Jay Bregman is a serial entrepreneur and the Founder & CEO of Thimble – Thimble delivers on-demand insurance by the job making insurance simple, helping small businesses to succeed on their own terms. Jay previously founded Hailo – a network that matches passengers and licensed taxi drivers, which was sold to Daimler – and eCourier – a technology-enabled services company, which was sold to the Royal Mail (the UK-equivalent of USPS).

Many small business owners are reassessing expenses from the ground up, and one particular expense that often comes to the top of the priority list is insurance. Getting the insurance coverage you need for a job usually entails a lengthy and often complicated process, and is cumbersome and expensive, not to mention hard to cancel. Jay shares how his company, Thimble, offers a new kind of insurance product – on-demand insurance by the job or even by the hour!

Jay lives in New York City.

Episode Topics & Questions include:

• What led you to solve the problem in the insurance industry?
  “By 2027, the majority of the U.S. workforce will work as freelancers. Thimble delivers on-demand insurance by the job to cover the 57 million people who work independently — such as photographers, handymen, DJs, and others — via our app. As more people freelance, many clients require them to be insured. These workers need easy, mobile access to quick, inexpensive, short-term insurance so they never lose a potential job or have to call an insurance broker. Thimble delivers this in seconds for as little as $5 for one hour and one million dollars of business insurance.”
• Who is your ideal customer? On-demand insurance is ideal for all types of small businesses and solopreneurs, including: Event Vendors, Entertainers, Freelancers, Consultants, Photographers, Videographers, Contractors, Handymen, Janitors, Cleaners, Landscapers, Hair & Beauty Professionals, Fitness & Personal Trainers, Pet Sitters, Drone Pilots.
• What type of insurance is available from Thimble?
  • General Liability Insurance – Protects your business when accidents happen to a third party, causing bodily injury or property damage.
  • Professional Liability Insurance – Covers claims that your work was unsatisfactory, late, or never done. It’s also called errors and omissions insurance.
  • Business Owners should also carry general commercial liability insurance, auto insurance, etc?
  • What’s not covered?
• Sounds a bit too good to be real. How are you able to provide this insurance product?
• How can a small business owner get started with trying your product?

Episode Host: Henry Lopez is a serial entrepreneur, small business coach, and the host of this episode of The How of Business podcast show – dedicated to helping you start, run and grow your small business.

Resources:

Books mentioned in this episode:
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• Why We Sleep: Unlocking the Power of Sleep and Dreams by Matthew Walker PhD

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