Newly-rebranded Thimble allocates $22M to take flexible insurance to the gig economy

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Thimble founder and CEO Jay Bregman I iTMunch

Thimble, which gives flexible, short-term insurance to small businesses and freelancers, is stating that it has raised $22 million in a Series A funding round managed by IAC.

Until today, the startup was identified as Verifly, a name attached to the company’s primary aim of giving insurance to drone pilots. 

However, founder and CEO Jay Bregman who earlier founded ridesharing company Hailo said that thanks to consumer demand, the team kept adding insurance for various types of businesses and now it is rebranding to show that broader vision.

More About Thimble

It is easy to talk about Thimble consumers as being part of the “gig economy.” 

Bregman saw that these are not just people driving for Uber or delivering for Postmates.

Only 4% of the company’s consumers classify as gig economy workers.

He said that there is this more significant thing called the gig economy where people are working in flexible ways and on their terms.

Thimble now states that it gives liability coverage for consumers in more than 100 professions, which includes handymen, landscapers, DJs, musicians, beauticians and also dog walkers. 

Policies can be bought straight from the Thimble website or app by the hour, day, week, month or year.

Thimble has obtained administrative approval to sell insurance in 48 states as of now.

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Gig Worker’s Influence 

Bregman was questioned whether the broader political debates about whether gig workers are employees could influence the company’s business.

 In response, he pointed over to the fact that the vast majority of Thimble customers don’t think of themselves as gig workers.

Their only worry is that in attempting to solve a very critical problem with long-term gig employment, a few of the laws may accidentally scare off certain freelancers.

As for the investment, IAC’s chief strategy officer Mark Stein confirmed that the digital media operating company doesn’t make several early-stage, minority investments. 

But he mentioned that deals like this are about “planting seeds.”

According to him, they need to discover these sorts of significant, addressable market events now in the hopes of building huge, industry-changing businesses in the future.

Former investors Slow Ventures, AXA Venture Partners and Open Ocean also joined in the round, making Thimble’s total funding to $29 million.

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