms. Its flexible insurance policies are designed with small businesses in mind, who face great uncertainty in normal times, and are now on the road to economic recovery. Available by-the-month or for as little as one hour, Thimble coverage takes less than one minute to obtain and can be scaled up, adjusted or paused at any time. Thimble has sold over 100,000 policies representing over $125B in coverage since launching in 2016.

Founded by Jay Bregman and Eugene Hertz, Thimble is based in New York City and has raised over $29 million in funding from IAC and other top firms. All General Liability and Professional Liability policies are underwritten by Markel Insurance Company. For more information, visit www.thimble.com.