From Jay Bregman, CEO/Co-Founder of Thimble:

If there’s one thing I’ve learned building an insurance startup, it’s that while it is hard to make insurance fun, it’s even harder to make it simple.

We started Verifly in 2016 to make insurance accessible to drone operators, but it quickly became clear we were just scratching the surface of a much bigger opportunity. Work was becoming more transactional, not just for pilots, but for handymen, photographers, and landscapers. By applying our innovations more broadly, we could make insurance simple for millions of small businesses and independent workers across hundreds of professions.

2016 (Verifly)

Today (Thimble)

Insurable Professions



While we lovingly built Verifly, both as a brand and as a product, she was never intended to take on this ambitious challenge. So, after months of hard work behind the scenes, we’re finally ready to introduce not only a new brand but an entirely new platform for small business insurance.

Meet Thimble.

Why Now?

In 2010, I started Hailo, a ridesharing app which connected passengers to licensed taxi drivers. It was sold to Daimler (as in Mercedes-Benz) a few years later and now flourishes in Europe as Free Now. Together with companies like Uber, Lyft, TaskRabbit, and Postmates, we gave rise to the “gig economy.”

What started as a means of allowing people to earn more on the side, has devolved into “full-time” gig employment. This is not how it was supposed to end up. The relationship between modern workers and technology platforms is now contentious and fragile. I believe that, in launching Thimble, we have an opportunity to tip the scales in favor of small businesses and independent workers and get back to the true essence of the gig economy: enabling people to work on their own terms.

The Mission

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

We believe that anyone who wants to earn a living should be able to do so on their time, in their own way of working, not on terms set by their insurance company. Thimble is the first and only platform where you can get flexible General Liability insurance by the hour, day, or month, and do it in seconds.

We’ve focused on three key areas to address some of the biggest frustrations of traditional liability insurance for the modern worker:

  1. Instant. We’ve removed a ton of barriers, from hold music to lengthy applications, so you can get a Certificate of Insurance within seconds of your next job.
  2. On-demand. You can buy policies only for the time you need, whether that’s a month, a day, or even just a single hour.
  3. Flexible. Once you purchase your policy you can extend, change, or even cancel it right from our app.

So Far, Real Good.

Although this is day one for Thimble, we first introduced Verifly in 2016, and since then we’ve sold 14,300,000 hours of insurance amounting to over $100B in coverage. We’re on track to end 2019 with over 100,000 policies arranged.

One of the signals that we’re most excited by, however, is that 75% of our customers have never had business insurance before – proof that we’re making insurance more accessible. This is important because 40% of sole proprietors don’t buy business insurance. And customers seem to be really liking us: we’re rocking a 4.8-star rating in the App Store.

Here’s what customers are saying:

“The biggest draw was the ability to plug in for coverage over a set time period. The fact that you can select daily, weekly, monthly, and even hourly coverage is ludicrous and I love it! I wasn’t 100% sure where I was going to go with my business—you never really are when you start out.” Jamie – Landscaper

“This is the easiest business app have ever used during my 25 years experience of contracting! Just started a new company, Custom Coated Painting, LLC. I’ve completed over $100 mill of work over my time with a goal for every client being 100% satisfied with all aspects of our process, always working together with each client on a personal level. I’m providing complete client satisfaction to all clients now using the Verify App. Perfect tool for streamlining my new Painting company.” – Steve

No wonder our Net Promoter Score is consistently above 80. That’s Peloton territory.

Speaking of apps, here’s a quick look at our all-new mobile experience, which has been painstakingly designed to make it super fast and simple to get a policy even if your next job is just an hour from now.

The Future of “Verifly”

By the way, building products for drone operators and those who helped us originally take off (pun intended), is still a big part of our business and passion. For that reason, the Verifly drone app will still exist and evolve – you can now visit to get started.

Planting Seeds

Today, we also announced $22M in Series A funding led by IAC bringing us to $29 million in total funding. Mark, our director and IAC Chief Strategy Officer, explained the funding as follows: “What we think about at IAC is: How can we go about planting seeds of growth for the future? What will become the next ANGI Homeservices? What will become the next Match Group?”


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