Today's entrepreneur: Jay Bregman

Steven Loeb · November 4, 2019 · Short URL:

I love finding problems in the world and obsessing about their solutions

Today's entrepreneur is Jay Bregman, co-founder and CEO of Thimble (formerly Verifly), a company who's  mission is to make insurance simple, enabling small businesses to succeed on their own terms.

Thimble, an on-demand, by-the-job insurance app aimed at the ever-growing economy of independent, freelance, and gig workers. Available across more than 100 professions in nearly 50 states, Thimble provides affordable, flexible liability policies to fit the dynamic nature of modern small businesses. 

The company recently raised a $22 million Series A round of funding, bringing its total raised to $29 million. 

Prior to founding Thimble, Bregman founded rideshare startup Hailo, which raised over $100 million before being sold to Daimler in 2016. He also founded on-demand, same-day delivery network eCourier, which was bought by Royal Mail in 2015. 

Bregman earned his Bachelor's Degree in philosophy from Dartmouth College, andd his Master's Degree in Media & Communications Regulation & Policy from The London School of Economics and Political Science.

Companies I've founded or co-founded:

Thimble, Halio, eCourier

Achievements (products built, personal awards won):

Patents (2): System and Method for Controlling the Transport of Articles, System and Method for Analyzing Drone Flight Risk

If you are an entrepreneur, why?

I love finding problems in the world and obsessing about their solutions. I had originally planned to be a lawyer, but then I took a course called “Philosophy and Computing” at Dartmouth that combined my love for technology with my passion for thinking critically about the world. I ditched the lawyer thing and spent the next two terms as a research assistant at the Berkman Center for Internet & Society at Harvard. I have been fascinated by experimentation from a very young age – I flew rockets, built RC planes, then eventually got into computers. My father also had an influence, since we shared a passion for technology – he was a surgeon who invented the intra-aortic balloon pump, which is a device that helps the heart rest after bypass surgery.

My favorite startups:

ArtistOnGo, Keyto, Lever, Classpass

Why did you start your current company?

I saw a need emerging as work fundamentally changed in our country and became obsessed with creating a solution to help a staid industry adapt. I’ve been convinced that technology would greatly impact our daily lives for decades, and I thought we were witnessing the dawn of something incredible with the increased engagement in the on-demand economy.

I discovered that the insurance industry has been stagnant and very slow to adopt this idea, especially when it comes to the modern workforce. To this day, most business insurance is still sold on paper. There was always only a one-size-fits-all annual insurance policy, and it has been holding back small business owners for years. Small businesses rely on flexibility and convenience, which the age-old business model cannot provide. Currently, 40% of sole proprietors in the U.S. don’t have business insurance, and 75% are under-insured, meaning they are not only at risk, but more importantly, they are being denied access to jobs that require proof of insurance. I started Thimble to provide protection down to a single hour for hundreds of different jobs in the ever-growing economy of gig workers, freelancers, and small business owners.

What's most frustrating and rewarding about entrepreneurship/innovation?

Entrepreneurs often see an opportunity that the world isn’t quite ready for, which can feel frustrating. Sometimes, you just have to wait for the world to evolve a bit. I experienced this with mobile technology, a space where there’s now a larger opportunity than could have ever been imagined. I first created Hailo in 2011, which at its simplest form, matched taxi drivers with passengers. But, the product we built was perfect for the future of consumerism, as it was designed to usher in the revolution of mobile commerce.

On the flip side, I’m an artist and a builder at heart, so it’s always rewarding to see a vision come together. I tend to identify problems and immediately start thinking about how I can fix them. I love experimenting, throwing around ideas, and constantly playing with technology until I develop a solution. This eventual “aha moment” is always the best part.

What's the No. 1 mistake entrepreneurs make?

Entrepreneurs need to have confidence in themselves and their inventions. Lots of people get discouraged before they even begin because they think they’ll never find the right idea, or discover the perfect solution. My advice: find a problem that needs solving and go out on a limb; you’ll hone the idea along the way.

What are the top three lessons you've learned as an entrepreneur?

1) Along the lines above, I would advise all young entrepreneurs to follow their passions, even in the face of criticism. For example, when my mother discovered I was buying drones, she genuinely thought I had become a military hazard. People associate drones with a negative, dystopian vision of society, but this hobby is ultimately what led me to starting Thimble.

2) I also learned that it has never been more socially acceptable to become an entrepreneur – it’s the new normal. Don’t be afraid of the risk or the backlash because more and more people, from young graduates to older members of the workforce, are deciding to start their own ventures.

3) Finally, you should always surround yourself with great people. Once you identify your world-changing solution, it’s crucial to put together an all-star management team. You can’t do everything by yourself, and it’s important to have different skill sets, as well as different viewpoints, as you continue to scale.

Support VatorNews by Donating

Read more from our "Today's Entrepreneur" series

More episodes

Related Companies, Investors, and Entrepreneurs



Joined Vator on

Thimble's mission is to make insurance simple, enabling small businesses to succeed on their own terms.



Joined Vator on

Hailo is a network that matches passengers and licensed taxi drivers, using a tool which helps to make cabbies’ days more sociable – and profitable. Hailo makes sure people are never more than two taps away from a licensed taxi, and that cabbies get more passengers when they want them.


Jay Bregman

Joined Vator on