Agency Intelligence

Agency Intelligence


Agency intelligence podcast, is your top insurance podcast with two unique series that let you hear from and learn from both agency owners and industry influencers. Agents Influence is your weekly guide to the latest and greatest thought leaders the industry has to offer. Agency Intelligence covers real data from real agents in real agencies.

In this episode of Agents Influence podcast, host Jason Cass interviews Jay Bregman, the Founder, and CEO of Thimble. Jay talks about his concept and ideas in building Thimble and the three lessons that he wrote back in May.

Episode Highlights:

Jason introduces Jay Bregman. (3:15)

Jay mentions that he did an internship at the Berkman Klein Center for Internet and Society at Harvard Law School in 1999. (8:54)

Jay shares that during his internship, he met a lot of law students but most of them were unhappy. They wanted to be entrepreneurs, rather than lawyers. (9:01)

Jay shares that he went to graduate school at the London School of Economics in London. He got together with his friend and they started a courier company. (9:25)

Jay mentions that they started this company without any knowledge on how to start a courier company based around technology. (9:35)

Jay mentions that in 2008, he had his first experience with a sudden downturn in the market. (10:15)

Jay shares how he came up with the idea of starting Thimble. (11:21)

Jay mentions that he was excited about Thimble because it was challenging and highly regulated. (12:23)

Jay shares a very interesting story of how they came up with Thimble as the name of their company. (13:15)

Jay mentions that the main idea of their company is to build this symbol of how these small businesses can succeed on their terms. (14:17)

Jay shares that they have a widget and brokers portal that the people can access, and they also have a mobile application that’s highly utilized. (18:02)

Jay mentions that he’s reading the book called Sapiens: A Brief History of Humankind, by Yuval Noah Harari. (35:45)

Key Quotes:

“I think everybody denies the privilege that they’ve had. I try to think very carefully about how much privilege I’ve had growing up, regardless of whether that was kind of on the spectrum between luck and not luck. I think everyone should be aware of that.” – Jay Bregman

“From our perspective, we’re a product based company. We say let the best product win.  We think that the agents will recognize that our product is a great product that people want. Everybody will benefit from that transaction.” – Jay Bregman

“When you’re running a small business, this happens. Not necessarily all the time, but it happens. And when it happens, it is kind of always existential because you’re a small business. The shockwaves do affect you more than larger businesses who have more layers of insulation against things like this.” – Jay Bregman

Resources Mentioned:

Agency Intelligence

Reach out to Jason Cass

Jay Bregman LinkedIn


Sapiens: A Brief History of Humankind


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