I had the pleasure of interviewing Jay Bregman. Jay is the CEO & Cofounder of Thimble, insurance that helps small businesses succeed on their own terms, and provides policies designed for the uncertainty of starting and
growing a business.

We discussed a number of topics. I asked him what makes Thimble unique in an industry that hasn’t seen a great deal of innovation. I asked him why he decided to enter a space that is difficult to enter. We discussed how Thimble is different, how they came up with pricing and what we can expect to see from them in the near future.

To date, Thimble has sold more than 150,000 policies representing over $175B in coverage to
small businesses across America via its award-winning app, partner APIs, and broker tools.
Thimble has raised $30M from investors including IAC (NASDAQ: IAC

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

My Website

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Music by Roger Clyne and the Peacemakers

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