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 also 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 is the ultimate serial entrepreneur. Prior to Thimble, he founded two startups in London, raised over $110 million, and successfully exited both businesses. After selling his second company, a ride-sharing app called Hailo, he became interested in the concept that several of his customers had multiple revenue streams and realized for a lot of people there was a new, much more flexible, way of working that would also require a new type of flexible insurance. Thimble was born out of this concept.
Launched in 2016, Thimble’s initial target market was drone pilots who would participate in drone races and needed to insure their drones for just a few hours a month. Jay and his team developed an insurance product that allowed drone pilots to get a policy in less than a minute. The product worked well, but they quickly realized a lot of their clients were not drone race pilots, but instead real estate brokers and photographers. At the same time, they were getting client requests demanding Thimble extend its coverage to other products and services while maintaining the flexible nature of their policy. At this point, Jay realized they were onto something and decided to build a product covering several types of small businesses.
As one might suspect, some of Thimble’s customers have been affected by the mandatory COVID shutdowns. However, they also serve various subgroups of clients who work in industries like landscaping or sanitation that have seen an increase in demand. Additionally, many small businesses have been persuaded to cut their annual insurance policies and migrate to Thimble for flexible monthly insurance that adjusts to the fluctuating needs of a small business. As Jay puts it, “Thimble is a cord-cutting product and it’s very similar to what has been done in telecoms and cable TV”. Interestingly, during this time their relationship with the regulator has strengthened and the government is even more committed to seeing InsurTech startups succeed.
The Road Ahead
According to Jay, the insurance industry doesn’t have a lot of startups because it isn’t yet considered an attractive space by many. He sees a lot of parallels to the ride-sharing industry in 2010 when investors didn’t believe transportation could be disrupted. Yet, he envisions massive potential for InsurTech and argues the $100 billion annual commercial insurance market is ripe for disruption. As for the future of Thimble, they are just getting started and although Jay recognizes there is a massive opportunity to execute Thimble’s business model around the world, he first plans to scale and grow locally before venturing outside the US.
If there is one reason Jay has been extremely successful in his entrepreneurial endeavors, it’s probably his passion. When asked for advice for future entrepreneurs, Jay tells us founders will go through multiple periods of time where all things won’t be going right at the same time. However, there are also periods you will experience that everything sort of goes right, the engine starts to work, and the customers start to love the product. For him, that’s worth waiting for and worth fighting for.
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.
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.
Reimagining Small Business Insurance with Jay Bregman, CEO and Founder of Thimble was originally published in Wharton FinTech on Medium, where people are continuing the conversation by highlighting and responding to this story.