Thimble, formerly known as Verifly, raised $22 million in new financing designed to fuel further expansion and diversification well beyond its original focus on on-demand drone insurance.

Existing investors Slow Ventures, AXA Venture Partners and Open Ocean participated in a round led by IAC, or InterActiveCorp, a media and internet company that includes consumer brands such as Vimeo and Dotdash, along with companies such as Angie’s List and Match Group’s online dating portfolio. Verifly unveiled its Thimble rebranding as part of the Series A venture financing.

“It’s a huge vote of confidence in the business and the market,” Jay Bregman, Thimble/Verifly’s co-founder and CEO, said during a Carrier Management interview held in advance of the company’s financing and rebranding announcement. “What it says is there is something in the product that deserves to be vastly accelerated.”

Jay Bregman, Thimble

New York-based Verifly launched in 2016 with a $2.7 million venture financing and a focus on providing on-demand drone insurance that started at $10 per hour and could be purchased through an easy-to-use app for both commercial and recreational drone users. Its policies, underwritten by Markel Insurance Company, have since expanded to cover areas and workers including events and entertainment, handymen and contractors, landscapers, beauticians, pet and fitness professionals. The coverage is branded as affordable and flexible, and half of Thimble’s policies involve coverage for a single day or less. Customers can buy the policies in seconds via the company’s app, the web or partner APIs.

Bregman said the rebranding from Verifly to Thimble is meant to address the company’s broader focus, which will continue to expand over time.

“Now we cover almost 120 types of small business,” Bregman said. “It became clear that we were becoming much bigger, the opportunity was much bigger and we needed a name that basically reflected how big this could be—how iconic—not just for one type of business but every type of small business.”

Plans call for using the new financing to grow product offerings and hire more employees. About 40 people work for Verifly/Thimble right now, though Bregman said total staff could grow between 50 and 100 percent within the next year to 18 months.

From Verifly to Thimble

Why Thimble? Bregman said a company name “doesn’t have to mean anything,” reflecting the practice of startups often having quirky brand names meant to make an impression. In this case Thimble does have meaning, he said, noting that a thimble, worn on the finger while sewing, offers “small protection” as the company itself does.

Bregman added that some of the younger employees at Thimble did not understand the reference but still appreciated the name. “It’s got a story behind it—it is something we feel like we can truly own that is a real object in the world.”

Looking ahead, Bregman said he wants to build Thimble into something big that stands on its own.

“Our long-term goal is to build the epic insurance business for small businesses that want to succeed on their own terms,” Bregman said. “They can work as they want, they can get their [insurance coverage] certification instantly, etc. We think this is the foundation of a very large, diversified business.”

Slow Build

Bregman said the company expects Thimble will take time to build, and he feels that IAC in particular will be a good partner that can help make that happen.

“We understand this is going to take time and investment,” Bregman said. “One of the reasons we were so thrilled to partner with IAC as in investor is their track record for making and supporting entrepreneurs with wild, long-term visions, and being patient as investors, as opposed to [demanding] returns quickly.”

Michelle Arbov, head of M&A with IAC, said that Thimble is an ideal investment for a key reason.

“Thimble is just the kind of company IAC likes to back—a smart team with a disruptive technology that aims to shake up a traditional category,” Arbov said in prepared remarks. “We’re excited to see what they can do.”

Bregman describes Thimble’s current status as “purposely unprofitable,” with an initial focus on building a business model that generates “supreme profit” later on.

The company has products approved by regulators in 48 states and claims to have sold more than $100 billion in aggregate exposure. Thimble said it is on pace to sell 100,000 policies by the end of 2019, and asserts that 75 percent of its customers are new to business insurance altogether.