The VentureFizz Podcast: Jay Bregman - Founder and CEO of Thimble

November 21, 2019

The VentureFizz Podcast: Jay Bregman - Founder and CEO of Thimble

For the 148th episode of our podcast, I interviewed Jay Bregman, Founder and CEO of Thimble.

Jay is a serial entrepreneur, who has a history of building companies that have reflected the trend towards the gig economy. From package delivery to the taxi industry’s answer to Uber, he has transformed multiple industries and his latest company is tackling the insurance industry.

If you are a small business owner or freelancer, it is probably smart to have insurance to protect yourself, but you probably don’t need insurance all the time. You probably just need it while you are actually providing your service. In the past, if you wanted coverage, you would have to purchase a plan for a full year. Thimble is disrupting the industry by providing essential risk protection with a flexible model where you can purchase coverage by the hour, day, or month - starting at just $5. The company recently announced $22M in Series A funding led by IAC.

In this episode of our podcast, we cover:

  • What its like building a company that ended up being an answer to a Jeopardy question.
  •  Jay’s background growing up and how he ended up in entrepreneurship.
  • His first two startups eCourier and Hailo, which both transformed an industry and led to an exit.
  • All the details on Thimble and how it is allowing small businesses and freelancers to get flexible insurance on demand.
  • Advice on hiring during the early stage of a company.
  • And more!

Our Job Board has over 4,700 positions listed, and we just went through a redesign of the job listing. It is a much cleaner design and you’ll find highly relevant information on each listing like employee testimonials, photos, video, and the latest featured story from VentureFizz. This way you can learn a lot more about the company and its culture direct from each job listing. Go to to check it out.

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Keith Cline is the Founder of VentureFizz. Follow him on Twitter: @kcline6.