Jay Bregman is CEO & co-founder of Thimble, insurance that helps businesses succeed on their own terms. Thimble’s customizable policies are designed for the uncertainty of starting, running, and growing a business in today’s economic landscape.

To date, Thimble has sold more than $175B in coverage to businesses across America via its award-winning app, partner APIs, and industry-leading broker tools. Their unique policies have attracted the likes of Hiscox, Lloyd’s, and Angi, who have partnered with the insurtech to provide innovative solutions to their customers. Thimble has raised $30M from investors including IAC, Open Ocean and top VCs.

Prior to Thimble, Jay founded Hailo, a ridesharing company in London backed by investors including Sir Richard Branson that was acquired by Daimler. Earlier, he founded and sold eCourier, a technology-enabled services company to Royal Mail.

Key points from the episode

• Thimble is simple business insurance created with small business in mind and the need for flexibility, especially in challenging times like we are facing today
• Jay's background was in the micro-employment and gig space, so he was watching how business consumers' needs were changing and insurance wasn't changing with them
• They started in drones, which was a space Jay was personally interested in and saw how the way people were using their drones for episodic income had no fit-for-purpose coverage
• In meeting the needs of drone pilots, those same people started asking for solutions for their other sources of income
• Aviation was easier to navigate the regulations on, but regulation became a major theme for Thimble as they spread to other lines by embracing the idea of working with regulators rather than fighting against them
• This may require lobbying to help move the thinking on some regulations that were created at a very different time and situation than the current environment or nature of work and exposure
• The economic shock of the pandemic has shifted how many companies work
  
  • Larger businesses decided they needed more flexibility than their annual policy, leading Thimble to see some larger risks than they had been seeing before
  • Smaller businesses with spikes in their revenue saw more spikiness, making the flexibility of Thimble's approach even more attractive
  • There has been more growth in the starting of small businesses that is unprecedented
• Insureds are used to "consumerized" experiences, and are increasingly intollerant of where this is missing
• Shifts coming - there is a shift in appetite for some of the startup carriers that had "simple" offerings early on (like Thimble when it was just offering drone coverage) to be able to compete on much more complex and complete offerings going forward once their platform is proven
• Making changes in a legacy carrier is possible, but you have to be willing to fight against your existing solutions that the change may be breaking, giving Thimble not just a head start, but a moat that should persist beyond just when legacy carriers start offering episodic solutions

This episode is brought to you by Medallia (Medallia.com), and the book series, "The Future of Insurance: From Disruption to Evolution" by Bryan Falchuk (future-of-insurance.com).

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of UPbeat Music, available to stream on Spotify, Apple Music, Amazon Music and Google Play. Just search for "UPbeat Music".